Looking for free events and discounts on events in Chicago? You're in the right place. Search our free & cheap Chicago events calendar for things to do and ways to have fun in the windy city. Look at upcoming events in list view, choose a specific date, or click on the month-view to see everything happening this month at a glance.
Don't forget to also check out our guide to what's free and cheap in Chicago this week, as well as some of our popular sections like Free Museum Days in Chicago, Half-Price Tickets to Chicago Entertainment, Things to Do with Kids in Chicago, and Chicago Restaurant Deals.
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International Jazz Day International Jazz DayTuesday, April 21, 2026 Commemorating 15 years of jazz music's role in fostering peace and intercultural dialogue, International Jazz Day is celebrated in 190 countries around the globe. On April 30, 2026, Chicago will host an all-star global concert, ... Read More » Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | International Jazz Day International Jazz DayTuesday, April 21, 2026 Commemorating 15 years of jazz music's role in fostering peace and intercultural dialogue, International Jazz Day is celebrated in 190 countries around the globe. On April 30, 2026, Chicago will host an all-star global concert, ... Read More » Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | |||||
Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Free admission for Illinois residents 10:00 am to 9:00 pm Free admission for Illinois residentsWeekly on TuesdayFree Tuesdays at the Museum of Contemporary Art for Illinois residents. Where: Museum of Contemporary Art, 220 E. Chicago Ave., 312-397-4010 When: 10am to 9pm Tuesdays; 10am to 5pm Wednesdays-Sundays; Closed Mondays. Free Tuesdays for Illinois residents with ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » |
Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayEven though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through ... Read More » Spring Flower Show 10:00 am to 5:00 pm Spring Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayWelcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » Spring Flower Show 10:00 am to 8:00 pm Spring Flower ShowSunday, March 1, 2026 Welcome the colors and excitement of the spring season with the annual Spring Flower Show at Garfield Park Conservatory. This year's show is called "Showers of Flowers" and runs through May 10, 2026. Wander through over ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Free admission for Illinois residents 10:00 am to 9:00 pm Free admission for Illinois residentsWeekly on TuesdayFree Tuesdays at the Museum of Contemporary Art for Illinois residents. Where: Museum of Contemporary Art, 220 E. Chicago Ave., 312-397-4010 When: 10am to 9pm Tuesdays; 10am to 5pm Wednesdays-Sundays; Closed Mondays. Free Tuesdays for Illinois residents with ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » | Cherry Blossom Season 9:00 am to 6:00 pm Cherry Blossom SeasonDailyThe delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April ... Read More » Chicago Mayfest 12:00 pm to 10:00 pm Chicago MayfestSaturday, May 16, 2026 Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood. This ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » |
Maxwell Street Market 10:00 am to 3:00 pm Maxwell Street MarketEvery 1 months on the 3rd SundayThere's no Chicago market more iconic than Maxwell Street Market. This year, the market runs on select Sundays, May 17 through October 4, 2026, 10 am -3 pm. Open since 1912, this bustling marketplace is ... Read More » Chicago Mayfest 12:00 pm to 10:00 pm Chicago MayfestSaturday, May 16, 2026 Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood. This ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Free admission for Illinois residents 10:00 am to 9:00 pm Free admission for Illinois residentsWeekly on TuesdayFree Tuesdays at the Museum of Contemporary Art for Illinois residents. Where: Museum of Contemporary Art, 220 E. Chicago Ave., 312-397-4010 When: 10am to 9pm Tuesdays; 10am to 5pm Wednesdays-Sundays; Closed Mondays. Free Tuesdays for Illinois residents with ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » Forte Happy Hour 4:00 pm to 7:00 pm Forte Happy HourWeekly on Tuesday Wednesday Thursday and FridayThe Symphony Center's new restaurant, Forte, is kicking off the year with happy hour specials that are sure to bring harmony to foodies searching for new culinary thrills. Located on Chicago's cultural mile, Forte at the ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » | Randolph Street Market 10:00 am to 5:00 pm Randolph Street MarketFriday, May 22, 2026 One of the most beloved events of the early summer season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on May ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » | Randolph Street Market 10:00 am to 5:00 pm Randolph Street MarketFriday, May 22, 2026 One of the most beloved events of the early summer season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on May ... Read More » Belmont Sheffield Music Fest 11:00 am to 10:00 pm Belmont Sheffield Music FestSaturday, May 23, 2026 For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026. The 40th annual celebration of community and local musicians ... Read More » Memorial Day Parade 12:00 pm to 3:00 pm Memorial Day ParadeSaturday, May 23, 2026 The annual Chicago Memorial Day Parade and Wreath Laying Ceremony honors all men and women who made the ultimate sacrifice in defense of our country. This year's parade is scheduled for May 23, 2026. Head to ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » |
Randolph Street Market 10:00 am to 5:00 pm Randolph Street MarketFriday, May 22, 2026 One of the most beloved events of the early summer season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on May ... Read More » Belmont Sheffield Music Fest 11:00 am to 10:00 pm Belmont Sheffield Music FestSaturday, May 23, 2026 For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026. The 40th annual celebration of community and local musicians ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Free admission for Illinois residents 10:00 am to 9:00 pm Free admission for Illinois residentsWeekly on TuesdayFree Tuesdays at the Museum of Contemporary Art for Illinois residents. Where: Museum of Contemporary Art, 220 E. Chicago Ave., 312-397-4010 When: 10am to 9pm Tuesdays; 10am to 5pm Wednesdays-Sundays; Closed Mondays. Free Tuesdays for Illinois residents with ... Read More » Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » Forte Happy Hour 4:00 pm to 7:00 pm Forte Happy HourWeekly on Tuesday Wednesday Thursday and FridayThe Symphony Center's new restaurant, Forte, is kicking off the year with happy hour specials that are sure to bring harmony to foodies searching for new culinary thrills. Located on Chicago's cultural mile, Forte at the ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » Happy Hour 3:00 pm to 6:00 pm Happy HourWeekly on Monday Tuesday Wednesday Thursday and FridayUnwind and celebrate the end of the work day with food and drink deals at Canal Street Eatery Monday through Friday, 3- 6 p.m. in the bustling West Loop neighborhood. Sip on $8 cocktails like Aperol ... Read More » | Under The Picasso Noontimes 10:30 am to 1:30 pm Under The Picasso NoontimesWeekly on Monday Tuesday Wednesday Thursday and FridayOne of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present ... Read More » Chicago Cultural Center Tours 1:15 pm to 12:00 am Chicago Cultural Center ToursWeekly on Thursday and FridayExplore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » | Free Docent-Led Tour 12:00 pm to 1:15 pm Free Docent-Led TourSaturday, May 30, 2026 Discover the dynamic culture of Puerto Rico and Chicago's strong link to the island by taking a free docent-led tour of the National Museum of Puerto Rican Arts and Culture in the Humboldt Park neighborhood. ... Read More » Do Division Street Fest 12:00 pm to 10:00 pm Do Division Street FestSaturday, May 30, 2026 Division Street in West Town comes alive with live music, food, boutique sales, fashion shows and family fun with the annual Do Division Street Fest on May 29-31, 2026. One of the most anticipated summer music ... Read More » Chicago RIverwalk and History Tour 2:00 pm to 4:00 pm Chicago RIverwalk and History TourWeekly on Thursday Friday and SaturdayChicago's skyline is legendary, our city's soaring architecture distinguishes it from every city in the world and there's no more scenic way to view it than from the Chicago Riverwalk. The Architecture Boat Tour is one ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » |
Celebrate German Culture at Maifest 12:00 pm to 10:00 pm Celebrate German Culture at MaifestSunday, May 31, 2026 Welcome spring at the traditional German celebration of the season, Maifest Chicago. The 26th annual festival runs from May 29 -31, 2026, in the heart of Chicago's German community in Lincoln Square. Chow down on lots of ... Read More » Do Division Street Fest 12:00 pm to 10:00 pm Do Division Street FestSaturday, May 30, 2026 Division Street in West Town comes alive with live music, food, boutique sales, fashion shows and family fun with the annual Do Division Street Fest on May 29-31, 2026. One of the most anticipated summer music ... Read More » Lincoln Park Blues and Gangster Tour 2:00 pm to 4:00 pm Lincoln Park Blues and Gangster TourWeekly on Sunday Friday and SaturdayChicago boasts a reputation for a lot of great things--architecture, food and a stunning skyline. The city's claim as the home of the blues is another great accolade but Chicago is also recognized for its ... Read More » WInterland at Gallagher Way 3:00 pm to 9:00 pm WInterland at Gallagher WayDailyDive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, ... Read More » |








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