TOP 15 PLACES TO PROPOSE IN CHICAGO

There’s no shortage of amazing locations in Chicago to ask the most incredible person in the world to spend forever with you. We’ve narrowed the choices down to these popular locations featuring the top 15 places to propose in Chicago. 

Looking for a covered indoor location to propose in Chicago in case of rain or snow? Check out The Best Indoor Location to Propose in Chicago

We have built relationships at these locations and can assist in securing permits, videography, musicians, floral arrangements and candles to complete an experience that your fiancé won’t ever forget. 
 
We invite you to explore our list of the top 15 places to propose in Chicago, enjoy our Chicago Proposal Photography portfolio and connect with us to learn how we can help you find your perfect place to pop the question in the Windy City. 

• 15. Garfield Park Conservatory
• 14. Fullerton Avenue Beach
• 13. Garden of the Phoenix | The Osaka Garden
• 12. Buckingham Fountain
• 11. Milton Lee Olive Park
• 10. Ambassador Chicago Hotel Astor Terrace Rooftop
• 9. Chicago Riverwalk
• 8. Millennium Park
• 7. Chicago Museum Campus
• 6. Alfred Caldwell Lily Pool
• 5. North Avenue Beach
• 4. The Honeycomb | People’s Gas Education Pavilion
• 3. The Cupola at London House Chicago
• 2. Gibsons Italia at River Point Park
• 1. Bridge at The South Pond in Lincoln Park Zoo’s South Pond Nature Boardwalk
• The Best Indoor Location to Propose in Chicago

All Photos © Jason Kaczorowski Photography

15. Garfield Park Conservatory

Location: Garfield (James) Park

300 N Central Park Avenue
Chicago, IL 60624

Proposal Permit: Required
Permit Fee: $45 + $35 application fee
Website: https://garfieldconservatory.org

Chicago’s Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. Often referred to as “landscape art under glass,” the Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. Year-round, visitors can enjoy the lush flora and tropical temperatures indoors, or more than 10 acres of outdoor gardens, nature play spaces for children, water lily pond, and much more.

Garfield Park Conservatory makes a great indoor location in case of rain or snow but make sure you make a reservation before visiting and book your permit online if you plan to have a proposal photographer there to capture your “Yes!” Reservations are currently required as of Summer 2023 but are free. 

14. Fullerton Avenue Beach

Location: 2301 Lake Shore Drive at Fullerton 

1601 N. Lake Shore Drive
Chicago, IL 60611

Proposal Permit: Not Required
Permit Fee: None

This lovely lakefront location offers plenty of space for social distancing while delivering unparalleled views of the Chicago skyline.

Buzzing with joggers, cyclists and Chicagoans enjoying an evening sunset, this location offers it all!

Street parking is sparse but often available early along Cannon Drive. You may also opt to pay to park at the Lincoln Park Zoo’s public parking lot located at 2400 N Cannon Drive Chicago, IL 60614.

13. Garden of the Phoenix | The Osaka Garden

12. Buckingham Fountain

Location: Center of Grant Park, and between Queen’s Landing and Congress Parkway

Proposal Permit: Required
Permit Fee: $45 + $35 application fee

Known as the crown jewel of Grant Park is one of the largest fountains in the world. The size is meant to symbolize the enormity of nearby Lake Michigan and uses as much as 15,000 gallons of water per minute.

At dusk, Buckingham Fountain comes to life and really puts on a show. Head to the park after sunset and you’ll be treated to a spectacular light and music display every hour.

If you wish to enjoy the fountain during the day, beware the hourly, 20-minute water show featuring the fountain’s center jet shooting water 150 feet into the air.

The fountain – including lights – is active from Mid-May through Mid-October.

11. Milton Lee Olive Park

Location: Adjacent to Jane Addams Memorial Park, Ohio Street Beach, north of Navy Pier and west of the Water Purification Plant. 

Proposal Photography Permit: Not Required
Permit Fee: None

Olive Park was created in 1965 to commemorate Milton L. Olive, III, a Vietnam veteran and the first African American to receive the Medal of Honor, who grew up and lived in Chicago.

The secluded urban oasis on Lake Michigan offers serene walking paths, circular fountains and spectacular skyline views predominantly showcasing Chicago’s John Hancock Building. This tranquil green space is a hidden gem in Chicago even though it’s located just north of Navy Pier and just east of the popular Ohio Street Beach.

10. Ambassador Chicago Hotel Astor Terrace Rooftop

Location: State Street between E. Goethe & E. Banks

1301 N State Pkwy
Chicago, IL 60610

Proposal Photography Permit: Required
Permit Fee: Prices vary. Please inquire.

Inquire
312-787-3700

This Chicago Jazz Age landmark hotel features one of the only private rental rooftops for proposals in Chicago.  The Astor Terrace offers unforgettable Gold Coast views to pop the question.

The Astor Terrace is located on 17th floor Penthouse of the hotel and features a private powder room, indoor conservatory (in case of rain), and the outdoor terrace with teak-lined flooring. The terrace features views to the North, East with lake views and south to the city. The Astor Terrace is 682 square feet indoors and 645 square feet on the terrace for a total of 1327 square feet.  

The Ambassador was once filled with A-list guests, including Frank Sinatra, Humphrey Bogart, Marilyn Monroe and Lauren Bacall.

The history of jazz and entertainment has clearly left its imprint on the halls, and Ambassador Chicago combines this sense of nostalgia with touches of modern hospitality. Focused around affordable luxury, Ambassador Chicago provides stylish ambiance and iconic boutique lodging. A little bit 1930s and a little bit 2017, the balance has been found.

Ambassador Chicago, originally named Ambassador East, opened its doors in 1926. With a brief stint as Public Hotel, Ambassador Chicago’s new name is a nod to its roots. Known as Chicago’s first boutique hotel, iconic celebrity visitors of note include Bill Murray and The Rolling Stones. Known for its sweeping views of Lake Michigan and easy access to Michigan Avenue, the Windy City’s main shopping boulevard, this hotel sits at the heart of the Gold Coast.

The building was added to the National Register of Historic Places on June 6, 1979 and was listed as a Chicago Landmark on January 28, 1983.

9. Chicago Riverwalk

Location: South bank of the Chicago River; extending from Lake Shore Drive and Lake Michigan to Lake Street. 

Proposal Photography Permit: Not Required
Permit Fee: None

The Chicago Riverwalk is a multi-use public space located on the south bank of the main branch of the Chicago River, extending from Lake Shore Drive and Lake Michigan to Lake Street.

The 1.25-mile long path has been constructed in phases and includes four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade.  The Chicago River is a treasured natural amenity in the urban canyon of world famous architecture. The Riverwalk allows for close proximity to the waterway where you can often find urban kayakers paddling this major artery for the city’s most popular residential and tourism based businesses.

8. Millennium Park

Location: 201 E Randolph Street Chicago, IL 60602

Proposal Photography Permit: Required
Permit Fee: $45 + $35 application fee

Many consider Millennium Park to be Chicago’s most important project since the World’s Columbian Exposition of 1893. At a total cost exceeding $475 million, the 24.5 acre park is a prominent civic center on the northwestern border of Grant Park near the Lake Michigan shoreline. 

The city’s most popular park is home to the Lurie Garden, The Jay Pritzker Pavilion, The Great Lawn, The Chase Promenade, Cloud Gate (aka “The Bean”), The Boeing Galleries, The Crown Fountains and Wrigley Square.

It is said that you can’t come to Chicago without visiting The Bean, one of the city’s most famous icons. Unveiled in 2005, British artist Anish Kapoor created her first outdoor public sculpture in the United States, and one of the largest sculptures of its kind in the world. The city’s skyline is reflected and distorted on Cloud Gate’s silky mirror-like surface which was inspired by liquid mercury.

Frank Gehry’s one-of-a-kind bandshell stands 120-feet tall, with a flowing crown of stainless steel ribbons and curving steel plates that make it a stunning and surreal place to see live entertainment. Plus, the pavilion has a state-of-the-art sound system designed to mimic the acoustics of an indoor theatre. Grab a seat or sprawl out on the Great Lawn with a picnic as you take in Millennium Park’s Summer Music and Summer Film Series, and a host of annual festivals, including the Grant Park Music Festival, the Chicago Blues Festival, the Chicago Jazz Festival, and the World Music Festival.

7. Chicago Museum Campus

Location: Solidarity Drive at Museum Campus Drive off S Lake Shore Drive

1400 S Lake Shore Drive
Chicago, IL 60605

Proposal Permit: Not Required
Permit Fee: None

The Chicago Museum Campus is a 57-acre park that sits on Lake Michigan and surrounds three of the city’s most notable museums, all dedicated to the natural sciences: the Adler Planetarium; the Shedd Aquarium; and the Field Museum of Natural History. It is also known for holding the Soldier Field football stadium and the Lakeside Center of the McCormick Place.

The Shedd Aquarium offers a very unique opportunity to learn about the Beluga Whale as you wade into the waters of the Grainger Beluga Encounter Habitat with an experienced trainer. After some up-close and personal time with the whales, they’ll swim to your love with a ring box in their mouth for a surprise porpois-al.  $75 (does not include admission to the Beluga Encounter)

You can also choose a 60-minute encounter where you’ll be introduced to the Magellanic penguins behind the scenes. You’ll learn how Shedd cares for and trains their penguins and the importance of how Magellanic penguins mate for life. $50 (does not include admission to the Penguin Encounter).

You can reserve the entire encounter to have a more intimate experience. With this option, you can bring additional guests or make it a private experience for you and your significant other. This encounter also includes champagne and strawberries (for two people) on a private balcony overlooking the Abbott Oceanarium.

Private Beluga Encounter: $1250 or $1000 for members
Private Penguin Encounter: $850 or $650 for members

6. Alfred Caldwell Lily Pool

Location: 125 W Fullerton Parkway Chicago, IL 60614

Lincoln Park Conservancy
2000 N. Racine
Suite 4800
Chicago, IL 60614
Email
T. (773) 883-7275
www.LincolnParkConservancy.org | Lily Pool

Proposal Permit: Required
Permit Fee: $150.00

Update Spring 2022: the Alfred Caldwell Lily Pool is no longer offering Closed/Private buyouts for proposals or portrait shoots. 

Email to receive a permit application. Review the guidelines, select the time of your session/event, return the completed application with payment via personal checks, Visa, MasterCard, American Express, and Discover.

The Lily Pool is open seasonally from mid-April through mid-November. It is also closed the Friday, Saturday and Sunday during the Air and Water Show along with select holiday weekends (Memorial Day, 4th of July, Labor Day).

The Alfred Caldwell Lily Pool, also known as Lincoln Park Lily Pool, is an important example of Prairie School landscape architecture designed by Alfred Caldwell. 

The site was originally part of a Victorian garden built in 1889 that displayed tropical lilies and other aquatic plants. When the Victorian-style garden fell out of popularity, the Lily Pool fell into disrepair until 1936 when Alfred Caldwell redesigned the pool and its surrounding area.

In 1997, the Lincoln Park Conservancy  adopted the Lily Pool and, with the Chicago Park District, created a Master Plan to restore Caldwell’s historic landscape and improve accessibility. Construction of the $2.4 million project began in 2000 and the re-named Lily Pool opened to the public in spring 2002 and the restoration earned the site National Historic Landmark and Chicago Historical Landmark status. 

5. North Avenue Beach

Location: North Ave. and Lake Michigan

1601 N. Lake Shore Drive
Chicago, IL 60611

Proposal Permit: Not Required
Permit Fee: None

As one of Chicago’s most popular beaches, the beach features a unique and popular beach house that forms a 22,000 square feet sleek, ocean liner-inspired building, decked out in a crisp blue and white, and boasts one of the best views in the city. The beach house has upper decks and portholes for looking at the magnificent Chicago skyline.

4.  The Honeycomb | People’s Gas Education Pavilion

Location: Southernmost end of the zoo, east of Café Brauer and Farm-in-the-Zoo

2121 N Stockton Drive
Chicago, IL 60614

Proposal Photography Permit: Required
Permit Fee: $125.00

This unique architectural landmark, located in Chicago’s Lincoln Park neighborhood, is called the “People’s Gas Education Pavilion” yet locals have come to refer to it as “The Honeycomb”.

The iconic Peoples Gas Education Pavilion was created by award-winning architectural firm, Studio Gang, (architect Jeanne Gang) who also designed Chicago’s exquisite Aqua building,  

The structure, which resembles a honeycomb from both the inside and out, faces south directly towards downtown providing a view which frames the John Hancock building through its arch. 

The honeycomb is located inside the Lincoln Park’s Zoo’s Nature Boardwalk – a lush Midwestern prairie ecosystem, this natural oasis provides unique opportunities for visitors to engage and connect with the natural world. Opened June 24, 2010, the former manmade pond is now revitalized as a haven of native trees, plants and animals. 

We strongly advise applying for a permit to discover if another wedding or portrait session has reserved the location. Additionally, weekends tend be very popular – especially between 2pm-5pm as wedding parties tend to gather for portraits as well as engagement & portrait sessions. 

3. The Cupola at London House Chicago

Location: 23rd Floor, London House Chicago. Two levels of hotel rooftop featuring cocktails & dining with indoor/outdoor seating & sweeping views of the Chicago skyline.

85 E Wacker Drive
Chicago, IL 60601

Proposal Manager: Manny Aganon
manny.aganon@londonhouse.com

Proposal Permit: Required
Permit Fee: Inquire

LondonHouse Chicago boasts some of the most impressive views of the Chicago River and the city’s architecture from its 22nd-floor rooftop terrace.

The most extravagant location in the entire city of Chicago to get engaged includes one bottle of Dom Perignon vintage champagne, rose petals, VIP elevator to the 23rd floor, private rooftop cupola, and the most stunning views of the Chicago skyline and river below. 

Work with the culinary team to craft a special menu of reimagined customizable cuisine to enjoy in LH Cupola’s original beaux-arts intimate space for memorable moments before and after s/he exclaims, “Yes!”

Please email Manny and inform him you wish to work with Jason Kaczorowski Photography when booking your proposal package at London House Cupola in Chicago. 

2. Gibsons Italia at River Point Park

Location: River Point Park. Where the Chicago River bends at N. Orleans Street, W. Lake Street & N. Canal Street; across from Wolf Point West

233 N Canal Street
Chicago, IL 60606

Proposal Permit: Not Required
Permit Fee: None

Gibsons Italia is a lavish three-level Italian steakhouse with outdoor dining, a bar and lounge on the first floor. The main dining room, which includes a private dining area in the back, sits on the second floor and the third floor features the retractable roof with another bar. All three floors feature stunning views of the Chicago River toward the east that lead north. The restaurant’s design plays off Italy’s northern Lombardy region for inspiration with high-end finishes throughout including white marble tables and backlit onyx walls.

Their signature Chicago cut, a 22-ounce bone-in rib eye, has been wet-aged for 40 days and is served with rosemary, roasted garlic bulb and sea salt flakes melt into the lightly charred top, capping perfectly marbled beef oozing with flavor. I also recommend trying the 7-Year Aged Acquerello Risotto with Viking village sea scallops, Parmigiano Reggiano & baby leeks or their house made, gold-extruded fresh pasta including the mouth-watering Ravioli Carbonara which is served with crispy prosciutto, Parmigiano Reggiano & winter black truffle. Check out their complete dinner menu and make sure to make a reservation for early as they tend to consistently book weeks in advance. 

River Point Park rests directly in front of Gibsons Italia and features not only jaw-dropping views of the Chicago river and skyline but also “Constellation” – the eye-catching, vibrant, red sculpture created by world-renowned Spanish/Swiss architect, structural engineer, sculptor and painter Santiago Calatrava.  The park, designed by world-renowned landscape architect, The Office of James Burnett, is the largest riverfront park in downtown Chicago and feature extensive seating, native and botanical gardens and public art.

1. Bridge at The South Pond in Lincoln Park Zoo’s South Pond Nature Boardwalk

Location: Southernmost end of the zoo, east of Café Brauer 

2121 N Stockton Drive
Chicago, IL 60614

Proposal Photography Permit: Not Required
Permit Fee: None

Located at the Lincoln Park’s Zoo’s South Pond Nature Boardwalk, the South Pond Bridge offers one of the best skyline views in Chicago within a city park. 

Because the Bridge itself is on public property, a permit is not required (unlike the South Pond’s “Honeycomb”). 

We love this location at sunset on weekends after the crowds have left the Zoo and wedding parties have conclude their portraits. Plan to arrive after 5:30pm. 

Best Indoor Proposal Location in Chicago: The Rookery Building

Location: La Salle & Adams

209 S La Salle Street
Chicago, IL 60604

Proposal Photography Permit: Required
Permit Fee: Range

Oriel Express
Access to the Oriel Staircase Only 
30 Minutes – $150.00
60 Minutes – $200.00

Rookery Memory Express
Access to the Oriel Staircase, Grand Staircase & Light Court
30 Minutes – $250.00
60 Minutes – $275.00

Option to Add
Access to the Burnham Library – $75.00
Access for each additional 10 Guests – $50.00/pp

Please Note 

• Up to 10 Guests allowed
• Only Checks are accepted as payment for permits and must be made payable to: THE ROOKERY, LP
• All checks are due prior to 3:00pm the Friday before your photo shoot date
• Glitter, sparkles, and confetti are prohibited

Scheduling
Monday-Friday: 6:00am-8:00am or after 5:30pm
Saturdays: After 2:00pm
Sundays: All Day

Contact
Natalie Walsh
Assistant Property Manager
The Rookery Building
209 S. LaSalle Street
Suite 625
Chicago, IL 60604
312-553-6102 
nwalsh@tjbc.com

Why We Love It

I am a preferred vendor at The Rookery and my team and I have captured more proposals (150+) and weddings (50+) there than anywhere else in the world! I’ve modeled my brand around the Art Deco stylings of The Rookery and the main image on my website features John Root’s famed “Oriel Staircase”. 

The Rookery can be rented in exclusive privacy which provides the ultimate seclusion for those seeking a location that is completely isolated from the rest of the world. 

The Rookery Building makes a great location in summer months when the weather is scorching, the Spring or Fall when rain is predicted, or in Winter when it’s just too cold to propose outdoors.

Because we are preferred vendors and work so frequently at The Rookery, we can facilitate photography permits on short notice (provided they have availability) which allows our clients to quickly pivot to an indoor location if there is unpredicted rain or snow in the forecast as we get closer to their proposal.  

* * *

The Rookery Building is a historic office building located at 209 South LaSalle Street in the Chicago Loop. Completed by architects Daniel Burnham and John Wellborn Root of Burnham and Root in 1888, it is considered one of their masterpiece buildings, and was once the location of their offices.

In 1905, Frank Lloyd Wright recast the famed Light Court in his signature Prairie style. In 1931 William Drummond modernized many of the interior elements, including new elevators, and brought period touches to the building, such as Art Deco detailing.

The Rookery has also been featured prominently in the 1987 film “The Untouchables” as the police headquarters of Eliot Ness. It was also used for filming “Home Alone 2: Lost in New York” in which the exterior and one of the lower levels were modeled as the toy store Duncan’s Toy Chest.

Why trust Jason Kaczorowski Photography to photograph your proposal?

These are the moments in life that you are worth investing in. Proposals are spontaneous events and there’s never any do-overs. This is a once-in-a-lifetime occasion! Don’t take chances on someone cancelling or not showing up on time to your proposal, missing the moment all together, or delivering anything less than amazing images of one of the most momentous moments in your life!   

I’ve been photographing proposals for more than a decade and capturing weddings for over 18 years. My team and I have photographed nearly 400 proposals and more than 650 weddings since 2005. 

I work with a dedicated team of Associate Photographers so even if I am personally already booked for your date, I can always assign the honor of capturing your “Yes!” to one of my trusted team of photographers.

I will always work with you every step of the way in planning your proposal and will be the one processing and perfecting your images so they share the same quality and consistency you admire about my portfolio. 

I’m so confident that you will love working with us that we will photograph your proposal for free. That’s right! I will rebate the entire amount of your Proposal Photography and apply it toward your wedding photography if choose to trust us to capture your wedding!

Riley trusted me to photograph his proposal to Molly in December of 2018. I captured their engagement session in the Fall of 2019 and then, due to several rescheduled dates based on Covid restrictions, their wedding in 2022 in Lake Geneva, Wisconsin.

Gavin trusted me to photograph his proposal in November of 2019 and loved working together so much that he flew my team and I to the Riviera Maya to capture his engagement session and wedding to Hillary in Playa del Carmen, Mexico in 2022.

Robby trusted me to photograph his proposal in July of 2021 and then photograph his wedding to Erin in 2022. 

How much does it cost to photograph my proposal in Chicago?

Contact Me today to start planning your proposal and I will send you “The Art of Proposing: A Guide to Planning the Logistics for Asking the Biggest Question of Your Life” just for reaching out.

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