Home・Blog・Best places to propose・IL・Chicago

Best Places to Propose in Chicago, IL

by Willyou.net * in Chicago IL

Chicago, or as we call it, Chi-Town, is the most populated city in Illinois and the third-most populated one in the United States. Located on Lake Michigan, its bold architecture and downtown skyline along with its well-reputed museums add to the city’s international appeal. Our locals and visiting tourists love our deep-dish pizza and Chicago-style hot-dogs, but what makes someone a true Chicagoan is sports team loyalty. We’re talking die-hard fandom and allegiance to our Bulls, Bears, Cubs, and Blackhawks. Visit multiple luxury local diamond jewelry stores in Chicago, IL, carrying the most exclusive diamonds that can be seen shining on ring-fingers at local upscale restaurants and nightclubs. The Windy City is the perfect place to propose.

Our local jeweler partners are always in the know on the best place to propose in Chicago, IL. We met with a few of them and picked their brains on the most romantic spots in the city and the best ways to pop the question:

Local Diamond Jewelers

“The Alfred Caldwell Lily Pool in Lincoln Park is hands down the most picturesque area to propose in Chicago, Illinois. Wedding Bands and Company has been privy to so many romantic proposal stories that took place in this serene location, and after having visited, we can attest to the site’s magic and allure. A perfect place to present your stunning diamond engagement ring.” – Wedding Bands and Company

Wedding Bands and Company, located in Chicago, Illinois, is a highly successful diamond jewelry company operated by master jewelry designer, Koorosh Daneshgar, who’s known for his unique engagement rings. The company has been serving its local and tourist customers since 1999. As one of the largest diamond jewelry stores in the Chicago area, Wedding Bands and Company strives to provide the most meaningful pieces at the best prices, and most importantly, the highest quality and service to their customers. They are located at 2 North Wabash Avenue, Chicago IL 60602, steps from Millennium Park in a private and spacious showroom. Keen on providing a personable, relaxing, and stress-free experience, their jewelry services include engagement rings, custom-designed rings, wedding bands, and more.

We met with the store’s manager, Koorosh Daneshgar, and asked: What is the most memorable proposal story you heard from a Chicago, IL customer?

“One of our favorite Wedding Bands and Company proposal stories is a Chicago classic. Our lovely customers first met on a blind date under the Marshall Fields’ Clock. We worked together to design a brilliantly unique diamond ring to resemble the clock and of course, the ring was presented on bended knee under the clock itself. Best proposal of all time!” – Koorosh Daneshgar

“We’re lucky to be located in the great city of Chicago, where there are amazing places to propose in our area. From restaurants and landmarks to the skyline near the museum campus and on top of the Hancock building, the proposal possibilities are endless!” – Windy City Diamonds

Windy City Diamonds has grown through four generations of the Zimmerman family, beginning in 1929. Today, they are in their 4th generation of working with friends, family, grandparents, parents, and now children. Their goal is to provide the finest jewelry, custom-designed engagement rings to their client’s specifications, and at the most competitive prices. Windy City Diamonds has one of the largest selections of GIA-certified diamonds in the Chicago area. Their jewelry experts work one-on-one with each person to meet all individual styles. They offer limitless options, as their expert designers guide each client in developing their ideas into a beautiful piece of jewelry.

We met with the store’s manager, Garry Zimmerman, and asked: Garry Zimmerman

What is the most memorable proposal story you heard from a Chicago, IL customer?

“A client and his girlfriend had just purchased a piece of property in the city together, in a building that had yet to be built. The client had a sign erected on the site asking his girlfriend to marry him, and then went to the top of the John Hancock building observation deck, pointed the binoculars to the deck at the sign and said, “Oh Look, we can see our new property from up here”, and then she peeked into the binoculars to see the proposal. Very creative and exciting.” – Garry Zimmerman

“Gato and Sons Jewelers suggests heading to Millennium Park for the perfect diamond engagement ring proposal. Get someone nearby to take a picture of you getting down on one knee in front of the famous “bean” and make a memory that will last you a lifetime.” – Gato and Sons Jewelers

Gato and Sons Jewelers is widely known to its Chicago, IL, residents as the best jewelers for engagement rings for women. Our staff is committed to exceeding your expectations, whether you chose a diamond engagement ring from our splendid selection, or opt to custom design one yourself. With years of experience in the craft and art of fine jewelry-making, Gato, and Sons Jewelers is committed to your utmost satisfaction.

We met with the store’s manager, Jose L Gato, and asked: What is the most memorable proposal story you heard from a Chicago, IL customer?

“Gato and Sons Jewelers loves hearing about our customers’ proposals. One of our favorites was a man who packed a bag and took his long-time girlfriend on a surprise trip to Hawaii. As if the trip itself wasn’t enough of a surprise, while they were sunbathing on the beautiful beach, he pulled out his custom-made diamond engagement ring and asked, “Will you?”. If it wasn’t clear before, the diamond ring helped- her answer was yes.” – Jose L Gato

“Millennium Park is one of the best places to propose in Chicago, Illinois. Located in the Loop of the city, there are fantastic views all around as well as housing the famous ‘Bean.’ There are lots of fantastic restaurants and events in the area as well. It’s an excellent place for a proposal.” Imperial Jewelry Company

Imperial Jewelry Company in Chicago, Illinois, is a local jeweler that offers a large selection of loose diamonds and diamond engagement rings at the lowest prices. They create custom diamond engagement rings, in-house, using the latest 3D technology.

We met with the store’s manager, Terry Te, and asked: What is the most memorable proposal story you heard from a CHICAGO, IL customer?

“One of our clients proposed on a boat with the entire family present. It was a dinner cruise, so in the middle of the meal, he proposed to his girlfriend with all their loved ones present.” -Terry Te

3 Best Places to Propose in Chicago, IL

1. Garfield Park Conservatory

You can present your love with her perfect diamond engagement ring at Garfield Park Conservatory, 300 N Central Park Ave, Chicago, IL, 42.1 miles (49-minute drive) from Chicago, IL, a 184-acre urban park that feels like Jumanji exploded in a glass aircraft hangar.

2. Wrigley Field

Or, help Clark cheer on our Cubbies at Wrigley Field, located at 1060 W Addison St, Chicago, IL, 33.7 miles (51-minute drive) from Chicago, IL, and we’ll be happy to display your proposal video up on the big board and let the crowd go wild.

3. Chicago Loop

Another classic proposal spot is at our famous Chicago Loop, 701 S State St, Chicago, IL, USA 38.2 miles (52-minute drive) from Chicago, IL, with its vibrant energy sure to suit your big moment. Enjoy fantastic music during either The Taste of Chicago or Lollapalooza music festival and get down on one knee in front of our famous “Cloud Gate” sculpture, commonly referred to as “The Bean”.

All Top 26 Places to Propose in Chicago, IL

The Art Institute of Chicago – 111 S Michigan Ave – Chicago – IL 60603 – USA
Millennium Park – 201 East Randolph Street – Chicago – IL 49534 – USA
Cloud Gate – 201 E. Randolph St – Chicago – IL 60601 – USA
Oriental Institute Museum – 155 E 58th St – Chicago – IL 60637 – USA
Frank Lloyd Wright’s Robie House – 5757 S Woodlawn Ave – Chicago – IL 60637 – USA
University of Chicago – 5801 S Ellis Ave – Chicago – IL 60637 – USA
Guaranteed Rate Field – 333 W 35th St – Chicago – IL 60616 – USA
National Museum of Mexican Art – 1852 W 19th St – Chicago – IL 60608 – USA
McCormick Tribune Ice Rink – Michigan Ave & Washington St – Chicago – IL – USA
DuSable Museum of African American History – 740 E 56th Pl – Chicago – IL 60637 – USA
Rockefeller Memorial Chapel – 5850 S Woodlawn Ave – Chicago – IL 60637 – USA
Argus Brewery – 11314 S Front Ave – Chicago – IL 60628 – USA
360 Chicago Observation Deck – 875 N Michigan Avenue – Chicago – IL 60611 – USA
Wrigley Field – 1060 W. Addison St – Chicago – IL 60613 – USA
Chicago Riverwalk – Chicago – IL 60601 – USA
The Field Museum – 1400 S Lake Shore Dr – Chicago – IL 60605 – USA
The Magnificent Mile – North Michigan Avenue – Chicago – IL 60611 – USA
Garfield Park Conservatory – 300 N Central Park Ave – Chicago – IL 60624 – USA
Lincoln Park Zoo – 2001 N Clark St – Chicago – IL 60614 – USA
Skydeck Chicago – Willis Tower – 233 S. Wacker Drive – Chicago – IL 60606 – USA
United Center – 1901 W Madison St – Chicago – IL 60612 – USA
Buckingham Fountain – Grant Park – Chicago – IL 60605 – USA
Lakefront Trail – 540 N Lake Shore Dr – Chicago – IL 60611 – USA
The Loop – 701 S State St – Chicago – IL 60605 – USA
Richard H. Driehaus Museum – 40 E Erie St – Chicago – IL 60611 – USA
Maggie Daley Park – 337 East Randolf Street – Chicago – IL 60601 – USA

Bottom Line…

No matter what time of year, come to Chicago, IL, for the most memorable diamond engagement proposal that will leave her sparkling and speechless! To dive deeper into popular choices and local trends, check out our detailed overview of engagement rings in Chicago IL