Tune2Love Blog

Online Dating and Relationship Advices

Your dates turned into a routine or even a duty? While planning your date night, you choose between watching movies or watching sports? Your sweetheart forgot how you look in festive attire or when the last time you had fun was?

All we need sometimes is a little inspiration. If you were looking for some tips, here we are!

We, the Tune2Love team, prepared several fresh date night ideas in Chicago that help you to spice up your relationships. There are no usual cafes or noisy bars, just the best and the most interesting venues. So, get ready to change your romantic time spending – you two won’t be bored with us!

1. Chicago Magic Lounge

The show at the Chicago Magic Lounge
Image source: https://www.instagram.com/chicagomagiclounge/

If you are looking for good food, a wide range of drinks, and entertainment for your date night in Chicago, spend your evening at the Chicago Magic Lounge.

Here you can see a true Chicago style of magic: the bar and table-side magicians with card tricks and performance on the stage. Art-deco interior and secret doors give this place a charming vibe.

Check their event calendar to learn what performance to expect on your special evening: it can be a Family show, a Signature show, a close-up performance with live music, experimental works, bar magic, etc.

Good for: Couples, Entertainment

Address: 5050 N Clark St., Chicago, IL 60640-4999

Working hours: Sun 11:30 AM – 1:00 PM, Sun – Wed 5:30 PM – 11:00 PM, Thu – Sat

5:30 PM – 12:00 AM

Phone: +1 312-366-4500

Website: https://www.chicagomagiclounge.com/ 

2. Drunk Shakespeare

Performance at Drunk Shakespeare, Chicago
Image source: https://www.instagram.com/drunkshakespeare/

At Drunk Shakespeare, you will find out that books can take a high place among Chicago date night ideas. 

This extraordinary place is a blend of a hidden library with more than 10 thousand books, a bar, and an improv show. This venue has an interesting idea: the actor drinks 5 shots of alcohol and then tries to perform one of Shakespeare’s plays. The audience also takes drinks and sits along the bookshelves, leaving a narrow passage-stage for the actor.

Good for: Couples, Entertainment, 21+ only

Address: 182 N Wabash Ave, Chicago, IL 60601-3624

Working hours: Wed 7:30 PM – 10:00 PM, Thu 7:00 PM – 10:00 PM, Fri 7:30 PM – 10:00 PM, Sat 5:30 PM – 10:00 PM, Sun 1:30 PM – 5:00 PM

Phone: +1 914-713-7865

Website: http://www.drunkshakespeare.com/ 

3. Blue Chicago

The performance at the Blue Chicago
Image source: https://www.bluechicago.com/

If you are looking for a great place with live music to add to your romantic date night ideas in Chicago, turn your attention to the Blue Chicago old blues bar. 

Here you can reserve a table for dinner or just take a drink and dance all night long close to artists. Great vibe, friendly staff, crafted cocktails and excellent music help you forget about all your daily troubles and enjoy pleasant company.  

Good for: Couples, Live music, Night drink

Address: 536 N Clark St, Chicago, IL 60654-7136

Working hours: Sun-Fri: 8:00 PM – 1:30 AM Sat: 8:00 PM – 2:30 AM

Phone: +1 312-661-0100

Website: https://www.bluechicago.com/ 

4. Maude’s Liquor Bar

The plate of seafood at the Maude's Liquor Bar, Chicago
Image source: https://www.instagram.com/maudesliquorbar/

Organize classic romantic date night in Chicago at the Maude’s Liquor Bar. Blue metal chairs and furniture in French vintage style, an endless number of vines and liquors, delicious French cuisine, fresh oysters, escargot, fondue, foie gras pate, and other gorgeous treatments help you feel like on France vacation. You can choose where to sit: indoors enjoying dim lighting or outdoors admiring a sunset.

Good for: Couples, Dining

Address: 840 W Randolph St, Chicago, IL 60607-2309

Working hours: Wed 5:00 PM – 9:30 PM, Thu 5:00 PM – 9:30 PM, Fri 5:00 PM – 9:30 PM,

Sat 12:00 PM – 9:30 PM

Phone: +1 312-243-9712

Website: http://www.maudesliquorbar.com/ 

5. The Escape Game Chicago

People on the Escape Game Chicago
Image source: https://www.instagram.com/theescapegamechicago/

Turn your exciting date night in Chicago into a breathtaking adventure: plan a prison break, the art heist, launch a spaceship, find the gold or try something else at the Escape Game Chicago. 

Their well-decorated rooms, a lot of details, fun puzzles create a uniquely immersive experience. The friendly staff will help you to dive into the scenario and get pleasure from the game.

Notice that you have 60 minutes to finish your mission.

Good for: Couples, Entertainment

Address: 42 E Ontario St, Chicago, IL 60611-2710

Working hours: Sun – Sat 8:00 AM – 12:00 AM

Phone: +1 312-453-7753

Website: https://theescapegame.com/chicago/ 


If you are single in Windy City, don’t be afraid, Tune2Love can help you find a matching person and build a strong romantic relationship. Don’t waste your time, your true love in Chicago is waiting for you. 

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