Chicago is one of the most cosmopolitan cities in the U.S. and a really fun place to visit! If you find yourself in the Windy City, whether for business or pleasure, you’ll be astounded by how much there is to do there.
You can drop a few dollars in Chicago, for sure, but there are ways to save.
If you want to see the sights, check out Chicago CityPASS — it lets you visit five of the most popular attractions in Chicago at one low price, while getting HALF OFF the price of individual tickets. Or, browse Groupon for discounts on lake cruises and city tours.
It’s easy to get around the downtown loop — because the area is highly walkable, plus Chicago is home to the nation’s second largest public transportation system, with 145 rail stations around town. Who hasn’t heard of the “El,” the city’s iconic elevated trains?
If you’d rather have the freedom of a car, start by booking with Budget car rental at Chicago’s O’Hare Airport (ORD) and be on your way to discover Chicago.
Besides the famous tourist destinations and pricey fine dining options in Chicago, you’ll be able to seek out plenty of free and cheap fun. (HINT: start by visiting our sister site, Chicago on the Cheap.) You can always travel on the cheap by visiting lesser known attractions, many of which are FREE!
Check out these hidden gems and quirky attractions in Chicago!
Garfield Park Conservatory
This stunning oasis on the city’s West Side is one of the largest botanical conservatories in the United States — and it is completely FREE to visit (you’ll need to make a reservation online). Year round, you can enjoy the indoor gardens that include the Palm House, Fern Room, Desert House, and more. There are also 10 acres of outdoor gardens.
Head to the Lincoln Park community for a fun romp through Oz Park. This public green space is FREE to visit and features a collection of statues of the famous storybook characters — including Dorothy, Toto, Scarecrow, Tin Man, and the Cowardly Lion. For kids, there’s an Oz-themed playground.
Bloomingdale Trail at The 606
Built on a former railway line, The 606 — also known as the Bloomingdale Trail — is an elevated park and trail system. It’s FREE to visit, so come by to walk, run, or bike in a relaxing environment with scenic lookout points and public art installations.
This is an editor’s pick! Promontory Point is a spot within Burnham Park, along the Lake Michigan shoreline. The Point is a man-made peninsula that juts out into the lake, offering a spectacular view of the Chicago skyline. There are trails, green spaces, and fire pits that you are free to use (safely, of course!)
Frank Lloyd Wright Home and Studio
Located in the suburb of Oak Park, this historic site offers guided tours of Frank Lloyd Wright’s former home, as well as the studio where he designed many iconic buildings. If you are an architecture enthusiast, make sure to include this in your list of must-visit places in Chicago. Tours are $20 to $30.
Alfred Caldwell Lily Pool
Nestled within Lincoln Park, the Alfred Caldwell Lily Pool is a hidden garden that features a lily pond, waterfall, and beautiful landscaping. It’s a popular spot for birders, and if you follow the stone path around the pond, you may see frogs, butterflies, turtles, and other wildlife. FREE to visit.
Head over to North Wolcott Avenue to see this hilarious metal sculpture of a pile of poop. Shit Fountain was inspired by the artist’s vexation with dogs doing their business just about anywhere, including his flower garden. This is a popular selfie spot, so plan to strike a pose and capture the attention of your friends on social media.
The Pilsen neighborhood is known for a vibrant Latin culture, overflowing with music, art, culinary traditions, and more. You’ll be amazed by the street art! Buildings are covered in colorful paintings and mosaics, making this area a living art museum. Stroll over to 16th Street to see more than 40 street murals along the embankment that runs between Halsted Street and Western Avenue.
Jane Addams Hull-House Museum
Located on the campus of the University of Illinois, the Jane Addams Hull-House Museum is dedicated to the social reform work of Jane Addams, a prominent American settlement activist. She was best known for her work in addressing the social and economic issues faced by immigrants and the poor in urban areas. Suggested donation is $5.
Ukrainian Village is a vibrant west side neighborhood, overflowing with art, culture, traditional food, glorious churches, and more. For a dive bar experience, check out the Rainbo Club there. It’s a tavern with a long local history and a quirky vibe. Have an adult beverage, play pinball, and listen to live music.