Valentines Day Ideas in Chicago

Looking for the perfect way to celebrate? Finding fantastic valentines-day ideas in chicago is easier than you think! This guide is packed with suggestions for romantic cafes, delicious restaurants, lively bars, and fun activities to make your Valentine's Day in the Windy City unforgettable.

Cafes & Coffee

Need a caffeine fix before or after your romantic outing? Chicago's cafes and coffee shops offer a cozy, intimate setting perfect for a relaxed Valentine's date, whether you're catching up over lattes or sharing a sweet treat.

Cafe Deko
Coffee shop

Cafe Deko

4.5

$

Cozy up at Cafe Deko for a budget-friendly Valentine's! Enjoy cute decor and delicious treats.

800 W Diversey Pkwy, Chicago, IL 60614

Café Calidá
Coffee shop

Café Calidá

4.9

$

Cozy up at Café Calidá for amazing coffee and a romantic, intimate vibe.

3455 W North Ave, Chicago, IL 60647

Restaurants

Looking to impress your sweetheart this Valentine's Day? Chicago's got you covered with a plethora of romantic restaurants, offering everything from intimate settings to delicious menus perfect for celebrating love.

Gibsons Italia
Italian restaurant
🍽️

Gibsons Italia

4.7

$

For a romantic night, Gibson's Italia offers stunning city views & delicious Italian.

233 N Canal St, Chicago, IL 60606

Boka
American restaurant
🍽️

Boka

4.7

$

For a romantic Valentine's, Boka's dimly lit, upscale vibe is perfect!

1729 N Halsted St, Chicago, IL 60614

Bars & Drinks

Looking for a spot to clink glasses and share sweet nothings this Valentine's Day? Chicago's bar scene is brimming with romantic options, offering everything from cozy vibes to dazzling city views perfect for sparking romance.

Cindy's Rooftop
Bar
🍸

Cindy's Rooftop

4.4

$$$

Snuggle up at Cindy's Rooftop for stunning city views and romantic vibes.

12 S Michigan Ave, Chicago, IL 60603

The Franklin Room
Bar
🍸

The Franklin Room

4.6

$

Cozy up at The Franklin Room, a dimly lit bar, for a romantic Valentine's with craft cocktails.

675 N Franklin St, Chicago, IL 60654

Activities

Looking for the perfect Chicago date this Valentine's Day? From romantic ambiance to exciting experiences, these activities offer something special to make your date unforgettable.

360 CHICAGO
Event venue
📍

360 CHICAGO

4.5

$$

Soar above Chicago at 360 CHICAGO for stunning views and a romantic Valentine's Day.

875 N Michigan Ave 94th floor, Chicago, IL 60611

Carnivale Chicago
Restaurant
🍽️

Carnivale Chicago

4.4

$

For a vibrant Valentine's, Carnivale's colorful, festive vibe and Latin flavors create a memorable date!

702 W Fulton St, Chicago, IL 60661

What Perfect Place Would Search For

Tell us about your date's preferences, and here's the kind of searches we'd run to find the perfect venues:

💖 Appreciates a romantic ambiance
romantic restaurants candlelit dinner restaurants with fireplaces intimate bars
🍸 Enjoys sophisticated cocktails
craft cocktail bars speakeasy upscale lounges restaurants with great cocktails
🎷 Is a fan of live jazz music
jazz clubs live music venues restaurants with live jazz intimate concert halls

The app finds actual venues matching these searches, ranked by how well they fit your date's personality.

No matter your style, Chicago offers countless ways to celebrate love this Valentine's Day. From cozy coffee shops to exciting experiences, we hope this guide has inspired you! For even more personalized recommendations and help planning your perfect date, be sure to check out the Perfect Place app to find the best valentines-day ideas in chicago.

More Date Ideas You Might Love

Get personalised date ideas

Perfect Place matches venues to their personality — so every date feels thoughtful.

Download Perfect Place now!