Cheap Chicago

Here are 10 tips to make a trip to the Windy City easy to afford.

Watch for free days at Shedd Aquarium and other popular museums.

View all images

Chicago is on a roll. Millennium Park is wildly popular, and it just keeps getting better, along with the rest of the city.

These days, tourists have to compete with hordes of conventioneers and suburbanites fleeing back to the city. Prices, of course, have gone up.

Still, there's a lot to do for free. Here are 10 tips for making a trip affordable.

In 2021, check in advance to see what's open.

For more tips, see Pinching pennies in Chicago.

1. Go when business people and vacationers don't. Hotels are cheapest in Chicago on the weeks before Christmas, a fun time to be in town, and in the depths of winter.

I've also gotten very good deals on the long Memorial Day and Labor Day weekends and in late October for Halloween, which is a big deal in Chicago. 

To get affordable hotel rates, avoid going when a big convention or event is in town. So before setting a date, check the Chicago convention calendar

2. Get there cheap. You may still find $1 tickets on the Megabus if you book early enough, though $60 is more typical.

Amtrak also can be inexpensive if booked early. 

Driving isn't cheaper once you pay for parking, which costs $40 and up per day.

3. Stay cheap The Hostelling International family hostel in the South Loop, three blocks from the Art Institute at Congress and Wabash, is quite posh, with pancake happy hours, an Internet room and a carpeted great room with foosball, ping-pong, a pool table and a communal kitchen.

It has private as well as shared rooms, along with the Freehand Hotel/Hostel, in a former 1927 hotel in River North, and the Chicago Getaway Hostel near Lincoln Park, a renovated women's boardinghouse.

For more, see Where to stay in Chicago.

You could also stay at an Airbnb; there are hundreds in Chicago. But they're not exactly cheap, partly because of a 23.4 percent tax on short-term vacation rentals.

In slow times (see No. 1), check Groupon Getaways or LivingSocial Escapes for deals. 

Or exchange your home for one there. That saves not only the hotel rate, but the hotel tax of 17.4 percent.

4. See what's free. Start looking at the Chicago Cultural Center and, across the street, at Millennium Park. They both host lots of free performances, including the summer-long Grant Park Music Festival, with orchestra concerts at Jay Pritzker Pavilion.

Check Choose Chicago's Chicago Style on a Budget page. Chicago's best-known free attraction is the Lincoln Park Zoo; the big park also includes the free Conservatory.

The ornate Cultural Center is home to a Chicago tourism office. When you're there, pick up a copy of the Time Out Chicago guide, which is full of tips. Navy Pier also offers many free events.

On Michigan Avenue, across from the John Hancock Building, the beautiful, neo-Gothic Fourth Presbyterian Church offers free noontime concerts on Fridays year-round.

The Chicago Tribune lists what's new and coming up. 

5. Get deals on theater, dance and comedy shows. Get half-price tickets at Hot Tix (online and at two downtown locations), Theatre in Chicago and Goldstar. You also have to pay a fee.

River cruises, opera concerts and walking and food tours also appear on the list occasionally.

6. Use public transit and bike-sharing. It's easy to use the CTA, which operates subways, El trains and buses. Get a Ventra Card, $10 for one day and $20 for three days.

If you buy and register the three-day card before you arrive, you can avoid the $5 fee for the reloadable card. If you buy it at the machine, you can register it later and get the $5 as a credit. 

For bicycling, pick up a blue Divvy bike at one of the many stations around town. A daily pass is $15 and a single ride is $3.30.

7. Eat cheap. It's not hard. Along Michigan Avenue, look for Cosi, the Corner Bakery, Naf Naf Grill, Panda Express and Chipotle; you can eat well for $10-$15 at all of them.

At the foot of the John Hancock Tower, try L'Appetito, a great but unassuming Italian deli at the foot of the John Hancock Tower.

On the mezzanine level of Water Tower Place, eat at foodlife, a bazaar of made-to-order kiosks. But be careful; the food has so much eye appeal it's easy to run up the bill, recorded on a magnetic card.

And you can get a loaded Chicago hot dog and fries for less than $5.

8. Use coupons. If you plan to visit the big museums, buy a CityPass, good for nine days. It provides general and special-exhibit admissions to Shedd Aquarium, the Field Museum, Skydeck Chicago, the Museum of Science and Industry or 360 Chicago (former the John Hancock Observatory) and Adler Planetarium or the Art Institute.

Before you visit, subscribe to Groupon, LivingSocial and other deals for Chicago. Many offers are aimed at locals, but some are for theater tickets and tours, and there are lots of restaurant deals.

The Entertainment book for Chicago isn't as good as it used to be, but check the offers if you'll be doing serious sightseeing and eating.

9. Go to museums on discount days. The big museums used to have one free day a week, but now they vary their schedules, except for the Art Institute of Chicago, which is free on Thursday evenings.

Mondays and Tuesdays in the off-season (which doesn't include December) are good bets, but sometimes museums schedule entire free weeks. There's a handy list of free days, mostly for Illinois residents, at Choose Chicago.

Check Shedd Aquarium, the Art Institute, Adler Planetarium and the Field Museum of Natural History (usually, second Monday of the month).

Because waits already are long at the Museum of Science and Industry, it may be best to avoid free day there.

And there are many other museums that are wonderful and also cheaper. Here's Choose Chicago's list of 20 Chicago Museums & Attractions for $10 or Less.

10. Have a Chicago Greeter show you around. Volunteer Greeters offer free tours of Chicago neighborhoods; reserve seven to 10 days in advance. There's also an Insta-Greeter service available at shorter notice.

More information

For more about architecture tours, neighborhood food tours, ethnic neighborhoods, bicycling on the Lakefront Trail, the Christmas season and traveling with kids, see Chicago stories.

Similar Stories

  1. 10 great getaways from Chicago
    Take a break to lounge on beaches, gawk at river canyons and go on brewery tours.
  2. Tales of the dead
    At Chicago's famous Graceland Cemetery, the graves have a lot to say.
  3. Cheap summer getaways in Michigan
    On the Upper Peninsula and Lake Michigan shores, vacation for as little as $100.
  4. Cheap summer getaways in Iowa and Illinois
    From quiet lake parks to the big city, vacation for $100 or less.
  5. Cheap summer getaways in Wisconsin
    No money, no problem: Here are 20 great vacations that are easy on the wallet.
  6. Cheap summer getaways in Minnesota
    No money, no problem: Here are 20 great vacations that are easy on the wallet.
  7. Wright in Oak Park
    After more than 125 years, the architect's first works still seem stunningly original.