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How to celebrate Valentine’s Day in Chicago

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

Valentine's Day candy
Photograph: Unsplash

The shelves at your local drugstore are stocked with heart-shaped boxes, giant stuffed animals and sappy cards for a reason: Valentine's Day is almost here. If you have a significant other, celebrate Valentine's Day in Chicago by making a reservation at one of the most romantic restaurants in Chicago or by getting them a big bouquet of flowers. If you're single, get together with friends at one of the best bars in Chicago for a couple of drinks—perhaps you'll strike up a conversation with a special someone. Regardless of your relationship status, there are lots of ways to make 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 another Valentine's Day in Chicago.

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 18 most romantic restaurants in Chicago
Restaurants

The 18 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 breakup songs
Music

The 50 best breakup songs

Most of the best pop music ever produced has sprung from its well of agony

Valentines for Chicago food lovers
Restaurants

Valentines for Chicago food lovers

Printable valentines featuring Rick Bayless, Paul Kahan, and other Chicago chefs and bartenders

More from How to celebrate Valentine’s Day in Chicago

The best things to do on Valentine's Day

It doesn't matter if you have a significant other or not—making plans on Valentine's Day sucks. If you're single, you need to find something to distract you from all the happy couples that you're suddenly intensely aware of. If you're in a relationship,...