Chicago is packed with festivals, art fairs, and other events all year long.
Some event organizers have announced dates of their events which I’ve updated below. Many events don’t finalize dates and event detail until closer to the actual date so check back for more info. Enjoy!
In summer we cover festivals and events that charge $10 or less admission and that are closer in and easy to access via public transit. Chicago residents aren’t required to pay entrance fees to street festivals. However many of these festivals are fundraisers for various neighborhood associations, schools and other organizations. More info here.
To find all events check the calendar here. To receive all the latest news on deals, discounts and free events in Chicago, sign up for the daily Chicago on the Cheap newsletter. You can also follow us on Instagram where I post additional deals in real time, Facebook and on Twitter. Cheers!
2019
February
- McCormick Ice Rink through March Millennium Park
- Maggie Daley Ice Skating Ribbon through March
- Lincoln Park Conservatory Spring Flower Show Feb 10-May 13
- Chicago Auto Show Feb 10-18
- Chinese New Year Events Feb -March 3
- Navy Pier: Global Connections Feb 10 and 24
- Garfield Park Conservatory Spring Flower Show Feb 10-May 13
NO DATES BELOW ARE UPDATED
March
- Free events at Daley Plaza under the Picasso
- Lincoln Park Conservatory Spring Flower Show through May 13
- Garfield Park Conservatory Spring Flower Show through May 13
- McCormick Ice Rink through March 11 Millennium Park
- Maggie Daley Ice Skating Ribbon through March 11
- Navy Pier: Global Connections March 4
- March in the Downtown Chicago St. Pat’s Parade March 17
- St. Patrick’s Day Parade March 17 Downtown
- Where to drink on St. Patrick’s Day
- Handmade Market at Empty Bottle March 10 Wicker Park To
- Southside Irish Parade March 11 Western from 103rd to 115th
- Northwest Side Irish Parade March 11 Raven from Neola to Northwest Highway to Harlem
- Chicago Flower & Garden Show at Navy Pier March 18-26
- Randolph Street Market March 24-25 West Loop
- Macy’s Flower Show March 25- April 8 Downtown
April
- Macy’s Flower Show March 25- April 8 Downtown
- Free events at Daley Plaza under the Picasso
- Free screenings Chicago Latino Film Festival No events 2018
- Lincoln Park Conservatory Spring Flower Show Feb 11-May 14
- Garfield Park Conservatory Spring Flower Show Feb 28-May 10
- Hellenic Heritage Parade (Greek Independence Day Parade) April 29
- One of A Kind Show and Sale Spring Show April 27-29
May
- Free events at Daley Plaza under the Picasso
- Kite Fest May 5 Cricket Hill/Montrose Beach
- Polish Parade May 5 Dearborn Street Downtown
- Lincoln Park Conservatory Spring Flower Show Feb 11-May 14
- Garfield Park Conservatory Spring Flower Show Feb 28-May 10
- Chicago Riverwalk Kick-off Celebration May 18-20
- Chicago Mayfest May 18-20 Lakeview
- Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
- Memorial Day Parade May 26 State Street Downtown
- Randolph Street Market May 26-27 West Loop
- Free Millennium Park House Party May 26
- Belmont-Sheffield Music Fest May 26-27
- Maifest Chicago May 31-June 3 Lincoln Square
June
- Gospel Fest June 1-2 Millennium Park
- Lincoln Park Greek Fest June 1-3
- Do-Division June 1-3 Wicker Park
- 57th Street Art Fair June 2-3 Hyde Park
- Chicago Blues Fest Preview Events June 4 and 7
- Chicago Blues Fest June 8-10 Millennium Park
- Ribfest Chicago June 8-10 Lincoln/Irving Park/Damen
- Andersonville Midsommarfest June 8-10
- Printers Row Lit Fest June 9-10
- Wells Street Art Fest June 9-10 Old Town
- Old Town Art Fair June 9-10 Lincoln at Wisconsin Lincoln Park
- Chicago World Naked Bike Ride June 9 Location TBA
- Taste of Randolph Street June 15-16 West Loop More info to come
- Pride Fest June 16-17 Boystown
- Gold Coast Art Fest June 17-18 Grant Park
- Pride Fest Navy Pier June 23
- Gay & Lesbian Pride Parade June 24 Boystown
- Ravenswood on Tap June 23-24
- Logan Square Arts Fest June 22-24
- Chinatown Dragon Boat Races June 23
- Free events at Daley Plaza under the Picasso
- Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
- Millennium Park Summer Film Series June 5 – August 21
- Grant Park Music Festival June 13-August 15 Millennium Park Wednesday Concerts
- Grant Park Music Festival June 15-August 17 Millennium Park Friday and Saturday Concerts
- Millennium Park Summer Music Series June 18-Aug 16
- Millennium Park Family Fun Festival June 25-August 10 (weekdays)
- SummerDance June 28-August 25 Grant Park
- Randolph Street Market June 23-24 West Loop
- Windy City RibFest June 29-July 1 Uptown
July
- Free events at Daley Plaza under the Picasso
- Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
- Millennium Park Summer Music Series June 12-August 21
- Grant Park Music Festival June 14-August 16 Millennium Park Wednesday Concerts
- Grant Park Music Festival June 16-August 19 Millennium Park Friday and Saturday Concerts
- Millennium Park Summer Film Series June 13 – Sept 5
- Millennium Park Family Fun Festival June 25-August 10 (weekdays)
- SummerDance June 28-August 25 Grant Park
- Free July 4 concert Millennium Park
- Millennium Art Festival July 6-8 Lake Street at Michigan Avenue
- West Fest July 6-8 Chicago Ave. between Damen & Wood West Town
- Taste of Chicago July 11-15 Grant Park
- Square Roots Music Fest July 13-15 Lincoln Square
- R0scoe Village Burger Fest July 14-18
- Bucktown Garden Walk July 14-15
- Southport Art & Music Fest July 14-15
- Chinatown Summer Fair July 15
- Taste of River North July 20-22
- Art Fest Michigan Avenue July 20-22 Downtown
- Disability Pride Parade July 21 401 S. Plymouth to Daley Plaza Route may be changing Check back
- Sheffield Garden Walk & Fest July 21-22 Lincoln Park
- Newberry Library Book Fair July 26-29
- Andersonville Sidewalk Sale July 27-29
- Wicker Park Fest July 27-29
- Taste of Lincoln Avenue July 28-29 Lincoln Park
- Randolph Street Market July 28-29 West Loop
August
- Free events at Daley Plaza under the Picasso
- Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
- Millennium Park Summer Music Series June 12-Aug 21
- Grant Park Music Festival June 14-August 16 Millennium Park Wednesday Concerts
- Grant Park Music Festival June 16-August 19 Millennium Park Friday and Saturday Concerts
- Millennium Park Family Fun Festival June 25-August 10 (weekdays)
- Millennium Park Summer Film Series June 13 – Sept 5
- SummerDance June 28-August 25 Grant Park
- Jeff Fest Arts & Music Festival Aug 3-5
- Edge Fest Aug 4–5 5900 N. Broadway Edgewater
- Chicago Hot Dog Fest August 10-12
- Retro on Roscoe Aug 10-12 Roscoe Village
- Ginza Holiday Fest Aug 10-12 435 W. Menomonee St. Lincoln Park
- Northalsted Market Days Aug 11-12 Boystown
- Clark After Dark Aug 16 River North
- Festa Italiana No event 2018 Little Italy
- Little Italy Festa Aug 16-19
- Glenwood Avenue Arts Fest Aug 17 – 19 6900N/1400W Rogers Park
- Chicago Air & Water Show Aug 18-19 North Avenue Beach/Downtown
- Pilsen Fest Aug 18-19
- Ukrainian Days Festival Aug 25-26
- Taste of Greektown Aug 24-26
- Randolph Street Market August 25-26 West Loop
- Logan Square Food Truck Social Aug 24-26
- Bucktown Arts Fest Aug 25-26
- Chicago Jazz Fest Aug 29-Sept 2 Chicago Cultural Center, Millennium Park and Harris Theater rooftop
- Fifth Star Awards No event 2018 Millennium Park
September
- Randolph Street Market September 29-30 West Loop
- Hyde Park Jazz Fest Sept 29-30
- Oktoberfest Chicago Sept 28-30 Lakeview
- Free Family Festival Lincoln Park Zoo Sept 28-Oct 28; Oct 8
- Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
- SummerDance June 23-September 10 Grant Park
- Millennium Park Summer Film Series June 13 – Sept 5
- Chicago Jazz Fest Aug 29-Sept 2 Chicago Cultural Center, Millennium Park and Harris Theater rooftop
- Taste of Polonia Aug 31-Sept 1 Jefferson Park
- German American Fest Sept 7-9 Lincoln Square
- Von Steuben German Day Parade Sept 8 Lincoln Square (part of German American Fest )
- Lakeview East Festival of the Arts Sept 8-9
- Festival on Prairie Avenue Sept 8 South Loop
- Annual World Music Festival Chicago Sept 7-23
- Chicago Turkish Festival Sept 13-15
- Ravenswood Art Walk Sept 15-16
- Lakeview Taco Fest Chicago Sept 15-16
- Printer’s Row Art Fest Sept 15-16
October
- Corn Mazes and Pumpkin Patches around Chicago
- Free Family Festival Lincoln Park Zoo Sept 28-Oct 28; Oct 8
- West Town Art Walk Oct 5-6
- Columbus Parade Oct 8 Downtown
- North Park Village Harvest Festival Oct 13
- Double Ten Parade in Chinatown Chicago Oct. TBD
- Open House Chicago Oct 13-14
- Free Fall Festival at Jesse White Park Oct 20
- Arts in the Dark The Halloween Parade and After Party Oct 20 Downtown
- Free Halloween events at Navy Pier No info
- Free Lincoln Park Spooky Zoo Oct 27
- National Museum of Mexican Art Day of the Dead Oct 28 Pilsen
- Maxwell Street Market Day of the Dead Celebration Oct 28 South Loop
- Randolph Street Market Oct 27-28 West Loop
- Clark Street Spooktacular Oct 28 Lincoln Park
- Logan Square Halloween Parade Oct 28
- Northalsted Halloween Parade Oct 31 On Halsted from Belmont to Addison
- Halloween on The 606 Oct 31
- Chicago Trick-or-treat and Halloween events
November
- 900 N. Michigan Holiday Tree Lighting Nov. 16
- Millennium Park Christmas Tree Lighting Nov 16
- Mag Mile Lights Festival Nov 16-17
- Randolph Street Market Nov 17-18 West Loop
- Thanksgiving Day Parade Nov 22
- Free day at Morton Arboretum Nov 22
- Maggie Daley Skating Ribbon Nov 16-March 2019
- Christkindlmarket Market Nov 16-Dec 24 Daley Plaza
- McCormick Ice Rink Nov. 16- March 4 Millennium Park
- Caroling at Cloud Gate Fridays, Nov 23-Dec 14, 2018 Millennium Park
- Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
- Garfield Park Holiday Flower Show November 23-Jan 6, 2019
- Wreathing of the Lions Nov 24 Art Institute of Chicago
- CTA Holiday Train Nov 23-Dec 21
- Lincoln Park Conservatory Holiday Flower Show and trains Nov 23-Jan 6
- CTA Holiday Bus Nov 27-Dec 23
- Old Town Tree Lighting Nov. 29
December
- Renegade Craft Fair Dec 1-2 Bridgeport
- Santa’s Misbehaving Dec 2 Downtown
- Made in Chicago Holiday Market Dec 3 West Loop
- One of a Kind Show Dec. 6-9
- Ugly Sweater Skate Dec 8 Maggie Daley Park
- Late Night Andersonville Dec 7 and 21
- Bucktown Holiday Art Show Dec 8-9
- West Town Winter Fest Dec 8
- Holiday Remix Chicago No dates on website Uptown
- Holiday Dose Market Dose Markets have ended permanently West Loop
- St Lucia Celebration No event 2018 Daley Plaza
- McCormick Ice Rink through March 2019 Millennium Park
- Maggie Daley Skating Ribbon Nov 16-March 2019
- Winter Wonder Fest Dec 1 -Jan 6 Navy Pier
- Garfield Park Holiday Flower Show November 23-Jan 6, 2019
- CTA Holiday Train Nov 23-Dec 21
- CTA Holiday Bus Nov 17-Dec 23
- Christkindlmarket Market Nov 16-Dec 24 Daley Plaza Select dates and times
- Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
- St. Lucia Fest Dec 13 Andersonville
- Randolph Street Market Dec 15-16 West Loop
- Jingle Fest Dec 15 West Loop
- The Chicago Santa Crawl Dec 15 River North
- Skate with Santa Dec 15 Maggie Daley Park
- Tuba Christmas Dec 22 Loop
- Free day at Morton Arboretum Dec 25
- avy Pier Fireworks Dec 31
2020
January
- Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
- Garfield Park Holiday Flower Show November 23-Jan 6, 2019
- McCormick Ice Rink through March Millennium Park
- Maggie Daley Ice Skating Ribbon through March
- Events below will be updated when info is available. Check back.
- Chicago Boat, Sports & RV Show Jan 10-14
- Chicago Restaurant Week Jan 26-Feb 8
- Randolph Street Market Festival Jan 28-29
- Chinese New Year Events Jan 28
February
Chicago Restaurant Week through Feb 8