Valentine’s Day in Chicago: Unique Date Ideas for Every Couple

The countdown to Valentine’s Day is on – and if you’re still searching for the perfect activity, reservation, or off-the-radar spot to bring your Valentine, we’ve got you covered. Whether you’re into cozy indoor activities, adventurous outings, or something totally out of the box, Chicago has plenty of romantic options. Read on for some of @properties Christie’s International Real Estate’s favorites. 

Image credit: Aire Ancient baths

1. Luxurious Relaxation at AIRE Ancient Baths

Set in a restored industrial building in River West, AIRE Ancient Baths is inspired by the traditional Roman, Greek and Ottoman experience of the bathhouse. Here, you and your Valentine can soak in thermal pools, unwind in steam rooms, and even indulge in a couple’s massage or wine bath.

Special for Valentine’s Day, AIRE is offering customizable experiences from February 14 to 19 Book now or surprise your Valentine with a digital gift card. 

Image credit: Avondale Bowl

2. Retro Bowling Fun at Avondale Bowl

If you and your plus-one are craving a little nostalgia, Avondale Bowl is your go-to. This vintage bowling alley is a serious throwback. For starters, there’s no digital scoring here and no bumpers – they weren’t invented until 1982. It’s all about enjoying the game (and getting a little competitive with your date, of course).

Post-game, grab a seat at the bar – theirs serves local brews and cocktails, making it a great spot to chill after a game or two.

Image credit: Block Club Chicago

3. Movie Night Under the Stars at Chi-Town Movies Drive-In

Speaking of retro, have a cozy date night from the comfort of your car at Pilsen’s Chi-Town Movies Drive-In. Park and watch a movie (or two) under the stars, with popcorn, tacos, wings, and pizza delivered right to your car.

Plan on heading to the drive-in on Valentine’s Day? Reserve your parking spot now to catch a screening of The Notebook or 10 Things I Hate About You. 

Image credit: Superdawg Drive in

4. Casual Cool at Superdawg

Rounding out the “retro” theme, consider heading to Superdawg – the original in Norwood Park or its north-suburban companion in Wheeling – for another classic drive-in experience, this time, with legendary Chicago-style hot dogs. It’s a fun, no-pressure spot and perfect for a low-key date night.

Image credit: Time Out Chicago

5. Jazz and Cocktails at Dorian’s Hidden Speakeasy

Hidden behind a record shop in Wicker Park, Dorian’s is a speakeasy that oozes cool and sophistication. With live jazz, creative cocktails, and an intimate setting, it’s the perfect spot for couples looking for good music, great drinks, and a relaxing vibe. This Valentine’s Day, Dorian’s is hosting singer Sophia Galaté. Rather get out on the weekend? Check out Proximity on Friday or Isaiah Collier & The Chosen Few on Saturday.

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6. Themed Fun at Crushed Heartbreak Bar

Whether you’re flying solo or coupled up this Valentine’s Day, consider stopping by the pop-up Crushed Heartbreak Bar at Virgin Hotels Chicago (203 N. Wabash). For $19 you can hang for 90 minutes and get a free Banish-Your-Ex welcome drink. Then, snap a photo on Cloud 9, get a tarot card reading, and enjoy light bites and Valentine’s-themed cocktails like the Stupid Cupid and Loves Me Not. Alternatively, book a table at Sunday brunch for an indulgent Valentine’s weekend.

Image credit: Emily’s Club

7. Curling at Stone’s Throw

If you don’t know the difference between a Free Guard Zone and Hog’s Line, check out Stone’s Throw at The Emily Hotel in Fulton Market to try your hand at curling. Take your turn at one of four onsite curling courts, then warm up with winter-themed drinks around the fire pits. It’s a fun, competitive way to spend the evening.  

Image credit: Moody Tongue

8. Decadent Desserts at Moody Tongue

If you’re dating a dessert lover, book a table at Moody Tongue, the world’s first Michelin two-star brewery. This Near South Side bar and dining room is renowned for its pairing menu, which includes items like a 12-layer German chocolate cake, which was constructed to complement characteristics of the beers it’s paired with. With seemingly endless brews, it’s the perfect spot to indulge your sweet tooth and explore new flavors.

Image credit: Trip advisor

9. Sky-High Thrills at IFLY Indoor Skydiving

Adventurous couples can get their adrenaline fix at IFLY Indoor Skydiving. At the three Chicagoland locations – Naperville, Lincoln Park, and Rosemont – you and your date can experience the thrill of skydiving, safely indoors. It’s perfect for chilly winter days – or times when jumping out of a plane just isn’t on the agenda.

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10. Gourmet Dining at Maple and Ash

If upscale dining is your taste, Maple and Ash in Chicago’s Gold Coast neighborhood offers a menu crafted by Michelin two-star Chef Danny Grant, and a wine list named “one of the most outstanding in the world” by Wine Spectator. Book a table in the dining room or patio, or order from the takeout menu – but either way, don’t wait. Space is limited and this is a very popular go-to for Valentine’s Day.

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11. Culinary Creations at Sur La Table
Rounding out the list is a year-round favorite: cooking classes at Sur La Table, which has locations in Chicago, Naperville and Skokie. For those who love to cook (or want to learn), Sur La Table offers a variety of cooking classes designed for couples. It’s a hands-on, fun way to bond over delicious food – and learn a new skill you can come back to even after Valentine’s Day.

Valentine’s Day classes include a Beautiful Bouquet of Cupcakes Rather wait for the weekend? There’s lotson the menu, including Classic French Croissants, Pasta Three Ways, Be Mine Macaron, and Perfecting French Pastries. 

Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.