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8 Perfect Chicago Date Night Ideas

Updated: Jun 17, 2023

Whether you’re on a baecation, staycation or just planning a weekend out, the city of Chicago has some pretty unique activities and restaurants to explore. Since February is often known as the month of love, many use it as the perfect time to celebrate and cultivate their most treasured relationships or woo that special someone. And you know me - I’m here to help! From the bougie foodies to the plain and simple, below are 8 perfect Chicago date night ideas.

Experience an immersive show at the Chicago Magic Lounge

Be amazed and awed at this tucked-away, magical speakeasy lounge where the art of illusion comes to life. Chicago may be known for its deep-dish pizza and incredible skyline, but did you know that in the 1900s, Chicago had a booming magic scene? The Chicago Magic Lounge brings the magic back to life at its art-deco and cabaret-style theater, where magicians dazzle the crowd with intimate tableside sleight-of-hand tricks and other illusions before the main show. They have small bites and signature cocktails with fun names like “How Houdini Died” and “Abracadabra.” We absolutely LOVED our evening spent here and would definitely return. I don’t want to give away too much, so see for yourself!

Chicago Magic Lounge

Cook up some romance at a Sur La Table class

Cooking up a little romance should always be on the menu. What better way to heat things up a little than taking an interactive date night cooking class. Sur La Table offers hands-on cooking classes conducted by personal chef instructors that can help you and your boo learn a few new skills to apply in the kitchen. Whether you’re in the mood for Italian cuisine or prefer to be swept up in the flavors of France, they have several different dates and menu options to choose from. They also have online cooking classes available if that tickles your fancy a bit more.

Indulge in a luxe lunch at 3 Arts Club

The 3 Arts Club cafe is a beautiful, posh restaurant inside the atrium of Restoration Hardware - an upscale home goods showroom featuring chic furniture, textiles, lighting & more. Simply put, this place oozes romance and is located in the heart of Chicago’s Gold Coast neighborhood. The cafe is adorned with chandeliers, plush couches, exposed brick, and an intricate flowing water fountain in the center giving it major chic appeal. The service is excellent, and the food is great! Whether you or your sweetie are architecture and design enthusiasts or self-proclaimed foodies who like a little swank, you will surely enjoy your time here.

Get whiskey at Untitled Supper Club

Time travel for the night back to the roaring 20s at the Prohibition Era-inspired Untitled Supper Club Chicago. This super-spacious spot is a triple threat - operating as a restaurant, bar, and live entertainment venue. If you or your lover is a whiskey drinker, Untitled also boasts having the largest selection of American whisky in the world in their Whiskey Library. This place is one to explore, where each room offers a different vibe, all tying back to the theme. Enjoy great cocktails and live entertainment like jazz bands, burlesque dancers, vocalists, or DJs spinning on the 1s and 2s. Whether you want to sit and chill or cut a rug, Untitled is a city hot spot.

Relax & relate at AIRE Ancient Baths

AIRE Ancient Baths quickly became one of my favorite experiences last year when I went on a solo date there in the name of luxe self-care. At AIRE Ancient Baths, you and your sweetie can immerse yourselves in their signature ancient thermal baths and indulge in spa add-ons like massages, fresh fruit juice, showers, and other amenities. Life is stressful enough, so why not take a break and snuggle up for some serenity and peace together. The ambiance here is worth every penny, and you’ll leave feeling refreshed and renewed.

AIRE Chicago

Take in the sights along the Chicago River Walk

A more cost-effective option is to take a scenic walk down the Chicago River Walk. You’ll have 1.25 miles to hold hands, stimulate conversation and soak in some world-famous Chicago architecture. There are also a few outdoor bars and restaurants you can stop at along the way to rest or grab a bite or sip wine on one of the patios. If you don’t want to walk, you can cruise down the river via an architectural boat tour. You can book water sports options like kayaks if you prefer a little adrenaline. When the sun goes down, the city lights begin to shine, & illuminate the water, ooooo weeee it’s beautiful!

Architectural boat tour. Alexa play “A Long Walk” by Jill Scott ;)

Show some amoré at Adalina

Don’t want to cook? Let your taste buds take you on a little journey to Italia. Located in the heart of the Gold Coast, Adalina Chicago is sure to offer a romantic evening with their upscale Italian cuisine, ambiance, and lavish decor. As soon you enter the place, you feel the vibes! They have excellent starters like gnocco fritto with prosciutto, whipped ricotta with honey drizzle, and delicious homemade pasta *chef’s kiss*. Oh, and if you know me, I’m a sucker for great service, and Adalina didn’t shy away. Come hungry and leave happy. Reservations are highly recommended.

Adalina Chicago

Put love to the test at an Escape Room.

If you and your sweetie like a little adrenaline rush, trying an escape room might be the move. Several places have been popping up over the city in the past few years, so you can pick your theme between breaking free from jail after being wrongly accused of espionage or trying to survive a zombie apocalypse. There are options suitable for both rookies and experts. Immerse yourselves in thrilling storylines that are sure to put your love to the test. But remember at the end of the day, love wins.

What are some of your favorite date night spots in Chicago? Let me know in the comments below or on IG @andthatsjustashley.


And That's Just Ashley

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