6 Surprising (And Red-Hot Romantic!) Date Ideas in Chicago

Who's still searching for Valentine's Day plans?

With Valentine’s Day right around the corner, love is in the windy, chilly Chicago air. Although more than one Top Chef star has a restaurant here, eating is far from the only thing to do in town — whether we're talking hot-date ideas for February 14 or beyond.

The ideas on this list bring you out of your comfort zone a little bit — all in the name of impressing and surprising your date. Cozy up and put your (ear-insulating) thinking cap on because it’s time to brainstorm the itinerary for a red-hot date night in the Windy City.

1.  The Signature Lounge

Check out the expansive view as seen from the top of the Hancock from The Signature Lounge. Grab a cocktail and take a stroll around the area, replete with floor-to-ceiling windows. The view here will be great at any time — the clear skies of the daytime will be invigorating just as the twinkling lights seen at night will be dazzling — but if you can time it right on a sunny day, why not aim for sunset?

2.  The Playground Theater

Admittedly, a comedy show can be relatively risky business for a first date, but even the worst case scenario (the comedian bites) can make for a great story and provide the two of you with conversation fodder for wherever you head off to next. With that said, the improv shows at The Playground Theater are known for being solidly good. The shows’ fees are by donation on Sundays — if you’d like to save a little bit to throw toward one of those Top Chef meals before or after — and you can BYOB any night of the week. How great is that?

3.  Kingston Mines

Music is inherently sexy... and each genre of music brandishes its own definition of the word. With that said, you can’t go wrong with taking a date to a legendary blues venue. Kingston Mines has been in its current location since 1982. There are two bands every single night, no matter which day of the year it is. Whether you spend your time there dancing up a storm or throwing back a classic drink while admiring the history of the place, you’ll be glad you chose this famous music venue as a backdrop for romance.

4.  Photo Booth Tour

As recommended by Thrillist, a photo booth tour is an absolutely genius idea for a date. Make a plan to grab a well-crafted drink at several bars — all of which have a photo booth — and watch how your date progresses through the photos. Bars to consider penciling in: Empty Bottle, Beauty Bar, and Skylark. If you hit up Empty Bottle, be sure to check out the concert calendar in case something you’re interested in overlaps. At Beauty Bar, you can have a martini and a manicure, which is an experience for the books. And Skylark not only has a pretty decent menu, but a solid music thing happening Monday nights.

5.  Promontory Point

This not-exactly-obvious beach spot is more secluded than most other spots in Chicago. Bring your date to Promontory Point in the summer for traditional beach lounging, of course, but in the winter, a bundled-up, beautiful walk along the surreal icy coast is unforgettable.

6.  Alder Planetarium

Alder Planetarium is gorgeous, but it isn’t at all off-putting in a nerdy way. With plenty of events that take place outside of the realm of normal astronomy, you can not only check this spot out as a cosmic addition to any date night but you might find that you can also incorporate one of their great events — like the Stellar Speakeasy night — into your perfectly planned date.

Remember: You might not be able to control the chemistry between yourself and your date, but you can certainly influence it with a meticulously thought-through itinerary!

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