40 Fun Date Ideas Around Chicago for Couples

Erin P. said:  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!

Kelly R. said:  Treat yourselves to the best view of the skyline from anywhere in Chicago. Adler After Dark is an adults-only event with open access to the museum at night, unlimited sky shows, and unique entertainment. Each month has a different theme with live entertainment, special guests and lectures, so the event is never the same. Buy tickets in advance, as this event is popular and often sells out.

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

Gina I. said:  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 said:  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 said:  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 said:  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.

Yoli B said:  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. said:  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. Put on your cocktail attire and get your tickets today!

Virtual magic shows can be designed for viewing at home via private Zoom, too.

Revival Food Hall is for the gastronomically adventurous couple who wants to try a few different, delicious food places in the city but doesn't have time to drive around all night. This is especially great if you are having the classic "what should we eat tonight?" debate because they have so many different high end options! And don't worry, they'll even have you covered for dessert too :)

Located on the ground floor of The National.

Gina I. said:  If you're looking for an excellent 'green' option for exploring the city, look no further than the Chicago Electric Boat Company! Their fleet of 100% electric boats have been certified as zero emissions watercrafts, and they are easy to drive even for the boating novice! Drive the boat yourself (they'll show you how)or you can hire one of their captains for the day. This is a river excursion, but in cases of hiring a captain, you can enter Lake Michigan. Boats can accommodate up to 10 - 12 passengers of all ages, and you are welcome to bring your own food and drinks.

Shila said:  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!

Kelly R. said:  Instead of popping into a bar for a drink on date night, why not learn to make your own? Hollow Leg offers hands-on mixology classes, where you can learn to make great original cocktails with a focus on local, seasonal, sustainable, and organic ingredients. Classes are held at different venues around the city and suburbs. See calendar.

Yoli B said:  Ever wonder what is behind that beautiful door in downtown Chicago? Now you can find out with Open House Chicago! One weekend a year the Chicago Architecture Center allows behind-the-scenes access to over 200 buildings around Chicago, giving you a glimpse of those never before seen tile floors or golden ceilings that are usually off limits. This event is great for design and history lovers. Don't miss it!!

Yoli B said:  Three Dots and a Dash is located in a dark basement in River North and somehow it is one of the coolest spots in town! The bar has a tiki theme and it shows in the food and the drinks as they come out. You can take your pick between the intimate lounge or boisterous bar area! What makes this place extra special is they cold press the juice for all of there cocktail creations, and also use the freshest ingredients for everything on the menu!