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Published January 23, 2024

How to Celebrate Valentine's Day in Chicago

Your guide to the best Valentine's Day restaurants, date ideas, and activities in Chicago. 💘

by Chicago Bucket List


Valentine's Day is around the corner, and whether you're looking for the perfect romantic restaurant, want to shake things up with a show, or just want a low-key night in with heart-shaped pizza and wine, Chicago has options.

Valentine's Day is also a good excuse to gather the crew and treat yourselves to an epic group dinner, or you can throw a Galentine's Day celebration with besties and enjoy mimosas and bloody marys at one of Chicago's best brunch spots. We rounded up some ideas to make sure you have a fun Valentine's Day no matter how you choose to celebrate.

12 Valentine's Day Ideas in Chicago

Visit The Crushed Heartbreak Bar

For a non-traditional Valentine's Day celebration, check out Crushed, a limited-time pop-up with themed cocktails/mocktails, photo ops, and activities like adding to the Crush List, taking photos on Cloud 9, and shredding love letters, photos, and mementos. A welcome shot is included with your ticket!

Where: Commons Club: 203 N. Wabash Ave 2nd Floor, Chicago, IL
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203 N Wabash Ave 2nd floor, Chicago, IL 60601, USA
Crushed Heartbreak Bar at Virgin Hotels Chicago
Starting at $19

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Get Creative at a Couples Spray Paint Workshop

Unleash your inner street artist! This interactive workshop designed for couples will allow you and your date the opportunity to create your very own original piece. Plus, you'll get acquainted 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 artists and staff who are happy to help along the way. Remember, couples who paint together stay together!

Where: The Graff: 3527 W. Grand Ave, Chicago, IL
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3527 West Grand Avenue, Chicago, IL, USA
Couples Spray Paint Workshop + Open Bar
Starting at $125

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Check Out Love Whims or Black Hearts

This immersive art exhibit at Whim showcases various art forms, including paintings, music, sculpture, and street art for a seasonal installation just in time for Valentine's Day. Explore art inspired by being in love (or out of love) alongside a seasonal menu, live performances, and a complimentary cocktail ot mocktail.

Where: 1225 W. Belmont, Chicago IL
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1225 W Belmont Ave, Chicago, IL 60657, USA
Love Whims or Black Hearts at Whim Chicago
Starting at $31

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Try a Fancy Tasting Menu

Esmé is a fine dining restaurant located in Lincoln Park and founded by a husband and wife pair of culinary experts. This special spot will offer a Valentine's Day tasting menu that showcases luxurious dishes and ingredients like white truffles, osetra caviar, 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
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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. You can order a Valentine's Dinner for Two from Sfera 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 heart-shaped pizzas (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 an upcycled vessel (or bring your own), and pour your very own candle in an instructor-led class with cocktail scents such as Barrel-Aged Bourbon, Old Fashioned Cocktail, or Whiskey & Sweet Tobacco. 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: Chicago Candle Co.: 1100 W Cermak Rd #419, Chicago, IL
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Whip Up Some Cocktails

If you want something a little more interactive than just dinner, try taking a mixology class together. Longman & Eagle is hosting whiskey classes where you'll learn how to make classic whiskey cocktails like Manhattans, Old Fashioneds, and more. Led by the whiskey experts at Longman, this hour-long course will provide you with everything you need to know to mix up your own cocktails like the pros, and Woodford Reserve will send you home with your very own cocktail kit.

Where: 200 N Columbus Dr, Chicago, IL
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2657 N Kedzie Ave, Chicago, IL 60647, USA
Longman & Eagle Whiskey Mixology Class
Starting at $55

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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
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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
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Share Fondue by the Fire at Geja’s Cafe

There are romantic dinners, and then there’s 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
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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
More information on Bordel and Chicago Speakeasies.


Take a Pizza Making Class with 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
More information

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

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