Things to Do

Museums, restaurants, parks, street festivals, concerts, shopping... Chicago has it all!  

Museums

• Art Institute of Chicago:  Second-largest art museum in the country and home to some extraordinary pieces
• Museum of Science & Industry
• Adler Planetarium & Astronomy Museum:  Great view of the city from here
• Shedd Aquarium:  Also a great view of the city from the grounds
• Museum of Contemporary Art
• Field Museum of Natural History
• Chicago History Museum
• Chicago Children's Museum

Landmarks

• Navy Pier:  Excellent in Summer months (very touristy too) to walk around; closest thing to having a carnival in the city
• John Hancock Observatory:  Make sure to stop at The Signature Room to get food, drinks, and a smashing view of the city
• Willis Tower:  Formerly Sears Tower; Step out into the glass box over the city on the 103rd floor of the iconic building
• Buckingham Fountain:  Located in Grant Park
• Tribune Tower
• Wrigley Building
• Trump Tower:  Has a bar and restaurant--both with amazing views--that is open to the public
• Water Tower
• Original Playboy Mansion:  Yes, it started here in Chicago and you can still walk by
• Cloud Gate:  Aka "The Bean"; Located in Millennium Park
• Marina City Towers:  Made famous by Ferris Bueller and Nik Wallenda, who walked across these two towers on a tight rope

Parks and Nature

• Lincoln Park:  Chicago's largest park; comes full of beautiful gardens and areas to relax and lounge with a backdrop of the city
• Lincoln Park Zoo:  Chicago's city zoo, which is free for everyone
• Lincoln Park Conservatory:  Three acres of lush, exotic plants that is open year-round; also free
• Alfred Caldwell Lily Pool:  One of the city's hidden gems and a place of complete serenity 
• Peggy Notebaert Nature Museum:  Located in Lincoln Park and home to various natural exhibits and an Exotic Butterfly Garden
• Millennium Park:  Home to "Cloud Gate" aka "The Bean"; hosts concerts in the Summer
• Grant Park:  Home to Lollapalooza, Taste of Chicago, Blues Fest, and many more events; also home to Buckingham Fountain
• Wicker Park:  Located in the heart of the artsy neighborhood that bears it's name
• The Beach along Lake Michigan:  Multiple entrances including North Avenue, Oak Street, Fullerton Parkway, and more.
• Garfield Park Conservatory

Sports

• Wrigley Field:  Home to the Chicago Cubs
• Cellular Field:  Home to the Chicago White Sox
• Soldier Field:  Home to the Chicago Bears
• United Center:  Home to the Chicago Bulls and the Chicago Blackhawks

Entertainment

• Concerts:  Lollapalooza, live music in the parks, concerts in United Center, House of Blues, music festivals through the summer, etc... there are plenty of music events to attend
• Fireworks on the lake:  Happens in the Summer 1-2 times per week; happens near Navy Pier area, but can be seen in multiple spots around the city
• Second City Theatre:  Almost any famous comedian (especially Saturday Night Live alumni) has passed through or gotten their start here
• Broadway in Chicago:  Major Broadway shows typically start here in Chicago before going to New York City in order to perfect the show; tickets are sometimes less expensive than buying them in NYC too
• Theatre:  There are so many different theaters (Steppenwolf, Chicago, iO, Bank of America, Auditorium, etc.) around the city with many wonderful shows
• Opera
• Architecture Boat Tour:  Takes passengers along the river to explore and learn about Chicago's architecture
• Dance: Joffrey Ballet, Giordano Dance Company, and many more! Chicago is home to many great dance companies that put on performances through the year
• Nightlife:  River North is the main area that attracts people for it's nightlife.  You'll find your larger nightclubs and bars around this area (Hubbard Street is the central of it all).  Other great areas to check out are all the amazing bars located in Wicker Park/Bucktown (The 6 Corners around Milwaukee Avenue is a good center of it all), West Loop for it's cuisine scene (Restaurant Row on Randolph Street), Boystown in Lakeview for the LGBT scene, Old Town for the bars, and many more.

Shopping

• Downtown:  Michigan Avenue is a main hub for visitors to check out shopping in Chicago.  (Personally, I do not prefer to shop down here, but there are good big retailers if thats your thing.)
• Lincoln Park/Old Town:  Great shopping and boutiques around Armitage & Halsted area, as well as along Clark & Diversey area.  Also bigger strip malls around North & Halsted.
• Wicker Park:  Local boutique heaven! So many amazing shops around this neighborhood and a lot of great thrift stores.
• Lakeview:  Good locations around Belmont & Clark area.  Also some great local spots as well as thrift stores.