Dating in Chicago

Whether you prefer singles bars or dating apps, fall in love the right way with our complete guide to dating in Chicago

Photograph: John Khuu

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.

The best date spots in Chicago

The best things to do on a first date in Chicago
Sex and dating

The best things to do on a first date in Chicago

There's no getting around it: First dates are awkward

14 Chicago bars and lounges for singles
Bars

14 Chicago bars and lounges for singles

From Andersonville to Pilsen, we’ve gathered the best Chicago bars for scoring a date

Let Time Out Chicago set you up on a blind date
Sex and dating

Let Time Out Chicago set you up on a blind date

C'mon, why not? 

The most romantic spots in Chicago
Sex and dating

The most romantic spots in Chicago

Believe it or not, Chicago is a city of romance

Valentine’s Day in Chicago
Things to do

Valentine’s Day in Chicago

The pressure is on

Romantic date ideas in Chicago
Things to do

Romantic date ideas in Chicago

These easy, low-key dates will definitely help spark romance

Fun date ideas in Chicago
Things to do

Fun date ideas in Chicago

Get better acquainted with your better half

9 adorable date ideas for when the temperature drops in Chicago
News

9 adorable date ideas for when the temperature drops in Chicago

Spice things up instead of “Netflix and chill"

The most romantic restaurants in Chicago
Restaurants

The most romantic restaurants in Chicago

From a hidden sushi haven to a fancy French steakhouse to an old-school fondue spot

The most romantic hotels in Chicago
Hotels

The most romantic hotels in Chicago

If romance is about setting the mood, then you should have no problem doing so at any of these picks. 

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Chicago dating stories

Dating IRL: Pilsen
News

Dating IRL: Pilsen

Dating IRL: West Loop
News

Dating IRL: West Loop

Dating IRL: Bridgeport
News

Dating IRL: Bridgeport

Dating IRL: Southport Corridor
News

Dating IRL: Southport Corridor

Dating IRL: Wicker Park
News

Dating IRL: Wicker Park

Dating IRL: Chinatown
Sex and dating

Dating IRL: Chinatown

Dating IRL: Andersonville
News

Dating IRL: Andersonville

Dating IRL: River North
News

Dating IRL: River North

Dating in Chicago

15 reasons dating in Chicago is better than dating in NYC
News

15 reasons dating in Chicago is better than dating in NYC

When it comes to finding love, Chicago reigns supreme to the Big Apple  

10 worst bars for a first date in Chicago
News

10 worst bars for a first date in Chicago

Hoping to make it to date number two? Avoid these places.

5 reasons for breaking up with someone that only make sense in Chicago
News

5 reasons for breaking up with someone that only make sense in Chicago

Sometimes, it just won't work out

11 people you’ll date in Chicago
News

11 people you’ll date in Chicago

You can’t help but run into a few characters along the way

Things that make you undateable in Chicago
News

Things that make you undateable in Chicago

Make space for change

The 12 people you'll meet on Tinder in Chicago
News

The 12 people you'll meet on Tinder in Chicago

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 our favorite winter pastimes is swiping through Tinder on a cold night and hoping to find someone who wants to spend all summer outside actually enjoying the city with us. These are the people you'll be sure to encounter when swiping from within city limits; which way you decide to swipe is entirely up to you.  The one who lies about being from the city. Schaumburg is not Chicago.  The one who just finished running the Color Run. We get it, you're sporty and you love a good 5K—we see those photos from the Shamrock Shuffle and Hot Chocolate Runs, too—but come on, it's been months since the Color Run. The Logan Square hipster. Has never ventured outside the square and only suggests dates at Longman & Eagle. Delicious, but it's time to try something new.  The one with the "skyline" view. Just because you can see the spire of the Hancock from your apartment does not mean you have city views. This is fine, but don't pretend.  The one posing with the Stanley Cup. Unless you're Jonathan Toews, we don't want to see a photo of you next to the Stanley Cup, we've all seen it, we get it.  The one who lives for summer street festivals. Their profile photos are just different shots of them in tank tops with a craft beer on every block of the city.  The bartender. Their profile photos behind the bar at your favorite hangout make

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Bars for dates

Best wine bars
Bars

Best wine bars

Think outside the box, from wine cocktails to wine on tap

Fantastic whiskey bars in Chicago
Bars

Fantastic whiskey bars in Chicago

Over the past decade, the city has really become a whiskey lover’s paradise

Restaurants and bars with fireplaces
Restaurants

Restaurants and bars with fireplaces

Our long winters have one big upside—getting cozy

Best cocktail bars in Chicago
Bars

Best cocktail bars in Chicago

We wouldn't blame you if you wanted to visit every bar on the list

Best beer bars
Bars

Best beer bars

Beer has officially entered the "something-for-everyone" territory

Best rooftop bars
Bars

Best rooftop bars

Drink with your love and the skyline

Best gay bars
Bars

Best gay bars

Chicago has a vibrant gay bar scene

The best beer gardens
Bars

The best beer gardens

There's no better place than a beer garden

Gift ideas for him or her

Chicago's best thrift stores for secondhand and resale shopping
Shopping

Chicago's best thrift stores for secondhand and resale shopping

Thrift stores in Chicago are true treasure troves

Find something for everyone at Chicago's best gift shops
Shopping

Find something for everyone at Chicago's best gift shops

For anniversaries, weddings, birthdays, the holidays or "just because"

The best Chicago flower shops
Shopping

The best Chicago flower shops

It can be tough to "pick" the best of the best

The best candy and chocolate shops in Chicago
Restaurants

The best candy and chocolate shops in Chicago

Whether you want to treat someone or just indulge yourself with a little chocolate

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