Download our app to stay updated on the latest experiences around you!

Bucket Listers




food & drink · arts & culture · music & nightlife ·

Published February 1, 2023

The Most Romantic Date Ideas For Valentine's Day in Chicago

The most romantic restaurants and date ideas to celebrate Valentine's Day all February long in Chi-Town. 💘

by Chicago Bucket List


Valentine's Day is around the corner, and thankfully the Windy City has all the ingredients you need to get the sparks flying with dazzling city lights, Michelin-starred restaurants, and dreamy waterfront spots to explore and admire. Whether you're looking for the perfect romantic restaurant, want to shake things up with comedy or a show, or want something a little more lowkey, our list of romantic date ideas has something for everyone.

Not feeling Valentine's Day this year? Check out this Bad Blood Break-Up Bar, where you can drink, sing, and dance along to Taylor classics. Valentine's Day is also a good excuse to gather the crew and treat yourselves to an epic group dinner. Or, attend a Galentine's Day dinner party with cute decor and festive drinks. You can also round up your besties for mimosas and bloody marys at one of Chicago's best brunch spots


15 Romantic Ways to Spend Valentine's Day in Chicago


Play Love Pong at SPIN Chicago

By combining an unusual mixture of sport, design, and entertainment, SPIN is the original ping pong social club. Grab your boo and go out for a night of friendly competition featuring DJs, specialty cocktails, surprise performances, and more! Tickets include a 2-hour open bar, access to ping-pong tables, paddles, unlimited balls, DJs, dancing, and more.

Where: 344 N. State St., Chicago, IL
More information on Love Pong at SPIN.


SPIN Chicago, North State Street, Chicago, IL, USA
Love Pong at SPIN - Chicago
Starting at $48

Book now

Go for a Wine Tasting at Uvae Kitchen & Wine Bar

Spend an afternoon sipping wines at Uvae Kitchen & Wine Bar in Andersonville. Uvae will offer a Valentine’s-themed wine tasting featuring “Sweetheart Wines” at the adjacent Fromagerie & Tasting Room on Saturday, February 11, at 3 pm. Guests will explore the holiday's history with four 4-ounce wine pours, plus small bites like Duck Pâté and a cheese plate.

For a grander Valentine's Day experience, Uvae will offer a 5-course Valentine’s Day Wine Pairing Dinner that will include Oysters three ways, Lobster Bisque, King Salmon, and a Petite Filet. Dessert will feature a white chocolate Soufflé with white chocolate, strawberry crème anglaise, biscoff, and meringue.

Where: 5553 N. Clark St. Chicago, IL
For more information on Uvae.


Get Creative at a Couples Spray Paint Workshop

Unleash your inner street artist! This interactive workshop designed for couples will allow you and your SO the opportunity to create your very own original piece. Plus, you'll get aquatinted with the ins and outs of working with spray paint and stencil application. Not the most creatively inclined person? Have no fear—this workshop will be curated by Studio W.I.P. artists and staff, that are happy to help along the way. Remember, couples who paint together stay together!

Where: The Graff: 3527 W. Grand Ave, Chicago, IL
More information on Couples Spray Paint Workshop + Open Bar.


3527 West Grand Avenue, Chicago, IL, USA
Couples Spray Paint Workshop + Open Bar
Starting at $125

Book now



Experience a Fancy Tasting Menu

Esmé is a fine dining restaurant founded by a husband and wife pair of culinary experts and located in Lincoln Park. Featuring artfully crafted dishes, this special spot will offer a Valentine's Day tasting menu that showcases luxurious dishes and ingredients like white truffles, burnt onion consommé, white sweet potato ice cream, osetra caviar return, and more. At Bar Esmé (located within the same space), diners can select a four-course menu for $150.00 per person. Menu items include Duck Ravioli, Monk Fish a la Normandie, Wagyu Au Poivre, and more.

P.S. As if the indulgent menu and husband and wife duo aspect weren't enough, Esmé translates to "beloved" in French, putting this date night spot off the charts in the romance category.

Where: 2200 N. Clark St, Chicago, IL
For more information on Esmé and bar Esmé.


Make and Sip Valentines Cocktails

Check out a special Valentine's Day-themed cocktail experience. Gold Coast Social will be decorated for Valentine's Day, and you and your date will get to create two different festive cocktails. When you're done mixing, enjoy your drinks alongside a Valentine's Day-themed flatbread.

Where: Gold Coast Social: 7 W Division St, Chicago, IL
More information on Love at First Sip Cocktail Class.

7 W Division St, Chicago, IL 60610, USA
Love At First Sip Cocktail Class
Starting at $55

Book now


Share a Heart Shaped Pizza

If you want to avoid the dinner crowds, but still want to share a romantic evening together, there's always the forever favorite heart-shaped pizza. Plan a night in and queue up a classic rom-com or your favorite romantic film, light some candles, and bust out some wine or bubbly to enjoy with your festive pizza. Order Valentine's Dinner for Two from Sfera, offering appetizers, salads, a heart-shaped Sfincione, two cannoli, and cocktail bases to mix up your own drinks at home. Or, surprise your partner with their favorite pizza in the shape of a heart from Robert's (you can even get an ice cream heart pizza!).

Other restaurants offering a heart-shaped pizza (both in-person and for delivery) include Bartoli's, Lou Malnati's, Giordano's, Eataly, Homeslice, and Dimo's.

Where: Various locations.


Make Your Own Candles

Set the mood with a DIY candlemaking experience. Choose from a wide selection of vessels, scents, and add-ins, then measure, mix, and pour your very own candle in an instructor-led class. This experience is also BYOB, so feel free to sip a glass of wine while you wait for your candle to set, and then take it home and get cozy. Bonus: you'll be reminded of your date every time you light it up.

Where: 4999 Old Orchard Center, Unit K11, Skokie, IL 60077
More information on Blank Mason Candle Bar.

Multiple locations
Blank Mason Candle Bar
Starting at $45

Book now


Take a Cooking & Cocktails Class Together

If you want something a little more interactive than just dinner, try taking a cooking class together, where you can learn a new skill and enjoy delicious food. Cozy up with your date at the Fairmont Lodge’s Cooking & Cocktail Classes. From 6:00 pm to 8:00 pm, learn how to make popular dishes and cocktails from Fairmont Chicago’s team of talented chefs and local mixologists. Each class will center around how to make favorites, including an inspired cocktail (with a recipe included so you can make it at home), fresh pappardelle pasta, and a celebratory cheese and charcuterie board.

Where: 200 N Columbus Dr, Chicago, IL
For more information on Cooking & Cocktails Classes.

Multiple locations
Cooking & Cocktail Class
Starting at $55

Book now


Explore a Museum or Gallery Together

There's something so charming about wandering through a museum, exploring art, and learning something new together. The Art Institute is a classic and offers world-class art, plus some dreamy spots like the Tiffany window. Head to Adler Planetarium and look to the stars to see if you and your date are meant to be, or explore the various art galleries of River North.

P.S. See our list of free and discounted museum days here.

Where: Various locations.


Sip Champagne at 3 Arts Club Cafe

This posh restaurant is inside the Restoration Hardware store, but don’t let that fool you into thinking this place doesn’t ooze romance. The stunning interior is located in the atrium and is surrounded by glowy lights and glass, creating the perfect moody ambiance for a romantic date night. Choose a bottle from their lengthy wine list, and you’re on your way to having an unforgettable evening. 

Where: 1300 N Dearborn St., Chicago, IL
For more information on 3 Arts Club Cafe.


Laugh the Night Away at a Stand-Up Comedy Show

Who said romance has to be boring? Laugh off any date night jitters at a fun comedy show featuring today's biggest names. On February 14, Laugh Factory will host a Valentine's special, and the world-famous stage will be transformed to reflect the holiday of love. These local comedians will deliver something for every taste and style of comedy, and many of the greats have come through the city!

Where: Laugh Factory: 3175 N Broadway, Chicago, IL 60657
For more information on Stand Up Comedy Tickets.


Share Fondue by the Fire at Geja’s Cafe

There are romantic dinners, and then there’s dining at Geja's. One of Chicago's most romantic restaurants is serving up a Valentine's Day Special that includes an appetizer of Swiss Gruyere cheese fondue with assorted breads, vegetables, and fruits for dipping, and an entree of Beef Tenderloin, Australian Lobster Tail, and Gulf Shrimp. Top it all off with Geja’s Belgian Chocolate fondue flamed tableside and served with marshmallows for roasting.

Where: 340 W Armitage Ave., Chicago IL 60614
For more information on Geja's Cafe.


See a Live Show at a Hidden Speakeasy

Few things feel sexier than slipping into a hidden speakeasy. Bordel is a cocktail bar and cabaret inspired by the sultry energy of Paris’ Pigalle and Montmartre. You and your date will make your way through the hidden door and up the leopard print stairs and find yourselves inside a plush candlelit lounge complete with pink velvet sofas and curtains, tasseled chandeliers, and ornate bronze sconces.

Enjoy surprising cocktails along with nightly entertainment that includes a premier cast of jazz musicians, burlesque performers, flamenco artists, magicians, cabaret dancers, and DJ performances.

Where: 1721 W Division St., Chicago, IL
For more information on Bordel and Chicago Speakeasies.


Attend a Beauty and the Beast Cocktail Experience

Is anything more romantic than a literal fairytale love story? Gift your Valentine tickets to this immersive cocktail experience that's an escape room, a theater show, and an adventure all blended into one. Based on the Jeanne-Marie Leprince de Beaumont fairytale, guests are invited to come along on a 90-minute journey and step into the enchanted and cursed world of Beauty & The Beast. Dress up in your most elegant Victorian-inspired costumes and enjoy crafting two bespoke-themed cocktails, solving riddles and challenges, and more!

Where: Esmerelda's Lounge: 2539 W Division St., Chicago, Illinois 60622
For more information on Beauty and the Beast Cocktail Experience.


Esmeralda's Lounge, 2539 W Division St, Chicago, Illinois 60622, United States
Beauty And The Beast Cocktail Experience: Chicago
Starting at $45

Book now



Take a Pizza Making Class and Sip Wine

Spend a romantic evening making handmade Neopolitan pizzas and sipping on your choice of beer and wine at this DIY Pizza and sip class at Millennium Hall. Choose from a number of toppings, sauces, meats, and cheeses, and then make a selection from the open bar while you enjoy some quality conversation and one-on-one time. When the pizza is ready, you can choose to take it home or indulge together at the restaurant.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602
For more information on DIY Pizza and Sip.


11 N Michigan Ave, Chicago, IL 60602, USA
DIY Pizza & SIP
Starting at $29

Book now


Never miss out on a new experience!

Create a Bucket Listers account to access exclusive offers and the latest news in your city


Make Every Day An Adventure with Bucket Listers! We make it easy to find & book the best things do in your city, all in one place.

All cities

Support Center

Privacy policy

Terms of use

Contact us

Frequently asked questions

About Bucket Listers

About us


Partner with us

Find experiences on our new app!

apple app store