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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Lincoln Park Conservatory Winter Flower Show 10:00 am to 3:00 pm Lincoln Park Conservatory Winter Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayLincoln Park Conservatory's beloved Winter Flower Show will explore the enchanting beauty of fireplaces and poinsettias with this year's show, "Fireside," which runs from November 26, 2025, to January 4, 2026. Cozy up at the enormous ... Read More » Garlfiel Park Conservatory Holiday Flower Show 10:00 am to 5:00 pm Garlfiel Park Conservatory Holiday Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayThe Chicago holiday season is never complete without the natural beauty of the Garfield Park Winter Flower Show. This year's theme is Merry & Bright, celebrating the festive colors and foliage of the season through ... Read More » Malcolm X College Kwanzaa Celebration 10:00 am to 6:00 pm Malcolm X College Kwanzaa CelebrationDailyThe exuberant seven-day African American tradition of Kwanzaa will be celebrated with seven days of free music, dance, culture and community at Malcolm X College on December 26, 2025-January 1, 2026. The annual Malcolm X College ... Read More » Winter Wonderfest 10:00 am to 10:00 pm Winter WonderfestFriday, December 5, 2025 Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from December 5, 2025, to ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Lincoln Park Conservatory Winter Flower Show 10:00 am to 3:00 pm Lincoln Park Conservatory Winter Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayLincoln Park Conservatory's beloved Winter Flower Show will explore the enchanting beauty of fireplaces and poinsettias with this year's show, "Fireside," which runs from November 26, 2025, to January 4, 2026. Cozy up at the enormous ... Read More » Garlfiel Park Conservatory Holiday Flower Show 10:00 am to 5:00 pm Garlfiel Park Conservatory Holiday Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayThe Chicago holiday season is never complete without the natural beauty of the Garfield Park Winter Flower Show. This year's theme is Merry & Bright, celebrating the festive colors and foliage of the season through ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Lincoln Park Conservatory Winter Flower Show 10:00 am to 3:00 pm Lincoln Park Conservatory Winter Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayLincoln Park Conservatory's beloved Winter Flower Show will explore the enchanting beauty of fireplaces and poinsettias with this year's show, "Fireside," which runs from November 26, 2025, to January 4, 2026. Cozy up at the enormous ... Read More » Garlfiel Park Conservatory Holiday Flower Show 10:00 am to 5:00 pm Garlfiel Park Conservatory Holiday Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayThe Chicago holiday season is never complete without the natural beauty of the Garfield Park Winter Flower Show. This year's theme is Merry & Bright, celebrating the festive colors and foliage of the season through ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | ||||
Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Lincoln Park Conservatory Winter Flower Show 10:00 am to 3:00 pm Lincoln Park Conservatory Winter Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayLincoln Park Conservatory's beloved Winter Flower Show will explore the enchanting beauty of fireplaces and poinsettias with this year's show, "Fireside," which runs from November 26, 2025, to January 4, 2026. Cozy up at the enormous ... Read More » Garlfiel Park Conservatory Holiday Flower Show 10:00 am to 5:00 pm Garlfiel Park Conservatory Holiday Flower ShowWeekly on Sunday Wednesday Thursday Friday and SaturdayThe Chicago holiday season is never complete without the natural beauty of the Garfield Park Winter Flower Show. This year's theme is Merry & Bright, celebrating the festive colors and foliage of the season through ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Winter Wonderfest 10:00 am to 10:00 pm Winter WonderfestFriday, December 5, 2025 Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from December 5, 2025, to ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Winter Wonderfest 10:00 am to 10:00 pm Winter WonderfestFriday, December 5, 2025 Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from December 5, 2025, to ... 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 » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... 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 » 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... 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 » |
Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » |
Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Sky Rink 10:00 am to 8:00 pm Sky RinkWeekly on Sunday Friday and SaturdayIce skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with ... Read More » | Free Martin Luther King Day Chicago events All Day Free Martin Luther King Day Chicago eventsMonday, January 19, 2026 Martin Luther King Jr. Day offers opportunities to celebrate the legacy of Dr. King by supporting racial justice causes, giving back to the community, and attending events that reflect his fight for equality and civil ... Read More » Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... 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 » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Chicago International Puppet Theater Festival 11:00 am to 9:30 pm Chicago International Puppet Theater FestivalDailyDive into the fanciful world of puppetry at the Chicago International Puppet Theater Festival, which presents master puppeteers from around the world in an array of performances throughout the city. The fest hosts over 100 ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » Rudolph's Rooftop 11:00 am to 12:00 am Rudolph's RooftopSunday, December 21, 2025 Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » |
Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » | Free things to do during Chicago Winter All Day Free things to do during Chicago WinterDailyChicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the ... Read More » Chicago Restaurant Week Chicago Restaurant WeekDailyChicago Restaurant Week returns on January 23, 2026- February 8, 2026, with lots of tasty opportunities to dive into the city's award-winning food scene. Technically, it's not just a week, it's a 17-day eating extravaganza. ... Read More » Ice Skating at Gallagher Way Ice Skating at Gallagher WayDailyEmbrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl ... Read More » Chicago Architecture Biennial Chicago Architecture BiennialSunday, January 11, 2026 The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city ... Read More » |








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