Skip the Sears Tower
Chicago’s most iconic building, the Sears Tower, is overrated. Even with the addition of the new glass-bottomed balconies, $15 is a bit much to pay for a view.
Instead, head to the John Hancock Center where you can skip the admission fee by ascending to the 96th-floor Signature Lounge. Drinks are on the pricey side, but the chance to take in the views (which many feel are better than those offered by the Sears Tower anyway) from the comfort of your own seat is worth the cost.
See summer shows on the cheap
Street fests almost always feature live music, and admission is just a few bucks.
For both big-name and local acts, pack a picnic and head to the lawn at Ravinia. You can bring your own beer and wine and listen to music under the stars for around $10.
Grant Park also hosts free concerts several nights a week.
Bring your own
Chicago’s liquor laws allow restaurants to offer BYO (bring-your-own) service. With hundreds of BYO restaurants to choose from, serving all varieties of cuisine in every corner of the city, there’s no reason not to take advantage and save yourself a few bucks.
Some restaurants charge a nominal “corkage fee” for your beer or wine, but you’ll still save considerably when you bring your own. For more info, check out 10 Spots in Chicago for BYOB Dining.
Ride the El
You can reach most attractions in the downtown area by foot, but to explore Chicago’s many diverse neighborhoods, you’ll need some sort of transportation.
Cab fares add up and parking is virtually impossible in many areas, so cut costs by riding the El, the city’s elevated train (which actually runs underground in parts). Single rides are $2.25 and day- and week-long passes are a great deal.
Riding the El is not only cheap, but watching the city go by from the elevated tracks is also a quintessential Chicago experience.
Forgo a full dinner
Chicago is home to some of the most celebrated restaurants in the country — many of which require you to order an expensive tasting menu of four to upwards of twelve courses. Save money by skipping the multi-course menu in the dining room and instead ordering a la carte at the bar.
If you’re absolutely committed to dining on fancy fish at L2O, for example, you can opt out of the $110-per person, four-course meal and order small plates for $10-20 each in the lounge.
Likewise, if you can’t splurge on a several hundred dollar meal at Tru, you can try a cheaper sampling of dishes in the bar, or book a “dessert-only” tasting for around $50 per person.
Save your shopping for neighborhood boutiques
Shopping at the designer stores on Michigan Avenue is a dream for many tourists. Paying off the credit card bill afterward, however, will be a nightmare.
Add in the fact that the influx of lower-cost chains like Forever 21 and H&M is taking some of the luster away from the experience, and shopping on the “Magnificent Mile” is no longer all that appealing.
For unique and affordable duds, check out the independent boutiques in Wicker Park, Bucktown, Lincoln Park, and Lakeview. You’ll find one-of-a-kind pieces that’ll impress your friends back home — without spending a fortune.
Pay less to ride the river
An architectural cruise along the Chicago River is a great way to learn about the city’s many notable buildings. But it ain’t cheap.
Instead, take a more budget-friendly ride on the water taxi that runs from Michigan Avenue to Chinatown. These go for just two bucks and pass many of the city’s most famous structures.
Score free admission
If you’re planning a visit to one of Chicago’s many museums, check each one’s website for a list of free-admission days scattered throughout the year.
The Lincoln Park Zoo is free every day.
Looking for other Matador community members in Chicago to connect with? Search for them in our destination pages.
And for all you cheapies out there, make sure not to miss these guides: