Top Chicago Skyline Views For The Best Surprise Proposal Photos
With so many different iconic Chicago skyline views it can be hard to choose just one for the perfect Surprise Proposal to your forever partner. If you are feeling overwhelmed and can’t choose which view is the best, you have come to the right place. I have photographed and planned over 100 surprise proposals in Chicago and have experience with every skyline view location in the city. You may think all Chicago skyline views are the same but in fact they each have different characteristics. It’s good to choose one that is logistically and aesthetically a good fit for your proposal. I am excited to provide you with an at-a-glance list of the best skylines in Chicago and what makes them unique.
Locations for most impressive larger than life skyline : North Avenue, Olive Park
Locations with some privacy: Grant Park Garden, River Point Park
Locations with BOTH skyline and Lake Michigan views: Olive Park, North Ave Beach, Adler Planetarium, Fullerton Ave
Locations popular for tourist attractions: Buckingham Fountain, The Bean, Lincoln Park Zoo Bridge, Adler Planetarium, Olive Park
North Avenue Beach
Pros:
This is likely the most popular view in the city because the view makes the city look larger than life. There is a small paid parking lot within feet of the beach ( in the summer months its usually full ). You can get both skyline views and Lake Michigan views.
Cons:
During the months of April through November it’s a very busy place with a lot of runners, bikers and tourists. The parking lot is usually full. It’s a very difficult place to get drop-off/pickup from an Uber. It’s not a walkable distance to downtown or dinner places. It’s a very public tourist spot and you may be one of many proposals on any given warm summer or fall evening.
Click here to see a complete North Ave Proposal Blog
Olive Park ( Milton Lee Olive Park )
Pros:
It’s view of the city is in a unique tucked away park near Navy Pier. It has a one of a kind walkout ledge over the lake. It’s a walkable distance to the downtown area and dinner spots. There are endless spots to propose and get a good backdrop so you don’t have to time your proposal in the spot everyone wants a photo at. It’s an easy place to get an Uber pickup/dropoff. The sunsets behind the skyline and makes for gorgeous sun flares during golden hour.
Cons:
There is no parking. It’s a 5+ minute walk from drop off to the proposal spot. It’s a very public tourist spot and you may be one of many proposals on any given warm summer or fall evening.
Click here to see a complete Olive Park Proposal Blog
Adler Planetarium ( Museum Campus )
Pros:
Easy to get to! There’s lots of paid museum parking and an additional large lot. Makes for a prime location near many museums which makes for an easy storyline reason to get your partner to make it a day of visiting museums. There are endless spots to propose and get a good backdrop so you don’t have to time your proposal in the spot everyone wants a photo at. Very easy Uber drop-off/pickup. This location provides the longest view of the skyline.
Cons:
During the months of April through November it’s a very busy place with a lot of runners, bikers and tourists.
Click here to see a complete Adler Planetarium Proposal Blog
Buckingham Fountain
Pros:
There are endless spots to propose and get a good backdrop so you don’t have to time your proposal in the spot everyone wants a photo at. Very easy Uber drop-off/pickup. There are endless places to take more photos with diverse backdrops, such as the Grant Park South Garden and North Rose Garden and is a short walk to all the Michigan Ave tourist locations and dinner spots.
Cons:
The Fountain only stays on during early May through mid October. During summer months it’s a very busy place with a lot of runners, bikers and tourists. There is close paid parking but most of the summer and fall is full.
It’s sometimes closed due to large summer festivals like Lollapalooza, Taste of Chicago and many other festivals of which the list gets bigger every year with new events added.
Fullerton Avenue Lookout
Pros:
You will likely be the only proposal happening in this spot as it’s at the top of the list of well known locations. This skyline location includes Lake Michigan views.
Cons:
There is no parking and it’s also a difficult spot for Uber pickup/drop-off. There is a restaurant next to this location! Make sure to check the hours as they can be limited.
Lincoln Park Zoo Bridge ( Nature Boardwalk )
Pros:
This is the most popular place to propose because its in the heart of the city. The Nature Boardwalk has many diverse backdrops to make for the ultimate engagement session. It includes many trees that adds lush green in the summer and rich reds and yellows in the fall to the entire landscape. The skyline view at this location is between a lot of nature including the boardwalk and the zoo ( which is free ! ) Its an easy Uber pickup/drop-off location if you enter from the Stockton Drive entrance. There is a massive paid parking lot which is part of the zoo that never fills up and can be accessed from Fullerton Ave. There is very little walking involved to get to the prime proposal spot. This is also a prime location to grab a celebratory dinner after in the neighborhood.
Cons:
During the months of April through November its a very busy place with a lot of runners and tourists. In fact its not only the #1 place to propose but it’s the #1 place to do a photoshoot of any kind including but not limited to; Family Sessions, Wedding Party Photos, Quinceañera Sessions, Maternity and Graduation Sessions. It’s a very public tourist spot and you may be one of many proposals on any given warm summer or fall evening.
Click here to see a complete Lincoln Park Zoo Proposal Blog
Grant Park ( South Garden )
Pros:
This location hasn’t become widely known yet so it’s still relatively low foot traffic and considerably private. This location’s unique skyline view is surrounded by a highly manicured garden that gives upscale vibes. There are endless spots to propose and get a good backdrop so you don’t have to time your proposal in the spot everyone wants a photo at. Very easy Uber drop-off/pickup. There are endless places to take more photos with diverse backdrops, such as The Buckingham Fountain and North Rose Garden and is a short walk to all the Michigan Ave tourist locations and dinner spots.
Cons:
There is close paid parking but most of the summer and fall is full. It’s sometimes closed due to large summer festivals like Lollapalooza, Taste of Chicago and many other festivals of which the list gets bigger every year with new events added.
Oak Street Concrete Beach
Pros:
This spot has a unique view! It’s a rare spot for proposals. If you don’t mind the walk its relatively close to Michigan Avenue and all it has to offer for celebratory dining and shopping.
Cons:
It’s complicated to get to. Once you get to an access point by walking from under Lakeshore drive, you then have to walk more. There’s no parking lot and no Uber drop-off/pickup. During the months of April through November its a very busy place with a lot of runners and bikers. This skyline view only includes a small chunk of the skyline.
River Point Park ( River Walk )
Pros:
This location is off a highly traveled street. It’s one of the more private locations. Its the only location on The Chicago River Walk. It’s an easy spot for Uber pickup/drop-off. Some paid parking only 2 block away. Not a high foot traffic area. Walkable to all the downtown restaurants and bars. Located behind Gibson’s Italia on Canal which makes for a close place to celebrate.
Cons:
Can be tricky to find, I suggest mapping out the directions with the only entrance off Lake Street. Moderately popular for proposals, but not the highest in demand. You don’t get the traditional full skyline view, it’s a different kind of skyline that features downtown bridges and buildings and not the tops of the most iconic skyscrapers.
If you are looking for more tips on planning a surprise proposal in Chicago, check out my blog on How to Plan a proposal here. If you are looking for the perfect location for your surprise proposal, check out my blog on popular Chicago locations here.
When you are ready to book please reach out to me so we can get your desired date locked in! Contact Me Here!
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