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19 Cheap Date Night Ideas in Chicago

Elizabeth SanFilippo
Aug. 3, 2017

Book a babysitter, grab your honey, and enjoy a one-of-a-kind night out in the Windy City on the cheap.

Cheap Date Night Ideas in Chicago, Illinois
Image via Unsplash.com/lomogee

“There is something magical about Chicago. The city is the perfect mix of glittery skyscrapers and natural beauty,” says Christine Arreola, a blogger at The New Abides. “It has everything you need for a great date night."

But as a big city, a night out in Chi-town can come with a hefty price tag. So how do you keep it fun without blowing the week's grocery budget? Arreola and Patti Feinstein, owner of Chicago-based America’s Dating Coach, offer 19 great date night ideas that are inexpensive or free.

Now, the only thing left to do is lock down your babysitter or nanny for the big night!

  1. Museum "Free Days"
    Many Chicago museums have free admission days, so plan your dates around those times. The Art Institute of Chicago, for example, has free admission on Thursdays from 5-8 p.m. "Try the affordable small plates offered in the museum cafe for dinner while you're there,” recommends Arreola. The Museum of Contemporary Art Chicago offers free admission to all Illinois residents every Tuesday.

  2. Catch a Sports Game
    Whether you're a fan of baseball, basketball, football or hockey, there’s always something going on in this city. Grab a ticket and head to the game to cheer on your favorite team together. Save money by attending a lower level division or high school game.

  3. Turn Into Pinball Wizards
    If you're looking for a date night idea that taps into your inner child, look no further than Logan Arcade. With 30 pinball machines and 47 video games, this place is a mecca for gamers of any age. The arcade offers a healthy selection of new and old-school games -- the latter of which will appeal specifically to the Millennial/Gen-X-er crowd. (Check out their game list to get an idea of what they've got.) And, as if it couldn't get any better, Logan Arcade also serves alcoholic beverages that you can consume (responsibly) as you walk down memory lane.

  4. Play Ping Pong at Happy Village
    Happy Village is a real favorite among locals because it truly has something for everyone. This spot offers some of the cheapest drink specials in Chicago, and they even have an outdoor beer garden where you can sit and enjoy your drink special as you get some fresh air. If you're feeling competitive, head into their ping pong room and get a few games going -- and if you're feeling REALLY lucky, start a tournament with the other ping pong enthusiasts there.

  5. Enjoy the Lakefront
    While there’s plenty of architecture and buildings to check out around town, there are also plenty of spots to hang out in the beautiful outdoors. “Enjoy Lake Michigan and views of the city on the Chicago Lakefront Trail or wander the grounds of the Peggy Notebaert Nature Museum,” says Arreola. “During late spring to early autumn, visit Buckingham Fountain which is lit by 820 shimmering lights at night.”

  6. Take in a Free Outdoor Concert at Millennium Park
    What better -- or cheaper -- way to celebrate summer in the city than by catching a free outdoor concert during the Millennium Park Summer Music Series? Shows are held on Mondays and Thursdays at the Jay Pritzker Pavilion in Millennium Park.

    The best part about them? “Concerts put on by the city of Chicago are free,” Arreola shares. “Bring a picnic basket, a bottle of wine, and listen to the music under the stars together."

    The schedule usually follows a June-August schedule, but that may obviously change from year to year. Check out the City of Chicago's website to see what the lineup is for each week.

  7. Try Out Some of the Chicago Park District Activities
    Not only are there free concerts, there’s also a plethora of free Chicago Park District venues and events. “Go for a stroll in the conservatory if you are a gardener,” says Feinstein. Other activities she recommends include volleyball and kite boarding.

  8. Spend the Day at a City Park
    Let your imagination guide you to find your own activity at one of the city’s many parks. Bring your rackets and play tennis or toss a Frisbee around. Afterward, set up a romantic picnic.

  9. Visit the Lincoln Park Zoo
    You may have to pay for parking, but admission to the Lincoln Park Zoo itself is free, making it the perfect place for animal lovers to date during the day.

  10. Go Out to Lunch
    The dining scene in Chicago is unlike any other. But that doesn’t mean you have to wait for dinner. “Many restaurants have less expensive menus for lunch and you can skip waiting a long time for a table,” suggests Arreola.

  11. Make Your Own Farm-to-Table Meal
    Dates often revolve around food, but that doesn’t require eating out. “You can also shop at one of Chicago's farmer’s markets, then go home to cook up your own romantic dinner together,” says Arreola.

  12. Treat Yo'Self...to Dessert
    If you prefer to go out, splurge on dessert instead of a full meal. Chicago has plenty of restaurants that serve stellar desserts -- from the banana cream pie at Bandera to the concrete ice creams at Scooter’s -- but it’s up to you if you want to share the spoon.

  13. Attend Festivals Galore
    Festivals in Chicago aren’t just about food, although many feature great eats, too. Catch some music at Jazz Fest or the Gospel Music Fest. Share your love of books at the Chicago Tribune’s annual Printer’s Row Festival. Discover local gardens with the Sheffield Garden Walk and Festival.

  14. Visit a New Neighborhood
    Every Chicago neighborhood has something different to offer, so hop on the el, train or car and check out all the enclaves from Chinatown to Little Italy to Greek Town to Andersonville.

    “Andersonville has become a happening and inexpensive hangout joint,” says Feinstein. “Go see a novel show, stand up comedians, etc. If you enjoy the arts, there are even interactive radio improv shows that include you in the fun." Find one for you using metromix.

  15. Attend a Chicago Public Library Event
    Make your date time intellectual with a trip to the Chicago Public Library’s (CPL) events. “The CPL routinely has published authors on a variety of topics. They come in and talk about both their work and process. These are typically free and on weeknights, as well as weekends,” says Feinstein.

  16. Go Ice Skating
    Not only is ice skating inexpensive, it’s also fun and healthy wintertime activity. “Men typically bond on activities, where women bond on self-disclosure,” says Feinstein. “This is a fun, non-pressure situation where you must interact with one another."

    Arreola agrees and suggests ice skating at Millennium Park, which is free (if you bring your own skates). Otherwise you can rent them. “Afterward, warm up together with hot chocolate next door at the Park Grill.”

  17. Attend an Improv Show
    Chicago is also home to a number of wonderful comedy venues, and there’s nothing better than sharing a laugh with your date. Check out improv shows at the infamous Second City, or smaller venues, where ticket prices are often a bit cheaper.

  18. Head Out to Happy Hour and Catch a Show
    Happy hour is usually a draw in and of itself, but if you'd like some smooth jazz or a stand-up routine to pair with your beer, head to places like The Gallery Cabaret. This fun, funky bar offers tons of great live comedy shows, musical performances, and open mic nights every week. Check out their extensive events calendar to see if they've got anything coming up that's in your wheelhouse.

  19. Check Out the Holiday Lights
    “Our wedding anniversary is in late November, so my husband and I started the tradition of heading downtown to see the holidays lights on Michigan Avenue. Grab a cup of coffee and window shop down the Magnificent Mile. Request a window seat at a restaurant, order dinner and watch the hustle and bustle go by,” says Arreola.


UP NEXT: "The 7 Best Free Things to Do in Chicago When Your Kids Say, ‘I’m Bored’"


Originally written by Elizabeth SanFilippo. Updated by Katie Bonadies on 7 July 2017.

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