Top 12 Romantic things to do in Chicago

Last Updated on February 23, 2024 by Emily Johnson

Chicago is one of the most romantic cities in the United States. Known for its stunning architecture, vibrant culture, amazing food scene and lively nightlife, the Windy City has so much to offer couples looking for a getaway filled with passion, fun and lasting memories.

Lincoln Park StrollExplore gardens and conservatories in one of Chicago’s largest public parks.
Lake Michigan Sunset CruiseEnjoy evening cruises with skyline views and complimentary drinks.
Theater District ShowsExperience Broadway-style shows and productions in historic venues.
Chicago Botanic GardenVisit 27 gardens and four natural areas across 385 acres.
360 Chicago Observation DeckView the city from 1,000 feet above at the John Hancock Center.
Downtown Carriage RideTour downtown Chicago by horse and carriage past top attractions.
Live Blues and JazzDiscover historic blues clubs and intimate jazz venues.
Dinner with a ViewDine at sky-high restaurants or alfresco dining spots with panoramic views.
Millennium Park WalkEnjoy public art, lush gardens, and outdoor concerts.
Comedy at The Second CityLaugh together at this iconic improv and sketch comedy venue.
Sleigh Ride in NapervilleExperience one-horse open sleigh rides through Tunker Grove Forest Preserve.
Art Institute of ChicagoView iconic works and enjoy a romantic setting in one of the oldest US museums.

From picturesque walks through lush gardens to sunset cruises on Lake Michigan, exciting shows and concerts, cozy cafes and Michelin-star restaurants, Chicago has something for every taste and budget. Whether you want to pop the big question, celebrate an anniversary or simply treat your significant other to an unforgettable experience, Chicago won’t disappoint.

In this article, we have compiled a list of the top 12 most romantic things to do in Chicago that are sure to make your next trip full of romance.

1. Take a stroll through Lincoln Park and the Lincoln Park Conservatory

Name and Location: Lincoln Park is a 1,200 acre park located along Lake Michigan in the community area of the same name in Chicago, featuring the Lincoln Park Conservatory and Zoo.

History and Significance: Dating back to the 1860s, Lincoln Park is one of Chicago’s largest and most popular public parks. Key attractions include the Lincoln Park Zoo, Chicago History Museum, Peggy Notebaert Nature Museum, Alfred Caldwell Lily Pool and the Lincoln Park Conservatory.

What to Expect: Visitors can enjoy walking, running and biking along the park’s paths and trails, visiting one of its many attractions, or simply relaxing by the pond. The park hosts various concerts, festivals, and events during warmer months.

Visitor Information: As a public park, Lincoln Park is free and open daily from 6am-11pm. Parking garages as well as CTA bus and train routes offer accessibility with stops throughout.

Lincoln Park is one of the largest and most popular public parks in Chicago. The park’s beautiful gardens, scenic walking trails, charming cafes and free Lincoln Park Zoo make it a great place for a romantic stroll. Make your way over to the Lincoln Park Conservatory. This tranquil oasis features lush ferns, palms, orchids and other exotic plants from around the world housed in glass greenhouses. Admire the peaceful setting with your loved one and snap some photos surrounded by gorgeous greenery. Don’t miss the tranquil Japanese garden with arching footbridges and calming koi ponds.

2. Cruise Lake Michigan at sunset

Name and Location: Lake Michigan sunset cruises depart from Navy Pier, located along Chicago’s waterfront at 600 E. Grand Avenue in downtown along the shore.

History and Significance: Navy Pier has been a docking spot and recreational pier since 1916, with tour boats and dinner cruises departing daily – many offering a chance to take in romantic views of the Chicago skyline illuminated against Lake Michigan’s glittering waters at dusk.

What to Expect: Lake Michigan sunset tours typically last 1-1.5 hours as visitors relax onboard with a drink in-hand, listening to live commentary on Chicago’s architecture while soaking up magnificent golden hour vistas of the cityscape reflecting off the vast lake.

Visitor Information: Tours generally run May through October and cost $45+ per person. Advance booking through operators like Seadog or Shoreline is recommended, though walk-ups based on availability possible.

One of the most romantic things to do in Chicago is taking a sunset cruise on Lake Michigan. There are many operators offering evening cruise options with skyline views of the city. Cruises typically include complimentary drinks and snacks for a few hours of quality time on the water. Watching the sun dip below Chicago’s striking skyscrapers while cuddling with your special someone on the upper deck is an incredibly romantic experience. Some cruises even feature live music for that extra special ambiance.

3. Catch a show at the Theater District

Name and Location: The Chicago Theater District, also known as the Loop or Downtown theater district, spans along N. State Street from Congress Plaza to Randolph Street in downtown Chicago.

History and Significance: Dating to theaters built after the 1871 Great Chicago Fire, the early 20th century saw iconic venues like the CIBC Theatre and Cadillac Palace Theatre arise during Chicago’s cultural renaissance – many of which host Broadway tours today alongside Chicago’s vibrant comedy, improv and arts scene.

What to Expect: The Theater District dazzles with restored Art Deco marquees and grand lobbies across storied venues like the PrivateBank Theatre and James M. Nederlander Theatre hosting award-winning musicals, dramas, comedy shows and concerts from traveling productions and local talent.

Visitor Information: Individual theaters sell tickets for their programming and schedule tours of their historic buildings. Parking garages and metered street parking provide nearby access, along with CTA trains and buses.

Chicago’s Theater District, located in the heart of the Loop, is home to exceptional Broadway-style shows and productions. Treat your loved one to an evening of entertainment at one of these historic venues like the CIBC Theatre or Cadillac Palace Theatre. Popular shows like Hamilton, Wicked and The Lion King often run in Chicago. If you’re looking for something more intimate, try a jazz or comedy show at a smaller venue like The Greenhouse Theater Center. End the night with a romantic dinner nearby.

4. Stroll through the Chicago Botanic Garden

Name and Location: The Chicago Botanic Garden spans 385 acres across nine islands in Glencoe, Illinois, 25 miles up the shore of Lake Michigan just north of metro Chicago.

History and Significance: Opened in 1972, the Chicago Botanic Garden’s diverse gardens, woodlands and water features provide a living museum protecting over a million rare plants while educating visitors on conservation efforts around the globe through immersive exhibits.

What to Expect: Visitors traverse bridges and pathways viewing 27 distinct gardens like the tranquil Japanese garden, serene English walled garden, scenic waterfall garden and more across this National Historic Landmark, with events and classes offered year-round.

Visitor Information: The Botanic Garden is open daily 8am-sunset April-October with an entrance fee of $12-25 for access to all exhibits, trails and seasonal displays like the holiday lights.

Spread out over 385 acres, the Chicago Botanic Garden is home to 27 different gardens and four natural areas. The romantic English Walled Garden features cascades, pergolas covered in wisteria and thousands of tulips in spring. Other highlights include the serene Japanese Garden, the Grunsfeld Children’s Growing Garden and the Model Railroad Garden. Pack a picnic, rent a bike built for two, or dine at the Garden View Cafe. Every turn reveals new romantic photo backdrops like waterfalls, flowers and secluded benches.

5. Share the views from 360 Chicago Observation Deck

Name and Location: 360 Chicago Observation Deck overlooks the city and Lake Michigan from 875 N. Michigan Avenue on the 94th floor of the John Hancock Center skyscraper in downtown Chicago.

History and Significance: Completed in 1969 as one of Chicago’s original skyscrapers, 360 Chicago’s 1,000-foot-high observatory reveals unobstructed views of Chicago’s skyline and sweeping vistas spanning across Lake Michigan and four neighboring states from its floor-to-ceiling windows.

What to Expect: In addition to panoramic views up to 50 miles, the observatory features interactive multimedia displays explaining Chicago’s architecture and history alongside bars and open-air terraces on the 94th floor letting visitors enjoy bird’s eye perspectives high above the Magnificent Mile.

Visitor Information: 360 Chicago is family-friendly, open daily 10am-10pm with tickets $21-26. Advance online booking recommended for sunset visits. Bars serve drinks and small plates onsite.

Soar 1,000 feet above Chicago at 360 Chicago Observation Deck, located on the 94th floor of the iconic John Hancock Center. Panoramic views stretch for miles across Chicago, Lake Michigan and four neighboring states. The views are incredible at any time of day, but visiting at sunset when the city lights begin to twinkle is especially romantic. Purchase a cocktail at the bar to enjoy the views together. They also offer private tables and romantic packages for couples looking for extra special treatment.

6. Take a carriage ride around downtown

Name and Location: Chicago horse-drawn carriage rides meander through key downtown sights along Michigan Avenue, State Street, and Grant Park available for booking in multiple locations.

History and Significance: Though cars have replaced equine transportation, horse-drawn carriages help visitors tour Chicago’s past and present by clopping through key landmarks around the Magnificent Mile and Museum Campus, hearing little-known tales from knowledgeable guides.

What to Expect: Typical Chicago carriage tours last 20-40 minutes with stops for photos opp at attractions like Millennium Park’s “The Bean” sculpture. Blankets provide warmth during the ride while narration brings the city to life from new perspectives.

Visitor Information: Carriage rides can be booked via vendors at major downtown hotels and plazas like Michigan Avenue. Prices start around $45+ per carriage for groups up to 4 with private and special event booking available.

Channel a romantic movie scene and tour downtown Chicago by horse and carriage. Several companies offer private carriage rides that take you past many top attractions like Millennium Park, the Magnificent Mile, the Chicago Riverwalk and more. Cuddle under a blanket and enjoy the leisurely pace and intimate setting. Many carriages have clear plastic sides so you can still get great views and photos. Prices are generally 40 to 60 minutes for $100 to $200.

7. Listen to live blues and jazz

Name and Location: Chicago’s lively blues and jazz scene concentrates in neighborhood music venues across the city, centered downtown along State Street and robust in areas like Pilsen.

History and Significance: Chicago’s been pivotal in blues and jazz music history since pioneers like Louis Armstrong, Jelly Roll Morton and Benny Goodman arrived from New Orleans. Iconic clubs like Kingston Mines carry on traditions in a city considered America’s blues mecca.

What to Expect: Authentic Chicago blues and jazz clubs emanate a mix of gritty and sophisticated energy fueled by hearty drinks, finger-licking barbecue and skilled performers channeling soulful rhythms through vocals, bass, brass, keys and more as crowds cheer.

Visitor Information: Downtown venues like Blue Chicago and Jazz Showcase host nightly acts with $10-30 cover charges. Explore club-rich areas like Pilsen and Uptown using rideshare or CTA to catch a range of local artists.

Chicago has amazing live music venues, many featuring soulful blues and smooth jazz perfect for couples. Head to historic blues clubs like Buddy Guy’s Legends in the South Loop or Rosa’s Lounge in Logan Square. Andy’s Jazz Club is a popular intimate venue to hear talented jazz musicians. The Green Mill is an iconic 1920s-era jazz joint that inspired the show Cheers. Split a pizza and take in the nostalgic vibe.

8. Savor the views over dinner

Name and Location: Elevated dining options with panoramic skyline views can be found across downtown Chicago high-rises, like Cindy’s Rooftop at the Chicago Athletic Association Hotel overlooking Millennium Park.

History and Significance: As one of the world’s tallest cities filled with architectural icons, experiencing Chicago’s exceptional cityscape over a gourmet meal has been a bucket list fine dining pursuit for visitors and locals alike since legendary towers arose in the early 1900s.

What to Expect: Venues like Cindy’s feature craft cocktails and upscale American plates alongside unobstructed views of Chicago’s steel and glass jungle – including celebrated buildings like the Tribune Tower, Wrigley Building and Willis Tower through wall-to-wall or open-air vistas.

Visitor Information: Many rooftop restaurants require reservations be made 30+ days in advance. Business casual dress code; weather dictates indoor/outdoor seating. Cost ranges $$$.

Impress your date with dinner and drinks at one of Chicago’s sky-high restaurants. The 95th floor lounge at the Hancock Building has gorgeous city views from 1500 feet up. Other romantic options include Cindy’s rooftop patio bar overlooking Millennium Park, the elegant Alinea with fireplace seating, and the Signature Room on the John Hancock’s 96th floor with stunning views. If you prefer alfresco dining, visit trendy River Roast along the Chicago River or IO Rooftop with panoramic skyline views.

9. Walk through Millennium Park

Name and Location: Millennium Park spans 24.5 acres in the Loop area of downtown Chicago, bordered by Michigan Avenue, Randolph Street, Columbus Drive and Monroe Street.

History and Significance: Completed in 2004 on former rail yard space, Millennium Park has become a popular Chicago attraction and event venue, known for public artworks like Anish Kapoor’s Cloud Gate “Bean” sculpture, the facespouting Crown Fountain, and Frank Gehry’s Pritzker Pavilion bandshell.

What to Expect: Visitors enjoy exploring Millennium Park’s contemporary monuments with free access to lawns hosting fitness classes, food trucks and rotating cultural festivals from May through September against the epic backdrop of Chicago’s skyline.

Visitor Information: As a public city park, Millennium Park is freely accessible 24/7 with family-friendly walking paths. Parking garages nearby; CTA trains/buses stop steps away.

Millennium Park is one of the top attractions in Chicago, covering 24.5 acres in the Loop. The park’s public art installations, lush gardens, historic monuments and outdoor concert venue offer many romantic things to do. Snap photos in front of Cloud Gate aka “The Bean,” then head to the Crown Fountain’s two glass brick towers for a kiss under cascading water. Take a break at the serene Lurie Garden before enjoying a concert at the Pritzker Pavilion.

10. See a comedy show at The Second City

Name and Location: The Second City comedy club operates at 1616 N. Wells Street in Chicago’s Old Town neighborhood, known as the training ground for comedians like Tina Fey, Stephen Colbert, Bill Murray and more.

History and Significance: Founded in 1959 by Bernie Sahlins and alumni of the University of Chicago, The Second City pioneered improvisational theater through satirical revues and sketch comedy performances that became the foundation of late night shows and sitcoms over 60+ years while showcasing rising talent.

What to Expect: Shows like “The Best of The Second City” improvise zany sketches lampooning Chicago living, current events and human relationships through physical humor with minimal props, engaging audiences of locals and tourists with intimate, interactive comedy theater.

Visitor Information: Various shows perform Wednesday-Sunday year-round, typically 8pm & 11pm on weekends. Tickets $15-$55 available onsite, online, and by phone 1-2 months ahead. Food/drink minimums enforced.

Since 1959, The Second City has launched comedic legends from Alan Arkin to Tina Fey. This Chicago institution offers hilarious improv and sketch comedy shows every night of the week. Laughing together is a great bonding experience for couples and sets a lighthearted mood for the rest of your date. Ticket prices usually range from $15 for student rush seats to $55 for prime weekend shows.

11. Cozy up for a sleigh ride in Naperville

Name and Location: Horse-drawn sleigh rides amble along the paths of charming downtown Naperville just west of Chicago during the holiday season, departing from locations like Naper Settlement.

History and Significance: A throwback to earlier eras when sleighs traversed snow-covered lanes, horse-drawn rides celebrate old-time tradition allowing visitors to feel immersed in nostalgia while admiring village scenes straight from a Christmas card.

What to Expect: Bundled beneath cozy blankets, passengers toast with hot cocoa as Belgian draft horses lead tours across bridges and trails past historic buildings illuminated under twinkle lights and decorated trees, with holiday tunes filling the air.

Visitor Information: Naperville sleigh rides typically operate late November through December, weekends only with rides lasting 25 minutes. Fares $10 kids/$15 adults; private bookings available.

About 30 miles west of Chicago, the quaint suburb of Naperville offers romantic one-horse open sleigh rides from November through February. Bundle under wool blankets as you’re pulled through Tunker Grove Forest Preserve by a Clydesdale horse with jingle bells ringing. Afterward, warm up with hot chocolate or coffee. Rides cost $25 per person and last 25 to 30 minutes. Make a whole day of it by also visiting Naper Settlement, a living history museum set on 13 acres.

12. See priceless artworks at the Art Institute of Chicago

Name and Location: The Art Institute of Chicago occupies a grand Beaux-Arts building on 111 South Michigan Avenue along Grant Park in downtown Chicago, housing one of the oldest and largest art museums in the U.S.

History and Significance: Founded in 1879, the esteemed Art Institute collects iconic Western works spanning 5,000 years, including the largest holdings of impressionist and post-impressionist art anywhere. Its diverse masterpieces have cemented Chicago’s reputation as a world-class cultural capital.

What to Expect: Visitors view an Encyclopedia Brittanica’s worth of iconic paintings, sculptures, textiles, antiquities and more from revered artists like Monet, Van Gogh, Picasso, Warhol and Hopper across the Art Institute’s two million square feet of gallery space.

Visitor Information: Open daily 10:30am-5pm (Thu-8pm), the museum sits steps from the Loop charging $25 admission. Timed-entry tickets help manage capacity and should be booked online in advance when possible.

A date at the Art Institute of Chicago allows you to view iconic works by Monet, Renoir, Picasso, Warhol and more while admiring your own priceless work of art. Founded in 1879, it’s one of the oldest and most prestigious art museums in the U.S. Stand hand-in-hand before Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. Find a quiet bench to sit close together and take in a Monet waterlilies painting. End with cocktails at the chic Modern Wing restaurant Terzo Piano overlooking Millennium Park.


Chicago has no shortage of romantic things to do for couples seeking quality time together. From picturesque gardens and serene lake cruises to exciting shows, comedy clubs and breathtaking city views, the Windy City sets the perfect scene for romance. Pack an overnight bag and treat your significant other to a memorable Chicago getaway filled with beauty, culture, laughter and passion you’ll both cherish.

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