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Cheap Chicago

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

A theater in Chicago.

© Beth Gauper

Check Hot Tix for discount tickets to productions in the downtown theater district.

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.

But Chicago is a populist town, and there's a lot to do for free. Here are 10 tips for making a trip affordable.

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. A quick look at Hot Rooms also will give you an idea of what rates will be.

2. Get there cheap. The Megabus still costs only $1 each way, if you book early enough, though $60 is more typical.

Amtrak also can be inexpensive if booked early. Spirit Airlines offers round-trips for less than $100 from some cities, and Southwest can go that low during sales.

Driving isn't cheaper once you pay for parking, which costs $30 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 new 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 home; there are hundreds in Chicago.

Shedd Aquarium in Chicago.

© Beth Gauper

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

In slow times (see No. 1), check Groupon Getaways or LivingSocial Escapes for deals. Or use Priceline to get rooms in good three- and four-star hotels for as little as $70.

Or exchange your home for one there. That saves not only the hotel rate, but the hotel tax of 16.5 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 Always Free Attractions page. Chicago's best-known free attraction is the Lincoln Park Zoo; the big park also includes a 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 Student 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.

Metromix Chicago lists lots of festivals, many in the neighborhoods, and most are free.

5. Get deals on theater, dance and comedy shows. Get half-price tickets at Hot Tix (online and at three 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 24-hour pass is $7, including unlimited half-hour trips. A trip that lasts up to an hour incurs an extra $2.

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 about $10 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.

Bands at the Chicago Blues Festival.

© Torsten Muller

Concerts in Grant Park, including the Chicago Blues Festival, are free.

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 pile of fries for less than $4.

8. Use coupons. If you plan to visit the big museums, buy a CityPass, $98 and 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 books for Chicago North and Chicago South & West aren't as good as it used to be, but check the offers if you'll be doing serious sightseeing and eating.

They start at $35 in fall, and the price drops to as low as $5 as the year progresses. Buy online for such bonuses as free shipping, a $25 restaurant coupon and/or two books for the price of one.

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.

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.


Last updated on January 18, 2017