12 Free and Cheap Date Ideas to Try in Chicago

The Chicago River
The Chicago River | © Pedro Lastra / Unsplash

An awesome date takes planning and preparation but not necessarily big bucks. In fact, Chicago has some pretty sweet date options that cost little to no money, from romantic walks to spectacular sights. Just bring the romance.

1. Lincoln Park Zoo

Zoo, Park

Lincoln Park Zoo, Chicago
© Ron Cogswell / Flickr / Derivative from original

One of Chicago’s top attractions also makes a pretty sweet date. For a zoo of its size to be free is remarkable—and don’t expect second-rate animals either: a polar bear, lions, a tiger, giraffes, gorillas, and plenty more will keep you occupied. For extra romance, go at twilight to enjoy beautiful views as the skyline lights up.

2. The Signature Lounge at the 96th

Restaurant, Bar, Cocktail Bar, American

View from the John Hancock Center
© tpsdave / Pixabay

No one in the know pays for a view in Chicago, and the best free view is undoubtedly from the Signature Lounge on the 96th floor of the John Hancock Center. As there’s no fee to go up, there’s a small price hike on the food and drinks, but it’s more than worth it for amazing 360-degree view of the city. Again, going at night adds that extra touch of romance.

Walk the Lakefront Trail

Beautiful coasts are often romantic, evoking memories and ideas of travel and excitement. Luckily for Chicagoans, Lake Michigan is so vast, the city feels like it’s on the shores of an ocean. What better way to step away from the hubbub of the city than with a romantic stroll on the Lakefront Trail or a picnic on one of the city’s famous beaches?

Chicago SummerDance

Ready to wow your date with your moves? The Chicago SummerDance program includes both lessons and free dancing in Grant Park. Between June 23 and September 10, 2017, are parties with live music and DJs. For those looking to polish up their footwork, dance lessons take place at selected times throughout the weekend.

DIY architecture tour

It’s not hard to put together a tour of Chicago’s best architecture. Whether you like the city’s original giants, Art Deco masterpieces, the Second Chicago School, or the latest modern skyscrapers, there’s plenty to choose from. Choose a theme, and you have a great cheap date ahead.

3. Buckingham Fountain


Buckingham Fountains spectacular water and light show
© Chris Pelliccione / Flickr

Time a visit to Buckingham Fountain right and see one of the world’s most spectacular fountain displays. Once an hour during the summer months, water and light combine to make a stunning 20-minute show. To make your data that extra special, why not add a walk around Grant Park?

Public art tour

In 2017, the Chicago Library held an exhibition highlighting the worst public art the city had seen over the years, but those failures are few and far between. Today, amazing art can be found all over the city for free. From murals of blues legend Muddy Waters to giant flamingo sculptures, there’s something for everyone.

4. Chicago Riverwalk

Park, Architectural Landmark

Looking down onto the Riverwalk in downtown Chicago on a warm summer day.
© D Guest Smith / Alamy Stock Photo

If soaking up the sights and sounds of the city is enough for a date, there aren’t many better spots than on the ever-growing Chicago Riverwalk. Watch the boats go by, look up at some of the city’s best buildings, or just enjoy a bit of people-watching. For a cheap boat ride, try the Chicago Water Taxi; one-way tickets start at $5.

Get on your bike

Any one of the almost 6,000 Divvy bikes in Chicago can be rented for $15 a day, providing a great value way to string together a number of sights for a great date. Enjoy the 606 urban park trail as the sun sets, watch the city lights from miles away on the Lakefront Trail, or zip around the Loop to grab some late-night eats.

A taste of Mexico in Pilsen

The National Museum of Mexican Art

One of the largest collections of Mexican art in the country is available for free at the National Museum of Mexican Art in Pilsen. Not only that, but there are also amazing murals dotted around the neighborhood to make for an awesome and free art-filled date. Pilsen is also full of authentic Mexican food at great prices.

5. Get your skates on


If you need a cheap date idea during the long winter months, ice skating is always a winner for romance. The Skating Ribbon in Maggie Daley Park is free as well as cool, giving you a chance to show off your skills on the track rather than the crowded rink in Millennium Park. Skates can be rented for $12 during the week and $14 at the weekend.

Grab a theater bargain

Chicago has some great options when it comes to theater, from independent productions to Broadway shows, and while tickets can be pricey, there are still bargains to be found. Head to Hot Tix for half-price tickets in advance for the current week and future dates as well as day-of discounts, or try TodayTix for discount tickets up to 30 days in advance.

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