Date Night Chicago: 17+ Unique Ideas and Restaurants

Is there anything better than being in love? There is! It’s being in love in Chicago. Between the dramatic skyline, the sweeping views of the lake, the best-in-class restaurants and the glistening lights, Chicago is an excellent backdrop for falling head over heels for someone. There’s only one thing more difficult than finding a special someone, though: deciding what to do on date night Chicago. With so many options, how can you be sure to sweep that person off their feet?

Don’t worry. We’re here to help you work some magic.

Chicago has a fantastic array of date night activities that will spark the romance between any couple, old or new. We’ll take you through some of the city’s most swoon-worthy spots, titillating experiences, and heart-skipping ideas, so you can blow away your sweetheart. We have 16+ unique date night ideas that will take your breath away.

Date Night for Those Looking to Wine and Dine 

They say the way to a man’s heart is through his stomach, but we firmly believe in inclusion: We say the way to anybody’s heart is through their stomach. If the only thing you and your partner love more than each other is food, then read on for some great date night ideas that will leave you deeply satiated.

#1 Enjoy Five Date Nights in One With a Chicago Food Tour

West Loop Chicago Things To Do

Photo Credit: Chicago Food Planet

Instead of spending the whole night in one trendy Chicago restaurant, hit five hotspots in one evening. Chicago Food Planet’s Gateway to the West Loop Food Tour takes guests around Chicago’s most renowned foodie neighborhood and helps you connect with food and the area in unexpected ways. Our knowledgeable guides will show you around the epicenter of the city’s culinary revolution, while entertaining you with stories on the West Loop’s history, architecture and quirky landmarks.

If that’s not enough:

Couples will get a bite of classic Italian amore at Formento’s, Mexican tradition at Cemitas Puebla, and artisan sweetness at Do-Rite, plus more. Adult beverage pairings are also available for those who may be in the mood to celebrate their love in a big way.

Insider Tip: Foodie couples visiting Chicago can have a lip-smacking good time exploring the city’s signature dishes, including the Buttermilk Old Fashioned Donut at Do-Rite. What are other must-eat foods in the city? Check out 20+ Signature Dishes You Must Try on Your Next Visit for our all-time faves.

#2 Indulge in a 5-Star Meal without the 5-Star Prices at Kai Zan

West Loop Restaurants Kai Zan

Photo Source: @kaizanchicago

Humboldt Park’s Kai Zan has all the elements of a fancy night out. Reservations are hard to come by, the space exudes minimalist chic, the food is sophisticated, and it’s executed impeccably.

Despite all this, one of Chicago’s best Japanese restaurants is still considered a steal. Plus, you can make your date feel extra special by asking the chefs to create individualized makis and sushis based on your sweetie’s preferences.  

For the true gourmands, Kai Zan offers two different omakase menus.

#3 Spice Up Your Romance with a Cooking Class

Chicago cooking classes

Photo Source: The Chicago Lifestyle

Done correctly, cooking can be an extremely sensual experience. Think about it!

You’re tasting, biting, chewing, licking, even steaming. Share this intimate activity with your one-and-only with one of the many courses at The Social Table. The inviting space feels more like an evening inside someone’s private apartment instead of cooking school. Their classes are structured in much the same way.

Though their experienced chefs will guide you through a recipe, the mood is that of a BYOB dinner party but without any of that pesky clean up. Bring your appetites and wow that special someone with your newfound skills.

#4 Get a Taste of the City of Love at Café Marie Jeanne

date night chicago ideas

Photo Source: Chicago Mag

Don’t have the time or budget to whisk your honey away to Paris? Take them somewhere that’s closer to home but with that certain je ne sais quoi: Café Marie Jeanne.

This cozy Humboldt Park restaurant has all the vibes of a Left Bank bistro and exquisite food to boot.

The dinner menu showcases French staples like steak frites and mussels as well as a wide variety of smoked and pickled fishes, omelets, soups, and appetizers. Daily specials are listed on their chalkboard for those who want to venture beyond their standard menu.

The best part?

You can get a decadent meal at Café Marie Jeanne without breaking the bank. They have a happy hour on weekdays from 3 to 6 p.m., a $36 prix-fixe dinner every Wednesday night, and a $20 burger, beer and fries deal on Thursdays.

#5 Grab Drinks — With a Twist — at KOVAL Distillery

chicago couple drinking KOVAL Distillery

Photo Source: Whole Foods Market

Meeting up for drinks gets a whole new meaning with KOVAL Distillery’s Chicago cocktail classes. Famous for being Chicago’s first distillery since the 1800s, their facilities offer tours, whiskey workshops, and a store where you can purchase the spirits they produce.

Wanna really get the party started?

Check out their cocktail classes. History lovers can sign up for a session focused on Prohibition-era cocktails, Mad Men enthusiasts will flock to the old fashioned class, and those with a creative streak can opt for a workshop on building your own classic cocktail.

Instructors pepper their lessons with fun facts on the history of spirits and libations. What a way to stir up some romance.

Quirky Date Ideas for Quirky Love Interests

Did you finally find the weirdo who understands your weirdness? Do all your conversations end with a breathless,  “me too”? Have you already dreamed up your themed wedding and it may or may not involve at least one Lord of the Rings character?

If your love is kooky, but true, we have some cute date night ideas that scream soul mate.

#6 Get Moonstruck at Adler Planetarium

chicago date night adler planetarium

Photo Source: Adler Planetarium

Embrace geek love at Adler After Dark, the planetarium’s exclusive 21+ evening event. Every third Thursday of the month, the Adler opens its doors after 6 PM for a night of live entertainment, special guests, and full access to its exhibits and galleries, including the Doane Observatory (weather permitting). Every month features a different theme like “Planetary Prom,” “Solar Eclipse (of the Heart)”, and “A Night in the Afrofuture.”

The truly nerdy among us can partake in lectures, sky shows, and other educational programs but, even if you don’t, the view of the skyline is well worth the price of admission. Get your tickets early because the event does sell out.

#7 Jazz Up Your Night at The Green Mill

date night chicago jazz club green mill

Photo Source: Michael Novo Photography

Nothing says Chicago romance like a night of classic cocktails, lavish art deco booths, and jazz standards. The Green Mill has been serving up smooth, smooth sounds since 1907 and they still maintain a timeless feel.

On any given night, couples can lounge the night away while listening to jam quartets, swing orchestras, brass bands, string sextets, jazz collectives and so much more.

Share your favorite facts on obscure trumpeters or impress your darling with your encyclopedic knowledge of all things Miles Davis. Its low mood lighting makes it the perfect, intimate spot to be seduced by the power of music.

#8 Write Your Own Romance at Volumes Bookcafe

Chicago couples night volumes cafe chicago

Photo Source: @volumesbooks

They say you can find out a lot about a person by looking at their bookshelves, but that may be too forward for a first date. Instead take them to Volumes Bookcafe, a charming bookstore in the heart of Wicker Park.

Flip through the pages of the latest bestseller or check out that new fiction novel you’ve both been hearing so much about, all while discovering who is the bigger bookworm. Volumes also has a café where you can indulge in their signature lattes, yummy teas, or even order a glass of wine to help take the edge off.

Sweeten the deal:

You can also rent board games, attend one of their many literary events, or simply take the time to write each other some love poems.

#9 Reenact That Scene from Ghost at a Pottery Class

date night chicago ideas

Photo Source: Chicago Catalyst

You may not have the moves of Patrick Swayze or the doe eyes of Demi Moore. There’s a very high probability that you are also not a ghost. That doesn’t mean you can’t fulfill one Hollywood’s most romantic fantasies!

Act it out:

Snuggle up to your paramour at Penguin Foot’s popular BYOB Wheel Throwing Happy Hour class. Instructors teach participants the basics of using a potter’s wheel and then help them create their own take-home pieces.

The experience is hands-on, interactive, but also very laid back. “Unchained Melody” soundtrack not included.

Have a Summer Fling with These Easy, Breeze Dates

Summer is in the air as soon as Memorial Day hits in Chicago. Maybe it’s because we’re no longer hiding under twenty piles of layers, but the warm months are prime time for romance in the city. Woe your sweetheart with these hot, Chicago romantic things to do and best date ideas.  

#10  Dinner and a Movie, but Make It Unique with Movies in the Park

chicago date night movies in the park

Photo Source: Chicago Parks District

There’s a reason why dinner and a movie is a classic but there’s no need to be lazy about it. Instead of hitting your local multiplex, grab your favorite picnic basket and a blanket and head outdoors.

Every summer, the Chicago Parks District’s Movies in the Park program features blockbusters, indie favorites, and golden Hollywood standards in parks all over the city on almost any given night of the week. Admission is free, but the memories are priceless and a great Chicago date idea to consider

#11 Discover Your Adventurous Side in Chinatown

Chinatown Chicago date night

Photo Credit: Chicago Food Planet

Date night can be an exciting opportunity to get out of your usual routine and dare to try something new. How about exploring Chinatown, one of Chicago’s most vibrant and intriguing neighborhoods? On Chicago Food Planet’s Chinatown Adventure Food Tour, you and your significant other will learn more about the community’s culinary history via Hong Kong dim sum, spicy Szechuan specialties, and the oft-overlooked treats in Chinese bakeries.

Wait, there’s more:

Besides being a total sensory experience for your taste buds, Chinatown is also home to some of the most memorable spots in the city and summer is the perfect time to explore them. The hidden side streets are perfect for stealing sweet glances, a Buddhist Temple will make you feel like you’re on a dream vacation, and the neighborhood’s serene park will give you so many feels.

Insider Tip: The couple that tours together, stays together. At least that’s what we like to think. If you’re interested in other tour options in the city, head over to our guide on the 15+ Best Chicago Tour Companies.

#12 Imagine Growing Old Together at Royal Palms Shuffleboard Chicago

chicago shuffleboard royal palms

Photo Source: Urban Matter

Chicago’s premiere shuffleboard institution is here to inspire a love that lasts a lifetime. Wicker Park’s Royal Palms looks like yet another hip and of-the-moment bar with its rotating selection of food trucks, a roof deck and a DJ spinning the latest indie darlings… until you realize it also includes eleven regulation-sized shuffleboard courts.

As far as we’re concerned, a sport best associated with Grandpa and Meemaw is exactly the kind of activity you want to do when envisioning a future together. Grab a Mai Tai, push some biscuits, and see if this is a forever kind of relationship.

#13 Get to the Next Level at Navy Pier’s Centennial Wheel

navy pier chicago centennial ferris wheel

Photo Source: Navy Pier

Add some dramatic flair to date night by hopping on Navy Pier’s Centennial Wheel, Chicago’s iconic Ferris Wheel. With unobstructed views of Lake Michigan and the city’s skyline, this may be the one time during the night that you’ll be able to take your eyes off each other.

Insider Tip: Planning on spending a whole day at Navy Pier, and not just a date? You’re in luck! Why not start with the Chicago Food Planet Navy Pier Signature Tour, then head over to the Centennial Wheel for a fantastic finish?

Get Ready for Snuggle Season with Our Favorite Winter Dates

If Chicago’s cold temperatures inspire you to run into your crush’s arms, we don’t blame you! Stave off the long winter nights, with these fun and romantic Chicago winter date night ideas that will warm you up for months on end.

#14 Get Lost in Each Other’s Eyes at Lost Lake

chicago couples bars lost lake

Photo Source: @lostlaketiki

If your idea of romance includes lush landscapes, tropical drinks, and the irresistible sexiness of oversized Hawaiian shirts, then head over to Lost Lake. The tiki bar that restored tiki bars to their former glory offers an escape from the cold with bae.

Picture this:

You and your date can laugh over cheeky cocktails like “Salty in All the Right Places” and “Nobody’s Business” or even share a punch bowl the size of your love like “Hula Hips of Heaven.” Nosh on some Asian-inspired bar bites, bob to the vintage vinyl sounds, and cuddle up in bamboo chairs.

Squint hard enough — or drink long enough — and soon Lost Lake’s floral walls will convince you both you’re actually in paradise.

#15 Put a New Spin on Date Night at Whirlyball

Whirly ball chicago

Photo Source: @whirlyball

Some couples like to be wined and dined, others like to spin and win. If you’re the latter, then Whirlyball is exactly the place you want to be on date night. A cross between basketball, lacrosse and bumper cars, each will get your engines and hearts racing.

Show off what a great team you are by knocking out the other players or flirt up a storm with some friendly competition by being on opposite sides of the court.

That’s not all:

The massive indoor Bucktown complex also holds a bowling alley, laser tag, and a full-service restaurant. With so much to do under one roof, it’s an easy way to spend a winter night or rainy Saturday.

Insider Tip: Looking to bond with your colleagues instead? (In a completely professional, platonic way, of course.) Whirlyball is a great way to blow off steam, collaborate, and have fun with a big group. For this and other team-building ideas, read our guide 17+ Kickass Ideas to Kickstart Your Next Team-Building Event.

#16 Kiss Under the Mistletoe at Christkindlmarket

date night chicago winter ideas

Photo Source: @christmaschi

With enough Christmas magic to fuel at least five Lifetime holiday movies, Chicago’s annual Christkindlmarket will make your heart grow three times its regular size. The cherished outdoor market is held right in Daley Plaza and is open daily from late November to Christmas Eve.

Stroll the stalls hand-in-hand, indulge in a nutella crepe, and toast each other with some gluhwein. On any given night you may also be serenaded by the angelic voices of a holiday choir, captivated by the twinkling beauty of lighting ceremonies or simply thrilled by the communal joy found in currywurst.

#17 Kick It Old School with Skate Night at the Chicago Athletic Association Hotel

chicago athletic hotel date night

For a crush that feels a lot like puppy love, no date might be better than the wickedly fun Skate Night at the swanky Chicago Athletic Association Hotel.

The beautiful and historic Stagg Court is turned into a roller rink for a throwback event that manages to feel brand new. Dance to the sing-out-loud tunes of powerhouses like Drake, cheer on the choreographed stylings of Chicago Roller Talent, and sip on some of the hotel’s refined cocktails.

Don’t get locked out:

Attendees can rent or bring their own skates, but tickets are a must. The event is only held during the winter months.

Connect With Your Partner & Food In Unexpected Ways


Enjoy Gateway To The West Loop Food Tour on the #1-Rated Date Night Activity

Meet the chefs, learn their stories & devour specialty dishes at top restaurants

Offered daily; Includes visits to Kuma’s Corner, Bonci Pizza & Do-Rite Donuts 


$60 Adult Tickets (Food Included)
VIP Tickets Available (+ Drink Pairings)

Learn More