25 Best Places to Propose in Chicago

Chicago has a glorious skyline, beautiful gardens and parks, a pretty lakefront, and world-renowned cultural institutions and restaurants. It’s no wonder many consider it a grand proposal venue. With its vibrant backdrops, this magnificent city boasts various magical places to pop the question. The choices vary from a romantic date night on a hotel rooftop to basking in nature in a botanical garden or getting cultural in a museum. Regardless of your preference, here are 25 great proposal venues.

1. Lincoln Park

Lincoln Park is the largest park in Chicago and stretches seven miles on Lake Michigan’s shoreline. Bordering the park is the upscale Lincoln Park neighborhood. Here are a few great proposal spots:

• The honeycomb structure is a walk-through art installation inside the Lincoln Park Zoo. It resembles a tortoiseshell, and its gentle arch creates a fancy frame of the city skyline.
• The bridge that overlooks the South Pond is a delightful bridge with a beautiful view of the Chicago skyline. The high architecture is a lovely contrast to the park’s natural beauty, and it ties in with Chicago’s “City in a Garden” motto!
• Alfred Caldwell Lily Pool is a beautiful hidden oasis that connects people with nature. There are several sweet spots to sit and unwind in this garden, and it’s an intimate option to ask your partner to marry you.

2. North Avenue Beach

You can find North Avenue Beach at 1600 North Lakeshore Drive via Lake Michigan’s shore. This venue is scenic and romantic with its blue waters, gorgeous city skyline views, and pretty shoreline. Whether winter or summer, North Avenue Beach is always breathtaking. It’s busier during summer, so planning your proposal for dusk or dawn is advisable to be free of the crowds.

3. Garfield Park Conservatory

Commonly called “landscape art under glass,” the Garfield Park Conservatory hosts thousands of plant species worldwide, set in eight indoor garden displays. It’s one of the country’s biggest and most beautiful botanical conservatories. You can visit all year round and feast your eyes on the lush flora and relax in the tropical indoor temperatures. In the case of rain, Garfield Park Conservatory is an ideal indoor location for popping the question in Chicago. Reservations are essential before your visit, and you have to book a permit online if you’d like your proposal to be photographed.

4. Chicago Riverwalk

There are several cute proposal points along this gorgeous Riverwalk, which is 1.25 miles long and connects the lakefront with the Chicago River downtown. The steps leading to the river outside the historical Wrigley Building or one of the many bridges are great spots for photographs.

5. The Osaka Garden | Garden of the Phoenix

This is one of Chicago’s glorious hidden gems and provides a unique, pretty proposal setting. A 10-minute stroll from the Museum of Science and Industry, it’s a nice secluded location. Imagine wooing your loved one with the sweet smell of flowers in bloom, lush greenery, and the soothing sound of slow-flowing water. This garden’s tranquility and beauty will only enhance your precious proposal moment and leave you with special memories.

6. Café Brauer – Lincoln Park Zoo

Café Brauer is a historic landmark that has a Prairie School style. You can view the amazing Chicago skyline overlooking Lincoln Park’s South Pond. A magnificent hall with stained-glass windows, high ceilings, and Tiffany-inspired chandeliers contribute to a majestic proposal venue. Due to being close to the Lincoln Park Zoo, it has several pretty walkways for those romantic couple shots.

7. Chicago Botanic Garden

This delightful 385-acre botanic garden has captivating woodlands, lush green gardens, and tranquil lakes, making it a magical proposal venue option. You could take a Grand Tram Tour to see the expanse of this majestic space from outside the city. Better still, there are various gardens to take your pick from for your romantic proposal.

8. Waldorf Astoria Chicago Hotel

If you’re feeling extra luxurious, include a fancy weekend getaway along with your proposal at the Waldorf Astoria Chicago Hotel. This iconic hotel is in the heart of the Gold Coast and has a Parisian feel, giving an ideal backdrop for the perfect proposal without needing a passport. After your partner has agreed to be yours forever, you can enjoy your stay at the hotel and indulge in an award-winning spa treatment and haute cuisine. You’ll enter dreamland in an apartment-style room for a lavish, memorable experience.

For those who love a luxurious weekend getaway.

9. Thompson Chicago

Another delightful location in the heart of the Gold Coast features a popular arch-shaped floor-to-ceiling window in the Froines Room, which promises an iconic photo op. Just a few steps away, you can find historic mansions and sophisticated boutiques and experience Lake Michigan’s beauty. You can spend a night here and experience elevated dining and personalized service in a bi-level penthouse. What a way to make your proposal memorable.

10. The Willis Tower

If your love is on cloud nine, why not propose there, too? The Skydeck at this magnificent tower lets you ask the most important question of your life high above the clouds. Afterward, you can have a delicious dinner with cocktails at the luxurious Metropolitan. It’s member-only but worth joining for an extra memorable experience. Get fantastic shots on The Ledge, a glass balcony extended in the air by 1,353 feet. That’s guaranteed to take your partner’s breath away! 

For the daydreamer up in the clouds…

11. Shedd Aquarium

The Shedd Aquarium is world-renowned and has 32,000 aquatic species and various fun interactive experiences like a Shark Feeding Tour or meeting a beluga. Besides the adventure, you can propose in front of the Lakefront Terrace, which has lovely Chicago skyline views, or the stunning Caribbean Reef & Aquarium Galleries. For those who’d like to include family and friends in their engagement, there are Insta-worthy opportunities in the Soundings event space. It has gorgeous views of the lake and provides full access to special exhibits and the main aquarium galleries.

12. Millennium Park

This is one of Chicago’s most popular parks and is home to The Chase Promenade, The Lurie Garden, The Great Lawn, The Jay Pritzker Pavilion, The Crown Fountains, The Boeing Galleries, Cloud Gate (aka The Bean), and Wrigley Square. The Bean, a towering sculpture, is one of Chicago’s most famous and popular icons. You’ll see Chicago’s skyline distorted and reflected on Cloud Gate’s mirror-like surface. Choose the ideal spot to propose to your special one from Millennium Park’s various options.

13. River Roast Social House

You’ll find the River Roast Social House on the scenic Chicago River. You can grab a river taxi for a unique way of experiencing downtown Chicago, and you may feel inspired to propose this way. Otherwise, River Roast Social House has magnificent evening cityscape backdrops with sparkling-lit buildings. To celebrate your engagement, you can host a fabulous dinner using their acclaimed menu by the James Beard award-winning Chef Tony Mantuano and Executive Chef John Hogan.

 14. Milton Lee Olive Park

Milton Lee Olive Park is an urban oasis found on Lake Michigan. It offers a secluded spot with peaceful walking paths, impressive skyline views showing Chicago’s John Hancock Building, and delightful circular fountains. It’s located east of Ohio Street Beach and north of Navy Pier.

15. The Signature Room on the 95th Floor

The 95th floor of the John Hancock Building hosts the Signature Room, which will take your breath away with its unmatched views of the Chicago skyline and Lake Michigan. You can spoil your betrothed with a dinner for two in an Art Deco-styled private dining area. One floor above, why not treat yourselves to a special cocktail in the lounge with even more spectacular views?

16. Ace Hotel Chicago

This West Loop hip hotel is a fast walk from the busy Randolph’s Restaurant Row and the energetic Fulton Market. It has a Prairie garden terrace providing vast city views, a blue geodesic dome, a picture-perfect garden, and many other photographic spots. The Midwestern-style rooftop bar, Waydown, is perfect for a post-proposal celebration. And for a glamorous staycation with your soon-to-be spouse, book a fancy loft suite.

17. Adeline’s Sea Moose

For something a bit different, opt for a romantic yacht treat with Adeline’s Sea Moose on Lake Michigan. The spacious yacht is 68 feet in length and has a lounge and modern bar. You’ll experience the continuous panoramic Chicago skyline and Lake Michigan views from various decks. And if you book a yacht when there’s a Navy Pier firework show, you’re bound to have a glittering proposal experience your partner will never forget.

For those who are always up for an adventure…

18. The J. Parker

This is another excellent proposal venue for rooftop view enthusiasts. The J. Parker offers fantastic views of Lake Michigan and Chicago’s glorious skyline for stunning photo backdrops. Additionally, for weather protection, you can utilize the fully-retractable glass roof. If you want to celebrate your engagement with those close to you, rent out the whole rooftop.

For the Chicago rooftop enthusiast.

19. City Winery Chicago

Keep your glass half full and experience the romantic feel of Tuscany with this urban chic downtown Chicago winery. It has an open-air romantic Wine Garden with string lighting and ivy-covered walls, creating a fairytale setting for a special proposal. You could also do a fun activity like a winery tour and tasting or get a custom wine label made as an additional proposal keepsake.

20. Navy Pier

Navy Pier is a well-known tourist destination, and a romantic proposal from the air in the iconic Centennial Wheel will be a great story to tell! You and your someone special can partake in fun activities, such as a psychedelic funhouse maze, a private charter, and a visit to the Chicago Shakespeare Theater. For a post-engagement celebration, choose from one of the many fantastic venues like the Lakeview Terrace, which has mesmerizing views of Chicago’s skyline.

21. The Hoxton Chicago

if you’re looking for a vibrant open-house feel for a proposal venue, Hoxton Chicago’s got you covered. There’s a rooftop pool area that gives you unending city views perfect for a proposal backdrop. There are three dazzling BOKA Group acclaimed restaurants to celebrate your engagement with family and friends. The Cira, Cabra, and Lazy Bird.

For the eclectic enthusiast…

22. Galleria Marchetti

This spot is ideal for those who want their proposal to be a grand surprise! You can experience a comforting 72-foot-long fire pit in the tented Pavilion and a beautiful European-style garden. There are several terraces, parks, and dining halls.

Host an epic engagement party in La Pergola, an open-air boutique with a retractable roof and delectable cuisine made on-premise

23. RPM Events

For the foodies, RPM events have many fantastic restaurants: RPM Steak, RPM Seafood, RPM Italian, and RPM on the Water. These guarantee you and your partner a memorable dining experience with high-quality ingredients and exceptional service. RPM Italian is more romantic, where you can seal your engagement with a heavenly dessert.

24. Chicago History Museum

The Chicago History Museum is one of the city’s oldest institutions and has marvelous Georgian colonial proposal backdrops. You can propose to your betrothed in front of the museum’s fantastic façade, then take a tour of the exhibits that promise unique photo ops. There are great nearby attractions like strolling through Lincoln Park, a skit at Second City, and choosing a Rover North fancy restaurant to have an engagement celebratory dinner.

For the Chicago history buff…

25. Theater on the Lake

This Prairie-style building set on the lake is one of the best proposal spots in Chicago. With great city views, it’s one of the only lakefront venues in Chicago, and ideal for a cozy post-engagement celebration party.

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.

Talk to a Diamond Expert

Your proposal venue is significant, but what good is a proposal without a ring? If you haven’t found one yet, Estate Diamond Jewelry has some exceptional vintage or antique engagement ring varieties. Contact us for assistance viewing our best options for your specific budget and design preference.