Romantic Things to Do in Chicago: Love Affair with the Windy City
Chicago, also known as the ‘windy city’ surprised us and quickly became one of our favourite cities in the US. Ishi and I spent three full weeks living, working and falling in love with it, but on a much deeper level. We weren’t just visitors; we became part of the rhythm of the city. And through morning riverside strolls, rooftop date nights,and unexpected discoveries, we realized just how romantic Chicago can be. Whether you’re planning a special anniversary, a honeymoon add-on, or just a getaway to reconnect, here are the most romantic things to do in Chicago, from our hearts to yours.
You know us by now, we’re not weekend warriors or checklist travelers. We work full-time jobs remotely and slow-travel through cities for weeks at a time. I lived in the U.S. for five years before moving to Canada and I’ve always had a soft spot for Chicago. But during our three-week stay, we got to know it like locals. Every recommendation below is something we personally experienced (and gushed about afterward). It’s not just a guide, it’s a love letter to the city.
Best Time to Visit Chicago for Romance
If you’re aiming for long, scenic walks and rooftop cocktails, visit from mid May to mid June and late August to late September. The weather is warm but not humid, the skies are painterly and the crowds are manageable.
We personally visited in August, and it was absolutely perfect. The summer warmth worked to our advantage, it gently masked the cool breeze coming off the lake, creating a balance that made every moment outdoors incredibly pleasant. The mornings started warm and breezy, and after logging off from work, we’d often head out to catch the golden hour light that softened the city’s edges. Whether we were strolling the Riverwalk, grabbing a drink on a rooftop, or finding a quiet spot by the lake, the soft glow and balmy air made every outing feel effortlessly romantic. There’s something incredibly romantic about the way Chicago feels in August: lively, golden, and full of long, lingering sunsets that invite you to pause and savor it all.
If you want a splash of quirky romance, come in March for St. Patrick’s Day, when the city dyes the river bright green. It’s festive, over-the-top, and honestly kind of magical. It’s still on our bucket list, but we’ve bookmarked it for a future trip.
If you’re looking to do what we did (travel while working full-time) we wrote a whole guide on how to make it happen: How to Travel While Working Remotely.
Top 5 Romantic Things to Do in Chicago
1. Take a Sunset Cruise on the Chicago River
You haven’t truly felt Chicago until you’ve glided along its emerald river during sunset. We boarded an architecture cruise on a crisp evening, drinks in hand, watching the golden glow bounce off skyscrapers. As we floated beneath the glowing bridges, with a gentle breeze brushing past and the lights flickering on in the skyline, it was easy to imagine the city’s history unfolding right beside us.
Pro Tip: Take the later cruise around golden hour for the most romantic ambiance. Bring a light jacket and let the wind play with your hair.
2. Watch the City Light Up from a Rooftop Bar
We’re both suckers for a good rooftop, and Chicago has so many. But three rooftops really stood out for their views, vibes, and romance factor:
LondonHouse Rooftop
If you want the most iconic view of the Chicago River, this is it. We went up just as the sun set and the bridges lit up like golden threads. LondonHouse is pricey but for us it was worth every moment.
Cindy’s Rooftop
Cindy’s overlooks Millennium Park, the Bean, and Lake Michigan. We came here for brunch, stayed through drinks, and almost forgot we had afternoon meetings. The vibe is relaxed, the drinks are playful and the view is expansive.
ROOF on theWit
If you’re looking for a rooftop that blends city energy with stylish ambiance, ROOF on theWit in the Loop is a fantastic pick. Perched 27 stories high, it offers sweeping skyline views, moody lighting, and a fun, modern vibe. We loved the DJ sets in the evening, the cozy fire pits and the cocktails that were just as bold as the view. Plus, it’s often less crowded than LondonHouse or Cindy’s, which makes it even easier to snag a table and enjoy a quieter, more personal atmosphere.
Pro Tip: Reserve in advance, especially for LondonHouse and Cindy’s. Sometimes searching for a table for 4 gives better availability than for 2.
3. Stroll the Chicago Riverwalk – Day and Night
Every morning before logging in to work, we’d walk or jog along the Riverwalk. And in the evenings, it transformed into a romantic riverside promenade. Alfresco wine bars, gelato stands, and street musicians make it lively but never overwhelming.
One night, we grabbed a deep-dish pizza from the famous Giordano’s, found a step overlooking the water, and just sat there. Watching boats glide by, listening to the hum of the city, it was perfect.
4. Jazz & Cocktails at the Green Mill Lounge
Stepping into The Green Mill is like entering a time capsule. This legendary jazz bar, once frequented by Al Capone, oozes vintage charm. We cozied up in a booth, sipped on classic cocktails, and got lost in the sound of a live jazz trio that played like they had nothing to prove. It’s romantic, sultry, and absolutely timeless. One of our favorite drinks was the French 75, it added the perfect sparkle to our romantic night.
Pro Tip: Arrive early on weekends, it fills up fast and they do not take reservations!
5. Sunset Picnic at Promontory Point
If you’re craving a quieter escape with skyline views, pack a picnic and head to Promontory Point in Burnham Park. It’s where the locals go to watch the sun dip behind the buildings from across Lake Michigan. We brought sandwiches, a bottle of Prosecco (shhh) and a blanket. There were barely any crowds – just us, the sound of waves, and the city shimmering in the distance. It was pure magic.
Note: Officially, alcohol isn’t permitted in Chicago parks without a special permit. That said, many locals discreetly enjoy a drink in a solo cup or other non-glass container. Just keep it subtle, respectful and clean up after yourself.
Pro Tip: Bring bug spray and get there 30 minutes before sunset for the best view.
Our Most Romantic Moment in Chicago
It has to be our sunset picnic at Promontory Point. We were looking for something peaceful and away from the buzz, and this spot gave us just that. As the sun dipped low and painted the sky in hues of orange and pink, the waves gently lapped at the rocks below us. We didn’t talk much, we just soaked it in.
That quiet, serene moment, far from the skyscrapers and crowds, was our favorite of the entire trip. It reminded us how sometimes, the most romantic memories come from the simplest moments.
Related Read: Planning a road trip filled with romance and adventure?
Check out our guide to 10 Epic Day Trips from Las Vegas, they’re perfect for couples craving variety and natural beauty.
Where to Stay for a Romantic Chicago Getaway
Your stay can set the tone for your entire romantic getaway, and Chicago offers plenty of dreamy options. Whether you’re planning a splurge or keeping it simple, here are our top picks for where to stay as a couple:
Budget-Friendly & Cozy
- Freehand Chicago – Stylish and budget-friendly with a cool bar.
- Hotel Lincoln – Right across from Lincoln Park, artsy vibes.
- Moxy Chicago Downtown – Modern and fun, perfect for young couples.
Luxury & Dreamy
- The Langham – Posh riverside hotel with a romantic spa.
- Waldorf Astoria Chicago – Gold Coast luxury and Parisian aesthetics.
- LondonHouse Chicago – Stay here for romance-in-the-clouds.
Romantic Restaurants to Try in Chicago
A romantic city like Chicago deserves an equally unforgettable meal to go with it. These restaurants are perfect for couples, whether you’re after cozy charm or elevated rooftop dining:
- Geja’s Café – A Chicago classic known for its intimate fondue experience. Dim lighting, private booths, and a warm ambiance make it a favorite for special occasions.
- Aba – A trendy Mediterranean rooftop restaurant in the Fulton Market District with lush greenery, soft lighting, and mezze that’s perfect for sharing.
- Le Colonial – A vintage Parisian-Vietnamese restaurant in the Gold Coast. Think colonial-era elegance, romantic décor, and flavors that feel both nostalgic and exotic.
FAQs: Romantic Things to Do in Chicago
Is Chicago a good place for a couples’ trip?
Yes! It’s full of hidden romantic gems, river views, skyline bars and cozy restaurants.
What’s the best way to get around in Chicago?
Uber or walking. It’s affordable, and it lets you enjoy the night without parking stress.
Is the safe to walk Chicago riverside at night?
Yes! It’s well-lit, patrolled and full of other nighttime strollers.
Departing Words
Romance in Chicago isn’t forced, it’s ambient. It’s in the way the lights dance on the river. It’s in the rooftop views and riverfront conversations. For us, it was in stolen moments between meetings, unplanned adventures and intentional pauses. We hope you experience the same kind of magic. Now go plan your trip, make a reservation or two and let Chicago romance you too!
