The best cheap things to do in Chicago for fun on a budget

Winter in Chicago can be a brutal, unforgiving time when residents dread the thought of ever leaving their home. But it doesn’t have to be all bad. In fact, it can even be rather fun, especially if you spend some time ice skating the Ice Skating Ribbon at Maggie Daley Park. Visits to the popular downtown rink require a reservation, but you can bring your own skates to save some money.

Price: $17-$19 with skate rental Monday-Thursday, free with own skates

Chicago is well-known as one of the great architecture cities in the world, but the architecture tours only go so far (specifically, the Loop). Beyond the gleaming skyscrapers, there are other structures that prove that Chicago is rightly-acclaimed for its architecture, including homes designed by famed architect Frank Lloyd Wright, especially the Robie House in Hyde Park. Glances of the exterior are free, of course, but tours of the interior of the historic house are only $20, making it a budget-friendly way to explore one of the city’s most creatively-designed homes—an early example of Prairie School architecture.

Price: $20

For comedy fans, there are few stages as hallowed as the ones at the Second City, where comedy greats like Chris Farley, Jordan Peele and Amy Poehler got their start. While Main stage shows can cost a pretty penny, student shows typically only cost about $10. Second City has student shows most nights (be sure to check the online schedule), and they feature students currently involved in the comedy training center’s many programs, including acting, writing, improv and stand-up.

Price: $10

As the birthplace of Ferris wheels, it only makes sense that Chicago still boasts a magnificent one. The Centennial Wheel in Navy Pier doesn’t come with the history of the original wheel, built for the 1893 World’s Columbian Exposition, but it doesn’t take away from the great views it offers of Lake Michigan. The current attraction was built in 2016, featuring contemporary luxuries like enclosed, climate-controlled gondolas that operate year-round. The wheel lifts riders up 200 feet into the air, giving them not only a great view of the rest of Navy Pier, but a spectacular look at the city’s skyline.

Price: $15-$18

Chicago doesn’t lack for museums, and has such a wide variety of them where you can learn about everything from Impressionist art to dinosaurs, but what if you want to learn about the city itself? That’s where the Chicago History Museum comes in. The museum, founded in 1856, is a relic itself and houses more than 22 million artifacts, documents and photos. There are also permanent exhibitions on topics like Abraham Lincoln and his experience in the city, and one where you can hop aboard an early “L” train car.

Price: Free for Illinois residents under 18, $17 for students (19-22) and seniors, $19 for adults

As one of the largest cities in the country, it’s almost guaranteed that most musicians will make a stop in Chicago while they’re on tour. Since 1992, the Empty Bottle has been one of the preferred places to catch rising acts, including early shows by bands like The Strokes and The Mountain Goats, as well as rare opportunities to see artists like Jack White in an intimate setting. The small dive bar’s stage offers a great opportunity to see live music up close and personal. All shows are 21 and up, and tickets to most shows are usually affordable. Plus, shows on Monday nights are usually free!

Price: Varies, usually less than $20

Just a bit outside of the city in Glencoe, the Chicago Botanic Garden is a lush and floral oasis for those looking to escape the urban setting. Stroll through the dozens of exhibits (both indoor and outdoor) that have aquatic flowers, fruits, roses, prairie plants and woodland vegetation. On top of the amazing views, the Chicago Botanic Garden is super affordable—adult admission is around $17. The garden grounds span almost 400 acres so you'll be sure to have plenty to see during a day trip.

Price: $17 adults, $12 children ages 3-12, free for children ages 2 and under

Some of the country’s greatest writers, and the tools that they’ve used to craft their stories, are on display at the American Writers Museum. The museum houses a wide-ranging collection of exhibits, even hosting some virtual exhibits on local writers like Ray Bradbury, as well as important authors such as Frederick Douglass and Hisaye Yamamoto. Don’t miss the Wintrust Chicago Gallery, which highlights some of the city’s most beloved writers and their works including novelist Saul Bellow and film critic Roger Ebert.

Price: $16 adults, $10 seniors and students, free for children

Want to spend an affordable day appreciating nature? Head out to suburban Lisle to soak in the 1,700-acre expanses of the Morton Arboretum, home to more than 222,000 live plants from around the world. Explore winding trails and forests or check out the Arboretum's calendar of events, where you'll find tons of nature-related activities and other outdoor programming. Don't forget to secure a reservation from the Morton Arboretum website before you head out to save $2.

Price: Adults start at $15, seniors and children start at $9

Any night can be a movie night at home, but Alamo Drafthouse in Wrigleyville makes movie night into an event. The cinema chain, which has a strict policy on no texting and no talking, has a large number of special screenings and themed events, as well as extensive food and beverage menus. Plus, servers will bring anything you order straight to your seat. On Tuesdays, tickets are just $7.

Sure, you can sing in your car or in the shower, but it’s fun to belt your heart out to your favorite song on a stage as well. That can happen every weekend at the tropical-themed Trader Todd’s, a karaoke bar in Lakeview. While the karaoke is free (tips to the DJ are encouraged), what’s karaoke without a bit of liquid courage? The bar’s tropical-themed drinks range in price from $9 for the house margarita, which comes in a variety of flavors, to the $12 spicy paloma featuring Jose Cuervo, grapefruit and lime juices, habanero simple syrup, splash of soda and cayenne pepper. The bar also offers a variety of beers.

Price: $9-$12 for most cocktails

Sure, you can go on a crime tour and learn about Chicago’s seedy past, but if you want to hear about the good of the city, look no further than Jane Addams Hull-House Museum. The building was originally a settlement house run by Jane Addams that housed and provided employment to immigrants, but it’s now a museum that serves as a memorial to Addams and her work. The Hull-House Museum, located on the campus of University of Illinois-Chicago, tells the story of the people who utilized the space, and the work they created while living there, including textile pieces and pottery produced by artists living at Hull House.

Price: $5 suggested donation

Sick of playing Monopoly for the millionth time? This Logan Square cafe offers more than 800 board games, and guests are welcome to hang out and play anything they desire for up to two hours for just $7 per person. There's a full food and drink menu, and if you're looking for a partner to play with, Thursdays are mix-and-mingle nights.

Price: $7 game admission

A lot can happen in an hour, and if you’re attending one of the Neo-Futurists’ productions at the group’s Ravenswood theater, that’s undeniably true. Every weekend, Friday through Sunday, the performers and writers of the Neo-Futurists put on 30 plays in 60 minutes, all combined into one show called The Infinite Wrench. Seeing one play downtown is likely to set attendees back a pretty penny, but the 30-play show at the Neo-Futurist Theater costs just $20.

Price: $20

Of course it’s fun when the beloved home teams, such as the Bears, Cubs, Blackhawks, Bulls and White Sox are winning throughout the season and heading deep into the playoffs. But it’s not always economically feasible to watch a contender. So if you’re just a fan of going to cheap sports games, root for the teams during their “rebuilding” seasons to score inexpensive seats. Or, if you’re brave enough, head out to a game in rough conditions, like the December 24, 2022 Bears game when the windchill was -11 degrees Fahrenheit but ticket prices were as low as $8 on the resale market.

This isn't where Goose Island got its start (that'd be the original Clybourn brewhouse that closed in 2023) but plenty of beer has been brewed here since the facility opened up in 1995. Learn about the company's history and get a peek behind the curtain with a tour of the brewery. After meeting in the adjoining taproom, you'll make your way through the brew deck, fermentation cellar, packaging line, innovation brewery and barrel-aging program. Beer is being made 24/7, so you're nearly guaranteed to spot some brewers hard at work. You'll also sample a variety of beers during the tour and take home a custom pint glass.

Price: $15 per person

Founded in 1940, the University of Chicago's single-screen Doc Films theater is on record as the longest continuously running student film society in the country. While it began featuring documentaries, the current screening schedule showcases classic films from a variety of genres, appealing to film aficionados as well as casual moviegoers. Tickets go on sale a half hour before each showing in Ida Noyes Hall and all screenings are open to the public.

Price: $7

Get your game on at this River North arcade bar, where all the cabinets are free to play. Whether you're a Street Fighter veteran or trying to set a new personal high score at Pac Man, the more than 70 retro arcade and pinball machines will keep you entertained all night long. And by saving quarters, you can spend your money on drinks and bites.

Price: Beers start at $7

If you're in the Loop and want to visit a museum but you're looking for something a bit smaller (and more affordable) than the Art Institute or anything on Museum Campus, might we recommend the Museum of Contemporary Photography? The relatively compact galley regularly rotates its exhibits, making it easy to stop by and see some amazing photos when you have an hour or two to spare. 

Price: Free, donations welcome

If you’re coming to Chicago and not getting some sort of sports experience, you’re missing out. The city's various teams have racked up a number of trophies through the years, but getting a glimpse of the teams in action can sometimes get a bit costly. A more affordable option? Paying tribute to Chicago’s best at the Chicago Sports Museum, a wallet-friendly stop that charges just $10 for admission. At the museum’s "Measure Up" exhibit, visitors can compare their jump heights to Michael Jordan’s, or their wingspan to Scottie Pippen’s. It also hosts the “Curses and Superstitions” exhibit, exploring the reasons why some fans believe the Cubs went 108 years without winning a World Series.

Price: $10, or free with minimum purchase at Harry Caray's 7th Inning Stretch

The South Side Community Art Center, the oldest African-American art center in the country, is a constantly evolving exhibition space of seasoned and contemporary artwork. With showcases of Chicago legends and emerging artists, there's always something to learn at this city landmark. On top of an enriching experience, admission is always free, with donations welcomed.

Price: Donations encouraged

Explore labor history and more in Pullman, the Far South Side neighborhood that was once home to the infamous Pullman Company-planned community. The Historic Pullman Foundation offers guided tours (featuring attractions like the Pullman National Monument) on the first Sunday of every month from May to October, but visitors are always welcome to take a free, self-guided look around the neighborhood with the help of a walking tour brochure.

Price: $20 adults, $15 students and seniors for guided tour; self-guided tour is free

Looking for an affordable way to appreciate local artists? Check out the Bridgeport Art Center every third Friday of the month for Open Studios. At the monthly event, artists in the building open up their creative spaces to the public and give art enthusiasts the opportunity to buy one-of-a-kind pieces. Whether you're looking for a new addition to your gallery wall or just want to view some cool art, Open Studios is a great option.

Price: Free

When he founded the Oriental Institute more than 100 years ago, University of Chicago professor and archeologist James Henry Breasted insisted that civilization began in the ancient Middle East, rather than in Greece or Rome. This museum has continued to explore the mission set forward by its founder, featuring more than 350,000 artifacts that have been uncovered by the museum’s own archeologists, including a nearly 3,000 year old sculpture that previously stood at the entrance of the Kingdom of Assyria’s throne room as early as 700 BC.

Price: $10 suggested donation

This cafe-rescue-lounge hybrid is the perfect place for cat lovers on a budget. By reserving ahead of time, you'll be free to hang out with feline friends in the Catcade lounge as they roam freely. Whether you're looking to adopt or just need a friendly pick-me-up, stopping by the Catcade is a great way to support an independent non-profit shelter.

Price: $20 per hour

On any given day at the Chicago Cultural Center, you might find a free classical concert being performed, an art exhibition on display in one of the building’s many galleries or tourists marveling at the world’s largest stained-glass Tiffany dome. Don’t worry about paying for admission—nearly everything that happens in this building is free and open to the public.

Price: Free