My Favorite Chicago Engagement Session Locations

If you just came from my nature locations post, you’ve already heard me say this… but it’s worth repeating. : ) 

Blake and I love taking photos on our anniversary trips, and one thing I’m always so grateful for is when the photographer we’re working with shares their favorite spots. It makes the whole process feel so much easier.

And honestly, even if you’ve lived in Chicago your whole life, it can still feel a little tricky to figure out where to take engagement photos.

Maybe you’ve seen inspiration you love, but you’re not quite sure where it was taken.

Or maybe you just want a spot that feels like you, but don’t know where to start.

That’s exactly what this post is for!

Below, you’ll find a few of my favorite Chicago locations along with photos so you can choose the location you’re most excited about.

And if you’re looking for more nature-inspired spots instead, you can check out that post here. : )

Lincoln Park + North Avenue Beach

Meet Up Address: Parking lot Entrance, 41.925314, -87.633456
Parking: Paid parking lot
Public Restroom to Change: No (best option is your car)
Are Dogs Allowed? Yes at Lincoln Park. Not allowed on the beach.
Photography Permit: None required (Lincoln Park Zoo does require one)

This is one of my all-time favorite spots because of the variety.

We can start in a more natural setting near the zoo, walk over Lake Shore Drive, and end at North Avenue Beach with a skyline view that just feels iconic Chicago.

A couple quick notes:

• Here are the coordinates for the parking lot entrance (maps have been a little weird lately): 41.925314, -87.633456
• Bring comfy shoes… we’ll be walking between locations
• The beach can get windy, so a brush is always a good idea
• On our walk between locations, we’ll pass your car, which makes outfit changes easy

This is easily the most popular location for our city engagement sessions and it’s because you really get everything with this spot! Nature, skyline and beach. A favorite of our couples and myself. : ) 

Milton Lee Olive Park

Meet Up Address: E Ohio St, Chicago, IL 60611
Parking: Paid parking (SpotHero highly recommended)
Public Restroom to Change: No
Are Dogs Allowed? Yes. This is actually a dog park!
Photography Permit: None required

This location has one of the best skyline views in the city.

We’ll typically start at Milton Lee Olive Park, make our way through the tree-lined paths, and then head down to Ohio Street Beach to end with a softer, lakefront feel.

A couple quick notes:

• The park closes at 8:00 PM sharp
• In the summer, I love ending the session on the beach since we often have light until about 8:30 PM
• There’s not a great place to change here, so plan outfits accordingly. 

Bonus option:

If you’re up for about a mile walk, sometimes couples will start at the Wrigley Building for a more architectural, downtown feel, then walk over to Milton Lee Olive Park to finish with skyline and beach views. A little bit of everything in one session AND this makes changing easy since we can pop into Target between stops. 

Museum Campus

Meet Up Address: Shedd Aquarium – 1200 S Lake Shore Dr, Chicago, IL 60605
Parking: Paid parking (SpotHero recommended, usually a bit of a walk)
Public Restroom to Change: Usually. It’s between the Shedd and MSI at the Museum Campus Cafe
Are Dogs Allowed? Not recommended
Photography Permit: None required

This spot feels classic and elevated. The skyline views with the city perfectly framed. Stunning architecture from the museums. Nature, water, and city all in one place. : ) 

There’s also a marina nearby, which can be really fun if we have extra time! Truly, one of my favorite spots because of how versatile it is. : ) 

A quick note: Bring a brush… it can get windy here too!

Indoor Options (Perfect for Winter!)

While I always prefer outdoor sessions when possible, Chicago Winters are COLD! If we’re planning a Winter engagement session, these are my two favorite indoor options that still feel intentional and beautiful. : ) 

The Art Institute of Chicago

Meet Up Address: 111 S Michigan Ave, Chicago, IL 60603
Parking: Millennium Park Garage recommended
Public Restroom to Change: Yes
Are Dogs Allowed? No
Photography Permit: None required, but they do require admission.

• Hours: Typically 11:00 AM – 5:00 PM || See Full Hours Here.
• Best Time: Morning sessions
• Admission:
  • $27 IL residents
  • $32 non-residents
  • $20 Chicago residents

This is such a special, unique location.

A couple quick notes:

• It will be busy, so we’ll be working around people
• If you’re a little camera shy, just something to be aware of
• You’ll need to check any bags larger than a small purse
• I recommend bringing your second outfit, checking it, and then changing on site

Lincoln Park Conservatory

Meet Up Address: 2391 N Stockton Dr, Chicago, IL 60614
Parking: Street parking / nearby lots
Public Restroom to Change: Limited
Are Dogs Allowed? No
Photography Permit: $90 (2026)

• Hours: 10:00 AM – 4:30 PM (Closed Mondays & Tuesdays)
• Best Time: Morning sessions

This is my go-to indoor nature option.

It’s warm, full of light, and gives you that lush, green feel even in the middle of winter.

A couple quick notes:

• I recommend booking at least two weeks in advance
• Reservations are required for everyone attending
• Reservations open 30 days out
• You’ll need both your permit and reservation confirmation to enter. If you don’t have both, they can turn you away due to capacity limits. YIKES! 

Final Thoughts

We are so lucky to have access to a city like Chicago. Each of these locations offers a completely different view of the skyline, and honestly, you can’t go wrong with any of them.

I hope this post was helpful to you as you are thinking about what location you would like for your engagement session.

No matter where we end up, we’re going to create something beautiful together. : )

Much Love,