Home» Chicago Marriage Proposal Ideas
Romantic Picnic Marriage Proposal
- Stumble upon a romantic setup on a park or beach that is set up ahead of time by a Proposal Planner
- Enjoy a romantic picnic for two in Chicago
- Propose while enjoying the views as the sun sets on the horizon
Moonlight Kayak and Dinner
Marriage Proposal
- Experience a private moonlit kayak ride down the Chicago River
- Disembark for a surprise riverside candlelight picnic
- Propose under the stars overlooking the moonlight river
Romantic Room Makeover
Marriage Proposal
- Romantic room makeover at the location of your choice
- Room is decorated with rose petals, LED candles, and pictures of you and your partner by a Proposal Planner
- Champagne and toasting flutes are provided
Musical Serenade Marriage Proposal
- Walk with your partner to one of Chicago’s iconic locations as you are approached by a musician
- The musician hands your partner a beautiful bouquet of flowers and serenades her with a beautiful love song
- After the song, you turn to your partner and propose
Skydiving Marriage Proposal
- Get your adrenaline fix and skydive with your sweetie
- Propose with a personalized “Will You Marry Me?” sign upon landing
- Celebrate with a champagne toast and take home commemorative glasses
Photo Tour Marriage Proposal
- Explore a famous or unknown part of Chicago on a fake “Walking Tour” arranged by a Proposal Planner
- Your partner thinks they are on a Walking Tour and a photographer is along taking pictures of your special day out
- Propose at a romantic location chosen by you and your proposal Planner and everything is caught on camera
Sand Sculpture Marriage Proposal
- Experience a unique moment on the beach with a customized sand sculpture featuring icons selected by you
- You and a Proposal Planner design a collage of up to 4 icons and have them crafted by professional sand sculptors prior to your arrival
- Propose with views of Lake Michigan and a gorgeous sand sculpture as your backdrop
Private City View Dining
Marriage Proposal
- Enjoy a romantic 4 course meal in a private dining room overlooking the entire city of Chicago
- Sip on Dom Perignon at your candlelit table decorated with a dozen roses
- Propose as a soloist musician plays romantic love songs
Private Limousine Tour Marriage Proposal
- Travel like a celebrity in a stretch limousine
- Experience an intimate tour of famous cites in Chicago designed by a Proposal
Planner - Limousine chauffeurs you to a romantic location for your proposal
Private Chef Marriage Proposal
- A private chef arrives at your home and prepares an exquisite meal
- You enjoy a candlelight dinner and listen to soft music in the background
- Propose to your partner and enjoy a glass of celebratory champagne
Private Helicopter Marriage Proposal
- Enjoy a private chartered helicopter tour for two arranged by a Proposal Planner
- Fly over downtown Chicago and see Millennium Park, Sears Tower, Navy Pier, and the magnificent skyline
- Celebrate with a champagne toast after you land
Custom Designed Marriage Proposal
- Your partner’s dream proposal is created by you and a professional Proposal Planner
- The perfect proposal location and vendors are hand selected by an experienced Proposal Planner
- Enjoy your stress free proposal and let your Proposal Planner handle all the details








