Chicago Guide
Chicago Jazz Festival
The Chicago Jazz Festival is free and open to the public the weekend of our event, Thurs-Sun! This is a large, annual, long-standing festival that brings a lot of wonderful performers to the Chicago area. Performances held at Millenium Park and other downtown locations - check out the website!
Logan Square Farmers Market
Open Sundays, 9am-3pm
The Second City
Shows every night of the weekend! We recommend checking out the Main Stage or "UP Comedy Club" productions, but you can't go wrong with any offering at this iconic Chicago comedy venue!
The Art Institute of Chicago
#1 place to visit in Chicago! A great place to beat the summer heat and take in some world-famous art (and have your Ferris Bueller moment).
Chicago River Boat Architecture Tours
A great way to get on the water and see the city from another perspective! These are informative and fun. We recommend the Chicago Architecture Center's boat company, but Wendella offers a nice tour as well. Alternately, we might recommend hopping on the water taxi and taking an inexpensive and beautiful ride down to Chicago's Chinatown neighborhood.
Green City Market Lincoln Park
Open Saturdays, 7am-1pm
Improvised Shakespeare Company
Hilarious, weird, and affordable entertainment!
Millennium Park
Visit the Chicago postcard icons like "The Bean" and Buckingham Fountain. Please be aware the the Jazz Festival will take over most of this area during the August 30th weekend!
Zanies Comedy Night Club
This and the Laugh Factory are great spot for standup comedy! Shows throughout the weekend with several time offerings.
The Green Mill
Great for late night jazz and a drink! A quintessential live music venue in Chicago. Kingston Mines is another great spot that's a little closer to downtown.
Garfield Park Conservatory
Reserve a timeslot before you go! This is a great free venue to take in some lush greenery - we always love to pair a visit here with a visit to Spinning J's for a treat (make sure to check their hours!)
Lincoln Park
Swing by the free zoo, the conservatory, the nature museum, the beach...a stunning and sprawling park to take a stroll or rent a local "Divvy" bike for a nice afternoon outdoors! The Central Park of Chicago :)
Museum Of Contemporary Art Chicago
A more consolidated, modern, and low-traffic art venue. Worth visiting if you're staying in the downtown area/near the lake!
Portillo's
Find out what a Chicago Dog is all about (vegan dogs also available!)
Dark Matter Coffee - Meddle
Get freshly roasted
Wicker Park
A great neighborhood to explore - good coffee, quick bites, vintage shops, small storefronts, and great vibes!