Chicago’s Top Photo Session Locations – A Comprehensive Guide

If you’ve found this blog post you’re likely looking for inspiration for your next Chicago photo session – welcome to your one-stop shop! In this guide, you’ll find my list of Chicago’s Top Photo Session Locations and what you should know about them.

You’re probably confused about how to pick the best spot – Chicago has an unlimited amount of amazing session locations that it can be entirely overwhelming. From larger questions like what area of the city, to what kind of ~vibe~ you want, and down to how busy the area gets and parking details, I’m here to divulge all my best-kept secrets about Chicago’s top couples/engagement session locations.

While there are an infinite amount of options to pick from for your engagement session location, I’ve narrowed down my top 5 for you based on my years of experience photographing in the hustle and bustle of Chicago – plus a few bonus locations at the end 🙂

Picking Your Location/Background

If you’re having a hard time deciding on your engagement session location, I recommend starting with a “vibe.” Do you envision the city skyline? Maybe a parking garage picnic? Lots of greenery? A cozy in-home session?

Give yourself some time to dream and settle on the vibe first. Check out my Pinterest board for Chicago Engagement Session Inspiration for more examples of different types of locations.

Like what you see? Reach out via my Contact Form to get your session at your top photo location in Chicago on my calendar 🙂

1. A Location Important To Your Story

Ok, so this isn’t a technical location in Chicago.

BUT, I’m a firm believer that when you take an intentional approach to make your session unique to you and your story, it adds an underlying layer of magic to your images that make your gallery that much more meaningful in the end. 

Start with the places that have the most meaning to your relationship:

– Photos at the place where you met for your first date or at your first home together.
– Recreating one of your favorite memories like a picnic on the beach or taking photos where they proposed. 
– Or maybe it’s something smaller like just taking a stroll through your neighborhood or walking your dog at your favorite park.

The options are endless for incorporating you and your love’s story into your engagement session. I promise you won’t regret it!

2. North Avenue Beach

Now, North Avenue Beach is my absolute favorite on my list of Chicago’s Top Photo Session Locations. The classic skyline view in that spot you’ve seen all over Instagram – it truly can’t be beaten. From the beauty of the lake to the skyline-and-beach combination, it’s a versatile location that’s great for any session type.

Parking at North Avenue Beach:

Speaking on logistics for this classic Chicago photography location, North Avenue Beach has a paid parking lot right by the beach and boardwalk. Current rates as of summer 2022 are $21 for less than 2 hours. This is the only parking option right by North Ave without walking underneath Lake Shore Drive. There are plenty of garages in the Lincoln Park area that go for cheaper than this lot, but you’ll have to compromise and walk for about 10 minutes to make it to the beach.

Overall Experience:

Speaking to the overall session experience, when photographing at this location, I like to make my couples aware of a few things. During the summer, there are a number of sand volleyball leagues that play on weeknight evenings. This won’t affect how your final photos turn out, but you should know that there will be a lot of people around during your time at North Avenue Beach. Couples that are shy or would be very distracted by two hundred-or-so people playing volleyball near them may want to steer in another direction during the summer.

I don’t think this should dissuade you from this location in any way as North Avenue Beach truly is my favorite location in the city, but it’s definitely something to consider when choosing your engagement session location in Chicago. Most often, the players ignore you entirely, because there are usually 5+ other couples taking photos every evening at North Ave anyway!

3. Lincoln Park’s Nature Boardwalk

Lincoln Park’s Nature Boardwalk area is next up on this list of the Top 5 Chicago Photo Locations. If North Avenue Beach was my favorite skyline view, Lincoln Park is my favorite spot for greenery!

This area near the Lincoln Park Zoo is perfect for couples looking for a little taste of all that Chicago has to offer. There are many different areas that include lots of foliage, views from the Bridge Over South Pond with the skyline, and the Education Pavilion/Honeycomb.

Parking at Lincoln Park’s Nature Boardwalk:

Parking is a little more challenging in this area on weeknight evenings in the summer. There’s free parking all along Stockton Drive, but you and the rest of the city are also trying to find those coveted free parking spots to enjoy a beautiful Chicago evening.

If you’re not able to snag a free spot, this parking lot will usually have spots open if you’re willing to pay the $16+ price tag. It does fill up during beautiful summer evenings, so don’t count on always having this option available. Worst comes to worst, I recommend driving along Clark Street for metered parking spots with a short walk to the Bridge Over South Pond, or driving Stockton again in case someone left while you were checking out the rest of the road.

Overall Session Experience:

Speaking of the overall session experience in this location, there are much fewer distractions than at North Avenue Beach. There are definitely still lots of people walking around in the summer evenings so it’s not quiet by any means, but there are a few places to sneak away you won’t be around so many people.

Overall, Lincoln Park Nature Boardwalk is a great option to get a little flavor of both the Chicago skyline and greenery! You have the option to cut out the skyline and only include greenery if you’re hoping for a more ambiguous foliage look for your engagement session.

Education Pavilion:

Now you’ve probably seen this large honeycomb structure all over Pinterest for Lincoln Park photography inspiration. This is called the “Education Pavilion.” Something to note is that like the Bean, or “Cloudgate,” this is an art installation through the City of Chicago so you’ll technically need a permit in order to photograph at this specific spot.

Oftentimes, the Honeycomb is rented out entirely for private events. I personally have never had issues at this location, but I don’t recommend basing your whole session around this spot unless you book a permit/reserve the space.

4. The Board of Trade Building

So, we’ve talked about my favorite locations for viewing the Chicago skyline and for my favorite park. Now, if you’re interested in having your engagement session in downtown Chicago amidst the hustle and bustle, The Board of Trade Building is for you. Here’s why:

This photography location is situated in the financial district, so once the 5 pm rush of office workers is over the area clears out from people.

Parking at The Board of Trade Building:

The parking situation is also one of the easiest out of my Top 5 Chicago Photo Locations. There’s plenty of paid metered parking around the area as well as parking garages. We love an easy way to park in the city!

Overall Session Experience:

As opposed to The Wrigley Building, this area of town is much calmer. While you’ll have people walking to and fro throughout your session, it’s nowhere near the chaos of Michigan Avenue. (see the end of this article for more details on the Wrigley Building).

This area of town is prime for those large landscape photos of downtown Chicago. Not only do you have a great view of the Board of Trade Building itself, but there are endless opportunities to play with the composition of skyscrapers surrounding the area.

As an added bonus, this location is also close to the river. If you’re interested in a 2-for-1, you can stop by during your session to create photographs near the iconic Chicago River.

The amazing views combined with the more chill vibe make this my favorite photo location in downtown Chicago!

5. Milton Lee Olive Park

Closing out my list of Chicago’s Top Photo Session Locations is Milton Lee Olive Park. Situated on an outcropping into the lake, Milton gives a unique perspective of the skyline than the rest of its peers in the city.

Parking at Milton Lee Olive Park:

Parking at this location is tough – it’s easiest to book a spot at Navy Pier and budget time to walk over. Alternatively, you can forgo your car and uber to the entrance. Since it’s situated so tightly between Lake Shore Drive and Navy Pier, there’s, unfortunately, no place close by to park.

Overall Session Experience:

My favorite thing about photographing at Milton Lee Olive Park is that even if there are a lot of people present, you can always find a spot on the mile-long lakefront trail. This location is ideal for getting those skyline views – without having to deal with the crowds at the Wrigley Building or North Avenue Beach.

Once you make it out onto this beautiful Chicago lakefront property, you won’t regret it. Your time spent walking out onto the water will be worth the stunning views this location offers.

BONUS: Honorable Mentions

I can’t help but include a few of my other favorite locations in Chicago that didn’t make the top 5. Chicago truly has an unlimited number of locations to photograph at. There’s definitely a location that fits you two and your story best!

The Wrigley Building

The perfect spot for those amazing Chicago river views. This location would have made the top 5 locations if the area wasn’t so crowded!

At every time besides sunrise, this location is one of the busiest in the city. Since it’s situated on Michigan Avenue, there are a LOT of people around at all times.

If you’re interested in this location, we’ll absolutely make space to capture the stunning views of this classic Chicago photography location.

Rooftop Parking Garage

This is one of my favorite unique Chicago skyline views. Situated on top of my secret parking garage, you’ll have the entire location to yourself. Plus, there’s already parking here!

Note: Since it’s an open parking garage, I can’t guarantee that we will have the full skyline without parked cars. (Every time I’ve been there, it’s been empty!)

This is my favorite spot on the west side of town for a more unique view of the skyline than most lakefront locations.

Ping Tom Park

If you’re looking for a variety of different looks at one location, Ping Tom Memorial Park is definitely for you!

Starting with the beautiful access right along the river, to the unique murals, and finally to that amazing skyline view, this location has plenty to offer you as a potential pick.

Situated on the north end of Chinatown, it’s perfect for grabbing an authentic bite to eat once your session is over 🙂

In Summary…

While there truly are unlimited locations for couples photography in Chicago, there are a few locations that stand out amongst the crowd. My list for Chicago’s Top Photo Session Locations include:

  1. A Location Important To Your Story
  2. North Avenue Beach
  3. Lincoln Park Nature Boardwalk
  4. Board of Trade Building
  5. Milton Lee Olive Park

And as a bonus, here are a few honorable mentions that just barely missed the top 5 for Chicago’s Top Photo Session Locations:

  1. The Wrigley Building
  2. My Secret Rooftop Parking Garage
  3. Ping Tom Memorial Park

Check out my Pinterest board for Chicago Engagement Session Inspiration for more examples of Chicago engagement photography!

Like what you see? Reach out via my Contact Form to get your session at your top photo location in Chicago on my calendar 🙂

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