10 Best Proposal Locations in Chicago
Chicago offers many romantic locations for a memorable proposal. Whether you’re seeking a peaceful park or a museum with breathtaking architecture, there’s a perfect place for every couple.
Here is a list of the top Chicago proposal locations to ask your partner to spend forever with you.
1. North Avenue Beach
Location: 1601 N. Lake Shore Drive, Chicago, IL 60611
With its breathtaking view of Lake Michigan and Chicago’s city skyline, North Avenue Beach has been a long time favorite. The beach itself, with the sound of the waves and stunning views of the water, offers a perfect spot for a proposal. If you’re seeking a more relaxed experience, the nearby grassy areas are perfect for enjoying a picnic before your proposal.
Here is a detailed guide on how to propose at North Avenue Beach.
2. Milton Lee Olive Park
Location: E Ohio St., Chicago, IL 60611
Milton Lee Olive Park is a hidden gem in the middle of downtown that makes it a popular spot for proposals: the beach, city skyline, and surrounding trees provide a beautiful setting. Make your proposal even more special by planning it around the sunset by the lake.
Thinking about a public proposal? Keep in mind that while the park offers stunning views and a romantic vibe, it’s not always completely private. Sometimes you’ll find joggers, cyclists, or the occasional tourist wandering through. If your partner loves a little excitement and doesn’t mind a few onlookers, the energy of the city in the background could make your moment feel truly epic. On the other hand, if they’re more on the shy side, you might want to scout for a quieter time of day or find a tucked-away spot near the trees for a more intimate atmosphere. No matter your style, Milton Lee Olive Park offers a balance of dramatic skyline and peaceful lakeside that’s hard to beat. Just remember to consider what feels right for both of you, whether that’s sharing the moment with the world or keeping it just between the two of you.
Here is a detailed guide on how to propose at Milton Lee Olive Park.
3. The Art Institute of Chicago
Location: 111 S Michigan Ave, Chicago, IL 60603
The Art Institute of Chicago has both historic artwork and stunning architecture. Not only are the interiors breathtaking, but the outdoor South Gardens has beautiful greenery in the heart of the city, especially in the spring when flowers are in full bloom.
If you and your partner are art lovers, this spot offers a truly romantic and refined atmosphere for your proposal. Wander through the galleries, pause in front of a favorite painting, or step outside into the peaceful gardens, there are countless corners to create a memorable moment. The grand staircase and iconic bronze lions make for classic proposal backdrops, while the museum’s blend of timeless beauty and contemporary design gives you endless options for a unique experience.
Here is a detailed guide on how to propose at The Art Institute of Chicago.
4. LondonHouse Chicago
Location: 85 E Wacker Dr, Chicago, IL 60601
LondonHouse Chicago is a popular location for both engagements and weddings. Available by reservation only, the Cupola at LondonHouse provides a luxurious and romantic atmosphere, offering a stunning city backdrop for your special moment.
Here is a detailed guide on how to propose at LondonHouse Chicago.
5. Chicago Botanic Garden
Location: 1000 Lake Cook Rd, Glencoe, IL 60022
The Chicago Botanic Garden is a perfect choice for nature lovers, with 385 acres of vibrant greenery. The expansive grounds also offer plenty of opportunities for a more intimate proposal, just be sure to check the weather. Find out more about this location on their website.
Here is a detailed guide on how to propose at the Chicago Botanic Garden.
6. The Rookery Building
Location: 209 S La Salle St, Chicago, IL 60604
The Rookery Building is a historic landmark celebrated as one of the best examples of early Chicago architecture. Available by reservation only, this building features stunning interiors perfect for an intimate proposal.
Here is a detailed guide on how to propose at The Rookery Building.
7. The Adler Planetarium
Location: 1300 S DuSable Lake Shore Dr, Chicago, IL 60605
With its breathtaking views of Lake Michigan and city skyline, the Adler Planetarium stands out as one of the most stunning spots in the city. Consider proposing at sunrise on the Skyline Terrace when the golden light creates a romantic atmosphere perfect for your unforgettable moment.
Here is a detailed guide on how to propose at Adler Planetarium.
8. Lincoln Park Honeycomb
Location: Lincoln Park Zoo, 2121 N Stockton Dr, Chicago, IL 60614
The Lincoln Park Honeycomb, officially known as Peoples Gas Pavilion, is a modern architectural gem. Nestled in Lincoln Park, this unique structure is surrounded by lush greenery, ponds, and walking trails. It’s open to the public and doesn’t require a reservation for a proposal.
Why Propose at the Lincoln Park Honeycomb?
This spot offers a perfect blend of urban and natural beauty. The honeycomb pavilion provides a backdrop for photos, while sweeping views of the city skyline peek through the arches, especially dramatic at sunrise or sunset. Set within the larger grounds of Lincoln Park, you’re just steps away from ponds, gardens, and shaded walking paths. It’s ideal for couples who want the best of both worlds: a private moment in the heart of the city.
Nearby Highlights to Make Your Day Extra Special
Lincoln Park Zoo: One of the last free admission zoos in the country, home to over 1,200 animals. Spend a day wandering the exhibits or strolling through the gardens.
Alfred Caldwell Lily Pool: Just a short walk away, this peaceful, historic garden is perfect for a quiet escape or a few extra engagement photos.
North Pond: Enjoy a scenic walk along the water or book a nearby restaurant for a celebratory meal after your proposal.
Whether you’re planning an intimate moment or want to explore everything Lincoln Park has to offer, the Honeycomb Pavilion lets you create a proposal as unique as your love story.
Here is a detailed guide on how to propose at the Lincoln Park Honeycomb.
9. Terrace 16 at Trump Hotel
Location: 401 N Wabash Ave 16th Floor, Chicago, IL 60611
Terrace 16 is the perfect spot for couples looking to celebrate their love in a luxurious and unforgettable way. Perched on the 16th floor of the Trump Hotel, this stunning venue features an outdoor rooftop patio with stunning views of the Chicago Riverfront for a truly romantic experience. Making reservations is required to propose here.
Here is a detailed guide on how to propose at Terrace 16 at Trump Hotel.
10. Garfield Park Conservatory
Location: 300 N Central Park Ave, Chicago, IL 60624
The Garfield Park Conservatory is one of the largest botanical conservatories in the country and is open year round, no matter the weather. If you plan to propose here, reservations are required.
Here is a detailed guide on how to propose at the Garfield Park Conservatory.
Additional Spots:
Ignite Glass Studios
Looking for something a bit more unconventional? Ignite Glass Studios, located at 401 N. Armour Street, Chicago, IL 60642, offers a creative and artistic environment that’s perfect for couples seeking a truly unique proposal. Here you can propose surrounded by glass artwork and afterward make your own glass keepsake together to celebrate. This dynamic venue blends art, hands-on experiences, and modern event spaces, making it a memorable choice for those who want a proposal as unique as their love story.
You can contact Ignite Glass Studios by calling (312) 465-2389 or sending an email to info@igniteglass.com.
Here is their official website for more information.
Millennium Park
Location: 201 E Randolph St, Chicago, IL 60601
Millennium Park is one of Chicago’s most iconic public spaces, making it a favorite destination for unforgettable proposals. Set in the heart of downtown, the park is famous for its vibrant blend of art, architecture, and green space. Couples come here for photos with the Cloud Gate (aka The Bean) and to take in the city views, gardens, and people.
What makes Millennium Park especially popular for a proposal? Its romantic ambiance is hard to beat, whether you’re strolling with the city’s skyline view or sharing a quiet moment by the Crown Fountain. Flexible, free, and open to everyone (no reservation required), this location truly offers something for every couple.
Chicago Riverwalk
Location: 22 E Wacker Dr, Chicago, IL 60601
The Chicago Riverwalk is loved by both tourists and locals in the heart of the city, a vibrant walkway stretching along the south of the Chicago River. With scenic river views, city skyline, and boats passing by, it has become an iconic backdrop of Chicago. Whether you’re looking for a lively atmosphere with restaurants and bars, or a quiet moment at sunrise, the Riverwalk offers both options for a beautiful proposal.
Enjoy public art, nearby museums, or simply enjoy downtown Chicago from a fresh perspective. The Riverwalk perfectly balances the energy of Chicago with calm moments, making it a favorite spot for many couples. No reservations are needed, just find your perfect corner, and let the city set the stage for your proposal.
Here is a detailed guide on how to propose at the Chicago Riverwalk.
Willis Tower Skydeck
Location: 233 S Wacker Dr, Chicago, IL 60606
If you’re dreaming of a proposal that feels like you’re floating above the city, Willis Tower Skydeck is hard to beat. High up the 103rd floor, the Skydeck features “The Ledge”, a series of all-glass boxes that extend out from the building, allowing you to stand 1,353 feet above Chicago with the city directly below your feet. With cityscapes stretching in every direction, it promises an unforgettable setting for popping the question. Keep in mind, it’s a popular attraction for both locals and visitors, so plan ahead and consider visiting during quieter weekday mornings for a more intimate moment.
Here is their official website for more information.
360 Chicago
Location: 875 N Michigan Ave, 94th Floor, Chicago, IL 60611
Want to propose 1,030 feet above Chicago? 360 Chicago is famous for panoramic views of the city and Lake Michigan from the 94th floor of the John Hancock Center. What really sets this place apart is “TILT,” a moving platform that tilts you outward over the city. Open daily from morning to late evening, 360 Chicago has the perfect city backdrop, whether you’re looking for golden hour or city lights.
Here is their official website for more information.
Union Station
Location: 225 S Canal St, Chicago, IL 60606
Looking for a proposal spot with lots of history? Union Station is an indoor venue right in the heart of Chicago. Known for its Great Hall, soaring ceilings, dramatic columns, and timeless marble, this iconic train station is a beautiful place to propose.
If you and your partner appreciate architecture or simply want a classic Chicago look in your engagement photos, Union Station is a good choice. It’s also a perfect backup proposal spot in Chicago if the weather forecast is looking bad. While it’s a public space with plenty of everyday hustle, a little timing and creativity can give you a quiet moment.
Here is their official website for more information or call 312-322-6777.
Calder’s Flamingo
Location: 50 W Adams St, Chicago, IL 60610
Calder’s Flamingo is an iconic red sculpture located in downtown Chicago. If you and your partner love modern art or you’re looking for a spot that's vibrant and colorful, Calder’s Flamingo is a great spot. I’ve done many photoshoots here and still love this spot!
The red color of the sculpture looks beautiful in photos and the open plaza means your proposal moment can happen right in the heart of downtown Chicago.
Romantic Restaurants for Proposing in Chicago
Chicago’s restaurants offer plenty of amazing proposal spots.
Beatnik on the River
Nestled along the Chicago River at 180 N. Upper Wacker Drive, Beatnik on the River pairs Mediterranean flavors with lush decor. The combination of riverfront views, creative cocktails, and atmosphere makes it a memorable spot for a proposal.
Chicago Winery
Located in River North, Chicago Winery allows you to toast with wine glasses in a beautiful space that’s both inviting and intimate. The restaurant offers seasonal dishes designed for sharing and if you’re looking for a twist, the wine barrels provide a unique backdrop to your proposal.
Helicopter Proposal Over Chicago
If you're hoping to truly take your proposal to new heights, a helicopter ride offers an unforgettable twist. Imagine proposing above the city’s most iconic landmarks, from Lake Michigan and Mag Mile to the rooftops of Wrigley Field and lights of Navy Pier.
A private helicopter tour isn’t just about the view. With room for up to three people, you can keep the moment intimate or invite a friend or photographer to capture the proposal.
You’ll cover 70 miles of cityscape in a single flight, leaving plenty of time for nerves to settle.
This high-flying adventure adds a sense of excitement and exclusivity to your engagement story. Your proposal will create a once-in-a-lifetime experience you’ll both remember for years to come.
Tips for Proposing in Chicago
Chicago offers countless romantic locations for a proposal. To ensure your engagement goes as planned, keep these tips in mind:
Photo Permit Requirements: Many locations in Chicago require a photo permit, especially if you're planning to reserve part of the space for a private event. Some venues can be slow to respond, so it's best to begin the planning process at least two weeks in advance.
Plan for Weather: Chicago’s weather can be unpredictable year-round. If you're planning an outdoor proposal, identify nearby locations as backup options. This way, you can quickly adapt and still enjoy your moment.
Add a Personal Touch: Thoughtful additions like a romantic picnic or a bouquet of flowers can make your proposal even more special.
The Essentials for a Smooth Proposal
Ring: At the heart of every proposal is the ring. Make sure it reflects your partner and your relationship.
Plan Ahead: Decide if you want your proposal to be public and grand or private and intimate. Choose a location that will be meaningful for both of you.
Have a Backup Plan: From rainy days to unexpected closures, things don’t always go as planned. Have an alternate location in mind just in case.
What to Say: You don’t need a long, memorized speech, but think about what you want to say from the heart. Those genuine words will mean the most.
Celebrate Together: After the proposal, plan something to celebrate, whether it’s a gathering with friends or family or simply enjoying the night together somewhere special.
Should You Propose in Public or Private?
Deciding between a public or private proposal is a big choice and there’s no one right answer. Both have their own advantages and drawbacks, so it’s important to think about what makes the most sense for you both.
Pros of a Public Proposal:
Memorable Atmosphere: Proposing in a public space like the Lincoln Park Honeycomb often creates an unforgettable setting, highlighted by Chicago’s beautiful backdrops.
Celebration: Some couples love the idea of sharing their proposal with nearby people, who might cheer and clap for you, turning your proposal into an exciting celebration.
Stunning Photos: Many public locations offer breathtaking scenery you just can’t get at home. If you want photos with Chicago’s skyline, a public venue has you covered.
Cons of a Public Proposal:
Less Privacy: Being surrounded by strangers can make an intimate moment feel a bit less personal, especially for those who shy away from the spotlight.
Unpredictable Weather: Weather and unexpected interruptions are part of public spaces.
Logistics: Photo permits, reservations, and timing all factor in (especially in Chicago).
A Private Proposal Might Be Best If:
Your partner prefers more personal moments over grand gestures.
You’re planning to have a large group of family and friends come along to celebrate.
The best option really comes down to your partner’s personality and what feels best in your relationship, as long as it reflects who you both are as a couple together!
Are You Ready To Get Engaged?
If you're ready to get engaged, then please contact me as soon as you can so I can help you plan your awesome proposal!
You can fill out this form at https://calebschaftlein.com/contact for more info!
You can check out my engagement pricing HERE!
I’m a Chicago Wedding and Engagement Photographer and would love to make your proposal extra special!
You can view more photos of Chicago’s best proposal locations on my blog.
