Move over, Paris. Chicago is the real city of love.

Chicago has a beautiful lakefront and a stunning skyline. Our charming neighborhoods are made for hand-in-hand strolls. We have festivals, culture, art, music, and a seriously impressive ferris wheel. What more could a happy couple ask for?

Don’t even get us started on Chicago’s swoon-worthy restaurants.

Ready to experience the most romance Chicago has to offer? Let’s dive in!

Romantic Spots In Chicago You Must Explore

#1 Explore Authentic Chicago On Randolph Street

Romantic spots in chicago

Photo Source: Charissa Johnson Photography

We love downtown Chicago. But, the West Loop neighborhood is where couples in the know go for a memorable day of foodie-friendly restaurant hopping — virtually free of tourists.

What once was Chicago’s meatpacking district has transformed to today’s Restaurant Row, home to so many up-and-coming chefs, we won’t even begin to list them. Randolph Street is alive with fun-filled patios and dotted with plenty of backdrops for that #couplegoals selfie.

Insider Tip: Not sure exactly which restaurants to visit and make a meal of it?  Wish you could hit up more then one or two in a single outing?  Leave the planning to Chicago Food Planet and hit five Chicago must-eat restaurants in three hours on the Gateway to The West Loop Food Tour. Their expert guides take care of every detail, providing architectural commentary, culinary and architectural insight and will even introduce you to the celebrated chefs behind Bonci Pizza, Kuma’s Corner, Cemita’s Puebla and more while you eat like kings and queens. You and your sweetie can just focus on devouring, drinking (yes, there are incredible drink + food pairings!) and having the time of your lives while getting to know your city, and each other, even better.

#2 Discover Ping Tom Memorial Park In Chinatown

romantic ideas chicago chinatown

Photo Source: Elizabeth Greve Photography

If Millennium Park is a “been there, done that” for you two, here’s your chance to keep your significant other on their toes. Chinatown’s beautiful 17-acre Ping Tom Memorial Park is still very much under the radar, so it’s an idyllic spot to steal away together for an afternoon.

The Chinese design of the padoga-style pavilion is the park’s crown jewel, but it doesn’t stop there. Check out the views from the second story patio of the field-house. Rent a kayak from the boathouse to float down the Chicago River together. Or grab some dim sum from Triple Crown in Chinatown for a unique park picnic.

Want to discover even more hidden secrets in Chinatown? Visit a Buddhist temple, learn about the Chinese Zodiac, walk through the glorious Ping Tom Memorial Park and more on the Chinatown Adventure Food Tour.  Three hours, five sit-down tastings at off-the-beaten-path, authentic restaurants and deep insight into the cultural and ethnic pageantry that defines Chinatown awaits.  

Bonus: Brush up on your Chinatown knowledge before you go. Check out our guide to the 22+ best restaurants and things to do in Chinatown, and show your sweetheart around Chinatown like an expert.

24 Hours of The Most Romantic Chicago Dining

#3 Grab Coffee & Stick Around At A Beloved Chicago Coffee Shop

free romantic things to do chicago

Photo Source: @ipsento

Sure, you could make a Starbucks run before the day’s adventures with your better half. Or, you could cozy up together at one of Ipsento’s two locations in Wicker Park or Bucktown.

It’s your quintessential intimate neighborhood coffee shop, made for long talks over Nutella Mochas. After all, the word Ipsento is Latin for self-discovery, so what better place to get to know each other even better?  

Insider Tip: In love with a true coffee lover? Plan a fun day date at Ipsento’s Coffee 101 class. They’ll drink up all the nerdy coffee knowledge, and even learn how to make you one awesome cuppa.

#4 The Best Way To Say: “I Love You A Brunch”

most romantic things to do in chicago

Photo Source: Facebook

The two of you make the perfect couple. The perfect union of barbecue and breakfast at Chicago q is a very close second, though. Brisket hash benedict? That’s a match made in heaven.

The portions are enormous at this upscale Gold Coast institution, excellent for sharing. We highly recommend the Bloody Mary Bar for a boozy brunch date that might just stretch into dinnertime.

Fun Fact: Oprah’s personal chef, Art Smith, is the pitmaster here. Go ahead – work that humblebrag into your Instagram caption.

#5 A Chicago Picnic Lunch With The One You Picked

chicago picnic ideas romantic

Photo Source: Video Blocks

There are few things sweeter than taking your sweetheart on a picnic in the park. But if the packing and planning makes you sweat, The Goddess & The Grocer has you covered.

Order the perfect packed lunch online, choosing from the gourmet grocery’s selection of sandwiches, salads and soups. Don’t forget the heavenly desserts, plus adult beverages of course. Pick it up from one of their four locations in Chicago. You’ll get a “Wow!” for sure. Whew.

#6 Magic Is Afoot At Romantic Chicago Restaurant Goosefoot

chicago romantic things to do

Photo Source: Time Out Chicago

Don’t be intimidated by the avant garde six-course tasting menu. Goosefoot boasts a Michelin star, yes, but the petite restaurant is actually an adorable tribute to the owners’ love story.

The dining room seats just 24, and the welcoming chef Chris Nugent is ever-present during your meal along with his charming wife, Nina. After your unforgettable dinner, Chris may send you home with a handcrafted chocolate bar, or Nina might press some seeds for your garden into your hands.

Insider Tip: Goosefoot is BYOB, so don’t forget to stop at the wine shop next door first to select the perfect bottle.

#7 Put A (Donut) Ring on It At Do-Rite Donuts

best romantic things to do chicago

Photo Source: Collin Pierson Photography

If your partner memorizes black & white movies and hunts for vintage finds, Do-Rite Donuts could be your new spot.

The award-winning chef at Do-Rite has perfected the Old-Fashioned donut — no frills, no gimmicks, just ridiculously delicious, gourmet donuts made fresh on premises.

Insider Tip: The behind-the-scenes visit to Do-Rite Donuts on the Gateway To The West Loop Food Tour always impresses. It’s the most popular Chicago tour for proposals and special occasions!

Go All In With These Romantic Grand Gestures

If you really want to impress your special someone, it might be time to step it up from dinner and a movie.

Sure, there is a time and a place for a Chicago date night in the city. But if you’re celebrating a birthday, anniversary or even popping the question? These romantic adventures might just be perfect.

#8 Come Fly With Me On A Chicago Helicopter Tour

helicopter tours chicago romantic ideas

Photo Source: CHE Facebook page

You don’t need reality TV producers to take off on a romantic helicopter date.

Scrape the sky right along with Chicago’s iconic architecture, and snuggle up while you take in the sparkling lakefront together.

Heights not really your thing? The plush leather seats, noise canceling Bose sound system and friendly, experienced pilots will make you feel right at home – if home happened to be 1,000 feet in the Chicago sky.

Insider Tip: Here’s your permission to be extra. Spring for the Chicago Helicopter Experience Date Night package. Spoil each other with dinner and drinks for two, then get to da choppa.

#9 Sail Away On A Spirit of Chicago Sunset Dinner Cruise

cheap romantic things to do in chicago

Photo Source: Spirit of Chicago

Show her you really are King of the World on a sunset dinner cruise on Lake Michigan – or at least get your chance to re-enact that Jack & Rose flying scene (with a much happier ending, of course).

Fantastic views of Chicago from the open-air observation deck are entertainment enough. But, there’s also an onboard DJ, games like giant Jenga, and let’s not forget that delicious dinner buffet.

Insider Tip: Make your plans early so you can snag one of the coveted window tables reservations for unbeatable views.

#10 Take A Chicago Couples Retreat At Chuan Spa

romantic things to do in chicago for couples

Photo Source: Chuan Spa Chicago

In Chinese, chuan means “flowing water,” and couples should step into Chuan Spa in the The Langham Chicago ready to go with the flow.

Before your scheduled pampering, you and your partner will embark on a series of Chinese relaxation steps called the Chuan Bathing Ritual. We recommend that you arrive at least an hour prior to your appointment, though, to luxuriate in the heated relaxation recliners with a hot cup of herbal tea.

And after your spa treatments, bask in that tranquil togetherness by slipping into sensory relaxation pods. They’ll surround you with calming sounds, light, and vibrations. Ahhhh.

Insider Tip: For an extra steamy spa day (and we mean that literally), indulge in a shower with your sweetie in those luxurious extra-large bathrooms.

You Can’t Top These Romantic Chicago Rooftops

Everything is just more romantic on a rooftop – and the Chicago skyline is an unbeatable backdrop for a special moment with your special someone.

These three Chicago rooftop bars are sure to set the mood.

#11 Steal Away To This Lush Rooftop Patio In Chicago

chicago date night ideas

Photo Source: Celeste

The intimate rooftop patio at Celeste feels like a secret garden. Tucked away in River North, this place drips with glamour, so put on your best dress and channel your inner starlet.

While the furnishings at Celeste are inspired by the Victorian era, their drink menu is cutting edge. So if the one you love enjoys inventive hand-crafted cocktails, we definitely recommend you two settle into a loveseat here.

Insider Tip: This rooftop patio is enclosed in the winter, so you can cozy up together at Celeste year round.

#12 Take It To The Next Level At LondonHouse Chicago’s Rooftop Bar

chicago romantic things to do ideas

Photo Source: CitySavvy Imaging

Each floor of this upscale hotel in the Loop is impeccably designed. Seriously: every piece of artwork was especially commissioned for LondonHouse Chicago to evoke the historic building’s roots in the 1920s.

But it’s the top three floors that truly bring the romance.

Level 21 is a sophisticated indoor bar with excellent dining to match, and it’s on Level 22 where you’ll discover the al fresco ambiance.

Trust us – you must pair those epic views of the city with a Chicago Cocktail. It’s cognac and sherry topped with champagne. You’ll both feel on top of the world.

Insider Tip: Got a certain question on your mind? We propose you reserve the breathtaking domed cupola on Level 23 for any memorable moments.

#13 Chicago’s MOST Romantic Rooftop? Cindy’s

fun romantic things to do in chicago

Photo Source: Cindy’s Rooftop

If there’s one place we point couples on Chicago food tour, it’s this one. Whether it’s brunch, dinner or late night drinks, the views of Lake Michigan and Millennium Park at Cindy’s are guaranteed take her breath away.

Cindy’s is a permanent guest at the beautiful and historic Chicago Athletic Association Hotel. If you pull out all the stops and book a room, you’ll have first dibs on the best tables — plus the chance to check out the swankiest roller rink you’ve ever skated.

Insider Tip: Definitely reserve one of the Lakeview Couches if you’re celebrating something special. The views are stunning and you’ll have more privacy from the bustling patio. 

Connect With Your Sweetheart and Food In Unexpected Ways


Enjoy Gateway To The West Loop Food Tour on the #1-Rated Date Activity

Meet the chefs, learn their stories & devour specialty dishes at top restaurants

Offered daily; Includes visits to Kuma’s Corner, Bonci Pizza & Do-Rite Donuts 


$60 Adult Tickets (Food Included)
VIP Tickets Available (+ Drink Pairings)

Learn More