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Summer Proposal Ideas In Chicago

June 14th, 2024

As the summer sun warms the city streets and the skyline glistens against the blue sky, love is in the air, and what better time to pop the question than amidst the beauty and energy of the Windy City? Whether you're seeking a backdrop of glittering skyscrapers, serene lakeside views, or hidden gems off the beaten path, Chicago offers an array of unforgettable settings for that perfect moment. Join us as we explore the most romantic and picturesque spots to get engaged in Chicago.

Chicago Botanic Garden

Located in the northern suburbs of Chicago, the Chicago Botanic Garden features 27 gardens! Although selecting a specific location to propose at this location may seem daunting, a few popular gardens are the Rose Garden, Water Garden, and Japanese Garden. There’s a map that can be useful for planning your proposal location. If you plan on hiring a photographer, a photography permit is required, so be sure to contact Chicago Botanic Garden at 847-835-6801 or email customersupport@chicagobotanic.org.

Navy Pier

Navy Pier has so much to offer in beauty, history, and things to do. It’s a classically romantic location that can make for an excellent proposal spot. You can reserve a spot for a Navy Pier Dinner Cruise, taking in stunning scenery and dining on the lake. Navy Pier also has Fireworks on Wednesdays at 9 pm and Saturdays at 10 pm. The Ferris Wheel can also make for a romantic proposal spot, as long as you’re not afraid of heights! 

Top Of The Washington Library

Perched atop the Washington Library in Chicago lies a beautiful domed room, with skylights flooding natural light into the elegant space. Located on the 9th floor of the library, the atmosphere of what's called The Winter Garden creates an enchanting ambiance for a proposal. As the city hums with life below, the quiet intimacy of this place provides the perfect setting to pop the question, making it a truly unforgettable moment.


On a Chicago rooftop, the city's skyline stretches endlessly before you, creating a stunning backdrop for a memorable moment. If it’s evening you’ll have the city's lights twinkling below and the stars above, or the backdrop of classic Chicago architecture during the day. Against a breathtaking urban panorama, getting engaged becomes a cherished memory framed by the grandeur of the cityscape.

360 Chicago

The John Hancock observation floor has a beautiful view of the Chicago skyline and offers event packages, including proposal accomodations. You can view the city from all sides of the observation floor, admiring Chicago from above while you plan for the perfect moment to get down on one knee.

LondonHouse Chicago - The Copula

Photo Credit: anamariavieriuphotography

LondonHouse in Chicago makes for an elegant, picture-perfect proposal spot. Be sure to plan ahead for this one since reservations are required. LondonHouse is located in downtown Chicago with the Copula being a romantic domed arch with pillars on the LondonHouse rooftop overlooking a city view. Be sure to do your research and look into some proposal tips for proposing at this location. It is also ideal for an engagement photo session. Contact LondonHouse Chicago at 312-787-8500 or email rsvp@londonhouse.com to inquire about reserving the Copula. 


James & Sons loves to be part of your story, so be sure to tag us in any photos! And if you’re still looking for a ring, stop by any of our jewelry stores in Chicago, Naperville, Orland Park, and Schererville and we can help you find the perfect one.