150+ Fun Things to Do in Chicago IL

Being the largest city in the midwest, the windy city is a a must visit tourist destination. There are countless amounts of fun things to do in Chicago. With a rich cultural music history and well known sports teams, Chicago has plenty of landmarks like The Bean to visit and jazz clubs to be entertained at. Find something epic to do in Chicago today, and even more to do in Illinois tomorrow!

Type of Activity

Season

Indoor/Outdoor

Free/Paid

Spend an entire day exploring Humboldt Park
outdoor – free – Website >> Reviews >>
Avoid the traffic and walk through Chicago’s underground pedway
indoor – free – Website >> Reviews >>
Be one with nature at Lincoln Park’s North Pond
outdoor – free – Website >>
Watch a spectacular show at the Full Moon Fire Jam
outdoor – free – Website >>
Get a great view of Chicago skyline from Promontory Point
outdoor – free – Website >>
Admire the architecture inside Chicago Cultural Center
indoor – free – Website >> Reviews >>
Visit Lincoln Park Zoo and see the amazing animals
outdoor – free – Website >> Reviews >>
Touch the Cloud Gate at Millennium Park
outdoor – free – Website >> Reviews >>
Catch a live event at Millennium Park
outdoor – free – Website >> Reviews >>
Spot the strangest flower in Lurie Garden
outdoor – free – Website >> Reviews >>
Get your cardio workout and bike the Lakefront Trail
outdoor – free – Website >> Reviews >>
Play catch with your lovable pet at Montrose Dog Beach
outdoor – free – Website >> Reviews >>
Hang out at Wicker Park
outdoor – free – Website >> Reviews >>
Attend the Renegade Craft Fair and find interesting handcrafted items
outdoor – free – Website >>
Find your inner peace at Baha’i House of Worship
outdoor – free – Website >> Reviews >>
Take a tour of the Money Museum and get free (shredded) money
indoor – free – Website >> Reviews >>
Be captivated by nature’s beauty at Garfield Park Conservatory
outdoor – free – Website >> Reviews >>
Know more about history at the Hull-House Museum
indoor – free – Website >> Reviews >>
View the Museum of Contemporary Photography’s diverse collection
indoor – free – Website >> Reviews >>
Visit the City Gallery in the historic Water Tower
indoor – free – Website >> Reviews >>
See the corpse flower at Chicago Botanic Garden
outdoor – free – Website >> Reviews >>
Find a great bargain at Michigan Avenue
outdoor – free – Website >> Reviews >>
Put on your walking shoes and stroll along Mag Mile
outdoor – free – Website >> Reviews >>
Visit the Holy Name Cathedral
indoor – free – Website >> Reviews >>
See the Enchanted Forest at Maggie Daley Park
outdoor – free – Website >> Reviews >>
Make a wish at the Buckingham Fountain
outdoor – free – Website >> Reviews >>
Travel back to the ancient world at Oriental Institute Museum
indoor – free – Website >> Reviews >>
Find out whose face will appear next at Crown Fountain
outdoor – free – Website >> Reviews >>
Take a romantic stroll on Chicago Riverwalk
outdoor – free – Website >> Reviews >>
Spend the afternoon relaxing at Lincoln Park
outdoor – free – Website >> Reviews >>
Find the best places to dine and shop at the Loop
outdoor – free – Website >> Reviews >>
Look at the pretty flowers in bloom at Lincoln Park Conservatory
indoor – free – Website >> Reviews >>
Walk around University of Chicago’s Harper Quad
outdoor – free – Website >> Reviews >>
View the rocks from all over the world at the Tribune Tower
outdoor – free – Website >> Reviews >>
Take a closer look at the Agora at Grant Park
outdoor – free – Website >> Reviews >>
See the water taxis while chilling at Michigan Avenue Bridge
outdoor – free – Website >> Reviews >>
Visit the Rockefeller Memorial Chapel
indoor – free – Website >> Reviews >>
Get a glimpse of Inez Clarke at Graceland Cemetery
outdoor – free – Website >> Reviews >>
Go book hunting at Myopic Books
indoor – free – Website >> Reviews >>
Locate hard to find books at Powell’s Bookstore
indoor – free – Website >> Reviews >>
Discover rare finds at Salvage One
indoor – free – Website >> Reviews >>
Enter another era at the Rookery
indoor – free – Website >> Reviews >>
Spot the “Picasso” in Daley Plaza
outdoor – free – Website >> Reviews >>
Escape the city and relax at Alfred Caldwell Lily Pool
outdoor – free – Website >> Reviews >>
Take a pic of the iconic Wrigley Building in the morning and another at night
outdoor – free – Website >> Reviews >>
Look at old and new books at Harold Washington Library Center
indoor – free – Website >> Reviews >>
See the bridge lift at McCormick Bridgehouse
outdoor – free – Website >> Reviews >>
Visit the National Museum of Mexican Art and see a unique exhibit
indoor – free – Website >> Reviews >>
See the sunrise at North Avenue Beach
outdoor – free – Website >> Reviews >>
Find the Tin Man, Scarecrow, Cowardly Lion, Dorothy and Toto at Oz Park
outdoor – free – Website >> Reviews >>
Attend a free concert at Willie Dixon’s Blues Heaven Garden
outdoor – free – Website >> Reviews >>
Look at Chagall’s Four Seasons, a mosaic masterpiece
outdoor – free – Website >> Reviews >>
Walk around Andersonville and local shops and restaurants
outdoor – free – Website >> Reviews >>
Get a nice skyline view at Milton Lee Olive Park
outdoor – free – Website >> Reviews >>
Go upward and onward at 606
outdoor – free – Website >> Reviews >>
Take a selfie with Calder’s Flamingo
outdoor – free – Website >> Reviews >>
Explore Devon Avenue
outdoor – free – Website >> Reviews >>
See the cool graffitti and street art at Pilsen
outdoor – free – Website >> Reviews >>
Explore the colorful Boystown neighborhood
outdoor – free – Website >> Reviews >>
Break away from the city and visit Lambs Farm
outdoor – free – Website >>

fun things to do in Chicago

This epic list of things to do in Chicago may not encompass everything, but we tried to include the most valuable attractions that need to be checked out. However, if you hate that we missed your favorite place in the city, don’t hesitate to reach out and yell at us! Looking to get out of the big city? Check out all of the things to do in Rockford!