10 Ideas to Help You Plan the Perfect Proposal in Chicago

It’s official! You’ve made the decision to propose to the love of your life. What better place to do so than the Windy City itself?! You realize that you want this to be the most PERFECT day for a proposal – which means you need to brainstorm the best spots and ideas to pull this thing off. But WHERE do you start? Don’t worry, I got you…Here’s 10 ideas to help you plan the perfect proposal here in Chicago!

1. Know What Events are Happening in Chicago

This is a big first step, and sometimes an overlooked one. Chicago is an amazing city, which means it’s home to some big events throughout the year – Lollapalooza, Taste of Chicago, Air and Water Show, Cubs games, and marathons… just to name a few. And some of these events will limit spots for your proposal. Barricades, traffic, parking, and people can all influence how all your ideas come together. So before you fall deep into planning, double check your date and preferred location for any local events at that time!

2. Consider Your Proposal Date when Booking Your Photographer

When deciding on your proposal date, being flexible is key while booking with your photographer. Since we’re in the business of weddings, A LOT of our weekends and Fridays are booked. This means you may need to be open to a weekday, or off-season weekend for your proposal if you’re wanting to book with an experienced photographer.

3. Choose a Location That Means Something to You

Proposing is more than just asking a question. It’s your whole past life with your partner falling into place for your future together! The location you choose should have significance for you as a couple. Whether it’s where you had your first date or a spot that represents your personalities, Chicago has tons of places that are perfect to share this amazing memory:

• Lincoln Park Conservatory: Greenery in the big city! A great spot for foliage AND great for a warm location in those colder or rainy months. 
• The West Loop: Known for its dining and nightlife, pop in and out of your favorite restaurants for some fun flash photos!
• Lincoln Park: From the honeycomb to the Alfred Lily Caldwell Pond, this location is great for that nature meets urban vibe. Plus it’s close to North Ave Beach and downtown Chicago streets for some different backdrops!
• Michigan Ave: Prime downtown feels. Bring your proposal ideas to life by stopping on the bridge or perusing the streets of Chicago for that genuine urban feel.

4. Understand That There will be People Around

With a population of 2.6 million and being a popular tourist destination, Chicago is ALWAYS bustling. Unless you’ve booked a private space, there will most definitely be people around. If your idea of a perfect proposal includes a more private moment, I’d recommend a sunrise proposal! There is always less commotion while the city sleeps, so many of the popular proposal spots will feel a little more intimate during this time, plus you’ll get some dreamy golden hour light!

5. Use Your Photographer’s Expertise

Once you’ve booked your photographer, don’t hesitate to ask questions and rely on them to help with the best strategy and tips. We want to help execute any ideas you have by guiding you on best locations, timing, lighting, etc to capture the BEST proposal!

6. Discuss the Proposal with Your Partner (Without Giving it Away!)

In the months leading up to the proposal, sneak in some well placed, intentional questions that will help determine what your partner’s dream proposal would be. Do they want something more intimate? Look into booking a private location or sunrise proposal. Would they prefer greenery or city vibes? Maybe your partner would also love to meet up with family and friends afterwards to celebrate, or perhaps a private dinner might be more their speed!

7. Come Up with a Plan to Get Them to Your Chosen Location

All your planning and prepping doesn’t work if we can’t get your partner to the proposal spot! You can work with your photographer for ideas and suggestions on the best way to get them to the location and what signal to give right before you pop the question.

8. Recruit Friends and Family to Help

This is a HUGE moment for you two, and there’s no doubt your friends and family will want in on this day. Don’t forget to ask them for help coming up with ideas on how, where, and when to execute the plans of your proposal in Chicago. From the brainstorming sessions, to helping get your partner to the chosen location, recruit them for all steps. You both will love looking back on this time knowing all your loved ones had a hand in writing your next adventure. 

9. Share Your Location with Your Photographer

THIS is so important to flawlessly execute your proposal (technology is an amazing thing)! Make sure you keep your photographer in the loop on where you’re at once you are headed to your chosen location. Chicago traffic can get wild, so sharing your location directly is the easiest way to do this without looking suspicious by being on your phone the whole time! This way there’s no lapse in communication and everything is up to date for your photographer to place themselves accordingly.

10. Be Present and Enjoy the Moment!

We can oftentimes lose ourselves in our own thoughts, technology, and anxiety. Your proposal is a moment you never will want to forget – so make sure you’re periodically refocusing on the moment with your special person. Your partner will love that you’re truly present, and you’ll love that you have this memory!

Planning your proposal should be as stress free as possible. Bring your ideas to life and make sure to follow these tips to have the best day (aside from your wedding day of course) for your proposal in Chicago. From choosing the perfect proposal spot, to sharing this moment with friends and family, I’m here to help document ALL the details of the beginning of your next chapter. Make sure to reach out to me if you’re looking for a photographer for this special day!