The Most Romantic Date Spots In Chicago
The Most Romantic Date Spots In Chicago

The Most Romantic Date Spots In Chicago

Author Pic By Chicago Bucket List

Come in from the cold with your special someone. πŸ₯‚πŸ₯°

Published April 20, 2021

We get it: romance has required way too much creativity during lockdown. But the light is in sight – private indoor dining is easing back in, businesses have evolved with healthful procedures, and a new world of ingenious date options for Chicagonians to enjoy have begun! 

The Windy City has all the ingredients you could need to get sparks flying, with sultry speakeasies, skyline views, and twinkling igloos galore. Below is our list of worry-free, spicy date spots to take your SO, be it a first date, anniversary, or an entire magical weekend getaway.

Aire Ancient Baths

Photo credit: Aire Ancient Bath 

Thermal baths, candlelight and a temple world where time doesn’t exist—is there a more romantic environment out there? Aire Ancient Baths is a newly formed spa experience inspired by ancient civilizations. We recommend enjoying their Wine Bath because well, wine obviously. 🍷


Where: 800 West Superior St.

For more information.


Three Dots and a Dash 

Photo credit: Three Dots and Dash

There’s something sexy about a speakeasy. Let your date in on the secret of Three Dots and a Dash, Chicago’s premier tiki bar hidden below the streets of River North. The hidden gem – named one of The World’s 50 Best Bars by Drinks International – creates jaw-dropping tropical cocktails using the freshest exotic fruits and spices, the finest rums and distilled spirits, and juices and elixirs that are cold-pressed and concocted in house every day. It’ll transport you both on to an island-getaway state of mind, guaranteed. 

Where: 435 N Clark (Entrance is in the alley east of Clark St, between Hubbard and Illinois. )

For more information.


Catch a Drive-In Movie 

The nostalgic date-fave is a sweet choice to  make, especially with ChiTown Movies playing the perfect romantic comedies and dramas week after week – The Notebook, and La La Land of course. Best of all, moviegoers will have the option to have popcorn, tacos, frozen mangos and more delivered right to your car. 

Where: 2343 S. Throop Street, Chicago, IL 60608

For more information. 


Road Trip to the Ice Castles

Photo credit: Ice Castles

Built in four cities across North America, Ice Castles is a once in a lifetime, interactive frozen, extravagant attraction to see. The experience is built entirely by hand using hundreds of thousands of icicles hand-placed by professional ice artists. The castles include breathtaking LED-lit sculptures, frozen thrones, ice-carved tunnels, slides, and fountains. Well worth the ~2 hour drive from Chicago, if we do say so ourselves. Tickets are currently sold out, but there's always a chance they release later dates depending on weather. If not, be sure to add it to your 2022 winter plans. 

Where: Geneva National Resort & Club, 1091 Hidden Cottage Cir, Lake Geneva, WI 53147

For more information.


Geja’s Cafe

Photo credit: Geja Cafe

This warmly lit fondue spot’s tagline is “Chicago’s Most Romantic Restaurant” for a reason. While sitting in their candlelit rooms, being serenaded by the music of Flamenco and classical guitar, we recommend ordering one of Geja’s three-course premier dinners

The dinner includes a starter cheese fondue with assorted breads, veggies and fruits, an array of meat entrees (from beef to australian lobster tail) served with eight gourmet dipping sauces, and their signature Geja’s Belgian chocolate fondue for you and your booo to enter food coma bliss together. 

Where: 340 W Armitage Ave

For more information.


Immersive Van Gogh 

Photo Credit: Immersive Van Gough 

Van Gogh’s signature masterpieces displayed over 300,000 cubic feet and 90 million pixels of flawless (and moving!) projections may be the most technically beautiful date spot of all.

Where: 108 W Germania Chicago, IL 60610

For more information.


Big Mini Putt Club

A little friendly romantic competition is healthy, right? Searching for a date idea that'll let you challenege each other? Look no further than the city's newest pop up, Big Mini Putt Club. Featuring a 9 hole course + bar with golf themed drinks, and more. Just don't let the competition get in the way of your connection too much!

Where: 1302 N Milwaukee Ave

For more information.


JoJo’s Shake Bar

Photo credit: JoJo’s Shake Bar

All things sweet are celebrated next with JoJo’s Shake Bar. The pop-up will showcase six different themes through the tent mimicking the CandyLand game board. Specifically for date night, we’re eyeing the Love Shack room, where they’ll serve their signature Love Shake (a raspberry and red velvet concoction, a giant heart sugar cookie, oversized cheesecake slice with raspberry drizzle, topped off with a chocolate covered strawberry and sprinkle pretzel). There’s also plenty of hearty diner food and cocktails if you don’t want to go purely desert. 

Where: 23 West Hubbard Street 

For more information.


Rooftop Igloo at I|O Godfrey

Photo credit: I|O Godfrey

I|O is a sensuous, swanky escape with unparalleled views of the southern Chicago skyline. Enjoy a date-night out there, or a date-night in with their take-home espresso martini kit.

Check here for an extensive list of COVID-safe outdoor dining options.

Where: 1800 N. Halsted 

For more information.


Hornblower Cruise

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Come aboard for a few hours of unbeatable views (especially from the Odyssey glass ceilings) and culinary excellence. Whether you’re looking for a dinner, brunch, or cocktail hour date, you and your partner can enjoy in style on the Spirit and Odyssey by Hornblower.

Where: 455 N. Cityfront Plaza Drive

For more information.


Sushi Making Classes

Keep things spicy with a hands-on socially distant cooking class together! You’ll learn to make a traditional cucumber roll, salmon avocado roll, and a Japanese veggie hand roll. Plus, guests are welcome to BYOB (wine, beer, and champagne only)

Where: 2620 W North Ave

For more information. 


Museum of Illusions

Photo credit: Museum of Illusions

For an extra playful date night, check out the Museum of Illusions! Designed to amuse, amaze, and stimulate the senses, the MOI features over 80 unique installations. Whether it's the spinning sensation through our Vortex tunnel, sizing up your partner in our Ames room, or defying gravity in our Reverse room, your mind will get a workout and your body will get a laugh. And they’ve extended their hours for Valentine’s weekend! 

Where: 25 E Washington St.
Use discount code BUCKETLIST421 for 20% OFF Mondays - Thursdays

For more information.

360 CHICAGO + TILT + Cocktails

Did you know that increased adrenaline creates increased attraction between individuals? We recommend testing that theory out at 360 CHICAGO—now open to the public with advanced safety measures. The spot offers breathtaking panoramic views of Chicago from 1,000 feet above the famed Magnificent Mile, and the observation deck is the home of Chicago’s highest thrill ride, TILT. After you’ve got your hearts racing, you can each calm your nerves at their bar and café, BAR 94, where you can relax, sip on a locally crafted beer or cocktails.

Where: 875 N Michigan Avenue, 94th Floor

Bucket Listers' Exclusive Package and Pricing. 

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