6 Chicago Proposal Packages—From Scenic Views to Romantic Picnics

Planning for a proposal can be a daunting task, which is why so many couples choose to use proposal packages that help guide the process. If you're planning to pop the question in the Windy City, these Chicago proposal packages are a great place to start. From scenic rooftops to romantic park settings, these packages truly showcase the best of Chicago. There are even custom proposal packages where you can choose a sentimental Chicago spot—or even your own home—to plan your proposal. With the help of a Chicago proposal planner, your dream engagement will come to life with ease. Whether you already have some ideas of how to propose or you are starting at square one, these proposal packages take all of the guesswork out of planning to ensure a seamless, stress-free experience.

1. Chicago Rooftop Proposal

Take advantage of breathtaking views with a Chicago rooftop proposal package from The Heart Bandits. Step off the elevator to a private rooftop terrace where you can pop the question with the dazzling lights of Chicago as your backdrop. In addition to booking the private rooftop venue, this package will give you access to a personal proposal planner to help facilitate the process.

• What's included: Private rooftop venue and professional proposal planner
• Price: From $2,049

2. Swanky Hotel Proposal

Photo: Drake Hotel

Chicago's Drake Hotel is a luxurious spot to plan your dream proposal. With a variety of packages to suit your personal preferences, you can rest assured that their team will handle all of the details of your proposal. Choose from the historic Sinatra Room, the starlight fountain or the charming gazebo as your Chicago proposal spot. You can also opt for add-ons such as dinner for two, a private photographer, overnight accommodations, flowers and chocolate-covered strawberries to enhance your Chicago hotel proposal package.

• What's included: One of three proposal spots, two cocktails or glasses of champagne and five photos with a professional photographer
• Price: Call The Drake Hotel for details.

3. Stunning Skydeck Proposal

Photo: Chicago Skydeck

The iconic Chicago Skydeck is a memorable proposal location that will take their breath away. Your proposal will occur on one of the five glass ledges with stunning views of the city and will be captured by Skydeck's in-house photo team. The 360-degree views of the city skyline at the Skydeck make the perfect backdrop for your engagement photos. Afterward, celebrate with your new fiancé and guests and pop some bubbly in the semi-private seating area.

---

FOR YOU

Private Proposal Ideas for the Two of You to Share

Create an intimate proposal à deux with these great private proposal ideas.

8 Las Vegas Proposal Packages for Your Big Moment

We've found exceptional Vegas proposal packages for you to explore.

15 Telltale Signs You're Ready to Propose

If you're thinking about taking the next step, you're already on the right track.

• What's included: Private proposal spot and professional photos
• Price: Call Skydeck for details

4. Park or Beach Picnic Proposal

Photo: Paparazzi Proposals

For the outdoorsy couple, a Chicago park or beach picnic is a romantic proposal spot. This proposal package in Chicago from Paparazzi Proposals includes everything you need for a surprise picnic proposal. Your partner will be left speechless when you stumble upon a picnic blanket decorated with red roses and a bottle of champagne. Afterward, you'll have a one-hour session with a professional engagement photographer to capture your special moment.

• What's included: A one-hour session with a professional photographer, picnic blanket, flower bouquet, sparkling cider with glasses and a consultation with a proposal expert
• Price: From $950

5. Customized Chicago Proposal Package

Photo: The Yes Girls

The Yes Girls have coordinated over 4,000 proposals since 2008 with their custom proposal packages. You tell them a little bit about your proposal ideas and budget, and they'll work with you to craft your dream proposal plan. Whether in Old Town, Lincoln Park or anywhere in between, The Yes Girls will go above and beyond to make your Windy City engagement special.

• What's included: Two custom proposal ideas, full-service planning and coordination and a personalized proposal day timeline
• Price: From $1,000

6. Scenic 360 Chicago Proposal

For a moment they'll never forget, surprise your partner with a scenic proposal at 360 Chicago. Whether you plan for dreamy sunset views or luminous night lights, you can't beat the jaw-dropping views at this proposal spot. You'll enjoy one hour in a private room where you and your new fiancé can take in the city views and celebrate this next chapter. One client called their 360 Chicago proposal "the ultimate way to celebrate our love for each other and this city."

• What's included: A private 360 Chicago space, Marry Me light-up letters, LED candles, rose petals, a 6' table with linens and a high-top table with linens and chairs
• Price: From $900/hour