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9 Free — or Super Cheap — Date Ideas in Chicago

Cheap date options in Chicago include visiting a museum on a free day and grabbing a hot dog.
Aug. 23, 2017
Managing Money, Personal Finance
9 Free — or Super Cheap — Chicago Date Ideas
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Cancel those restaurant reservations. The dinner date is an expensive, awkward and unoriginal rendezvous. Chicagoans can do better.

That’s because Chicago is bursting with activities that are cheaper and more interesting than making small talk across a table. Here are a few out-of-the-restaurant date ideas that cost nothing, or pretty close to it:


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Explore the city

1. Visit a museum

Many of the city’s museums host free-admission days or evenings, according to Chicago tour guide Clarence Goodman. You and your date can learn about each other by discussing exhibits, he says.

2. Discover city art

“There’s public art everywhere in Chicago,” Goodman says, including sculptures, statues, murals and architecture. Find free guides to Chicago’s architecture and public art on ArchDaily and the City of Chicago websites.

3. Tour a house of worship

“No matter what one’s religious affiliation is or is not, there are dozens of gorgeous houses of worship in downtown Chicago, many going back to the time of the fire,” Goodman says. “They put you in the mood to be close to another human being and the spirit or essence of that person.” Many of these places give free tours or allow visitors to walk in and explore, he adds.

4. Share your day

A day-in-the-life date costs next to nothing and shows your new beau how and where you spend your time. “Ride the L together and show one another the city through your eyes, based on your commute,” Goodman says. End the date by showing off your neighborhood. Or do the reverse: Check out your date’s commute and community.

Take in some nature

5. Go for a walk

“Chicago has a zillion beautiful, world class parks,” Goodman says. He recommends strolling through the Chicago Botanic Garden or the Lincoln Park Zoo, both of which are free.

6. Pack a picnic

Aside from a stroll, parks are perfect for picnics. Grab a blanket from home and pre-made appetizers from the grocery store, says Stef Safran, owner of the Chicago-based matchmaking service Stef and the City. “It looks like you spent a ton of time and money, when you didn’t,” she adds. Goodman suggests Jackson Park for a picnic, specifically its lagoon and the free, Japanese-styled Garden of the Phoenix, previously known as the Osaka Garden.

7. Catch an outdoor movie

Safran recommends taking advantage of the Movies in the Parks program, which shows flicks through early September. Bring snacks for a retro, inexpensive take on dinner and a movie. “It’s kind of reminiscent of the old-school drive-in,” Safran says.

Share a meal

8. Grab a Chicago-style hot dog

Skip the pricey sit-down dinner. In Chicago, there’s no shortage of places to load a hot dog with mustard, ketchup — just kidding! — onions, relish and other fixins. Because these hot dogs are so filling, Goodman says, “this is an extraordinarily cheap way to taste Chicago.”

9. Cook for each other

What’s more romantic than taking time and effort to create a meal for someone at home? (Never mind the benefit of spending $20 on groceries, rather four or five times that amount at a restaurant. You can be both romantic and frugal.)

The only catch is that sharing a meal at home is a pretty intimate date, Safran says. Save this invitation for after you’ve wowed your new partner with city tours, picnics and hot dogs.

More money-saving insights

Dating in the city doesn’t need to be expensive. And, ideally, these potential life partners agree with the Beatles: Money can’t buy them love.

But if you’re so cash-strapped that an occasional dinner date guts your bank account, it might be time to rethink your financial strategy. NerdWallet recommends devoting 50% of your earnings to necessities, 30% to wants — a date at the Chicago Theatre, anyone? — and 20% to savings. Here’s everything you need to know about budgeting. With a little financial TLC, you can go on cheap dates because they’re fun, not because you have to.

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