10 Free or Cheap Things to do in Chicago

You’ve got a weekend planned in the Windy City, but you’re already counting the cost. Museums, tours, and restaurants are all enticing and often rewarding experiences but can add up quickly. Here are some ways to enjoy the city without handing over your wallet.

Wander Millennium Park

This one is a no-brainer. Enjoy watching your reflection in the Cloud Gate sculpture, affectionately known as “The Bean.” Splash in the Crown Fountain. Marvel at the Jay Pritzker Pavilion, an outdoor amphitheater designed by Frank Gehry. Even better, catch a free concert there during the park’s Summer Music Series. Bring a blanket, some lawn chairs, and a picnic spread while enjoying a symphony concert under the stars.

Browse the Chicago Cultural Center

Right across the street from Millennium Park is the Chicago Cultural Center. An overlooked and free of charge attraction, the building was once the city’s library and memorial to the Grand Army of the Republic. The city spared no expense on materials; woodwork, mosaics, and marble are all prevalent in the design. On the library side is the world’s largest Tiffany dome, restored in 2008 to its former glory. Check the website for any special events – performances, lectures, art shows – that may be going on during your visit.

Stand on LaSalle St

If you’ve seen a movie – any movie, really – you’ll probably recognize the view on LaSalle anywhere south of the river. The street dead-ends into the art-deco Chicago Board of Trade Building and is famously featured in films such as The Untouchables, The Dark Knight, and Transformers: Dark of the Moon, among others. While you’re over there, step into the Rookery. Built in 1888 by the famous architect duo of Daniel Burnham and John Wellborn Root (with a remodeled lobby by Frank Lloyd Wright), it’s considered the oldest standing high rise in Chicago. They don’t build them like this anymore. Across LaSalle from the Rookery is the Federal Reserve Bank of Chicago museum, a small but free excuse to get out of the elements.

Walk the Magnificent Mile

While you won’t be saving bucks by shopping at Burberry, no one’s charging you to walk past or even take a peek inside. That being said, Michigan Ave, particularly near the river, features one architectural gem after another. These are the early skyscrapers, the ones that dared architects to dream higher. The Wrigley Building is worth a look, as are the walls surrounding the Tribune tower which feature bits and pieces of famous structures from around the world. There’s no better place to absorb Chicago than the Mile. Just don’t turn toward Navy Pier – it’s a classic tourist trap.

Grab drinks in the Signature Lounge

Want to go up a tower? I don’t blame you. The Chicago skyline is unbelievably photogenic. My vote is the John Hancock Tower. You have two options. You can pay nearly $20 for the observation deck, or you go to the Signature Lounge — one floor higher than the observation deck — and buy a drink. Your drink will be expensive, perhaps $8 for a bottle of beer, but now you have a beer and a view. You’re required to purchase something up there, but as long as you don’t go crazy on the cocktails, you’ll spend less in the Lounge than you would for the deck. Also, I hear the view from the woman’s bathroom is incredible.

Explore Lincoln Park

“The Lakefront by right belongs to the people,” Burnham wrote in his 1909 Chicago Plan. The spirit of that notion lies in Lincoln Park, 1200 acres of prime lakeshore real estate devoted to recreation and nature. Here, in the middle of the third-largest city in the country, are ponds specifically designed to cater to endangered migratory birds, a quiet lily pond, a conservatory, public art, statues, bike trails, and a zoo. None of it costs a cent. The Chicago History Museum and the Peggy Notebaert Nature Museum charge admission, but neither are very expensive.

Eat the Chicago way

It’s no secret that Chicago natives enjoy eating deep-dish pizza and Chicago-style hot dogs. The good news for visitors is that neither are very expensive. Portillo’s is a good place to start for hot dogs. As for pizza, Giordano’s and Pizzeria Uno are easily accessible while downtown. It’s a relatively affordable option when split amongst a group; most people don’t eat more than one or two slices. There’s no shortage of good things to eat in Chicago, so plan according to your budget. It’s probably best to avoid restaurants directly on Michigan Ave.

Booking.com

Beat the meters

Now about parking. Garages can be prohibitively expensive. Chicago is best explored on foot or by public transportation, but if you need a car, I recommend using an app that locates pay and display parking according to hour restraints. I used Meter Beaters during my last visit and it worked well. Consider parking somewhere outside of downtown – Old Town or Lincoln Park, perhaps – and taking the ‘L’ to the Loop.

If you need a quick parking solution downtown, there is metered parking on Columbus St. behind the Art Institute, but this is subject to road closures when there’s a festival in Grant Park. Otherwise, metered parking is easier to find, in general, north of the river than in the Loop.

Make a friend with an Illinois resident

If you are a resident of Illinois, the city offers free days for many of the city’s most prestigious museums. The Art Institute is free every Thursday night for Illinois residents. If you’re traveling with a local, take advantage of their zip code and save some major bucks. “Time Out Chicago” typically does a good job of rounding up these free museum days on their website.

Laugh at improv

Second City is great, but IO “Improv Olympics” are just as funny and have significantly cheaper tickets. In the same theater as IO is The Improvised Shakespeare Company, which takes one audience suggestion for a non-existent play title and runs with it. Years later, I still quote the show.

Conclusion

Yes, there are things you should do in Chicago that will cost money, whether it is take in a Cubs game, take an architecture cruise, or an Al Capone themed walking tour, but your Windy City trip does not have to break your bank.