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Valentine's Day in Chicago

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

Photograph: Martha Williams
Heart-shaped macaron from La Boulangerie

Ah, Valentine’s Day: When the pressure is, in fact, truly on. If you’re taken, you’re weighing whether to dish out at Chicago’s best fine dining. If you’re single, you’re probably out at your favorite bar trying to get laid. 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 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. Or, at the very least, you’ll survive it. 

Valentine's Day gifts and dates

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 in the ass

Valentine's Day dinner specials
Restaurants

Valentine's Day dinner specials

Show your adoration at some of the best Chicago restaurants with indulgent Valentine's Day dinner specials 

The most romantic hotels in Chicago
Hotels

The most romantic hotels in Chicago

Stay in for the night, soak in the neighborhood, enjoy a late dinner at these romantic spots

The best romantic date ideas in Chicago
Things to do

The best romantic date ideas in Chicago

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

The 10 most romantic restaurants
Restaurants

The 10 most romantic restaurants

From fancy French restaurants to a casual cocktail and pizza joints

Valentine’s Day movie screenings in Chicago
Movies

Valentine’s Day movie screenings in Chicago

See one of these enduring romantic movies that are getting special screenings on and around February 14

Garrett Popcorn releasing a special Valentine's Day flavor
Blog

Garrett Popcorn releasing a special Valentine's Day flavor

Meet the Sweetheart Mix, a combination of White Chocolate CaramelCrisp and Simply Strawberry

Portillo's is offering one of the sweetest Valentine's Day treats
Blog

Portillo's is offering one of the sweetest Valentine's Day treats

From February 10–14, Portillo's will be offering a heart-shaped version of its popular chocolate cake

Valentine's Day gifts for when it's complicated
Shopping

Valentine's Day gifts for when it's complicated

Not quite in a relationship, not quite single? We get it

7 great coffee shops for a Valentine's Day date
Blog

7 great coffee shops for a Valentine's Day date

Caffeinate with your crush.

Anti-Valentine’s Day ideas
Shopping

Anti-Valentine’s Day ideas

Reject the Hallmark holiday with these feisty options

The Chicago dating scene by the numbers
Sex and dating

The Chicago dating scene by the numbers

Remember, it might seem rough out there, but we're all just trying to not die alone

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

Find a shop that’s clean and comfortable

The best fun date ideas in Chicago
Things to do

The best fun date ideas in Chicago

Guarantee a good time

11 date ideas that aren't sitting in a bar
Blog

11 date ideas that aren't sitting in a bar

Get to know someone's better side

Valentine’s Day ideas for her
Shopping

Valentine’s Day ideas for her

These unique, fun, and thoughtful Valentine's Day gifts will make her swoon

Valentine's Day ideas for him
Shopping

Valentine's Day ideas for him

Give your guy the perfect gift with the help of our gentlemanly guide

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

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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
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.