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7 Actually Great Date Spots in Chicago

“Believe it, Chicago is a city of romance. And possibly even more so for all”
By Alex Glover May 27, 2021

7 Actually Great Date Spots in Chicago

“Believe it, Chicago is a city of romance. And possibly even more so for all”
By Alex Glover May 27, 2021

Believe it, Chicago is a city of romance. And possibly even more so for all the amorous pleasantries that go unseen during Chicago's brutal winters, in sweatpants, under blankets in heated living rooms with a movie on TV. You know, the unsexy kind of stuff so often portrayed on Midwestern sitcoms.

When the weather permits though, Chicago is one of the best cities for dating. If you're looking for venues with the best opportunities to make sparks fly or rekindle an old flame, search no further. These are the most romantic spots in Chicago!

1. Have an amazing date and see Buckingham Fountain


It doesn’t spew water in winter, but with its four Art Deco–style seahorses, Georgia pink marble and holiday light and music show, this fountain built in 1927 is still a sight to behold. From May through Labor Day, 20-minute shows every hour on the hour feature 14,000 gallons of water spouting from 133 jets. In summer, see the nighttime colored light shows, capped off with a center jet shooting 150 feet of water in the air. That's a magnificent show which will surely make you wanna kiss your date immediately in front of that incredible fountain!

2. Watch the latest art-house in Music Box Theatre


Who doesn't love movies? It's definitely a no-fail idea for a perfect date! For movie lovers who don't care for traditional Hollywood blockbusters, there's no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. It's gorgeous, and the main theater regularly hosts director Q&A's as well as weekly midnight screenings of cult classics. Also, the concession stand here tops its popcorn with real butter. you should totally try it!

3. Cosy up at a fireplace bar 

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Okay, so this one is technically just going to a bar and drinking, but there's definitely a romantic appeal to bars with fireplaces. And thanks to Chicago's 11-month long winters, this city has enough bars with fireplaces to go around. Nestle in with your date, a cocktail and a blazing fire, and we guarantee you won't want to leave anytime soon. Our choise is Chief O'Neill's pub, this cozy Avondale pub not only boasts a roomy patio that's perfect for summer lounging, it's also a great wintertime hang that will warm you up. Order up some rib-sticking pub eats with a Guinness, and kick back while the calories form a protective layer around your winter-worn body.

4. Feel the nature at Alfred Caldwell Lily Pool


Step through the Prairie-style Fullerton gate and enter a hidden garden of unmatched beauty. Only bird songs and the sound of a gentle waterfall break the restful silence. Follow the stone walk encircling the lily pool and discover a pavilion, council ring, and diverse native plantings. This is the vision of landscape architect Alfred Caldwell: a hidden garden for the people of Chicago designed to resemble a river meandering through a great Midwestern prairie. What can be more romantic? Take your significant other to such place and this date will totally be a date to remember!

5. Enjoy the unique view at Signature Room Restaurant


The Signature Room on the 95th floor of the John Hancock Center offers unparalleled panoramic views of Chicago for a dining experience with your date wholly unlike any other. The view at night is beyond gorgeous, it's absolutely stunning. An enviable location, exceptional service, impeccable menus and, of course, those unbelievable views will totally impress your date. Enjoy the magnificent panoramic views through floor-to-ceiling windows and make your special evening unforget.

6. Stroll down the Riverwalk together


The Riverwalk is still a pretty new commodity, so there's a good chance your date hasn't spent time down there yet. The huge strides Chicago has made along its backwards flowing river have created a date spot that doesn't fail to disappoint, with more and more great spots to stop for a glass of wine or bite to eat along the way. Venture down there on a Saturday or Sunday afternoon and you'll remember that the Loop is actually pretty gorgeous.

7. Try delicious seafood at GT Fish & Oyster


Ask to be seated in the back dining room, as the lighting and overall mood is a little sexier and more romantic, if you catch our drift (ha!), or go the casual date route by snagging a spot at the oyster bar - East Coast oysters are the winners here. Order at least four oyster po'boys (because you’ll regret it if you don’t), shrimp bruschetta, and the Maine lobster roll, but only if you don’t mind being really spendy. But who cares about money when we're talking about a foodgasm for you and your date?

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