What to do and see in Downtown / The Loop, Illinois (IL): The Best Events

December 29, 2021 Deane Carmody

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Chicago Blues Festival

337 E Randolph Dr, Chicago, IL 60601-7403 https://www.cityofchicago.org/city/en/depts/dca/supp_info/chicago_blues_festival.html/
Excellent
63%
Good
30%
Satisfactory
3%
Poor
0%
Terrible
4%
Overall Ratings

4.5 based on 30 reviews

Chicago Blues Festival

Held over three days each June in the city's beloved Green Park, the Chicago Blues Festival is one of the highlights of the city's summer lineup. Originally started to commemorate the death of Blues legend Muddy Waters, it has grown to be the largest free blues festival in the world. There are five stages of live music to choose from, featuring both established and up-and-coming artists. Previous performers have included Chuck Berry, Keith Richards, and John Lee Hooker, and each year there are a few surprises in store for blues fans.

2. Lollapalooza

337 E Randolph Dr, Chicago, IL 60601-7403 http://www.lollapalooza.com/
Excellent
53%
Good
30%
Satisfactory
13%
Poor
0%
Terrible
4%
Overall Ratings

4.5 based on 30 reviews

Lollapalooza

As well as being fun to say, Lollapalooza is also a heck of a lot of fun to attend. Filled with international talent but far from being a faceless international festival, Lolla celebrates the best in local life. Grab some of Chicago's best food, handpicked from local restaurants, and choose from one of the eight live music stages to chill out and listen to acts such as Paul McCartney, Florence and the Machine, and Sam Smith.

3. Chicago Jazz Festival

78 E Washington St, Chicago, IL 60602-4801 https://www.facebook.com/Chicago-Jazz-Festival-48931671436/
Excellent
69%
Good
31%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 13 reviews

Chicago Jazz Festival

4. Chicago Marathon

301 S Columbus Dr Grand Park, Chicago, IL 60605 +1 312-904-9800 http://chicagomarathon.com
Excellent
79%
Good
18%
Satisfactory
0%
Poor
3%
Terrible
0%
Overall Ratings

4.5 based on 34 reviews

Chicago Marathon

5. Taste of Chicago

337 E Randolph Dr, Chicago, IL 60601-7403 http://www.cityofchicago.org/city/en/depts/dca/supp_info/taste_of_chicago.html
Excellent
34%
Good
33%
Satisfactory
17%
Poor
9%
Terrible
7%
Overall Ratings

4.0 based on 96 reviews

Taste of Chicago

Taste of Chicago is the world's largest food festival, drawing millions of food lovers to Grant Park every summer since 1980. Soak up the sun and enjoy some of the best of Chicago's restaurants, food trucks, and pop-ups by guest chefs. A variety of musical genres are represented and big-name 90s headliners such as Erykah Badu and Weezer entertain guests enjoying a picnic on the lawn. Best of all, all ages are welcome and admission is free — just purchase scripts for your food items and grab a beverage from one of the tents set up throughout the festival.

6. Christkindlemarket

50 W Washington St, Chicago, IL 60602-1305 +1 312-494-2175 [email protected] http://www.christkindlmarket.com/chicago/
Excellent
50%
Good
0%
Satisfactory
50%
Poor
0%
Terrible
0%
Overall Ratings

4.0 based on 2 reviews

Christkindlemarket

7. Chicago Thanksgiving Parade

State St, Chicago, IL 60602 [email protected] http://ChicagoThanksgivingParade.com

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