Where is the most romantic place to propose in Chicago? After all, Chicago is home to a gorgeous lakefront, glittering skyline, and world-renowned restaurants and culture institutions. With such stunning backdrops at every turn, this vibrant city offers plenty of magical places to pop the question. At PartySlate, we know the best places to propose in Chicago.
For an epic date night that ends in a memorable engagement, consider a hip hotel rooftop with break taking views or an elegant restaurant with acclaimed cuisine. For an undeniably romantic setting, there’s lush garden spaces and city wineries. Iconic museums and cultural institutions offer an unforgettable day of engaging activities — along with one perfect photo op after another. No matter your style or personality, there’s a perfect Chicago venue awaiting you and your partner.
Make your engagement unique (not to mention, picture-perfect) by getting down on one knee at one of these romantic places in Chicago — or save them for your upcoming wedding shower, rehearsal dinner, or even wedding. And don’t forget to capture every special moment with a top Chicago photographer. Such a magnificent city (and of course, your love) deserves to be immortalized.
*In no particular order…
For the one with a green thumb…
- Experience 385 acres of lush-green garden space, tranquil lakes, and enchanting woodlands for a dreamy pre-proposal stroll
- For a unique experience, take a Grand Tram Tour to discover the majesty of this expansive green space just outside the city
- Head to one of the many beautiful gardens (such as the stately English Walled Garden or the lavish Rose Garden) for a romantic proposal site
For the one who loves a unique experience…
- Historic Prairie School-style landmark that boasts gorgeous skyline views over Lincoln Park’s South Pond
- The Great Hall at Café Brauer features soaring ceilings, stained-glass windows, and Tiffany-inspired chandeliers for a picture-perfect proposal site
- The close proximity to Lincoln Park Zoo means plenty of romantic walkways and photo ops
For the one who loves a dramatic view…
- Situated on the picturesque Chicago river with accessibility to river taxis for an exciting way to experience downtown Chicago
- Boasts stunning cityscape backdrops — especially at night — with twinkling lights from the surrounding buildings
- Celebrate your engagement with an outstanding dinner featuring an acclaimed menu created by James Beard award-winning Chef Tony Mantuano and Executive Chef John Hogan
For the one who appreciates the mysteries at the heart of the universe…
- Head to the largest museum in the Western Hemisphere and explore thousands of thrilling exhibits, such as a U-505 Submarine and the five-story Giant Dome Theater
- As the only remaining building from the 1893 World’s Columbian Exposition, this epic museum boasts jaw-dropping architectural details, making it a dazzling backdrop for a momentous engagement
- Consider hosting a magnificent wedding celebration under the 120-foot copper-domed ceiling of the Rotunda space or on one of the picture-perfect Outdoor Porticos near the Jackson Park Lagoon
For the one who loves a luxurious weekend getaway…
- Turn your engagement into a luxe weekend getaway at Waldorf Astoria Chicago Hotel in the heart of the Gold Coast
- This iconic hotel boasts Parisian charm, making it the perfect backdrop for a romantic engagement — without the need to hop on a plane
- Extend your stay and indulge in award-winning spa treatments, haute cuisine, and apartment-style rooms for an unforgettable and lavish experience
For the one who likes to be in the center of it all…
- Thompson Chicago is conveniently located in the heart of the Gold Coast, just steps away from sophisticated boutiques, historic mansions, and the beauty of Lake Michigan
- Get down on one knee before the iconic, arch-shaped floor-to-ceiling window in the Froines Room for the most stunning photo op
- Make sure to spend the night and enjoy everything from a bi-level penthouse loft to personalized service and elevated dining
For the Chicago history buff…
- Step inside Chicago History Museum, Chicago’s oldest cultural institution, for elegant Georgian colonial backdrops
- Propose in front of the building’s beautiful facade before taking a tour of the many riveting exhibits with unique photo ops such as the L car no. 1 or a vintage jazz club
- Spend the rest of the day enjoying nearby attractions such as a skit at Second City, a stroll through Lincoln Park, or head south to one of River North’s stylish restaurants for a romantic dinner celebration
For the romantic foodie…
- RPM boats many acclaimed restaurants, such as RPM Italian, RPM Steak, RPM Seafood, and RPM on the Water, for a romantic and elevated dining experience
- Celebrity couple Giuliana and Bill Rancic, as well as R.J. Jerrod and Molly Melman of Lettuce Entertain You Enterprises, team up to create an upscale dining experience that includes exceptional service and high quality ingredients
- RPM Italian is an especially romantic setting for an unforgettable dinner followed by a sweet proposal (and divine dessert)
For the daydreamer up in the clouds…
- Pop the question high above the clouds on the Skydeck at the Willis Tower and then head straight for a celebratory dinner and cocktails at the luxe, member-only Metropolitan (it’s worth joining, trust us)
- Pose for a picture (and get an adrenaline rush) on The Ledge, a glass balcony jutting out at 1,353 feet in the air
- Come back to celebrate your big day at one of the 16 private event spaces at The Metropolitan, complete with jaw-dropping views of the Chicago skyline
For the one with an artistic eye…
- Historic, world-renowned art museum with almost 300,000 works of art and awe-inspiring architectural details
- Features an impressive spread of galleries and gardens that offer ample opportunities to pop the question
- For an artistic photo op, head to the iconic Woman’s Board Grand Staircase or the sleek Bluhm Terrace in the Modern Wing with dazzling views of Millennium Park and The Pritzker Pavilion
For the one who loves a grand photo op…
- This world-renowned aquarium showcases 32,000 aquatic animals and numerous interactive experiences such as “Meet a Beluga” or a “Shark Feeding Tour”
- Propose in front of one of the magical Caribbean Reef & Aquarium Galleries or on the Lakefront Terrace with dramatic views of the Chicago skyline
- Stick around for an Instagram-worthy engagement party in the sleek Soundings event space that boasts stunning lake views and full access to the main aquarium galleries (as well as certain special exhibits)
For the one who loves beauty and romance…
- Located on the 95th floor of the John Hancock Building, The Signature Room at the 95th wows with unparalleled views of Lake Michigan and the Chicago skyline
- Enjoy a dinner for two or host an engagement party in one of the stunning Art Deco-styled private dining spaces for an unforgettable soirée
- Make sure to go one floor higher for a craft cocktail in the cocktail lounge; the views only get better
For the one who is always up for an adventure…
- Experience an intimate and romantic yacht ride on Lake Michigan with Adeline’s Sea Moose, a spacious 68-foot boat with a modern bar and lounge space
- Non-stop panoramic views of the Chicago skyline and Lake Michigan (from multiple deck spaces) makes this one of the best places to propose in Chicago
- Book a private yacht during the Navy Pier fireworks show or head on a destination charter to a nearby state for a wow-worthy proposal
For the Chicago rooftop enthusiast…
- The J. Parker offers dramatic rooftop views of both the Chicago skyline and Lake Michigan, ensuring your engagement photos are set against the most beautiful backdrops
- Rent out the rooftop for a post-engagement private party to celebrate your love and impending nuptials
- We especially love how this chic space has a fully-retractable glass roof for a weatherproof proposal in the Windy City
For the one who loves the lake…
- This historic Prairie-style building sits directly on the lake and offers sweeping city views, making it easily one of the best places to propose in Chicago
- Celebrate your engagement with dinner at The Lakefront Restaurant, drinks on the Lakefront’s Skyline Patio, and a show-stopping play at this intimate theater venue
- As one of Chicago’s only lakefront event venues, this unique space is also perfect for engagement parties, rehearsal dinners, and weddings
For the one whose glass is half full…
- Experience the beauty of Tuscany at this chic urban winery in downtown Chicago
- The Wine Garden offers a romantic, open-air space with ivy-covered walls and string lighting — making it a fairytale setting for a memorable proposal
- Enjoy a winery tour and tasting for a one-of-a-kind post-proposal activity, or create a custom-wine label for a treasured keepsake
For the explorer at heart…
- The Field Museum is one of the largest museums in the world, showcasing world-renowned exhibitions, artifacts, and scientific specimens
- Go for unique photo ops in front of the T-Rex named Sue in Stanley Field Hall or pose inside the three-story replica of an ancient Egyptian tomb
- Make sure to grab a souvenir at the gift shop for a keepsake of your most special day

For the book lover and intellectual…
- This grand research library, built in the Spanish Romanesque style, boasts soaring ceilings, large windows, and ornate detail work — making it a romantic and dramatic backdrop for your engagement
- Book lovers will adore the opportunity to discover over one million books that go back six centuries
- Make sure to head across the street to Washington Square Park for romantic photo ops
For the local who knows that Chicago has a lot to offer…
- While Navy Pier may be a world-renowned tourist destination, there’s nothing more romantic than a proposal high in the air on the iconic Centennial Wheel
- Spend the day and enjoy engaging activities such as a private charter, a stop at the Chicago Shakespeare Theater, and a psychedelic funhouse maze
- Celebrate post-engagement with family and friends at one of the many spectacular venues, such as the Lakeview Terrace with dazzling skyline views
For the one who loves a big surprise…
- Head to the tented Pavilion to experience the lush beauty of a European-style secret garden and the comforts of a 72-foot-long fire pit
- Host an epic engagement party in La Pergola, an open-air boutique with a retractable roof and delectable cuisine made on premise
- With its many terraces, dining halls, and gardens, Galleria Marchetti also makes a spectacular venue for an elegant wedding
For the trend-setter yet traditionalist…
- Set in the luxurious Viceroy Chicago, this upscale restaurant is inspired by American Country Club culture
- Features glamorous décor and gold-like lighting for a moody, romantic ambiance
- Part of the Boka Restaurant Group, with upscale American cuisine from Michelin starred Chef Lee Wolen
For the one who appreciates a classic date night…
- This iconic Chicago steakhouse is a favorite with couples looking to experience a delectable dining experience and exceptional service
- Pick a seat near the fireplace in the Gibsons Room for a romantic setting, especially on a blustery Chicago evening
- Consider returning to the place where your journey began and host an elegant wedding in one of the many refined venue spaces at Gibsons Bar & Steakhouse, Chicago
For the eclectic enthusiast…
- The Hoxton Chicago’s energetic, open-house vibe makes it one of the best places to propose in Chicago
- The rooftop pool offers sweeping city views for a dazzling proposal backdrop
- Celebrate getting engaged at one of the three acclaimed BOKA Group restaurants within the hotel: Cabra, Cira, and Lazy Bird
For the holiday lover…
For the hip urbanite…
- Hip hotel in the West Loop that is a quick walk from the vibrant Fulton Market and buzzing Randolph’s Restaurant Row
- Prairie Garden Terrace boasts expansive city views, a picturesque urban garden, and a bright-blue geodesic dome — as well as plenty of unique photo ops
- Head to Waydown, the Midwestern-style rooftop bar and lounge, for a post-proposal celebratory drink
- Don’t forget to book a suite or loft for a glam staycation in this vibrant Chicago neighborhood
Next Steps on PartySlate…
Make sure to hire a top photographer to capture the moment you get down on one knee. You can also find creative engagement photo ideas to make your proposal as picture perfect as can be.
Now that you’ve planned where to pop the question, it’s time to start thinking about an epic engagement party. Read Celebrity Event Planner Debi Lilly’s top tips for planning an unforgettable engagement party. For even more inspiration, check out these engagement party ideas.