44 Fun Date Ideas Around Chicago for Couples

Gina I.:  Grab a blanket, pack a picnic, and head to your local Chicago area park for Movies in the Parks! From old Hollywood classics and family friendly films to recent box office favorites, you're sure to find the perfect flick for your next date night. In fact, Movies in the Parks are have showings in dozens of Chicago area parks, so there is something almost every night of the week. Best of all, it's free!

Erin P.:  Bottle & Bottega/Painting With A Twist is a popular painting and pottery studio in Chicago with many locations throughout the area that feature wine and paint parties! This is a fun and non intimidating class that any one will love regardless of their artistic abilities. All classes are BYOB, and class themes can be quite unique. You'll walk out with a masterpiece!

Treat yourselves to the best view of the skyline from anywhere in Chicago. On Wednesday nights the Adler is open late, and is a great time to enjoy the award-winning sky shows and activities at this excellent Chicago planetarium. Best of all, Wednesdays are free admission for Illinois residents with proof of residency! Everyone should book their entry online in advance.

Joseph Kelley:  Jazz. Cocktails. The lake. Fireworks. And 32,000 animals. That's Jazzin' at the Shedd!

Gina I.:  Whether you are new to the city or were born and raised in Chicago, you've never seen the city quite like this! Chicago Segway Tours gives you and your honey the opportunity to explore the Windy City including the landmarks and beautiful buildings that border Lake Michigan. Tours are led by knowledgeable guides who will share lots of fun facts about the city. Be sure to bring your camera for plenty of fun photo-ops!

Lisa R:  Known as one of the best bowling alleys in Chicago, this upscale banquet hall and bistro has a menu that will please kids and discerning adults alike, making it perfect for both date nights and family celebrations. Patrons can enjoy their choice of craft beers, cocktails, or wine over a romantic meal or while playing a game of bocce or bowl. Check the events page of the location nearest you for special social events, trivia nights, tastings, and late-night hours.

Lisa R:  Consistently rated one of the best guided tours in Chicago, Bobby's Bike Hire has a range of walking and biking tours specially tailored for kids only, families, and date night. It's a great way to catch up on Chicago history, learn about new places that you'll want to return to again and again, and (best of all) learn obscure facts that will impress your work friends on Monday. Date night options include a City Lights at Night Tour, a Brewery Tour, Museums and Parks at Sunset, Sweets and Spirits, and a Craft Beer Tasting (walking only).

Kristy Pepping:  One of the most unique date ideas around Chicago occurs in the winter months. Warm up on a date with outdoor ice skating! The Ribbon is located in the heart of downtown Chicago and aptly-named as the ice winds through a rolling landscape providing an ice skating experience unlike any other. Limited spacing. Reservations required.

Vanessa M.:  Forget the cover fees! The City of Chicago hosts Chicago Summer Dance for free each summer. Live bands ranging from reggae to rock transform the Spirit of Music Garden in Grant Park into a happening urban dance space. Pack a picnic or grab some takeout and enjoy a lovely summer evening together. Get there early for free dance lessons!

Kelly R:  The Millennium Park Summer Music Series offers a lineup of free outdoor concerts at the Jay Pritzker Pavilion, held most Mondays and Thursdays throughout the Summer. The series features a wide variety of music from local, national and international artists. Bring along a picnic and a bottle of wine to enjoy.

Kelly R:  Spend a few hours wandering around The Art Institute of Chicago. General admission is free to Illinois residents every Thursday from 5 - 8 pm.

Yoli B:  You have so many options around town, but the Game Room at the Chicago Athletic Association will certainly be a great entertainment spot for date night. You can join in with others or compete against one another in pool, bocce, foosball, and many different board games! No matter what you choose you will have a great time in the beautiful game room.

Kelly R:  Treat yourselves to a magical night out at award winning magician Dennis Watkins' funny, lively, and sophisticated show held in an intimate 50-guest suite at the Palmer House Hilton.

Enjoy fun, live jazz music in an upscale room complete with cocktails and dinner options. The music is not so loud that you can't still carry on a conversation, and the occasion offers a great excuse to get dressed up, go downtown, and enjoy yourselves!

Shila:  Share your passion with someone special in a variety of private or small group cooking classes that are held frequently throughout the month. Example date night classes include Passport to Tuscany, Celebrate Chinese New Year, Italian Romance, Evening in Paris, Great Steak Dinner, and more!

Sur La Table Make & Take Classes are fun for stay at home date nights, too!