Valentine’s Day in Chicago

Take the pressure off with our guide to Valentine's Day ideas, including romantic restaurants and gifts

Photograph: Martha WilliamsHeart-shaped macaron from La Boulangerie

Valentine’s Day is right around the corner, which means the pressure is on. If you’re taken, you're probably weighing whether it’s really worth shelling out at one of Chicago’s best fine dining restaurants. If you’re single, you might be out at your favorite bar trying to get some action. And if you’re somewhere in between and don’t know whether you’re “doing” Valentine’s Day, well, best of luck. 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, making plans on Valentine’s Day is a total pain

The most romantic hotels in Chicago
Hotels

The most romantic hotels in Chicago

Stay in for the night at one of these top-tier spots

Romantic date ideas in Chicago
Things to do

Romantic date ideas in Chicago

We'll tell you where and how to get lovey-dovey all over the city

The most romantic places in Chicago
Sex and dating

The most romantic places in Chicago

Believe it, Chicago is a city of romance

How to have an amazing first date in Chicago
Sex and dating

How to have an amazing first date in Chicago

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

The 10 most romantic restaurants
Restaurants

The 10 most romantic restaurants

From fancy French restaurants to a casual cocktail and pizza joints

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"

10 Chicago bars and lounges for singles
Bars

10 Chicago bars and lounges for singles

You don't have to fly solo if you don't want to

Sex shops in Chicago for all your sex toy needs
Shopping

Sex shops in Chicago for all your sex toy needs

Get exactly what you're looking for at these sex-positive emporiums

The best fun date ideas in Chicago
Things to do

The best fun date ideas in Chicago

Guarantee a good time

Where to shop

The best Chicago flower shops
Shopping

The best Chicago flower shops

Find the freshest arrangements for your special someone

The 9 best gift shops
Shopping

The 9 best gift shops

Mark a romantic occasions with an amazing gift

The 10 best candy stores
Restaurants

The 10 best candy stores

There's no sweeter gift than a box of chocolates

The top jewelry stores
Shopping

The top jewelry stores

If you're looking to make a statement this year, we've tracked down the city's best jewelers

Show more

Romantic lists

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?

Valentines for Chicago food lovers
Restaurants

Valentines for Chicago food lovers

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

The 50 sexiest songs
Music

The 50 sexiest songs

Our playlist will lead you straight to the bedroom

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.

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Comments

3 comments
Amy M

Geez, what cynical Grinch wrote the copy for this page?!  "Pressure?" "Stress?" It's a sad commentary on our culture that a holiday celebrating love is considered a burden.  And why assume that single people "loathe" the holiday? Speak for yourself. I am blissfully single and I love celebrating Valentine's Day.  Life is my Lover.  365 days of the year.