The Best Places to Propose in Chicago: Ideas for Every Style
Looking for the ideal place to propose in Chicago, or curious about where couples have been getting engaged over the past year? We analyzed recent proposal trends to see what’s popular today. While many Chicago residents choose to mark the moment in their own city (or even their own homes), many opt for destination proposals beyond state lines.
In this article, we’ll explore the most popular proposal spots among Chicagoans—from iconic local landmarks to romantic locations around the globe.
The Most Popular Place to Propose in Chicago
We analyzed roughly 2,000 Chicago Google searches to learn more about where people are interested in proposing. By a landslide, the most popular place to propose in Chicago is the LondonHouse Chicago Hotel. LondonHouse offers a picturesque rooftop, with beautiful 360 views of downtown and the Chicago River.
When it comes to overseas proposal locations, most Chicago locals search for the Eiffel Tower. It’s no surprise that this is a popular place to pop the question, as Condé Nast recently named Paris the third most romantic city in the world.
Venues and Proposal Hot Spots in Chicago, IL
In no particular order, local blogs frequently name the following landmarks and venues as top places to propose:
- NoMI Restaurant: An upscale restaurant with stunning Magnificent Mile and Lake Michigan views, ideal for an intimate, fine-dining proposal with a romantic cityscape backdrop.
- City Winery Chicago: A chic urban winery that combines elegant ambiance with handcrafted wines, perfect for couples who want a sophisticated, cozy setting with a personal touch.
- Milton Lee Olive Park: A peaceful lakefront park with skyline views and a quiet, tucked-away feel. It’s great for a private, heartfelt proposal by the water.
- Lurie Garden: Nestled in Millennium Park, this hidden gem offers a serene, floral-filled atmosphere in the heart of downtown, ideal for a nature-inspired city proposal.
- Chicago Botanic Garden: A sprawling, beautifully landscaped garden just outside the city—a timeless spot for a romantic, nature-centric proposal surrounded by flowers and greenery.
- Chicago Riverwalk: Lined with restaurants, views, and public art, the Riverwalk blends urban energy with waterfront romance, perfect for a scenic stroll and a spontaneous proposal.
- Sears Tower (Willis Tower): Propose on top of one of the tallest buildings in the world! The Skydeck offers breathtaking views and the thrilling Ledge experience for a sky-high “yes.”
- CloudBar: This elevated cocktail bar delivers panoramic city views with a modern vibe, ideal for a sleek, sky-high proposal at sunset or under the stars.
- Cloud Gate: More commonly known as “The Bean”, this iconic Chicago landmark in Millennium Park is a playful, artistic, and instantly recognizable backdrop for a memorable and public proposal moment.
- Music Box Theatre: This historic, vintage cinema offers a nostalgic and cozy atmosphere—perfect for film lovers or anyone seeking a unique, retro-inspired proposal in front of a cinema marquee.
- Lakefront Trail: With 18 miles of lakefront beauty, this trail offers endless scenic spots for an active couple to stop, take in the view, and pop the question.
- Promontory Point: Located in Burnham Park, this stone peninsula juts out into Lake Michigan, offering unbeatable skyline views and a peaceful, natural setting for a heartfelt proposal. For extra romance, wait until sunset.
- Navy Pier: A classic Chicago destination with vibrant energy, waterfront views, and the iconic Centennial Wheel—great for a festive, fun, and photogenic proposal.
- Lincoln Park Conservatory: Step into a lush, tropical world inside this historic glasshouse, perfect for a year-round, plant-filled proposal surrounded by exotic greenery.
- Alfred Caldwell Lily Pool: Alfred Caldwell Lily Pool is a quiet, hidden garden in Lincoln Park with winding paths, a still pond, and beautiful stonework. This peaceful spot offers a natural setting that’s perfect for a private, heartfelt proposal.
- Buckingham Fountain: One of the largest fountains in the world, it’s a dramatic and romantic backdrop, especially at night when it’s beautifully lit with music and lights.
- Garfield Park Conservatory: The Garfield Park Conservatory is a beautiful indoor garden filled with exotic plants and eye-catching architecture. It’s a peaceful, romantic spot that’s perfect for a proposal, no matter the weather.
- Baháʼí House of Worship: Located in nearby Wilmette, this architectural marvel offers a serene, spiritual setting with beautiful gardens, ideal for a meaningful and peaceful proposal.
- Architectural River Tour: Glide through the heart of Chicago on a romantic river cruise while taking in the city’s iconic skyline and historic architecture, perfect for a surprise proposal with a grand urban backdrop.
- Humboldt Park: Humboldt Park is a large, vibrant park with a scenic lagoon, historic boathouse, and plenty of green space. It’s a great spot for a laid-back, picturesque proposal away from the busy downtown. You can even rent swan boats and ask the big question on the water.
What types of proposals do Chicago locals prefer?
Data shows that the vast majority of proposal searches were surrounding local spots, including restaurants and rooftops. However, the most popular type of proposal Chicago natives search for is at the beach. Whether you decide to propose over a beachfront dinner or private sunset walk, beach proposals range from fancy to relaxed and intimate.
After the beach, the second most popular type of proposal is grounded and practical: at home. Chicagoans could be choosing to propose at home due to a mix of factors, like wanting to have a private intimate moment, rebelling against flashy proposal culture, or the pure practicality of saving money in today’s economy.
The third most popular type of proposal is restaurants. Whether you’re looking for a dazzling rooftop view, historic location, or gourmet dining experience, Chicago has a restaurant for every type of proposal.
How to Choose the Right Proposal Spot in Chicago
Choosing the perfect place to propose can be challenging – there are many moving pieces to consider, like making reservations, finding a photographer, or planning an afterparty. The most important factor you need to determine is whether you prefer a private or public location, and overall how many people you’d like around. Is inviting family and friends important, or do you (as a couple) prefer private one-on-one moments?
Our favorite private proposal spots
- Alfred Caldwell Lily Pool: This part of Lincoln Park is a hidden gem, tucked away from the city bustle. Its winding stone paths, a reflective pond, and total tranquility make it ideal for a quiet, heartfelt moment.
- City Winery Chicago: For a cozy, upscale indoor proposal, this stylish urban winery is warm and intimate. Between the ambiance and the wine, it’s a perfect blend of sophistication and privacy.
- Garfield Park Conservatory: With its lush indoor gardens and peaceful corners, this conservatory is perfect for an intimate proposal any time of year, especially if you’re looking for a nature vibe without weather worries.
Our favorite public proposal spots
- Buckingham Fountain: This iconic location is romantic, cinematic, and offers a wow-factor backdrop that feels straight out of a movie. Ideal for a classic, high-impact proposal moment.
- Promontory Point: A scenic, natural setting with sweeping skyline and lake views, especially stunning at sunset. It’s technically public but often peaceful enough to feel semi-private.
- Chicago Riverwalk: Energetic yet romantic, this bustling waterfront space has gorgeous city views and just the right amount of passerby buzz for a lively but meaningful proposal.
The Perfect Ring for the Perfect Spot
From iconic city landmarks to intimate at-home moments, Chicago offers endless inspiration for a memorable proposal. But no matter where you choose to pop the question, the most important detail is the ring—because it’s the one part of your proposal that lasts forever.
At Christopher Duquet Fine Jewelry, we specialize in crafting custom engagement rings as unique as your love story. Whether you already have a vision or need help designing the perfect piece, our team is here to bring your dream ring to life.Ready to start your forever? Let’s create something beautiful together—schedule a consultation with Christopher Duquet today.
Methodology
In April 2025, Christopher Duquet analyzed 1,970 Google searches surrounding proposal spots from March 2024 – February 2025.
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Fair Use
When using this data and research, please attribute by linking to this study and citing Christopher Duquet.
