Chicago on the Cheap

Deals, discounts and free events in Chicago

2019 Events

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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, and Facebook. Cheers!

2019

April

  1. Macy’s Flower Show March 24 April 7 Downtown
  2. Free events at Daley Plaza under the Picasso
  3. Lincoln Park Conservatory Spring Flower Show Feb 9-May 12
  4. Garfield Park Conservatory Spring Flower Show through May 12
  5. Free screenings Chicago Latino Film Festival No events 2018

  6. Dates below not updated. Check back later for more info.

  7. Hellenic Heritage Parade (Greek Independence Day Parade) April 29
  8. One of A Kind Show and Sale Spring Show April 27-29

May

  1. Free events at Daley Plaza under the Picasso
  2. Kite Fest May 5 Cricket Hill/Montrose Beach
  3. Polish Parade May 5 Dearborn Street Downtown
  4. Lincoln Park Conservatory Spring Flower Show Feb 9-May 12
  5. Garfield Park Conservatory Spring Flower Show through May 12
  6. Chicago Riverwalk Kick-off Celebration May 18-20
  7. Chicago Mayfest May 18-20 Lakeview
  8. Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
  9. Memorial Day Parade May 26 State Street Downtown
  10. Randolph Street Market May 26-27 West Loop
  11. Free Millennium Park House Party May 26
  12. Belmont-Sheffield Music Fest May 26-27
  13. Maifest Chicago May 31-June 3 Lincoln Square

June

  1. Gospel Fest June 1-2 Millennium Park
  2. Lincoln Park Greek Fest June 1-3
  3. Do-Division June 1-3 Wicker Park
  4. 57th Street Art Fair June 2-3 Hyde Park
  5. Chicago Blues Fest Preview Events June 4 and 7
  6. Chicago Blues Fest June 8-10 Millennium Park
  7. Ribfest Chicago June 8-10 Lincoln/Irving Park/Damen
  8. Andersonville Midsommarfest June 8-10
  9. Printers Row Lit Fest June 9-10
  10. Wells Street Art Fest June 9-10 Old Town
  11. Old Town Art Fair June 9-10 Lincoln at Wisconsin Lincoln Park
  12. Chicago World Naked Bike Ride June 9 Location TBA
  13. Taste of Randolph Street June 15-16 West Loop More info to come
  14. Pride Fest June 16-17 Boystown
  15. Gold Coast Art Fest June 17-18 Grant Park
  16. Pride Fest Navy Pier June 23
  17. Gay & Lesbian Pride Parade June 24 Boystown
  18. Ravenswood on Tap June 23-24
  19. Logan Square Arts Fest June 22-24
  20. Chinatown Dragon Boat Races June 23
  21. Free events at Daley Plaza under the Picasso
  22. Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
  23. Millennium Park Summer Film Series June 5 – August 21
  24. Grant Park Music Festival June 13-August 15 Millennium Park Wednesday Concerts
  25. Grant Park Music Festival June 15-August 17 Millennium Park Friday and Saturday Concerts
  26. Millennium Park Summer Music Series June 18-Aug 16
  27. Millennium Park Family Fun Festival June 25-August 10 (weekdays)
  28. SummerDance June 28-August 25 Grant Park
  29. Randolph Street Market June 23-24 West Loop
  30. Windy City RibFest June 29-July 1 Uptown

July

  1. Free events at Daley Plaza under the Picasso
  2. Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
  3. Millennium Park Summer Music Series June 12-August 21
  4. Grant Park Music Festival June 14-August 16 Millennium Park Wednesday Concerts
  5. Grant Park Music Festival June 16-August 19 Millennium Park Friday and Saturday Concerts
  6. Millennium Park Summer Film Series June 13 – Sept 5
  7. Millennium Park Family Fun Festival June 25-August 10 (weekdays)
  8. SummerDance June 28-August 25 Grant Park
  9. Free July 4 concert Millennium Park
  10. Millennium Art Festival July 6-8 Lake Street at Michigan Avenue
  11. West Fest July 6-8 Chicago Ave. between Damen & Wood West Town
  12. Taste of Chicago July 11-15 Grant Park
  13. Square Roots Music Fest July 13-15 Lincoln Square
  14. R0scoe Village Burger Fest July 14-18
  15. Bucktown Garden Walk July 14-15
  16. Southport Art & Music Fest July 14-15
  17. Chinatown Summer Fair July 15
  18. Taste of River North July 20-22
  19. Art Fest Michigan Avenue July 20-22 Downtown
  20. Disability Pride Parade July 21 401 S. Plymouth to Daley Plaza Route may be changing Check back
  21. Sheffield Garden Walk & Fest July 21-22 Lincoln Park
  22. Newberry Library Book Fair July 26-29
  23. Andersonville Sidewalk Sale July 27-29
  24. Wicker Park Fest July 27-29
  25. Taste of Lincoln Avenue July 28-29 Lincoln Park
  26. Randolph Street Market July 28-29 West Loop

August

  1. Free events at Daley Plaza under the Picasso
  2. Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
  3. Millennium Park Summer Music Series June 12-Aug 21
  4. Grant Park Music Festival June 14-August 16 Millennium Park Wednesday Concerts
  5. Grant Park Music Festival June 16-August 19 Millennium Park Friday and Saturday Concerts
  6. Millennium Park Family Fun Festival June 25-August 10 (weekdays)
  7. Millennium Park Summer Film Series June 13 – Sept 5
  8. SummerDance June 28-August 25 Grant Park
  9. Jeff Fest Arts & Music Festival Aug 3-5
  10. Edge Fest Aug 4–5 5900 N. Broadway Edgewater
  11. Chicago Hot Dog Fest August 10-12
  12. Retro on Roscoe Aug 10-12 Roscoe Village
  13. Ginza Holiday Fest Aug 10-12 435 W. Menomonee St. Lincoln Park
  14. Northalsted Market Days Aug 11-12 Boystown
  15. Clark After Dark Aug 16 River North
  16. Festa Italiana No event 2018 Little Italy
  17. Little Italy Festa Aug 16-19
  18. Glenwood Avenue Arts Fest Aug 17 – 19 6900N/1400W Rogers Park
  19. Chicago Air & Water Show Aug 18-19 North Avenue Beach/Downtown
  20. Pilsen Fest Aug 18-19
  21. Ukrainian Days Festival Aug 25-26
  22. Taste of Greektown Aug 24-26
  23. Randolph Street Market August 25-26 West Loop
  24. Logan Square Food Truck Social Aug 24-26
  25. Bucktown Arts Fest Aug 25-26
  26. Chicago Jazz Fest Aug 29-Sept 2 Chicago Cultural Center, Millennium Park and Harris Theater rooftop
  27. Fifth Star Awards No event 2018 Millennium Park

September

  1. Randolph Street Market September 29-30 West Loop
  2. Hyde Park Jazz Fest Sept 29-30
  3. Oktoberfest Chicago Sept 28-30 Lakeview
  4. Free Family Festival Lincoln Park Zoo Sept 28-Oct 28; Oct 8
  5. Navy Pier Summer Fireworks Wednesdays and Saturdays May 26-Sept 1
  6. SummerDance June 23-September 10 Grant Park
  7. Millennium Park Summer Film Series June 13 – Sept 5
  8. Chicago Jazz Fest Aug 29-Sept 2 Chicago Cultural Center, Millennium Park and Harris Theater rooftop
  9. Taste of Polonia Aug 31-Sept 1 Jefferson Park
  10. German American Fest Sept 7-9 Lincoln Square
  11. Von Steuben German Day Parade Sept 8 Lincoln Square (part of German American Fest )
  12. Lakeview East Festival of the Arts Sept 8-9
  13. Festival on Prairie Avenue Sept 8 South Loop
  14. Annual World Music Festival Chicago Sept 7-23
  15. Chicago Turkish Festival Sept 13-15
  16. Ravenswood Art Walk Sept 15-16
  17. Lakeview Taco Fest Chicago Sept 15-16
  18. Printer’s Row Art Fest Sept 15-16

October

  1. Corn Mazes and Pumpkin Patches around Chicago
  2. Free Family Festival Lincoln Park Zoo Sept 28-Oct 28; Oct 8
  3. West Town  Art Walk Oct 5-6
  4. Columbus Parade Oct 8 Downtown
  5. North Park Village Harvest Festival Oct 13
  6. Double Ten Parade in Chinatown Chicago Oct. TBD
  7. Open House Chicago Oct 13-14
  8. Free Fall Festival at Jesse White Park Oct 20
  9. Arts in the Dark The Halloween Parade and After Party Oct 20 Downtown
  10. Free Halloween events at Navy Pier No info
  11. Free Lincoln Park Spooky Zoo Oct 27
  12. National Museum of Mexican Art Day of the Dead Oct 28 Pilsen
  13. Maxwell Street Market Day of the Dead Celebration Oct 28 South Loop
  14. Randolph Street Market Oct 27-28 West Loop
  15. Clark Street Spooktacular Oct 28 Lincoln Park
  16. Logan Square Halloween Parade Oct 28
  17. Northalsted Halloween Parade Oct 31 On Halsted from Belmont to Addison
  18. Halloween on The 606 Oct 31
  19. Chicago Trick-or-treat and Halloween events

November

  1. 900 N. Michigan Holiday Tree Lighting Nov. 16
  2. Millennium Park Christmas Tree Lighting Nov 16
  3. Mag Mile Lights Festival Nov 16-17
  4. Randolph Street Market Nov 17-18 West Loop
  5. Thanksgiving Day Parade Nov 22
  6. Free day at Morton Arboretum Nov 22
  7. Maggie Daley Skating Ribbon Nov 16-March 2019
  8. Christkindlmarket Market Nov 16-Dec 24 Daley Plaza
  9. McCormick Ice Rink Nov. 16- March 4 Millennium Park
  10. Caroling at Cloud Gate Fridays, Nov 23-Dec 14, 2018 Millennium Park
  11. Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
  12. Garfield Park Holiday Flower Show November 23-Jan 6, 2019
  13. Wreathing of the Lions Nov 24 Art Institute of Chicago
  14. CTA Holiday Train Nov 23-Dec 21
  15. Lincoln Park Conservatory Holiday Flower Show and trains Nov 23-Jan 6
  16. CTA Holiday Bus Nov 27-Dec 23
  17. Old Town Tree Lighting Nov. 29

December

  1. Renegade Craft Fair Dec 1-2 Bridgeport
  2. Santa’s  Misbehaving Dec 2 Downtown
  3. Made in Chicago Holiday Market Dec 3 West Loop
  4. One of a Kind Show Dec. 6-9
  5. Ugly Sweater Skate Dec 8 Maggie Daley Park
  6. Late Night Andersonville Dec 7 and 21
  7. Bucktown Holiday Art Show Dec 8-9
  8. West Town Winter Fest Dec 8
  9. Holiday Remix Chicago No dates on website Uptown
  10. Holiday Dose Market Dose Markets have ended permanently West Loop
  11. St Lucia Celebration No event 2018 Daley Plaza
  12. McCormick Ice Rink through March 2019 Millennium Park
  13. Maggie Daley Skating Ribbon Nov 16-March 2019
  14. Winter Wonder Fest Dec 1 -Jan 6 Navy Pier
  15. Garfield Park Holiday Flower Show November 23-Jan 6, 2019
  16. CTA Holiday Train Nov 23-Dec 21
  17. CTA Holiday Bus Nov 17-Dec 23
  18. Christkindlmarket Market Nov 16-Dec 24 Daley Plaza Select dates and times
  19. Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
  20. St. Lucia Fest Dec 13 Andersonville
  21. Randolph Street Market Dec 15-16 West Loop
  22. Jingle Fest Dec 15 West Loop
  23. The Chicago Santa Crawl Dec 15 River North
  24. Skate with Santa Dec 15 Maggie Daley Park
  25. Tuba Christmas Dec 22 Loop
  26. Free day at Morton Arboretum Dec 25
  27. avy Pier Fireworks Dec 31

2020

January

  1. Lincoln Park Zoo Lights November 23-Jan 6, 2019 Select dates
  2. Garfield Park Holiday Flower Show November 23-Jan 6, 2019
  3. McCormick Ice Rink through March  Millennium Park
  4. Maggie Daley Ice Skating Ribbon through March
  5. Events below will be updated when info is available.  Check back.
  6. Chicago Boat, Sports & RV Show Jan 10-14
  7. Chicago Restaurant Week Jan 26-Feb 8
  8. Randolph Street Market Festival Jan 28-29
  9. Chinese New Year Events Jan 28

February

  1. McCormick Ice Rink through March  Millennium Park
  2. Maggie Daley Ice Skating Ribbon through March
  3. Chicago Restaurant Week through Feb 8
  4. Chicago Theatre Week Feb 8-18 City wide
  5. Handmade Market at Empty Bottle Feb 10 Wicker Park
  6. Lincoln Park Conservatory Spring Flower Show Feb 10-May 13
  7. Chicago Auto Show Feb 10-18
  8. Chinese New Year Events Feb -March 3
  9. Navy Pier: Global Connections Feb 10 and 24
  10. Garfield Park Conservatory Spring Flower Show Feb 10-May 13

March

  1. Free events at Daley Plaza under the Picasso
  2. Lincoln Park Conservatory Spring Flower Show Feb 9-May 12
  3. Garfield Park Conservatory Spring Flower Show through May 12
  4. McCormick Ice Rink through March 11 Millennium Park
  5. Maggie Daley Ice Skating Ribbon through March 11
  6. Chicago Flower & Garden Show at Navy Pier March 20-24 Discount tickets available
  7. Downtown Chicago St. Pat’s Parade March 16
  8. St. Patrick’s Day Parade March 16 Downtown
  9. Where to drink on St. Patrick’s Day
  10. Southside Irish Parade March 17 Western from 103rd to 115th
  11. Northwest Side Irish Parade March 17 Raven from Neola to Northwest Highway to Harlem
  12. Handmade Market at Empty Bottle March 24 Wicker Park
  13. Randolph Street Market March 24-25 West Loop
  14. Macy’s Flower Show March 24 April 7 Downtown

 

 

 

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