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Spark Romance with Chicago’s Most Unique Date Spots

If you find yourself in Chicago, you may be wondering about unique date ideas. We all know you can take a summer Saturday and walk around the bean (ok, Cloud Gate) or Buckingham Fountain and have a fabulous date!

Cloud Gate

But what if it’s horrible weather out or you want to try something new that's not your usual stay-at-home-date? That's where this post comes in handy.

There are some affiliate links below, but they are all products I highly recommend. For more info, view my disclosure.

Casual (Also Affordable) Unique Date Ideas Chicago

If it’s a Wednesday and you don’t want to spend a lot of time and money on a date, you can try some of these ideas. Let’s face it, sometimes we don’t know how much we really like a person, and if we want to take the time and money on an elaborate date.

Photo Of Buildings


There are two great conservatories in Chicago. The Garfield Park Conservatory ( 300 N Central Park Ave, Chicago, IL 60624) And Lincoln Park Conservatory (2391 N Stockton Dr, Chicago, IL 60614). Both are free and open Wednesday through Sunday.

These are wonderful for the dead of winter when you want to feel like you’re on a tropical island. It's hot and steamy plus beautiful; perfect for your date.

Ice Cream

If you have a little money to spare, try Margie’s Candies. There are two locations, 1960 N Western Ave, Chicago, IL 60647 or 1813 W Montrose Ave, Chicago, IL 60613. This is a candy shop but also has ice cream.

I recommend getting any flavor ice cream made into a hot fudge sundae. It's a candy shop so hint, hint, they make their own hot fudge and it's scrumdiddlyumptious!

Chicago River Between Trees and City Skyscrapers

For A New Twist on a Classic Museum

Yes, you can go to any of our world-class Chicago museums and have a wonderful time with your date, especially if you are a sapiosexual.

But, for a truly unique date idea, you can go to a special event at one of Chicago's many museums. Most museums in Chicago have late night adults-only events where you can see new exhibits or listen to music while seeing classic exhibits.

Blue Universe

Adler Planetarium

My top pick for most romantic date is Adler Planetarium (1300 S Dusable Lk Shr Dr, Chicago, IL 60605). They have late nights every Wednesday, from 4:00 pm to 10:00 pm.

You can gaze at the stars with your significant other. Wednesdays are typically free days for Illinois residents, so this makes it super affordable too.

These nights are not necessarily adults-only but check back for future dates for adults. They may have them in the summer.

Shedd Aquarium

Shedd Aquarium (1200 S Dusable Lk Shr Dr, Chicago, IL 60605) also has nights for grownups only. Jazzin’ at the Shedd is available in the summer. In the fall, they have Shedd After Hours.

Museum of Science and Industry

The Museum of Science and Industry (MSI) Chicago (5700 S Dusable Lk Shr Dr, Chicago, IL 60637) used to do adults nights, but may have suspended them the past few years so check their website for updates.

Fun and Wild Date Ideas in Chicago

Sometimes you want to let loose, laugh, and just have fun with your date, not have serious conversations. That’s where these places come in.

Buddy Guys Legends

Buddy Guys Legends (700 S Wabash Ave, Chicago, IL 60605). Not only is this one of the best places to see up-and-coming blues artists but the legend himself (Buddy Guy) often sits in. It’s true! I met him several years ago; he was just chilling at the bar.

Also, little know fact, many famous musicians come here after their main concert is done for the night. People have spotted Mick Jagger, John Mayer, Eric Clapton, and other greats at this local club. So you will for sure get great blues music for your date but might even have the best night of your life where you meet a legend. Plus, it’s super sexy to dance to music and lean in close to your date.

Music Box Theatre

If you want truly hilarious and unique date ideas Chicago, head to Music Box Theatre (3733 N Southport Ave, Chicago, IL 60613) once a month at midnight for their showing of Rocky Horror Picture Show!

There are people up on stage acting out the show as it occurs, and it's a raucous good time. This theater also shows indie films, foreign films, and old movies that haven't been in a theater for a decade or two. Or four.

For a Private Night

The wild and fun nights are great but sometimes you want to have deep conversations. Then, you will need a quiet and private place to stare into each other’s eyes. These are great for unique date ideas Chicago.

There's a few restaurants, even in a busy city like Chicago, that are quiet or have private booths.

Sayat Nova

My favorite is Sayat Nova (157 E Ohio St, Chicago, IL 60611). It's right off Michigan Avenue, but you wouldn't know it because it's tucked away and quiet. The booths aren't exactly private but have that vibe because of the structure of them, like you're in your own oasis. The food is legit Armenian and so tasty and affordable.


This one actually does have booths with curtains you can close. The food is out of this world and Latin-inspired. Penumbra is Spanish for a space of partial illumination by candles. And, you guessed it, they have dim lights with candles at this restaurant. It’s very romantic. You can find this restaurant at 3309 W Fullerton Ave, Chicago, IL 60647.

Geja’s Cafe

Not only does this restaurant have private booths with curtains but the food is fondue.  Nothing sexier than cooking for each other and feeding each other. It's been named Chicago’s most romantic restaurant. I believe it because it's gorgeous, intimate, sensuous, and delicious. You can find this at 340 W Armitage Ave, Chicago, IL 60614.

IO Godfrey Hotel Winter Wonderland

In the winter, this hotel transforms its rooftop deck into a winter wonderland, complete with private igloos. Don't worry, the igloos are plastic, not ice, and heated. For the cost of a bottle, you can sit in the igloo with your special someone.

Bottles are not cheap, but if you want to impress, take your date here. Bottles range from $325 to $2500. Also, this isn't just for the holidays but stays open through March. If your date is during the summer, you can enjoy their regular rooftop deck.

You can find this at 127 W Huron St, Chicago, IL 60654 and the info about the Winter Wonderland is here.

Man in Gray Suit Standing Beside Woman in Green Dress

The Ultimate Sexy and Intimate Date Ideas

The next two bridge the gap between private and watching a show/music. They are two great burlesque shows in Chicago.

Untitled Supper Club

Untitled Supper Club does have some private booths with curtains but also has music or burlesque shows later. So, it may be loud, depending on the day and time. It's meant to mimic the speakeasy and their shows of the 1920s. But it is a very sexy and unique date idea. You can find it at 111 W Kinzie St, Chicago, IL 60654.


Bordel doesn't have curtained booths but does have thick velvet couches that are somewhat separate from other guests, plus sensual entertainment. It was designed after Paris during the Belle Epoque. There are a lot of red dim lights. If that doesn't get you in the mood, I don't know what will. It can be found at 1721 W Division St, Chicago, IL 6062 .

Unique Date Ideas Chicago

Well, now you have a list of some of the most special and fun date ideas in the Windy City. Whether you take a walk in a conservatory, visit a museum at night, dance the night away to legendary blues, hang out in a private booth in a romantic restaurant, or get steamy watching a burlesque show in a speakeasy, you are sure to find one-of-a-kind dates for you and that special someone.

Faith Mickley

Faith Mickley is a Chicago-based blogger and creative product creator. A single mom of a beautiful daughter, she's an avid dater and lover of all things Chicago (food, architecture, culture, etc.).

As a special needs advocate, Faith is passionate about making the world a more inclusive place for everyone.

When she's not blogging or creating new products, you can find her spending time with her family or exploring all that the Windy City has to offer. Click here to read more of her articles.

Spark Romance with Chicago’s Most Unique Date Spots

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