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Chicago Engagement Ideas in 2024

Finding the right Chicago engagement idea can be an overwhelming experience. Whether you are looking for an extravagant proposal in Chicago or a private proposal idea with just you, your significant other, and a photographer like Shane Welch Photographers, the options are seemingly endless. We will break down the best marriage proposal ideas in Chicago.

Places to propose in Chicago

Top Proposal Ideas in Chicago

Here are our picks for the best ideas for a proposal in the windy city.

  1. Alder Planetarium
  2. Olive Park
  3. North Avenue Beach
  4. Chicago Riverwalk
  5. LondonHouse Chicago Rooftop

Alder Planetarium Proposal

Address: 1300 S DuSable Lake Shore Dr, Chicago, IL 60605
Cost: Free (no permit required)

Alder Planetarium stands as an enchanting spot for a proposal in Chicago, offering an outstanding view of the skyline as well as the lake. Nestled along the picturesque lakeshore, it boasts unparalleled views of the majestic Chicago skyline, providing a romantic backdrop that amplifies the magic of the moment. Against the shimmering waters of Lake Michigan, the skyline’s iconic architecture becomes a breathtaking panorama, setting the stage for an unforgettable engagement in Chicago.

Olive Park Engagement

Address: E Ohio St, Chicago, IL 60611
Cost: Free (no permit required)

Olive Park, nestled along the tranquil shores of Lake Michigan in Chicago, is a beloved spot for romantic proposals. With its breathtaking views of the iconic city skyline as a backdrop, couples find themselves immersed in a picturesque setting ideal for declarations of love. The park’s serene ambiance, lush greenery, and peaceful atmosphere create a perfect stage for popping the question, making Olive Park a cherished destination for unforgettable moments of heartfelt commitment and celebration.

North Avenue Beach Proposal

Address: 1600 N. Lake Shore Drive, Chicago, IL 60613
Cost: $45 permit

North Avenue Beach in Chicago presents an idyllic setting for a memorable proposal against the backdrop of the iconic skyline. As the sun casts its golden glow upon the sandy shores of Lake Michigan, couples find themselves immersed in a romantic atmosphere filled with warmth and serenity. With the gentle lapping of waves and the city’s majestic skyscrapers painting the horizon, North Avenue Beach offers a picturesque stage for declarations of love and commitment, creating cherished memories to last a lifetime.

Chicago Riverwalk Engagement

Address: 22 E Wacker Dr, Chicago, IL 60601
Cost: Free (no permit required)

When it comes to proposal ideas for Chicago, one of the first places that comes to mind is the Chicago Riverwalk. The Riverwalk offers incredible views where couples can be immersed in the picturesque skyline with the river serving as the backdrop. If you are thinking about an engagement on the Chicago Riverwalk, try to plan it for the summer.

Wriggly Building Proposal

Address: 400-410 Michigan Ave, Chicago, IL 60611
Cost: Free (no permit required)

One of the most iconic buildings in Chicago is the Wriggly Building. The building itself is not the only great view when proposing at this landmark. There is also a white stone railing that offers another breathtaking view of the city and the beautiful blue water of the river. During the holidays there are ample opportunities for an engagement photoshoot featuring the Christmas decorations.

LondonHouse Chicago Rooftop Engagement

Address: 85 E Wacker Dr, Chicago, IL 60601
Cost: Free (reservation required for seating)

One of the best rooftop proposal locations in Chicago is found at LondonHouse. The perfect place to propose is in the Cupola of love which offers a circular stage for you to get down on one knee and propose. Beyond the columns of the Cupola you will enjoy beautiful views of the skyline and river from above. Be sure to call and make a reserve a date well in advance as reservations can be hard to come by.

Lakefront Park Proposal

Address: 400 S DuSable Lake Shore Dr, Chicago, IL 60605
Cost: $35 permit

Lakefront Park in Chicago offers an ideal setting for a wedding proposal, with its serene ambiance and picturesque views. Couples can savor intimate moments amidst lush greenery and the sparkling waters of Lake Michigan, creating memories to cherish forever. The backdrop of the iconic skyline adds to the romantic atmosphere. However, one drawback to consider is the potential for crowds, especially during peak times, which may detract from the intimacy of the moment.

Wilmette Harbor Engagement

Address: 20 Harbor Dr, Wilmette, IL 60091
Cost: Free (no permit required)

Wilmette Harbor in Chicago offers a charming setting for a memorable proposal. With its scenic views of Lake Michigan and the serene ambiance, couples can create unforgettable moments against the backdrop of sailboats and the distant skyline. The harbor’s peaceful atmosphere lends itself well to intimate gestures of love and commitment. However, one drawback may be the potential for crowds, particularly during peak times, which could eliminate this spot for couples seeking a private place to propose in Chicago.

3 Arts Club Café Proposal

Address: 1300 N Dearborn St, Chicago, IL 60610
Cost: Free (no permit required)

3 Arts Club Café in Chicago offers an enchanting setting for a restaurant proposal. Nestled within the elegant Restoration Hardware store, it provides a sophisticated atmosphere with luxurious décor and gourmet cuisine, perfect for a romantic occasion. The café’s intimate ambiance and upscale charm create a memorable backdrop for declarations of love. However, a potential drawback could be the bustling atmosphere, which can be noisy at times.

The Rookery Engagement

Address: 209 S La Salle St, Chicago, IL 60604
Cost: $150 permit

The Rookery Building in Chicago offers a distinctive indoor setting for a memorable proposal. Its majestic atrium, adorned with ornate ironwork and bathed in natural light, provides a captivating backdrop for declaring love and commitment. The building’s rich history and architectural significance add an extra layer of charm and sophistication to the occasion. Proposing at The Rookery allows couples to immerse themselves in timeless elegance while creating cherished memories in a unique and memorable location.

Yacht Rental Proposal

Address: Varies
Cost: Starting at $250

Proposing on a yacht rental in Chicago offers an unforgettable and romantic experience. With various yacht rental and charter services available, couples can choose the perfect vessel to suit their preferences and budget. Enjoying the breathtaking skyline views while cruising along Lake Michigan creates a magical ambiance for the proposal. The best time for this idea is during the warmer months when the weather is pleasant and the lake is calm, typically from late spring to early fall, enhancing the charm of the moment.

Millenium Park Engagement

Address: 201 E Randolph St, Chicago, IL 60602
Cost: $45 Permit

Millennium Park in Chicago offers several enchanting locations perfect for a memorable proposal. The Cloud Gate sculpture, affectionately known as “The Bean,” provides a reflective and intimate setting, ideal for capturing the moment against the backdrop of the city skyline. The serene Lurie Garden, with its lush greenery and tranquil atmosphere, offers a secluded spot for a romantic declaration of love. Additionally, the enchanting promenades and serene Nichols Bridgeway provide picturesque settings for couples to create cherished memories amidst the park’s iconic landmarks.

Buckingham Fountain Proposal

Address: 301 S Columbus Dr, Chicago, IL 60605
Cost: $35 permit

While Buckingham Fountain in Chicago is a beautiful and iconic landmark, it may not be the most ideal spot for a proposal due to its bustling tourist activity and lack of intimate ambiance. The fountain area is often crowded with visitors, which could detract from the privacy and romance of the moment. However, some couples may still find the grandeur of Buckingham Fountain appealing for a proposal, especially if they don’t mind the presence of onlookers. Ultimately, the decision depends on the couple’s preferences and comfort level with a public proposal.

Chicago Engagement FAQs

Do you need a permit to propose in Chicago?

While not every location mentioned in our list of the best places to get engaged in Chicago require a permit some do. While you could technically get away with a proposal without a permit in Chicago, it is best to ensure that your proposal goes off without a hitch.

Are there any free rooftops for proposals in Chicago?

There are a number of great rooftop proposal locations in Chicago. While many of them are accessible for free, you will likely need to get a reservation well in advance.

What are some private proposal spots in Chicago?

If want a private place to propose in Chicago it is best to avoid the touristy spots. Some of the parks and even the Alder Planetarium are good places to go to get a great backdrop and few crowds.

Are you allowed to propose on the Riverwalk in Chicago?

Proposals on the Chicago Riverwalk are in fact permitted. The Riverwalk is one of the most popular places to propose if you don’t mind the crowds in the summer.

What are some romantic restaurants for proposals in Chicago?

Chicago offers a ton of great restaurants that make fantastic places for a romantic proposal. Some restaurants to consider include Adalina, Beatnik West Town and Bazaar Meat by José Andrés.

Final Thoughts

In conclusion, Chicago offers a plethora of captivating locations for unforgettable marriage proposals. From the romantic shores of Lake Michigan to the iconic landmarks such as Millennium Park and The Rookery Building, couples can find the perfect backdrop to begin their journey together. With its diverse array of settings and atmospheres, Chicago sets the stage for cherished moments of love and commitment.