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Unforgettable Chicago Proposal Ideas & Best Places to Propose

You're ready to take the leap into marriage and you want your proposal to be special and memorable. Well, selecting the perfect spot to pop the question is crucial. Luckily, Chicago steps up to the plate with countless fantastic locations for your proposal. Whether you're after romance, breathtaking scenery, or a unique spot, we’ll help you uncover the best places to propose in Chicago. Surprise your partner with these amazing Chicago proposal ideas and make this moment unforgettable. 

When planning your marriage proposal in Chicago, it's essential to select a venue that resonates with you both. Picking a spot that holds sentimental value or aligns with shared interests adds a personal touch to this incredible life moment. Preparation is key, so scout your chosen location in advance, considering factors like privacy, lighting, and potential crowds. Don't forget to have a contingency plan for unpredictable weather, ensuring your big moment isn't dampened by rain or wind. Above all, prioritize creating a relaxed atmosphere where you and your partner can fully immerse in the joy of the occasion.

Best Time of Year to Propose in Chicago

As the weather heats up in the spring, Chicago comes alive with eye-popping flowers and a welcoming vibe that creates the perfect backdrop for getting down on one knee. Summer is another great option for a proposal, with its long days and stunning sunsets, giving you all the time in the world to find that perfect, Instagram-worthy spot. And don’t forget fall, when the city turns into a romantic scene straight out of a movie with all those incredible red and gold leaves. No matter the season, you've got beaches that catch the sunlight just right and parks that look like they've been waiting for your big moment. This is your call to make that proposal as epic as your love story! Get out there and make it happen.

The 16 Best Places to Propose in Chicago

Millennium Park - A Classic Choice

Location: 201 E Randolph Street
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour

In the heart of downtown Chicago lies Millennium Park, a favorite spot for a proposal amidst iconic city landmarks. The park's famed Cloud Gate sculpture, affectionately known as "The Bean," provides a reflective, mesmerizing backdrop perfect for the occasion. Beyond The Bean, the park's beautifully landscaped gardens and impressive cityscape views offer various romantic spots for getting down on one knee. Even more, you can heighten the ambiance by timing your proposal with one of the park's regular concerts or public events. While Millennium Park operates from 6 am to 11 pm, you'll want to keep in mind that peak hours and events may increase the number of spectators to your special moment.

Photo credit: Emma Mullins Photography

Lurie Garden - A City & Garden Proposal

Location: 201 E. Randolph St., between Monroe St. and Columbus Ave
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour

Pop the question at Lurie Garden, a magnificent five-acre sanctuary famed for its sustainable design and gorgeous perennial garden located at Millenium Park. This spot would offer a peaceful and visually striking setting for your marriage proposal. The contrasting scenery of native plants against the city's towering skyline provides a gorgeous backdrop, blending nature's beauty with architectural grandeur. Planning your proposal during the blooming season, from late spring through early fall, will showcase the garden at its most vibrant, making it a great choice for your special moment. In one word? Beautiful.

Photo credit: Christy Tyler Photography

Milton Lee Olive Park - A Secluded Proposal

Location: 500 N Lake Shore Dr, Chicago
Proposal Photography Permit: Not Required
Permit Fee: None

Step into Milton Lee Olive Park, a hidden gem away from the hustle and bustle, waiting to be the stage for your grand proposal moment! This isn’t just any spot; it’s where Lake Michigan meets the vibrant Chicago skyline, creating a magnificent canvas that's both wildly natural and unmistakably urban. For couples who chase extraordinary experiences, this park is the perfect spot for you to declare your love. Imagine—the privacy, the secluded paths, all leading to that one magical moment where you pop the question against a backdrop nothing short of spectacular. No permits, no fuss, just ensure you make your move before the clock strikes 11 pm. Here’s your chance to step up, embrace the moment, and mark the beginning of your forever.

Engagement at Milton Lee Olive Park - Chicago
Photo credit: JNA Visuals

360 CHICAGO - Sky-High Romantic Proposal

Location: 875 N Michigan Avenue
Proposal Photography Permit: Not Required
Permit fee: None
See Proposal Package

Transform your proposal into a landmark moment at 360 CHICAGO! Perched on the 94th floor of the former John Hancock Building, this observation deck gifts you a breathtaking 360-degree panorama that sprawls over Chicago and spills into the majestic Lake Michigan. Envision taking your love to new heights, proposing amidst a canvas of sunset or the city's luminous night lights. The Chicago Proposal Package is designed to fuel that romance with all the right touches. It offers you a private space with unmatched views, captivating "Marry Me" lights, a trail of rose petals, adrenaline-pumping TILT thrill ride tickets for two, and a duo of drinks from CloudBar's Sip Menu. Once there, you're invited to immerse yourselves entirely and stay as long as you like. Seize this opportunity to etch your moment in eternity, showcasing the unstoppable force of your love. Let 360 CHICAGO be the launchpad for your journey together. Propel your love story into the stratosphere, where it rightfully belongs!

Marriage Proposal at 360 Chicago

Lincoln Park - Nature's Beauty & Love

Location: 2001 N Clark St, Chicago
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session

Lincoln Park Zoo offers a whimsically romantic setting for those looking to pop the question amidst gardens, animals, architecture, and Chicago's skyline view. The enchanting backdrop of exotic animals and beautifully landscaped grounds provides a unique and lively atmosphere for a proposal. Whether you choose to kneel beside the tranquil swan pond, under the leafy embrace of the conservatory, or in front of your partner’s favorite animal exhibit, this location ensures an unforgettable moment. The zoo offers a playful setting that speaks to the adventurous spirit of love.

Lincoln Park Zoo in Chicago
Photo Credit: Paparazzi Proposals

The South Pond Bridge- For Nature Lovers

Location: Southern end of the zoo, east of Café Brauer  2121 N Stockton Drive
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session

Lincoln Park is a haven for nature lovers and a picturesque choice for a proposal. This expansive park is adorned with sprawling gardens, tranquil ponds, and scenic pathways, offering a variety of enchanting settings. Opt for a bridge overlooking the South Pond for a beautiful view that encapsulates the essence of nature in the city. Beyond its natural charm, this idyllic park is known for its peaceful ambiance that invites lovers to express their heartfelt feelings. Plus, with its proximity to neighboring eateries and fantastic cityscape views, your proposal can easily be extended into a romantic date, marking an unforgettable chapter in your love story.

The South Pond Bridge in Lincoln Park in Chicago
Photo credit:Paparazzi Proposals

The Alfred Caldwell Lily Pool - For a Secluded Proposal

Location: 125 W Fullerton Parkway Suite 4800
Proposal Permit: Required
Permit Fee: $150.00

Immerse yourself in nature's serenity at The Alfred Caldwell Lily Pool within Lincoln Park. This tranquil oasis is characterized by its meandering stone pathways, native plants, and, most notably, the picturesque lily pool that provides a serene and intimate location to pop the question. The Lily Pool is open to visitors from mid-April through early November, from sunrise to sunset.

Alfred Caldwell Lily Pool
Photo Credit:Nicole Defilippis Photography

The Honeycomb Structure - For Architecture/ Nature Lovers

Location: Southernmost end of the zoo, east of Café Brauer and Farm-in-the-Zoo 2121 N Stockton Drive
Proposal Photography Permit: Required
Permit Fee: $125.00

This architectural beauty in Lincoln Park creates a gorgeous setting for an engagement. The Honeycomb Structure, officially known as the People's Gas Pavilion, is a marvel of modern design, featuring a lattice-like steel network forming an expansive canopy above a lush green landscape. The interplay of light and shadow through its geometric patterns provides a visually stunning setting. Picture the moment you ask your person to marry you, enveloped by this architectural masterpiece, with nature as your witness. This spot not only offers a unique backdrop for such a pivotal moment, and also symbolizes the interconnectedness of your future together.

Chicago's Honeycomb Structure at Lincoln Park
Photo Credit:Caleb Schaftlein

Museum of Science and Industry - For Science Lovers

Location: 5700 S Lake Shore Drive
Proposal Photography Permit: Inquire 
Permit Fee: Inquire

Ignite a spark of discovery and innovation at the Museum of Science and Industry for your proposal. This place is especially appealing to couples who share a passion for science, exploration, and learning. This iconic venue, one of the largest science museums in the world, offers an extraordinary array of exhibits that provide a dynamic and interactive backdrop for popping the question. Imagine the excitement of proposing amidst groundbreaking scientific achievements, from standing under a massive suspended aircraft to the shadows of a towering dinosaur skeleton! It will be a moment that your loved one least expects. Check with Museum staff for any required permissions or fees related to events or photography. Operating hours vary, so make sure to plan your surprise around a time when your favorite exhibits are accessible.

Photo Credit:Ryan Inman Photography

North Avenue Beach - For Beach Lovers

Location: 1601 N. Lake Shore Drive
Proposal Photography  Permit: Not Required
Permit Fee: None

It's one of the city's most popular beaches, with some of the best views of the city and Lake Michigan, hands down! Imagine walking hand in hand along the sandy shores of North Avenue Beach, pausing as the sky is painted in orange and purple hues. At this moment, as the bustling city seems to stand still, presenting your beloved with the ultimate question here makes for an exceptionally picturesque and heartfelt moment. Not only is this location easily accessible, but it also does not require a permit for proposals, making it a cost-effective yet heartwarming choice. Keep in mind, though, that this public space is most peaceful during early mornings or late evenings.

North Avenue Beach one of the best places to propose in Chicago!
Photo Credit:Hanna Walkowaik

The Chicago Riverwalk - For A Scenic Stroll Proposal

Location: South bank of the Chicago River
Proposal Photography Permit: Not Required
Permit Fee: None

Take a stroll along the Chicago Riverwalk for an enchanting proposal experience. This waterside promenade weaves through the heart of the city with its captivating views. Lined with impressive skyscrapers and bridged by historic walkways, the Riverwalk provides a unique blend of natural beauty and architectural marvels. Choose a spot near one of the many iconic landmarks to pop the question, which will likely be very unexpected! The ideal time for a more serene moment would be in the early morning or late evening, avoiding significant crowd times, typically in the mid-afternoon and on weekends.

The Chicago Riverwalk: One of the best places to propose in Chicago
Photo Credit:Janet D Photography

The City Winery Chicago - For Wine Lovers

Location: 1200 W Randolph Street
Proposal Permit: None
Permit Fee: None; inquire about private space/dining and drink experience 

Do you and your partner love fine wines and an intimate setting? Look no further than the City Winery Chicago, which offers a lovely proposal location. Located on the vibrant Chicago Riverwalk, this venue combines urban sophistication with the charm of wine country, making it an idyllic spot for this special moment. With its customizable event spaces, you can curate an ambiance that reflects your love story, whether it's a private barrel room illuminated by candlelight or a scenic outdoor patio with river views. Although the City Winery does not require permits for small, informal gatherings, securing a private space for your proposal might involve a reservation fee and should be arranged directly with the venue. This ensures your moment is as seamless as it is memorable. Whether over a glass of their finest vintage or a custom dining experience, proposing at City Winery promises romance and tasty libations.

City Winery in Chicago - A Great place to propose
Photo Credit:Christy Tyler Photography

Buckingham Fountain - For Park & Fountain Lovers

Location: Center of Grant Park, 301 S Columbus Drive 
Proposal Permit: Required
Permit Fee: $35 application fee + $45 photography fee 

This historic fountain (Remember the opening scene of Married With Children?) is one of the largest in the world and provides a visually stunning background for your special moment with your love because of its rococo-style design and dazzling water displays. The fountain's water shows and Chicago's skyline in the background create a romantic atmosphere, especially during the evening light and music performances from April to October. For an added wow factor, plan for the proposal to happen when the fountain's water display is in full swing. The park is open from 6 am to 11 pm, offering flexibility for your proposal plans. However, be mindful of public events that might coincide with your planned date. Visiting the Buckingham Fountain will deliver a visually spectacular moment. 

Buckingham Fountain — A memorable place to propose in Chicago
Photo Credit:Ashley Hamm Photography

Chicago Botanic Garden - For Flower Lovers

Location: 1000 Lake Cook Rd, Glencoe, IL (20 miles from Chicago)
Proposal Photography Permit: Required 
Available daily 10 a.m., 12 p.m., and 2 p.m.
Permit Fee: $250 Includes parking for two passenger vehicles

Escape to a world where nature's beauty unfolds at every turn at the Chicago Botanic Garden. This sprawling sanctuary offers an idyllic setting for your proposal if your partner loves meticulously curated gardens and tranquil water features. Its vast array of landscapes, from the romantic English Walled Garden to the serene Japanese Garden, provides a variety of locations perfect for dropping to one knee. Choosing this location for your special moment ensures a backdrop filled with natural beauty and a tranquil atmosphere.

Chicago Botanic Gardens
Photo Credit:WS Photography

Navy Pier - For Amusement Park Lovers

Location: 600 E Grand Ave
Proposal Photography Permit: Not required
Permit Fee: Not required 

Looking for an engagement location that will deliver fun and energy? Navy Pier, stretching into Lake Michigan, offers a captivating backdrop for your proposal. This iconic Chicago landmark is home to the Centennial Wheel, providing a unique opportunity to pop the question high above the city with panoramic views of the skyline and lake. The pier's lively atmosphere, filled with gardens, restaurants, and attractions, adds a festive touch to your special moment. You won't have a private location, but you will have a blast for your big day.

Navy Pier Chicago Proposal
Photo Credit: Allison Williams Photography

London House Cupola - For An Elegant Proposal

Location: 23rd Floor, London House Chicago. 85 E Wacker Drive
Proposal Permit: Required
Permit Fee: Inquire

Perched atop the luxurious London House Chicago, The Cupola (a private outdoor section on the roof of London House) offers an intimate and breathtaking venue for a marriage proposal. This exclusive space boasts Chicago skyline views of the Chicago River, creating a dramatic and unforgettable scene. The Cupola's elegance and privacy make it ideal for a special moment away from the city below. The team at London House can top off your evening with a special dinner menu to celebrate your special occasion. 

London House Cupola - Best place in Chicago for a proposal
Photo Credit: Lakeshore in Love

Regardless of your selection, your Chicago Marriage Proposal is going to be grand! For more tips and ideas for enjoying Chicago, follow our blog for more information. 

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