You don’t need a booming bank account to revel in Chicago’s cultural coolness. Accommodation will cost you, but oodles of free things to do, discount ticket schemes, and relatively low cost of food and transportation help keep overall expenses in check. 

Here are our top tips for stretching your dollars in the Windy City.

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Figure out which Chicago airport is the cheapest to fly to

Chicago has two airports: O’Hare and Midway. Budget airlines fly into both, and transport costs to the city center are similar, though Midway is slightly cheaper since it is a few miles closer. In general, budget airlines Spirit and JetBlue fly to O’Hare, Southwest and Allegiant fly to Midway, and Frontier flies to both. O’Hare is also a hub for United and American Airlines, and they often have low-priced flights to the city.

Take the L train from the airport

Both airports have easy links to downtown via public transportation — specifically the L train — which costs about US$5 and takes 40 minutes from O'Hare, and about $3 and 30 minutes from Midway.

O’Hare has its own Blue Line station, while Midway has its own Orange Line station; trains depart from both every 10 minutes or so. This option is much cheaper than taxis, Uber or Lyft, which can cost 10 times more and take almost as long given Chicago’s heavy traffic. 

Pedestrians walk the streets of Chicago while buses and the L whiz by, blurred by motion
Make use of Chicago's extensive public transit system to save time and money © Andrey Denisyuk / Getty Images

Use Chicago’s public transit system to get around

Parking costs will drain your budget quickly. Downtown street meters charge about $7 per hour, with garages averaging around $40 per day. Plus, driving in the traffic-packed city is maddening – public transit is the way to go. 

Chicago’s L train system has eight color-coded lines that get you to most sights and neighborhoods. Buses pick up the slack in areas that the L misses. 

Ready for a bargain? An unlimited-ride day pass costs $5, valid on all trains and buses. Buy it at any L station (including the airports) or via the Ventra app. You can also buy a rechargeable Ventra Card, which saves around $0.50 per ride over disposable fare tickets for one-off rides. 

Hop on a water taxi

Chicago’s architectural boat tours are wildly popular, and no wonder. It’s awesome to glide along the river and stare up at the skyscrapers. But if you can’t afford to drop over $50 on a guided tour, don’t fret. The Chicago Water Taxi plies the river and charges around $10 for a day pass.

The boats travel from the Michigan Avenue Bridge to Madison Street and onward to Chinatown, so you’ll still get that wind-in-your-hair experience.

Visit in spring or fall to save money

Summer (June through August) is Chicago’s peak season, when lodging is typically more expensive. Winter (December through March) is the cheapest time to go, but the cold and snow aren’t very inviting. Spring and fall are the shoulder seasons when sweet deals and decent weather coincide.

Consider staying at a hostel

Chicago has a number of quality hostels. The stalwart HI-Chicago is right in the heart of downtown. Wrigley Hostel parties hard near the north side baseball park, and Chicago Getaway Hostel has been hosting travelers for years in the good-time Lincoln Park neighborhood.

Meanwhile, Freehand Chicago, Found Hotel and Selina Chicago are bar-laden, hostel-hotel hybrids recently opened at downtown’s northern edge. 

Top 7 winter day trips from Chicago 

Look for lodging beyond the core

Move away from the Loop, Near North, Gold Coast and West Loop — Chicago’s hotel-loaded central districts — and prices tend to be lower. Try neighborhoods like Lincoln Park and Lake View, both just north of downtown and filled with bars and restaurants, and Wicker Park, northwest of downtown, near buzzy nightlife and shops. 

Cool areas that are even cheaper include Logan Square, Pilsen, Ukrainian Village and Andersonville. Most accommodations in these outlying districts are apartment rentals, so you can save additional money by self-catering some of your meals. It's key to be near an L station, though, so check this before booking.

Crowds of people browse the Chicago farmers market located at Daley Plaza during summer morning
Snag some budget-friendly goodies from one of the city's many markets, like this one at Daley Plaza © Shelly Bychowski / iStock Editorial / Getty Images Plus

Graze through a market

From May to October, farmers markets pop up citywide and offer inexpensive meals. Green City Market lays out the largest spread, from pies to pickles to pastas, on Wednesdays and Saturdays in Lincoln Park. The Logan Square market adds live music to its array of fruits, veggies and prepared foods on Sundays. Downtown’s Daley Plaza erupts in fresh produce and Amish baked goods on Thursdays.

And while it’s more of a junk market than farmers market, Sunday’s Maxwell Street Market has become a hot spot for foodies craving homemade churros, tamales and other Mexican fare.

Best healthy food spots in Chicago 

Browse for cheap eats in Pilsen, Chinatown, Uptown and Humboldt Park 

Several neighborhoods are especially great for cheap eats, with lots of high-quality cafes and mom-and-pop restaurants to choose from within walking distance of each other. In Pilsen along 18th Street, Mexican bakeries and taquerias mix with hipster coffee shops and barbecue joints. Chinatown along Wentworth Avenue offers a smorgasbord of tart-filled bakeries and dim sum places. 

In Uptown along Argyle Street, Thai and Vietnamese noodle houses steam up the corridor known as “Little Saigon.” And in Humboldt Park along Division Street, homey spots serve strong coffee, roasted pork, spiced rice and other Puerto Rican specialties.

Find the food trucks

Chicago has a relatively small fleet of food trucks, but the ones that do roll serve lip-smacking tacos, Vietnamese sandwiches, soul food and more for modest prices. They generally prowl office-worker-rich zones like the Loop and Near North around lunchtime, and then nightlife-focused Wicker Park and Lake View in the evening. 

On summer Fridays, trucks congregate at Daley Plaza during lunch. Check Street Food Finder for locations.

The best things to do in Chicago 

Buy a discount pass to save on attractions

There are a couple of options that can save 30% or more on admission fees. CityPass gives access to five of the city's top draws, including the Art Institute, Shedd Aquarium and Willis Tower Skydeck, over nine consecutive days. 

The Go Chicago Pass offers some 25 sights, including all museums (except the Art Institute) and various bus and boat tours. You pay a flat fee for one, two, three or five consecutive days, and visit as many attractions as you want during that time frame. 

Chicago marathon participants run by the Chicago Theater with the red and white marquee lit up in the background.
 Score discounted tickets to Chicago's thrumming theater scene © Fernanda Paradizo / Shutterstock

Check Hot Tix for cheap theater tickets

Hot Tix sells same-week theater tickets for half-price. Drama, comedy and performing-arts venues citywide have seats on offer, including big-name venues such as the Lyric Opera and Steppenwolf Theatre. Book online or in person at the Hot Tix outlets downtown at 72 E Randolph Street and 108 N State Street. The earlier in the week you visit, the better the selection.

Know your baseball options 

Chicago has two pro baseball teams. The Cubs play on the city’s north side at historic Wrigley Field, which charms with its hand-turned scoreboard, neon entrance sign and other old-timey bits. The White Sox play on the city’s south side at Guaranteed Rate Field, a modern ballpark. 

Tickets to Cubs game are usually much more expensive, though the Upper Reserved Infield seats can be moderately priced. They're high up but have decent views. For the White Sox, tickets on Sunday and Monday typically offer the best deals.

Take advantage of free things to do

Chicago has a ton of sights and activities that are 100% gratis. You won’t pay a dime to hear summer concerts at Millennium Park, view terrific art exhibitions at the Chicago Cultural Center, wave to the animals at Lincoln Park Zoo, smell the flowers at Garfield Park Conservatory, tour the city with Chicago Greeter and much more.

Daily costs in Chicago

  • Hostel room: $35-55 (dorm bed)
  • Basic room for two: $150-275
  • Self-catering apartment (including Airbnb): $80-175
  • Public transport ticket: $5 day pass
  • Coffee: $3
  • Hot dog: $4-5
  • Dinner for two: $30-60
  • Pint of microbrew at the bar: $7-8

This article was first published May 26, 2022 and updated Jul 27, 2023.

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