Chicago Proposal Spots

Romance is around every corner in Chicago. The windy city is the perfect place to propose, from the dreamy art-deco architecture to the cosy jazz clubs and sophisticated art scene. This is a once-in-a-lifetime event (no pressure!), so take some time to get your Chicago proposal right. In your search for the best places to propose in Chicago, consider the setting, time of year, and whether you want to propose in public or create a more intimate moment.

You’ll also want to think about how to capture the moment, whether by organising a surprise engagement shoot or a simple post-proposal selfie. At ​​Flytographer, we easily connect people with trusted photographers for fun photo shoots and have captured over three million memories worldwide. We asked our local photographers to show us around all the very best places to propose in Chicago.

TLDR

  1. Lincoln Park: Chicago’s largest park stretches seven miles along Lake Michigan’s shoreline and is bordered by the upscale Lincoln Park neighbourhood.
  2. North Avenue Beach: A beautiful and popular spot, with epic skyline views of the city from the sand.
  3. Chicago Riverwalk: A scenic 1.25-mile path connecting the lakefront with downtown along the Chicago River.
  4. Millennium Park: A stunning open space in the heart of downtown Chicago where art and nature meet.
  5. River Point Park: Chicago’s newest public park and a hidden gem!

Photo: Lukas in Chicago for Flytographer. Nicole and partner celebrate a proposal in Chicago with a proposal photoshoot at Lincoln Park.

Best time of day to propose

The best time of day to propose will depend on your location and the season. If you’re an early riser, head to Lake Michigan in the summer for a stunning sunrise. There will be fewer people around to watch if you’re feeling nervous! A dawn proposal is symbolic of the new start you’re making together, plus it gives you the whole day to enjoy as a newly engaged couple.

Night owls may be less enthusiastic about an early morning outing and suspicious if you suggest setting the alarm. In this case, a sunset stroll makes more sense.

Although sunrise and sunset are beautiful times to propose during the summer, mid-afternoon is better during the cold Chicago winter. Overcast skies will diffuse the bright sunshine, creating a beautiful soft light for romantic photographs. This is the perfect opportunity to bundle up and head out to downtown Chicago’s famous public parks, where romantic fountains and stunning sculptures add drama to the setting.

Photo: Lukas in Chicago for Flytographer. Aaron and partner celebrate a proposal in Chicago with a proposal photoshoot at the Buckingham Fountain.

Best proposal tips for Chicago

You know your partner best—will they love a public proposal or a secluded spot? Will they want to be all dressed up when they say yes, or are they comfortable in casual attire? Creating a moment they’ll enjoy is key to a perfect proposal.

Picking a great outfit is crucial, as you’ll both want to be comfortable but cute for your proposal pics. Try booking somewhere sophisticated for brunch or dinner, so you can dress up without arousing suspicion. 😘

If you’re an out-of-towner, note that Chicago weather can be unpredictable. A warm summer day can include an afternoon downpour, and snowfalls are common in winter. Springtime is notoriously unsettled, with temperatures whiplashing from freezing to triple-digits in some years.

A backup proposal location somewhere indoors like Lincoln Park Conservatory, Adler Planetarium or Shedd Aquarium is a good idea. 🌷🪐🐠

Photo: Joe in Chicago for Flytographer. Francisco and partner celebrate a proposal in Chicago with a proposal photoshoot at BP Pedestrian Bridge.

Best places to propose in Chicago

Chicago has many romantic places, but the perfect spot for your marriage proposal must speak to you as a couple. Whether you love spending time in nature, admiring art, or fine dining, Chicago has somewhere to inspire the special moment. A little local knowledge goes a long way, and our Chicago photographers know all the romantic spots and hidden gems of the windy city. Here are their top five picks.

Photo: Flytographer in Chicago. Jack Lee and partner celebrate a proposal in Chicago with a proposal photoshoot at North Avenue Beach.

1. Lincoln Park

Chicago’s largest park stretches seven miles along Lake Michigan’s shoreline and is bordered by the upscale Lincoln Park neighbourhood. Here are some of our favourite Lincoln Park proposal ideas.

  • The honeycomb structure

The Honeycomb, as it is affectionately known locally, is a walk-through art installation located in Lincoln Park Zoo. Inspired by a tortoiseshell, the graceful arch frames the city skyline beautifully.

  • Alfred Caldwell Lily Pool

    Designed as a hidden oasis to connect Chicago residents with nature, there are many quiet places to sit and reflect in this garden. It’s perfect if you’re looking for an intimate spot to pop the question. The pond is open seasonally from mid-April to November and is especially beautiful in the fall.

  • Bridge overlooking the South Pond

The bridge crossing Lincoln Zoo’s South Pond is popular for wedding portraits, and it’s easy to see why. The sweeping view of Chicago’s skyline is one of the city’s best. The soaring architecture contrasts with the park’s natural beauty, perfectly encapsulating Chicago’s motto: City in a Garden. 🌳

Photo: Lukas in Chicago for Flytographer. Mark and partner celebrate a proposal in Chicago with a proposal photoshoot at Lincoln Park.

2. North Avenue Beach

North Avenue Beach, located at 1600 North Lakeshore Drive on the shore of Lake Michigan, holds a special place in the hearts of Chicagoans. In summer or winter, North Avenue Beach is always beautiful and popular, with epic skyline views of the city from the sand 🏖️. It’s busier in the summer, so head there during dawn or dusk to avoid the crowds.

Photo: Francisco in Chicago for Flytographer. Cat and partner celebrate a proposal in Chicago with a proposal photoshoot at North Avenue Beach.

3. Chicago Riverwalk

The Chicago Riverwalk is a scenic 1.25-mile path connecting the lakefront with downtown along the Chicago River. You’ll find many gorgeous proposal spots along the way, including outside the historic Wrigley Building, on the steps that lead down to the river, or on one of the bridges. 

Photo: Amanda in Chicago for Flytographer. Jared and partner celebrate a proposal in Chicago with a proposal photoshoot at the Chicago Riverwalk.

4. Millennium Park

Chicago’s Millennium Park is a stunning open space in the heart of downtown Chicago where art and nature meet. It’s home to some of the city’s most iconic sculptures, like The Bean.

  • The Bean

    Cloud Gate, or The Bean, as it’s affectionately known, is a public art installation located above McCormick Tribune Plaza in Millennium Park. The 33-foot-high stainless steel sculpture by artist Anish Kapoor reflects the skyscrapers, sky, and the park’s nature.

     

Short walk to Buckingham Fountain

Take a short walk south past the Chicago Art Institute from Millennium Park to Buckingham Fountain in Grant Park. One of the largest fountains in the world, it’s a beautiful landmark and one of the best places to propose in Chicago.

Photo: Joe in Chicago for Flytographer. Chris and partner celebrate a proposal in Chicago with a proposal photoshoot at Millennium Park.

5. River Point Park

River Point Park is Chicago’s newest public park and a hidden gem! The riverside park is 1.5 acres of green space connecting Chicago’s stunning skyscrapers with the water. Check out Constellation, a fire-truck red sculpture outside the River Point building – one of the best places to propose in Chicago.

Photo: Amanda in Chicago for Flytographer. Price and partner celebrate a proposal in Chicago with a proposal photoshoot at River Point Park.

Brunch spots for two in Chicago

Michelin-starred North Pond in Lincoln Park boasts fabulous city views and is ideal for a sophisticated post-proposal Sunday brunch. For a casual experience, head to local favourite Batter & Berries, a Lincoln Park restaurant famed for its delightful French Toast.

Are you looking to start the celebrations early? Chicago has a competitive brunch scene, and Fremont pulls out all the stops to stay on top. You’ll find a buffet, bottomless mimosas, a DJ, and a donut wall at this vibrant venue. 🍹

Photo: Lukas in Chicago for Flytographer. Mohit and partner celebrate a proposal in Chicago with a proposal photoshoot at the Chicago Riverwalk.

Lunch spots for two in Chicago

Take time out from strolling the scenic riverwalk for mouth-watering Italian-influenced food at Gibsons Italia in Riverpoint Park. Set over three levels, this modern steakhouse offers a refined seafood and steak menu with an extensive wine list (including vintage champagne! 😉)

For the wow factor, book a table at Alla Vita, which serves Italian-American classics in a sophisticated setting. The weekday prix-fixe menu is a budget-friendly way to enjoy a luxury lunch.

Photo: Amanda in Chicago for Flytographer. Jeremy and partner celebrate a proposal in Chicago with a proposal photoshoot.

Rooftop bars in Chicago to celebrate

Show off that engagement ring in style in one of Chicago’s buzzy rooftop bars! Grab a table at the world’s largest rooftop bar at Offshore, on Navy Pier. The panoramic views of the city and the lake don’t disappoint. If that’s not high enough, take a spin on Navy Pier’s Centennial Wheel, inspired by the original Ferris wheel.

If you want to go all out, book the proposal package at LondonHouse Chicago. For one hour, you’re granted exclusive access to the luxury hotel’s stone cupola on the 23rd floor, where rose petals are scattered, and a chilled bottle of Dom Pérignon awaits. It’s a grand romantic gesture they’ll never forget. 🥂🤩

Spectacular views pair well with cocktails, so head to The Signature Room on the 96th floor of 875 North Michigan Ave (formally known as the John Hancock Building) for sunset. If that’s not high enough, Skydeck is located on the 99th floor of Willis Tower, the tallest building in Chicago and one of the biggest in the Northern Hemisphere. For a special surprise, book the Skydeck for a private dinner after closing and enjoy a romantic dinner in the sky!

Photo: Flytographer in Chicago. Mike and partner celebrate a proposal in Chicago with a proposal photoshoot at the LondonHouse Hotel Rooftop.

Make it a day to remember

Connect with a local Chicago Flytographer to help plan and capture this special moment forever. Chicago proposal photographers know all the best spots and how to handle the city’s changeable climate, so you can focus on popping the question. Bonus: you won’t have to rely on a passerby to take your first picture as an engaged couple! Here’s to happily ever after. Cheers!

“Amanda was amazing to work with! She was so helpful in planning the surprise proposal and making sure it went off without a hitch. On the day she captured the proposal perfectly, then seamlessly transitioned to directing/posing us for additional photos to help commemorate the occasion. 10/10!!”





Price

Amanda in Chicago

Custom Route

“Working with Lukas was an absolute pleasure! I was quite nervous for my proposal shoot but Lukas did a great job ensuring we were on the same page before the big day. The day of shooting was as perfect as could be! He was on time and took the time to get to know us during the shoot. He did a great job of making me and my fiancé comfortable with him and the posing aspect! I’d recommend Lukas to anyone looking for great photos.”





Mark

Lucas in Chicago

Lincoln Park

“Monica was kind, courteous, professional, and a delight to work with. I chose the Fly On The Wall scenario and she did a great job of blending in and not making it obvious! Once my fiance said yes she spent more than the allotted time I paid for and was very patient and kind during the entire shoot.”





Ryan

Monica in Chicago

Custom Route