10 Best Places to Propose in Chicago (2025)

3. Chicago Riverwalk

The Chicago Riverwalk is a vibrant and scenic promenade that stretches along the Chicago River, offering a unique and romantic setting for a proposal. The waterfront views, combined with the bustling city life, create a lively yet intimate atmosphere. Proposing here in the evening, with the city lights reflecting on the water, ensures a magical and memorable experience.

4. Skydeck Chicago - Willis Tower

Proposing at the Skydeck of Willis Tower is an exhilarating and unforgettable experience, perfect for those seeking a unique and adventurous setting. As you step onto the glass ledge 1,353 feet above the bustling city, you'll be met with unparalleled panoramic views of Chicago, stretching out to the horizon.

5. Grant Park

Known as "Chicago's front yard," Grant Park is a sprawling green space that offers a beautiful and diverse backdrop for a proposal. The highlight of the park, Buckingham Fountain, is especially stunning during the evening light show, creating a captivating and romantic atmosphere.

6. Lake Michigan

Lake Michigan is one of the Great Lakes and offers a stunning and expansive backdrop for a romantic proposal. Its vast, clear waters, coupled with Chicago's beautiful skyline, provide a perfect mix of natural beauty and urban sophistication. Proposing at Lake Michigan gives you numerous options for scenic spots along its shoreline, ensuring a memorable and picturesque moment.

7. Vineyards

Located in Roselle, just outside of Chicago, Lynfred Winery is Illinois’ oldest and largest continuously operating family winery. The winery features beautifully landscaped gardens, a charming tasting room, and an elegant wine cellar. Situated in Long Grove, Valentino Vineyards & Winery offers a scenic and tranquil setting with its sprawling vineyards and rustic charm. The winery’s peaceful atmosphere and beautiful landscapes provide a perfect backdrop for a romantic proposal.

“Suzanne was amazing! I utilized the layaway service and it was a breeze. Ring made its way to Texas and was even more gorgeous in person."
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Romantic Destinations in Chicago

Chicago is full of romantic beaches and parks. These are some especially romantic locations for a proposal over a glass of wine, at a spectacular garden, or on a beautiful beach.

8. Montrose Beach

Montrose Beach provides a lovely and serene beach setting within the city, offering a perfect blend of urban convenience and natural beauty. The beach is less crowded, allowing for a more private and intimate proposal. The expansive views of Lake Michigan and the sandy shores create a romantic and tranquil atmosphere, ideal for a memorable proposal by the water.

If you and your partner are baseball fans, consider proposing at Wrigley Field, home of the Chicago Cubs. You can arrange for a special message on the scoreboard or a private tour of the stadium.

10. Chicago Botanic Garden

Located just outside the city, the Chicago Botanic Garden features beautiful gardens, including the Rose Garden and Japanese Garden, which are perfect for a romantic proposal. This lush and expansive garden spans 385 acres and features 27 distinct gardens, each with its own unique charm and beauty. The tranquil ambiance, filled with the sights and scents of blooming flowers and meticulously landscaped areas, creates a romantic and intimate atmosphere.

Best Places to Propose in Chicago

While it can be tempting to get wrapped up in elaborate proposal plans, sometimes the very best way to ask the question is a classic, heartfelt, on-one-knee moment. Whatever you and your soon-to-be fiance or fiancee enjoy, Chicago has beautiful and memorable places to propose. Make one of these romantic locations your special place by proposing with the perfect vintage engagement ring.

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Suzanne Sachs