Most Romantic Hidden Proposal Spots in Chicago
20 Hidden Gem Chicago Proposal Spots
Hidden gem city proposal spots
The city is a gorgeous backdrop for a romantic proposal. From the stunning riverwalk to the charming Lurie Garden, there are many ideal Chicago engagement photography locations. The city is a dream for beautiful engagement portraits.

01
Gibson’s Italia
This beautiful spot overlooks the river, the iconic Chicago Lake Street bridge and the glass buildings in the background.
02
Franklin Street
The last bridge before Wacker turns is a stunning spot to propose and it usually is pretty quiet.


03
Franklin Street Bridge
The last bridge before Wacker turns is a stunning spot to propose and it usually is pretty quiet.
04
Fulton Street Bridge
IThis bridge has a beautiful view of the river and downtown buildings. It tends to not have a lot of foot traffic.


05
Fulton Street
Unless you know this lovely spot is there, you’d likely walk by and never know it. Alfred Caldwell spent his own money to create this beautiful oasis for the public to enjoy. The pool eventually fell into ruin after years of neglect, but it was restored to its original beauty in 1997.
06
Riverwalk
This section of the Chicago Riverwalk for engagement shoots is my sweet spot! Anywhere around Michigan Avenue is always crowded, but there are a few secret spots where you can escape the crowds.


07
Michigan Avenue
While Michigan Avenue is always bustling with people, just below the crowds is a more secluded little spot with views of London House and the Dusable Bridge.
08
Riverwalk
Just below Michigan Avenue and the Dusable Bridge is a quiet little spot with the trifecta of iconic Chicago – the river, the bridge and the Wrigley Building.


09
Grant Park
South of the downtown area is a beautiful tree lined area of Grant Park with views of the city in the background.
10
Art Institute Garden
Right next to the Art Institute of Chicago is a beautiful garden with views of the city in the background.


11
Lurie Garden
Millennium Park has so many great spots. My favorite is the Lurie garden. The lush flowers and foliage against the cement and glass buildings are a beautiful contrast.
12
Olive Park
Located near Navy Pier, Olive Park is a gorgeous location for skyline and lake view. The jetty stretched over the lake makes a perfect spot to capture the lake with the city backdrop.


13
Millennium Park
Located near Navy Pier, Olive Park is a gorgeous location for skyline and lake view. The jetty stretched over the lake makes a perfect spot to capture the lake with the city backdrop.
14
Chicago Board of Trade
While this is not exactly a hidden spot, it tends to be pretty quiet on weekends with multiple beautiful spots for a proposal.


15
Federal Reserve
Right near the Chicago Board of Trade is the Federal Reserve Building. The gorgeous gold doors and massive columns make for a romantic and private spot.
16
North Avenue Beach
Any movie shot around the lakefront features this view. It’s the classic Chicago shot with the Drake Hotel and Hancock Building in the background, making it one of the top Chicago engagement photography locations.


17
North Pond
On the other side of Fullerton is a secluded pond that has a pier so you can feel like you are in the middle of the pond.
18
Union Station
An iconic Chicago landmark, Union Station is a gorgeous spot to propose.


19
Riverwalk
Just off State Street, this walkway has views of the city and is also covered.
20
Garfield Park Conservatory
If you are looking for a hot spot in the winter or just some lush green nature, the Garfield Park
Conservatory is a beautiful spot in the city. You will need to have a permit for engagement shoots and it’s definitely one of the Chicago engagement photography locations worth considering.


21
Lincoln Park Conservatory
Conservatory is a beautiful spot in the city. You will need to have a permit for engagement shoots and it’s definitely one of the Chicago engagement photography locations worth considering.
ROMANTIC PROPOSAL PHOTOGRAPHY
PLanning A proposal?
I’ll help you create the perfect plan to make your proposal a beautiful surprise. I provide same day sneak peek photos because I know you’ll want to share the news with photos! Proposals start at $850 for planning, capturing the moment and a mini engagement shoot.

