The Best Proposal Ideas in Chicago The Best Proposal Ideas in Chicago

The Best Proposal Ideas in Chicago

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Why propose in this city? Chicago’s location on the shores of Lake Michigan, the trove of architectural treasures, and abundance of off-the-beaten path romantic spots scattered around this massive city ensure that there’s truly something for every type of proposal. 

It’s easy to fall in love with its flourishing food scene, imposing architecture, and diverse, colorful neighborhoods. The nation’s third-largest city has so much to offer that it’s hard to pinpoint where exactly you want to have dinner, never mind where you’re going to pop the question to the one. A proposal is a day you’ll remember for the rest of your life, and you want every moment of it to be special enough to stick with you forever. And the first thing anyone talks about with a proposal is: “Where did it happen?” Luckily, we’ve got you covered. If you’re you’re going to get down on one knee in Chi-Town, these are the places that will ensure you and your special someone will never forget this moment.

Travel & Getting Around: The city’s located more or less in the middle of the country, making it easily accessible from just about anywhere. And it’s well-served from the air thanks to its two major airports: O’Hare — one of the world’s busiest and the hub for both American Airlines and United Airlines — and Midway, a major hub for Southwest Airlines. If you’re on a tight budget or just want to avoid the gridlock on the freeway, take the “El” from both airports into the city center or to many neighborhoods a bit outside the urban core. 

Being in the Midwest, Chicago gets snow in the winter. A lot of it. And it’s cold. Really cold. But it’s also a city of four seasons, so although winter can be bitterly cold and snowy, the summer is hot with long days — perfect for a day on Lake Michigan. Thanks to it being a city of seasons, Chicago can be perfect for a proposal all year round, depending on what kind you want. If a winter wonderland is your vision, Chicago’s for you. And if you want to be on the beach in a swimsuit, Chicago’s also for you.

Chicagoans are known for being no-nonsense folk who are kind but will never mince words. Despite its reputation as a tough and buttoned-up city, Chi-Town won’t fail to surprise you with plenty of spots that are sure to sweep your future fiancé or fiancée off their feet. Check out our list of the best places to propose in Chicago, with something for every type of person.

The Best Places to Propose in Chicago

  • Best Chicago Instagram Proposal: Cloud Gate (aka "The Bean")

    201 E Randolph St, Chicago, IL 60602, USA
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    Anish Kapoor’s Cloud Gate, also known as “The Bean,” is a sculpture that has been on every tourist’s must-see list since it was fully installed in 2006. And since the rise of Instagram, you can’t even say you’ve been to the Windy City unless you’ve posted a pic of this giant reflective work of art on your feed. It’s a tourist trap, yes, but if you could manage to clear the crowd just enough to get out of the frame of a photographer’s lens, you could have a dramatic and undeniably romantic proposal. Who can say no to a picture in front of an empty Bean? You’ll probably have to pay a pretty penny to clear out the entire area for your proposal, but if you don’t mind some other people in your photos, you could do this whole thing for minimal money. (Photo courtesy of Choose Chicago)

  • Most Chicago Proposal: The Signature Room at the John Hancock Center

    875 N Michigan Ave, Chicago, IL 60611, USA
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    Chicago is famous worldwide for its iconic architecture. One of the buildings that elevated the city’s profile on the world scene is the 1,500-foot-tall John Hancock Center. And on the 95th floor of this world-famous building, you’ll find The Signature Room, a Chicago institution since 1993. Treat your special someone to a romantic dinner, open a bottle of bubbly and pop the question far above the twinkling city lights below. It’ll be a night the two of you will never forget. (Photo courtesy of The Signature Room)

  • Best Fall Proposal in Chicago: Lincoln Park Zoo

    2001 N Clark St, Chicago, IL 60614, USA
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    Nothing says autumn like a big patch of trees with leaves changing colors all at once. If you’re planning a fall proposal, look no further than Chicago’s Lincoln Park, the North Side’s quintessential green space home to a famous zoo, among other things. What it also boasts, though, is impressive skyline views. And there’s a beautiful, stylized archway known as the Lincoln Park Zoo Pavilion that serves as a space for various classes and activities, but perhaps more importantly as a perfect frame for the iconic Gold Coast skyline. There’s no entrance fee to the park, so make an afternoon of it — bring a picnic and enjoy your time before roaming over to the pavilion and finally working up the courage to ask your significant other to spend the rest of your life with you. (Photo courtesy of Shutter Runner)

  • Best Proposal for Fitness Junkies in Chicago: Lakefront Trail

    Lakefront Trail, Chicago, IL, USA
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    If you’re a couple who enjoys staying fit together, plan your proposal for the Chicago Lakefront Trail, which lies on the eastern edge of the city and follows the Lake Michigan shoreline for 18 miles along a paved trail that’s open to pedestrians, runners, cyclists, and rollerbladers. The Trail passes through a number of Chicago’s best neighborhoods, like Edgewater, Lakeview, Lincoln Park, Hyde Park, and the South Loop, and the closer you get to the city, the better the background will be. The summer is when the Lakefront Trail is at its best, and thanks to the long days and late sunsets, there’s plenty of time to set up the perfect photos to remember this special day. Time the big ask to coincide with magic hour and you’ll have an almost impossibly romantic proposal. (Photo courtesy of Choose Chicago)

  • Most Artsy Proposal in Chicago: Museum of Contemporary Art

    220 E Chicago Ave, Chicago, IL 60611, USA
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    If you’re planning to marry someone with an eye for all things avant-garde and cutting edge, the Museum of Contemporary Art is the perfect spot for you to propose. The MCA has been one of the world’s largest venues for contemporary art since it opened in 1967, and has played host to some pretty incredible exhibitions over the years, including Frida Kahlo’s first U.S. show and Jeff Koons’ first solo show in a museum. It’s the perfect spot to bring someone who’s just a little bit more “enlightened” than the rest of us. A new wing was constructed in 1996, and it holds a geometric, spiraling staircase that would be a drop-dead gorgeous backdrop for a set of proposal photos. MCA doesn’t turn anyone away, but the suggested admission fee is $15 for adults, though it’s free for Illinois residents on Tuesdays. (Photo courtesy of the Museum of Contemporary Art)

  • Best Holiday Proposal in Chicago: Maggie Daley Park

    337 E Randolph St, Chicago, IL 60601, USA
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    Located in the northeast quarter of The Loop’s Grant Park, Maggie Daley Park has quickly become a wintertime hit for Chicagoans, in large part thanks to its Ice Skating Ribbon. Not your typical urban ice skating rink, the ribbon spans about a quarter of a mile in the shape of a … ribbon. Around the holidays, the park is decked out in lights and garlands, and its location in front of the Loop’s towering skyscrapers makes this a fantastic spot to pop the question in the cold winter weather. Let’s just hope there’s gently falling snow on the night you pick to add that extra dose of romance into the whole thing. (Photo courtesy of Maggie Daley Park)

  • Most Over-The-Top Proposal in Chicago: Willis Tower

    233 S Wacker Dr, Chicago, IL 60606, USA
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    Willis Tower — let’s be honest, though, everyone still calls it Sears Tower — is one of the most instantly recognizable buildings in the country, if not the entire world. What better way to make a statement that this girl or guy is the one for you than by taking them 1,353 feet up to the 103rd floor of the building to propose at The SkyDeck, or perhaps even inside The Ledge, a glass box that extends off the side of the building … 1,353 feet in the air — that’s over the top … of just about everything! Tickets to The Ledge cost $25 per adult, a small price to pay for memories and photos that will last a lifetime. (Photo courtesy of Skydeck Chicago)

  • Best Beach Proposal in Chicago: Oak Street Beach

    Oak Street Beach, Illinois, USA
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    Located in one of the more iconic corners of the city, where Lakeshore Drive takes a sharp turn and heads into the center of Chicago, Oak Street Beach is a sandy oasis in the middle of the concrete jungle that is Chi-Town. On a summer day, Lake Michigan really does seem like an ocean, with boats cruising off the shore, crystal blue waters, and no land in sight on the horizon. Save this spot for a summer proposal, as you’ll want to wait for the perfect and elusive magic hour — when the lighting is just right — to make your move. (Photo courtesy of Choose Chicago)

  • Best Restaurant Proposal in Chicago: Alinea

    1723 N Halsted St, Chicago, IL 60614, USA
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    Chicago’s dining scene is on par with some of the hottest cities in the country — if not the world — so anyone looking to keep it classic with a restaurant proposal will have a big decision to make. Luckily, one of the city’s most storied restaurants should certainly do the trick. Since 2005, Chicago’s Alinea has been wowing diners by putting on a show with each of the 18 to 22 courses that you’ll be served. It’s one of only 12 restaurants in the U.S. to receive a three-Michelin star rating and has been named the best restaurant in America three times. In other words, if you take your date here, you’re sure to impress. This is no casual date, however. The restaurant’s cheapest offering will run you $190 to $285 per person — without alcohol. (Photo courtesy of Alinea)

  • Best Bar Proposal in Chicago: Devereaux

    1112 N State St 18th Floor, Chicago, IL 60610, USA
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    Located on the 18th floor of the Viceroy hotel in Chicago’s Gold Coast neighborhood, Devereaux is a perfectly Instagrammable Art Deco spot where you can sip sophisticated cocktails in your best clothes before popping the question. In warmer months, there’s also an outdoor terrace with jaw-dropping views of the city skyline. Trimmed in metallic and gold, this spot would be ideal to rent out for you, your special someone, and all your friends to make it a night no one will be forgetting any time soon. (Photo courtesy of Devereaux)

  • Best Garden Proposal in Chicago: The Art Institute of Chicago

    111 S Michigan Ave, Chicago, IL 60603, USA
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    In a city of about three million people, it’s hard to find any spots that are away from the hustle and bustle of the city, but at The Art Institute of Chicago, there are two gardens — the North and South Gardens — where you’ll really feel a world away. With lots of tranquil fountains and plenty of greenery around, these gardens make for a perfect proposal that’s certainly off the beaten path of the rest of the city’s spots. Note, though, that the gardens are only open from around April to November, so make sure you’re aware of when you’re planning to pop the question if you’re going to pick this spot to do so. (Photo courtesy of The Cultural Landscape Foundation)

  • Best Proposal Spot for Urbanites: Cabana Club

    2018 W North Ave, Chicago, IL 60647, USA
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    Situated in Art Deco office building from 1929 at one of Chicago’s (in)famous three-way corners — at the intersection of Damen, Milwaukee, and North avenues — The Robey hotel is a supercool hangout in Chicago’s Wicker Park neighborhood, a rapidly gentrifying area that’s become a magnet for urban millennials. On the roof is a bar called the Cabana Club, which provides gorgeous panoramic views of the entire skyline as well as a tiny swimming pool. Rent out the space for you, your significant other, and a group of your closest friends and family members and you’ll have the perfect urban backdrop for the big question. Note that the Cabana Club is only open seasonally and will be open again in May 2020. (Photo courtesy of The Robey Chicago)

  • Best Proposal Location for a Sports Nut: Wrigley Field

    1060 W Addison St, Chicago, IL 60613, USA
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    There are few experiences in sports more iconic than watching America’s pastime at Wrigley Field in Chicago. Located in the appropriately named Wrigleyville area of the city, the ballpark opened in 1914 and is the nation’s second-oldest baseball stadium — Boston’s Fenway Park opened two years earlier in 1912. Home to the Chicago Cubs, Wrigley Field is the perfect place to take your sports-loving soulmate. Keep it low-key with an in-seat proposal, or pop the question with the assistance of the stadium’s video board. However you decide to do it, a proposal at Wrigley Field is sure to be remembered for years to come. Oh, and fly the W! (Photo by Michael Lehet)

  • Best Proposal for Adventure Seekers: In a Helicopter

    1339 S Wood St suite A, Chicago, IL 60608, USA
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    If your significant other is a thrill-seeker, book the both of you on a helicopter tour that will take you to new heights above Chicago’s world-famous skyline, and pop the question mid-flight. There are numerous operators to choose from, though several operators including Vertiport Tours have dedicated proposal packages that will provide you with a private helicopter tour, Champagne, chocolates, and a photographer and videographer (for an additional cost). A helicopter proposal above Chicago’s towering skyscrapers is sure to be a moment that will never be forgotten. You can expect to pay at least $850 for a proposal package. Still not enough? Plan your tour for the nighttime to make the setting even more dramatic — and romantic. (Photo courtesy of Vertiport Tours)

  • Best Proposal for a Luxury Lover: LondonHouse Chicago

    85 E Wacker Dr, Chicago, IL 60601, USA
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    Located at the corner of East Wacker Drive and North Michigan Avenue, the LondonHouse Chicago has been a staple of Chicago’s luxury hotel scene since 1923, underwent a total renovation, and joined Hilton’s Curio Collection in 2016. The renovation reestablished the hotel as one of the city’s top lodging options and has become a destination for fashionable Chicagoans thanks to its three-level rooftop space that provides unbeatable views of the Chicago River and the city’s skyline. On the top of the roof is a cupola that can be rented out for an unforgettable proposal. It comes complete with a bottle of Dom Perignon, a rose petal trail leading into the cupola, and a private dining room as a back-up plan in case the weather is less than ideal. It will set you back $1,000, but it’s money well spent for a high-end proposal that’s sure to wow your family and friends. (Photo courtesy of LH Rooftop)

  • Best Proposal for an Architecture Buff: University of Chicago

    5801 S Ellis Ave, Chicago, IL 60637, USA
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    Located in the Hyde Park neighborhood on Chicago’s South Side, The University of Chicago is one of the most picturesque sites in the whole city, with most of its original buildings designed to emulate the University of Oxford in England. Two of the best places on campus to pop the question are the very collegiate Main Quadrangle and the imposing Rockefeller Chapel. To be sure, when you’re standing in the Quad, you feel the history, knowledge, and the architectural significance of the place. The chapel takes up most of a city block and seats up to 1,700 people. Get the place to yourselves and the photos are guaranteed to be dramatic — and romantic. Bonus: Robie House, right across from the Quadrangle, is a Frank Lloyd Wright landmark building and open for tours. (Photo courtesy of the University of Chicago)

  • Best Proposal When You Want to Ball on a Budget: Navy Pier

    600 E Grand Ave, Chicago, IL 60611, USA
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    No discussion of Chicago is complete without a mention (or two) of Navy Pier, one of the most classic attractions in the city. Situated at the end of the pier is a gigantic Ferris wheel, called the Centennial Wheel, which was a replacement for an older, smaller wheel. The new wheel includes a special pod, known as the VIP Gondola, which can be rented out for a number of things, including a memorable proposal. You can rent out the entire car for $200, perfect for someone looking to make a big impact on a smaller budget. The VIP Gondola comes with a glass bottom, too, which means you’ll have epic views of both Lake Michigan and the city skyline. (Photo courtesy of Navy Pier)

  • Best Proposal for Someone Who Appreciates Serenity: The Alfred Caldwell Lily Pool

    125 W Fullerton Pkwy, Chicago, IL 60614, USA
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    If you and your significant other fancy a bit of calm and serenity in the middle of the nation’s third-largest city, consider a quiet, romantic proposal at the Alfred Caldwell Lily Pool, located within Lincoln Park on the north side of the city. Constructed in the late 1930s, the Lily Pool is a “hidden” garden within the huge park, is listed on the National Register of Historic Places, and designated as a National Historic Landmark. Alfred Caldwell designed the garden specifically to bring a bit of the calmer prairie lifestyle into the big city, complete with a Prairie School-style pavilion. There aren’t too many places in a city of almost three million people where you can be transported to a simpler time and place and pop the question with the sound of a gentle waterfall flowing in the background. (Photo courtesy of the Lincoln Park Conservatory)

  • Best Proposal for a Water Lover: On the Chicago River or Lake Michigan

    Chicago River, Illinois, USA
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    Chicago is a city on the water, which means that boats are an integral part of the life here — in the summer, at least. If your soulmate is most at home by the water, charter a yacht or a sailboat and go for a jaunt on the Chicago River or out on Lake Michigan and set up the perfect backdrop of Chicago’s glittering skyscrapers before getting down on one knee and popping the question. There are numerous charter companies to choose from, but you can expect to spend at least $1,000 for a sizable boat with a several-hour tour on a weekend day. (Photo courtesy of Choose Chicago)

  • Bottom Line

    Chicago is a city that has something for everybody. It has all the big-city attractions that make natural locations for a proposal, but also some hidden, under-the-radar spots where you can feel a world away from the hustle and bustle of city life. 

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