
The best things to do on a first date in Chicago
There's no getting around it: First dates are awkward
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Whether you prefer singles bars or dating apps, fall in love the right way with our complete guide to dating in Chicago
Dating: Everyone has an opinion on the subject. Some folks thrive on constantly meeting new people, others find comfort in long-term relationships, and for others still, the mere thought of getting drinks with a stranger insights unshakeable anxiety. Regardless of your personal convictions, let’s get one thing straight about dating: Chicago is a fantastic place to do it. (Pun intended, duh.) We’re home to a slew of cozy, romantic (not to mention delicious) bars and restaurants, world-class museums for daytime outings and lots of friendly, good-looking people. Even if dating itself isn’t your cup of tea, use our guide and you’ll fall in love with Chicago while looking for that special someone.
There's no getting around it: First dates are awkward
From Andersonville to Pilsen, we’ve gathered the best Chicago bars for scoring a date
C'mon, why not?
Believe it or not, Chicago is a city of romance
The pressure is on
These easy, low-key dates will definitely help spark romance
Get better acquainted with your better half
Spice things up instead of “Netflix and chill"
From a hidden sushi haven to a fancy French steakhouse to an old-school fondue spot
If romance is about setting the mood, then you should have no problem doing so at any of these picks.
When it comes to finding love, Chicago reigns supreme to the Big Apple
Hoping to make it to date number two? Avoid these places.
Sometimes, it just won't work out
You can’t help but run into a few characters along the way
Make space for change
Dating in Chicago isn't for the faint of heart. We spend half the year in hibernation, which can make finding a partner a little difficult. That said, one of...
Think outside the box, from wine cocktails to wine on tap
Over the past decade, the city has really become a whiskey lover’s paradise
Our long winters have one big upside—getting cozy
We wouldn't blame you if you wanted to visit every bar on the list
Beer has officially entered the "something-for-everyone" territory
Drink with your love and the skyline
Chicago has a vibrant gay bar scene
There's no better place than a beer garden
Thrift stores in Chicago are true treasure troves
For anniversaries, weddings, birthdays, the holidays or "just because"
It can be tough to "pick" the best of the best
Whether you want to treat someone or just indulge yourself with a little chocolate
Discover Time Out original video