Photographer : Rebecca Huang
The Best of | Chicago | Weddings

20 Best Places to Propose in Chicago

Where is the most romantic place to propose in Chicago? Good Question.

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. 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.

1. Ace Hotel Chicago

Dining area with Chicago skyline in the background at Ace Hotel Chicago | PartySlate

photo courtesy of & venue: Ace Hotel Chicago

For the hip urbanite…

Chicago, IL

  • 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

Ace Hotel Chicago

Chicago, IL

For an epic date night that ends in a memorable engagement, consider a hip hotel rooftop with break taking views.”

2. The Art Institute of Chicago

Bride and groom in of famous painting at The Art Institute of Chicago | PartySlate

photographer: Natalie Probst Photography

For the one with an artistic eye…

Chicago, IL

  • 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

The Art Institute of Chicago

Chicago, IL

3. Cafe Brauer at Lincoln Park Zoo

Bride and groom on green winding pathway at Cafe Brauer at Lincoln Park Zoo | PartySlate

photographer: Adams Photography

For the one who loves a unique experience…

Chicago, IL

  • 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

Cafe Brauer at Lincoln Park Zoo

Chicago, IL

4. Chicago Botanic Garden

Open gates at entrance of Chicago Botanic Garden | PartySlate

photographer: fourteensixteen

For the one with a green thumb…

Chicago, IL

  • 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

Chicago Botanic Garden

Chicago, IL

5. Adeline’s Sea Moose

A Beautiful and Surprising Buckingham Fountain Yacht Proposal at Chicago Private Yacht Rentals in Chicago, IL | PartySlate

photographer: Rebecca Huang

For the one who is always up for an adventure…

Chicago, IL

  • 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

Adeline’s Sea Moose

Chicago, Illinois

With such stunning backdrops at every turn, this vibrant city offers plenty of magical places to pop the question.”

6. City Winery Chicago

Dining area with by barrels behind paned glass and string lights at City Winery Chicago | PartySlate

photo courtesy of City Winery Chicago

For the one whose glass is half full…

Chicago, IL

  • 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

City Winery Chicago

Chicago, IL

7. Galleria Marchetti

Tented wedding at Galleria Marchetti with chandeliers and floral centerpieces | PartySlate

photographer: Tim Tab Studios

For the one who loves a big surprise…

Chicago, IL

  • 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

Galleria Marchetti

Chicago, IL

8. The Hoxton Chicago

Private event space with floor to ceiling windows and modern design at The Hoxton Chicago | PartySlate

photo courtesy of The Hoxton Chicago

For the eclectic enthusiast…

Chicago, IL

  • 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

The Hoxton Chicago

Chicago, IL

9. River Roast Social House

Outdoor area at the River Roast Social House with a chandelier and hardwood floors | PartySlate

photo courtesy of River Roast Social House

For the one who loves a dramatic view…

Chicago, IL

  • 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

River Roast Social House

Chicago, IL

10. RPM Events

Event space with couches and spherical lights at RPM Events | PartySlate

photo courtesy of RPM on the Water

For the romantic foodie…

Chicago, IL

  • 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)

RPM on the Water

Chicago, IL

For an epic date night that ends in a memorable engagement, consider an elegant restaurant with acclaimed cuisine.”

11. Shedd Aquarium

Two event spaces at Shedd Aquarium, outdoor dining area with pink floral centerpiece | PartySlate

photographer: WASIO photography Chicago

For the one who loves a grand photo op…

Chicago, IL

  • 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)

Shedd Aquarium

Chicago, IL

12. Somerset

Upscale restaurant with fancy bar area and modern design, Viceroy Chicago | PartySlate

photo courtesy of Somerset

For the trend-setter yet traditionalist…

Chicago, IL

  • 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


Chicago, IL

13. Theater on the Lake

Modern building with glass panels and vast view at Theater on the Lake | PartySlate

photographer: Grey Garden Creative

For the one who loves the lake…

Chicago, IL

  • 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

Theater on the Lake

Chicago, IL

14. Tortoise Supper Club

Red walls and chairs in private room at Tortoise Supper Club | PartySlate

photo courtesy of Tortoise Supper Club

For the holiday lover…

Chicago, IL

  • Unique Red Room space offers a whimsical and festive space to celebrate a holiday-time engagement
  • Mixologists on-site to create something special for the newly engaged couple
  • Celebrate with a Saturday date night in the Lounge for live jazz, moody lighting, and delectable cocktails

Tortoise Supper Club

Chicago, IL

15. The Newberry Library

Grand library proposal in Chicago in front of historical architecture building | PartySlate

photographer: JPP Studios

For the book lover and intellectual…

Chicago, IL

  • 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

The Newberry Library

Chicago, Illinois

16. Gibsons Bar & Steakhouse, Chicago

The Gibons Room at Gibsons Bar & Steakhouse, Chicago with hardwood floors | PartySlate

photo courtesy of Gibsons Bar & Steakhouse, Chicago

For the one who appreciates a classic date night…

Chicago, IL

  • 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

Gibsons Bar & Steakhouse, Chicago

Chicago, Illinois

17. Navy Pier

Miller Lite Beer Garden at Navy Pier at nighttime | PartySlate

photo courtesy of Navy Pier

For the local who knows that Chicago has a lot to offer…

Chicago, IL

  • 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

Navy Pier

Chicago, Illinois

18. Field Museum

T-Rex Sue at the Field Museum in Chicago with visitors looking | PartySlate

photo courtesy of Field Museum

For the explorer at heart…

Chicago, IL

  • 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

Field Museum

Chicago, Illinois

Iconic museums and cultural institutions offer an unforgettable day of engaging activities — along with one perfect photo op after another.”

19. Museum of Science and Industry, Chicago

Auditorium at Museum of Science and Industry, Chicago with blue lighting | PartySlate

photo courtesy of Museum of Science and Industry, Chicago

For the one who appreciates the mysteries at the heart of the universe…

Chicago, IL

  • 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

Museum of Science and Industry, Chicago

Chicago, Illinois

20. The Willis Tower

The Oak Room at the Metropolitan in the Willis Tower at Chicago | PartySlate

photo courtesy of The Metroplitan

For the daydreamer up in the clouds…

Chicago, IL

  • 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

The Metropolitan

Chicago, Illinois

But wait, there’s more:

Make sure to hire a top photographer to capture the moment you get down on one knee. Discover creative engagement photo ideas to make your proposal as picture perfect as can be. 

We’re not through yet:

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.