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Valentine’s Day in Chicago

Celebrate Valentine's Day in Chicago with our guide to romantic restaurants, date ideas and more

Heart-shaped macaron from La Boulangerie
Photograph: Martha WilliamsHeart-shaped macaron from La Boulangerie

If the heart-shaped candy and sappy cards at your favorite drugstore didn't already tip you off: Valentine's Day is just around the corner. If you're coupled up, celebrate Valentine's Day in Chicago at one of the city's most romantic restaurants or splurge on a fine-dining experience. Don't fret, singles: A visit to one of the best bars in Chicago is just what the doctor ordered. Regardless of your romantic situation, we’ve got a slew of ideas to make celebrating this manufactured holiday one of your favorite things to do during the winter in Chicago. Well, let’s not go that far—at the very least, you’ll survive it.

How to spend Valentine's Day in Chicago

The best things to do on Valentine’s Day
Things to do

The best things to do on Valentine’s Day

Whether you’re single or all bae’d up, make plans for Valentine's Day.

The 15 most romantic restaurants in Chicago
Restaurants

The 15 most romantic restaurants in Chicago

The most romantic restaurants in Chicago crank up the heat and set the mood.

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.

Romantic (and totally original) date ideas in Chicago
Things to do

Romantic (and totally original) date ideas in Chicago

Easy, low-key dates that will spark romance.

Get a room at one of the most romantic hotels in Chicago
Hotels

Get a room at one of the most romantic hotels in Chicago

Turn the city into an ideal backdrop for a romantic romp.

Romantic places in Chicago to visit with that special someone
Sex and dating

Romantic places in Chicago to visit with that special someone

Cozy up with your sweetheart at these surprisingly romantic spots.

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

Single? Apply to be set up for our feature, "Dating IRL"

The top fine dining restaurants in Chicago
Restaurants

The top fine dining restaurants in Chicago

Splurge this Valentine's Day with a reservation at one of these no-fail spots.

Where to shop

11 awesome flower shops in Chicago
Shopping

11 awesome flower shops in Chicago

Find the freshest arrangements for your special someone

The 19 best gift shops in Chicago
Shopping

The 19 best gift shops in Chicago

Mark a romantic occasions with an amazing gift

The 15 most decadent candy shops in Chicago
Restaurants

The 15 most decadent candy shops in Chicago

There's no sweeter gift than a box of chocolates

The best flower delivery in Chicago
Shopping

The best flower delivery in Chicago

These companies deliver quality arrangements, fast and without hassle

Set the mood

The 50 best love songs ever made
Music

The 50 best love songs ever made

Are you ready to fall head over heels with the best love songs of all time?

The 50 most romantic movies of all time
Movies

The 50 most romantic movies of all time

Prepare to swoon at our loveliest of movie lists.

The 50 sexiest songs
Music

The 50 sexiest songs

Our playlist will lead you straight to the bedroom

Anti–Valentine’s Day movies
Things to do

Anti–Valentine’s Day movies

Check out some streaming movies with the power to squelch out romance

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