Best Places to Propose in Chicago

You love Chicago, but you’re not sure where to propose. I got you! In this guide, I’m taking you through the city’s top spots for that big moment. As a photographer with over 8 years experience under my belt, mostly around Chicago, I’ve seen plenty of proposals, each as unique as the couple themselves.  Whether you’re looking for an epic city backdrop or a quiet, sentimental corner, I’ve got you covered. Get the lowdown on where to propose, plus some straightforward tips to make it a moment to remember, Chicago style. 

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Is Chicago a good place to propose?

Chicago has a vibe that’s just perfect for popping the question. It’s not just the buildings, though they are pretty cool with all their different styles, from sleek skyscrapers to those classic old beauties. And yeah, it’s kind of neat thinking about all the movies that have been shot here – it’s like you’re stepping into your own romantic film scene.

But really, it’s the feel of the place. Chicago has this unique blend of city buzz and cozy spots that makes it super special for a proposal. Whether it’s under the shadow of a towering skyscraper or in a quiet, historical corner, there’s a sense of being part of something bigger. So, if you’re thinking about asking that big question, Chicago’s definitely got the magic for it.

Best Places for a Chicago Rooftop Proposal

Couple embracing at LondonHouse, one of the recommend places in Chicago to propose.

LondonHouse Chicago Rooftop

If you’re thinking of a rooftop proposal, LondonHouse is a total gem. It’s right on Wacker Drive, up on the 22nd floor, so you’re getting those epic city views. It’s got this cool mix of old-school charm and modern style. Perfect for a romantic vibe.

Here’s the thing: it’s pretty popular, especially on weekends. So, if you’re looking for a quieter moment, maybe try a weekday or go earlier. Just remember to book ahead, this spot’s in demand! And hey, it’s right near the Magnificent Mile, so there’s lots to do around.

  • Address: 85 E. Wacker Drive, 22nd Floor, Chicago, IL 60601
  • Website: LondonHouse Chicago
  • Phone: +1 312-357-1200

Willis Tower Chicago Skydeck

Willis Tower Skydeck is another awesome choice for a proposal with a view. It’s way up on the 103rd floor, so you’re basically proposing in the clouds! The big draw is “The Ledge”, glass boxes that jut out from the building, giving you this crazy feeling of floating over the city. It’s a big hit for both locals and tourists, so it can get crowded. To dodge the long lines, try to go at an off-peak time, maybe early morning or on a weekday. It’s a bit pricey, but the views are worth it. Great for a high-in-the-sky, unforgettable proposal moment!

  • Address: 233 S. Wacker Drive, Chicago, IL 60606
  • Website: Skydeck Chicago
  • Phone: +1 312-875-9447
The view of Chicago from the observation deck at 360 CHICAGO.

360 Chicago

360 Chicago is all about the views – and what views they are! Sitting up on the 94th floor of the iconic building formerly known as the John Hancock Center, this place gives you a 360-degree look at Chicago’s skyline and Lake Michigan. But here’s the cool part: they’ve got TILT, a thrill ride that literally tilts you over the edge of the building for a heart-racing experience. It’s open daily from 9 am to 11 pm, so you’ve got plenty of time to soak in the sights. Perfect for a proposal that’s literally on top of the world!

  • Address: 875 N Michigan Avenue, 94th Floor, Chicago, IL 60611
  • Website: 360 Chicago
  • Phone: +1 888-875-8439

Cindy’s at Chicago Athletic Association Hotel

Cindy’s Rooftop at the Chicago Athletic Association Hotel offers an elegant and airy atmosphere, ideal for a romantic proposal. It’s known for its panoramic views of Millennium Park and Lake Michigan, adding a scenic touch to your special moment. The open-air terrace and chic indoor space provide a versatile setting, fitting for any weather. It’s a popular spot, so consider booking ahead to secure a good table, especially if you’re planning for a weekend. For a more relaxed experience, try visiting on a weekday or during off-peak hours.

  • Address: 12 S Michigan Ave, Chicago, IL 60603
  • Website: Cindy’s Rooftop
  • Phone: +1 312-792-3502

Best Restaurants to Propose in Chicago

Beatnik on the River

Beatnik on the River is a trendy spot located at 180 N. Upper Wacker Drive, known for its relaxed yet chic ambiance. It’s a great place to propose if you’re looking for a spot that combines great food, a cool vibe, and lovely views of the river. The outdoor seating is perfect for a sunny day, and the decor has a tropical feel which adds to the charm of the place.

This restaurant serves Mediterranean cuisine and is known for its cocktails, making it ideal for a romantic meal or a casual drink. It’s particularly good for small plates and vegetarians, and the atmosphere is suited for both casual and slightly more formal occasions.

  • Address: 180 N. Upper Wacker Drive, Chicago, IL 60606
  • Website: Beatnik on the River
  • Phone: +1 312-526-3345

Chicago Winery

Chicago Winery is a cool spot in River North. It’s got this great mix of a winery vibe with a city touch. Perfect if you want to propose with a glass of wine in hand. They’ve got the whole winemaking process on display, which adds a unique twist to the experience. Plus, they have a neat restaurant that serves up some tasty dishes. The place is all about sharing good times and great wine, so if that’s your scene, it’s worth checking out for a proposal or just a nice evening.

Website: Chicago Winery

Unique Proposal Spots in Chicago

Chicago Riverwalk

The Chicago Riverwalk is a fantastic spot for a stroll or proposal. It’s right along the south bank of the Chicago River and is bustling with public art, museums, water activities, and more. The vibe here is great, especially with the restaurants and bars along the path. It’s a scenic route through the city, perfect for seeing Chicago from a different angle. Plus, you can enjoy watching boats and the beautiful skyline. It’s a place that combines relaxation with the excitement of the city. Definitely a must-visit if you’re in Chicago!

Address: 22 E Wacker Dr, Chicago, IL 60601

875 North Michigan Avenue, the john hancock center view from Milton Lee Olive Park.

Milton Lee Olive Park

Milton Lee Olive Park is a hidden gem in Chicago. It’s this peaceful spot just north of Navy Pier, offering some amazing views. The park feels like a quiet escape in the middle of the city. It’s got nice grassy areas, perfect for a picnic or just chilling out. Plus, the views of Lake Michigan and the skyline are top-notch. If you’re thinking about a more low-key, scenic proposal spot, this park is a great choice. It’s a bit of a secret spot, so you might even have some privacy for your big moment!

Address: 500 N Lake Shore Drive, Chicago, IL 60611

Lincoln Park Zoo

Lincoln Park Zoo is a really unique place in the city, especially if you love animals. It’s one of the last free-admission zoos in the country, so that’s a big plus. They have over 1,200 animals, and you can take your time wandering around, checking out everything from seals and polar bears to penguins. It’s a great spot for a laid-back day, or even for a more casual, fun proposal if that’s your style. Plus, being right in the heart of Lincoln Park, you’ve got the rest of the park to explore too. Definitely a good pick for a relaxed, enjoyable day out.

  • Address: 2001 N Clark St, Chicago, IL 60614
  • Website: Lincoln Park Zoo
  • Phone: +1 312-742-2000

A Helicopter Ride with Heli Chicago

For an unforgettable experience, consider a helicopter tour with Heli Chicago. They offer a 45-minute Downtown Chicago Helicopter Tour for $795, covering 70 miles of flight. You’ll get to see iconic landmarks like Wrigley Field, Soldier Field, Adler Planetarium, “The Bean”, United Center, Navy Pier, and the Mag Mile. The price is for the whole helicopter, accommodating up to three passengers. It’s a unique way to experience Chicago from above.

  • ddress: 905 W Irving Park Rd, Schaumburg IL 60193
  • Website: Heli Chicago
  • Phone: (847) 602-1888

Millennium Park

Millenium Park in Chicago is a must-visit spot with iconic attractions like the Cloud Gate sculpture, also known as “The Bean.” It’s a great place for a romantic stroll or a unique proposal, especially with its beautiful open spaces and impressive city backdrop. The park is renowned for its artistic and architectural elements, making it a picturesque location in the heart of the city.

  • Address: 201 East Randolph Street, Chicago, IL 60601-6530
  • Website: Millennium Park

Calder’s Flamingo

Calder’s Flamingo is a striking piece of public art located in the heart of Chicago. Known for its bold, abstract design and signature red color, this sculpture stands out against the city’s tall buildings, making it a notable landmark in the area. It’s a great spot for art enthusiasts and those looking for a unique proposal backdrop, offering a blend of artistic flair and urban vibe.

Best Indoor Places to Propose in Chicago 

Rookery Building

The Rookery Building in Chicago is a historic architectural masterpiece, blending the designs of Daniel Burnham, John Root, and Frank Lloyd Wright. Its stunning light court and lobbies, remodeled by Wright, are a major draw. While most of the building is not accessible to the public, the ground floor and its beautiful lobby are open for viewing. It’s recommended to book a tour for a more comprehensive experience, though the lobby itself is worth a visit for its architectural beauty. For more information, visit the Tripadvisor page for The Rookery Building

Ignite Glass Studios

Ignite Glass Studios in Chicago is a unique venue that combines an art gallery, glassblowing classes, and event spaces. It offers a creative and artistic environment for events, making it an intriguing choice for a memorable proposal. The studio is located at 401 N. Armour Street in Chicago, IL 60642. You can contact them at (312) 465-2389 or via email at info@igniteglass.com. This venue is well-suited for those looking to add an artistic touch to their special moment.

For more information, you can visit their website.

Chicago Cultural Center

The Chicago Cultural Center, housed in the city’s former public library, is a stunning architectural gem. Renowned for its largest Tiffany glass dome, the building exudes historical charm and beauty. While it’s not a typical museum, it offers a glimpse into Chicago’s rich cultural and architectural history. The center hosts a variety of events and exhibitions, making it a worthwhile visit, especially since admission is free. It’s located near major attractions like Millennium Park and the Art Institute of Chicago, making it an easy addition to any sightseeing itinerary.

BONUS: Union Station

Union Station, right in the heart of Chicago, isn’t just your average train station. It’s a place where old-world charm meets the hustle and bustle of city life. With its stunning architecture and the iconic Great Hall, it’s like a little slice of history still alive in the modern world. It’s a cool, slightly unconventional spot for a proposal, especially if you love the idea of a grand, historic backdrop mixed with everyday city vibes.

Chicago Proposal FAQ

What do I need to get to propose?

Alright, so you’re gearing up for the big proposal? Here’s a relaxed rundown of what you might need:

  • The Ring: Pretty key item here. It doesn’t have to be the fanciest thing in the world – just something that says ‘you’ and ‘them’ all in one little sparkly package.
  • A Plan: Are you going big and public or sweet and private? Think about what would make your partner feel special. Maybe it’s a spot that’s meaningful to you both or just a chill night in.
  • A Backup Plan: Because, let’s be real, sometimes things go sideways. Rain, closed venues, lost reservations… you name it. Having a Plan B can save the day.
  • The Words: What do you want to say? You don’t need a speech, but a few honest words from the heart can mean the world.
  • A Camera or Photographer: If you want to capture the moment, either get a friend to hide in the bushes with a camera or hire a pro. 
  • Celebration Plans: After the “Yes!” (fingers crossed), maybe have something fun lined up like a nice dinner, a get-together with friends or family, or just a cozy night to yourselves.

Remember, the most important thing is the love you’re sharing. Everything else is just icing on the cake!

Is it a good idea to propose in public?

Public proposals definitely have their ups and downs. Like, if your partner is into big, showy moments, a public proposal could be a total hit. But if they’re more on the shy side, they might prefer something more low-key, just the two of you.

Public proposals can be super epic, but they’re not super private. And there’s always that bit of pressure – you know, how your partner might feel about everyone watching during such a big moment. Plus, you can’t really control stuff like weather or random people photobombing your big moment.

But hey, if you both love a bit of drama and excitement, a public proposal can be really romantic. Just think about what feels right for the two of you. There are quite a few public places in chicago to propose in without crowds. 

The Best Time of Year for a Chicago Proposal

In Chicago, each season has its charm for a proposal, but also a few things to consider:

Spring: The city blooms beautifully in spring. It’s a time of renewal, perfect for new beginnings. However, be mindful of the unpredictable weather, as rain showers can be frequent.

Summer: Warm and vibrant, summer in Chicago is full of life. The outdoor scenery is at its best, ideal for a sunny proposal. But it can get pretty hot and crowded, especially in popular spots.

Fall: Fall brings stunning foliage, creating a gorgeous, colorful backdrop. The weather is comfortably cool. Just remember, the days get shorter and the evenings cooler.

Winter: There’s a magical, snowy wonderland feel in winter, great for a cozy, intimate proposal. But Chicago winters can be harsh, with very cold temperatures and snowstorms, so plan accordingly.

Best time of day to propose in Chicago?

 In the summer, the best time to propose in Chicago would be around sunrise or just before sunset to avoid the intense heat and harsh sunlight. In the winter, a proposal in the early afternoon before the sun sets would be ideal to take advantage of the natural light and avoid the cold temperatures. Ultimately, the best time to propose will also depend on the specific location and setting you choose for your proposal. It’s always a good idea to consider the lighting and weather conditions to ensure that the moment is as magical as possible. 

How much are engagement/proposal photography packages?

The Novel – $2400

  • 3 hour session
  • Multilocation
  • Hair and makeup included
  • $500 print credit
  • Travel in Florida Included
  • Preview within 48 hours
  • High Res Digital Gallery
  • Tailored Planning Advice

The Story – $1200

  • 2 hour session
  • Multi-location
  • Preview within 48 hours
  • High Res Digital Gallery
  • Tailored Planning Advice

The Chapter – $800

  • 45-minute session
  • Preview within 48 hours
  • High Res Digital Gallery
  • Tailored Planning Advice

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