Chicago is a beautiful city full of countless options for your engagement photos. If you’re looking for engagement photos that are genuine, personal, and reflect who you are as a couple, you are in the right place. Here are 25 creative ideas to personalize your Chicago engagement photos.

1. Visit a record store.

Are concerts, listening to music, and/or collecting records your thing? If so, let’s hangout at a local record store for your Chicago engagement photos.

Alexandra and Brandon love music so we visited a record store for their session. Surrounded by vinyl records with music playing in the background, you can definitely see how these two were in their element.⠀⠀⠀⠀⠀⠀⠀⠀
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The record store owner was super sweet, and let us take photos wherever we wanted. At the end of the session, she even offered Alexandra and Brandon vinyls to take home to use as wedding decor ❤️

Just like their engagement session was unique and creative, this was also reflected in Alexandra and Brandon’s Starline Factory wedding.

Here are some record store locations for your Chicago engagement photos:

Reckless Records: 929 W Belmont Chicago IL 60657 | Dusty Groove: 1120 N Ashland Ave, Chicago, IL 60622 | Laurie’s Planet of Sound: 4639 N Lincoln Ave, Chicago, IL 60625

2. Let’s grab donuts and coffee for your Chicago engagement photos.

If coffee and donuts are your thing, then I can’t wait to meet you two! Whenever we are on vacation, I’m always on the lookout for the best local coffee shop or bakery. My husband and I event went on the Underground Donut Tour of Chicago.

That’s why I got even more excited when Allison and Jacob wanted to take some of their engagement photos at Stan’s Donuts. Incorporating your interests into your engagement session will make your photos that much more personal and fun. Also, who doesn’t love a coffee and donut break?

Here are some coffee and donut shop locations for your Chicago engagement photos:

Doughnut Vault: 401 N Franklin St, Chicago, IL 60654 | Stan’s Donuts: 259 E Erie St, Chicago, IL 60611 | Heritage Bikes & Coffee: 2959 N Lincoln Ave, Chicago, IL 60657 | Hero Coffee Bar: 22 E Jackson Blvd, Chicago, IL 60604

3. Visit Lincoln Park Conservatory or Garfield Park Conservatory.

These two Chicago greenhouses are some of my favorite locations in the city for engagement photos. I love how no matter what the weather is (cold, windy, rainy), these two indoor locations are the perfect option. You still get the greenery and outdoor feel, without having to deal with the weather.

Haley and Mike love the outdoors, but understandably didn’t want to be outside for too long on a windy December day in Chicago. The Lincoln Park Conservatory turned out to be the perfect spot for their engagement photos.

For Gabby and Scott’s Lincoln Park Conservatory session, they loved getting to be inside for their photos. It was only 6 degrees on this cold January day. We found refuge from the frigid weather inside the Lincoln Park Conservatory. It was so warm inside that we even ditched out coats.

Here are two conservatory locations for your Chicago engagement session:

Lincoln Park Conservatory: 2391 N. Stockton Dr. Chicago, IL 60614 | Garfield Park Conservatory: 300 N Central Park Ave, Chicago, IL 60624

4. Winter wonderland.

If you love snow and are ready to embrace the cold, then let’s head outside for your winter engagement photos in Chicago.

Check out Brant’s Cantigny Park proposal, and Logan’s Morton Arboretum proposal to see some winter photo inspiration.

For winter engagement photos, we recommend wearing layers and a jacket to stay warm.

Below are location ideas for your winter engagement photos in Chicago.

Milton Lee Olive Park: E Ohio St, Chicago, IL 60611 | North Avenue Beach: 1600 North Lake Shore Drive, Chicago, IL 60613 | Morton Arboretum: 4100 IL-53, Lisle, IL 60532 | Cantigny Park: 1 S, 151 Winfield Rd, Wheaton, IL 60189

5. Bring your fur babies.

We love when couples choose to incorporate pets into their engagement photos. Keep in mind that bringing a pet along often means that we’ll need to choose a pet friendly location.

Nikki and Alex brought their dog, Frankie, to their Chicago engagement session and we had the best time. It makes your photos that much more special to have you fur babies in them.

We recommend planning for your pet to be at the first part of your session and then having a friend take them home. We won’t use the pet in every single photo so it’s also nice to have a friend available to hold him or her in between shots.

If you’re going to bring a pet, exercise your pet before the session and bring your pet’s favorite treats! Depending on your pet’s fur type, it might also be a good idea to groom them before the shoot.

6. Include your Family.

If you have children, they are always welcome at your engagement session. It makes it that much more fun to capture, because I get to create photos that not only show your love for your partner, but your family too.

We recommend having a family member or friend bring your child at the beginning of the session and then taking him/her home.

7. Drinks at a winery, brewery or bar.

On date night, where do you like to go for drinks? It can be a fun way to end your engagement session with drinks at your favorite place. It’s also another opportunity to personalize your photos.

Shannon and Jerad love exploring new craft beers so we made sure to start off the engagement session at a local brewery called The Roaring Table.

Below are ideas for wineries, breweries, and bars to go to for your Chicago engagement photos.

City Winery: 1200 W Randolph St, Chicago, IL 60607 | Wild Blossom Meadery & Winery: 9030 S Hermitage Ave, Chicago, IL 60620 | Goose Island: 1800 W Fulton St, Chicago, IL 60612 | Guiness Brewery: 901 W Kinzie St, Chicago, IL 60607 | Cindy’s Rooftop: 12 S Michigan Ave, Chicago, IL 60603

8. Go on a picnic.

Picnics are such a cute activity for your engagement photos. Tim set up a picnic at Olive Park in Chicago for his suprise proposal to Erin.

These two met almost 3 years ago during the pandemic on Bumble. Because there weren’t many good date night options during that time, they started cooking together, and enjoy doing that even now. They also enjoy going on picnics together, but Tim wanted to make this particular picnic even more special.

When he got a text that Erin was on her way, you could tell Tim felt a little more nervous. He wanted everything to go perfectly for Erin. She arrived at the picnic and was ready to catch up and decompress after a long work day.

Tim surprised Erin first with dessert from her favorite place – The Killer Brownie Co. He wanted to throw her off a little bit, because he had a feeling she might be onto his real surprise. She excitedly gave him a kiss and then Tim took her hands in his as he knelt down on one knee to propose.

Here are some of our favorite Chicago engagement photo locations for your picnic:

Milton Lee Olive Park: E Ohio St, Chicago, IL 60611 | Ping Tom Memorial Park: 1700 S Wentworth Ave, Chicago, IL 60616 | Alfred Caldwell Lily Pool: 125 W Fullerton Pkwy, Chicago, IL 60614

9. Chicago engagement photos in front of the skyline.

I think Chicago has one of the prettiest skylines. The way the light reflects on Lake Michigan and the buildings – you seriously can’t beat it.

It also makes it makes it fun choosing a location for your engagement photos in Chicago. There are so many great options.

Below is a list of some of my favorite locations for skyline views for Chicago engagement photos.

Milton Lee Olive Park: E Ohio St, Chicago, IL 60611 | Lincoln Park Nature Boardwalk: 2121 N Stockton Dr, Chicago, IL 60614 | North Avenue Beach: 1600 North Lake Shore Drive, Chicago, IL 60613

10. Go on a hike for your Chicago engagement photos.

Since Illinois typically has a flat landscape, it’s always exciting to find locations with unique scenery. Drive about 2 hours outside of the city, and you will find beautiful rock formations and a breathtaking waterfall.

I had so much fun hiking and exploring this Matthiessen State Park with Juliana and Ryan. A bonus is that it’s also where they got engaged. How cool is that?

Below are a few parks with great hikes and views for your Chicago engagement photos.

Matthiessen State Park: 2500 IL-178, Oglesby, IL 61348 | Devil’s Lake State Park: S5975 Park Rd, Baraboo, WI 53913

11. Let’s go to the beach for your Chicago engagement photos.

If you love spending time at the beach then let’s incorporate that in your engagement photos.

For example, Jessica and David both coach and play volleyball. It made sense to take photos at North Avenue beach where they often play beach volleyball.

Here are some of our favorite beach locations for your Chicago engagement photos:

North Avenue Beach: 1600 North Lake Shore Drive, Chicago, IL 60613 | Indiana Dunes State Park:

12. Have art as your backdrop.

Galleries and murals can be the perfect way to incorporate an artsy feel into your Chicago engagement photos. One of my favorite locations in Chicago is the Art Institute of Chicago. The inside is beautiful and they permit photography in all of their permanent galleries.

Another reason why I love the Art Institute of Chicago is the south garden. You never would know it’s actually built on top of a parking garage with the beautiful trees and vines throughout the garden. It was the perfect location for Jay’s proposal to Lizzie in the south garden.

Here are my favorite locations for adding art to the backdrop of your engagement photos:

Art Institute of Chicago: 111 S Michigan Ave, Chicago, IL 60603 | Greetings from Chicago Mural: 2226 North Milwaukee Avenue, Chicago | Blue & White Flowers Mural: 1700 S Wentworth Avenue, Chicago

13. Chicago engagement photos with fall color.

October is a popular time for photos in the midwest. Make sure to get on our calendar as soon as possible if you are wanting a session date in October.

We love the warm tones that the changing leaves bring to your engagement photos. During fall, we love both the city and suburbs for your session.

Below are are two favorite locations for your fall engagement photos: Lincoln Park Nature Boardwalk: 2121 N Stockton Dr, Chicago, IL 60614 | Morton Arboretum: 4100 IL-53, Lisle, IL 60532

14. Spring flowers for your Chicago engagement photos.

Spring is such a fleeting season in the midwest, but if we get lucky, we can catch some of the prettiest spring blooms. It varies every year, but usually the end of April and beginning of May are the perfect time for your spring engagement photos.

One of my favorite locations for spring photos is the Morton Arboretum in Lisle. The trees that are planted there represent not only Midwest species, but also trees from all over the world. During Carson and Dalton’s spring engagement session, we were able to get so many different backgrounds for the photos, and it was all taken at the same location.

Here are are top spring engagement photo locations:

Morton Arboretum: 4100 IL-53, Lisle, IL 60532 | Cantigny Park: 1 S, 151 Winfield Rd, Wheaton, IL 60189

15. Go on a boat cruise for your Chicago engagement photos.

Do you love the water and want that incorporated into your photos? If you have a boat or lake house then that could a great option for your engagement photos. Or if you don’t have a boat, no worries! Chicago has so many choices for boat rentals or your could go on a boat cruise or architectural tour of Chicago on the water.

For example, after Evan’s proposal by the Chicago Riverwalk he surprised Julia with a boat cruise around Chicago to celebrate.

Here are some places you can rent boats or go on boat tours in Chicago:

Chicago Sailboat Charters | Chicago Electric Boat Company | Chicago River Architecture Tour

16. Dance to your wedding song.

An engagement session can be the perfect time to practice your first dance. Anytime we can bring movement into photos it makes it that much more fun and special.

17. Let’s go chasing waterfalls.

Waterfalls in Illinois? You might not think they exist here, but they do! We have a few favorite spots that we love.

Check out Juliana & Ryan’s Matthiessen State Park session and Christina & Dan’s Waterfall Glen session for some waterfall inspirations.

Chicago engagement photo locations with waterfalls:

Matthiessen State Park: 2500 IL-178, Oglesby, IL 61348 | Waterfall Glen: Lemont, IL

18. Explore a Destination.

While we photograph most of our engagement sessions in the Chicago and Nashville, we’ve photographed sessions everywhere from Oregon to Colorado to Minnesota. If you have a location in mind, let us know because if our schedules align, we might be able to take your engagement photos outside of our normal area.

I loved photographing Kayla and Joels engagement session at Haystack Rock in Oregon. This was my first trip out the the Pacific Northwest, and it sure didn’t disappoint. It amazes me how all the things I love (mountains, waterfalls, forests, vineyards, and beaches) can all be found in Oregon.

We are always up for a new adventure and would love to capture you two wherever that is.

19. Back to where it all started.

I love it when couples choose a location that has special significance to them. Going back to the place where you first met or had you first date, is a great way to add a sentimental and personal touch to your photos.

Avni and Whitney met while attending college at the University of Illinois. So it only made sense to head to Champaign to take photos and reminisce at the place where they met. Whitney and Avni walked around the campus with me, and I loved how each spot we visited brought back such good memories for them.

I’m all for choosing a location because it’s beautiful, but when it also has sentimental value it makes it that much more special. Hanging out with Whitney and Avni at their old college campus was so much fun.

20. Include your car in your Chicago engagement photos.

Maybe you have a classic car, motorcycle, truck or Jeep that you want to have at your session. For Alexis and DJ’s engagement session, they brought their Jeeps along since they both love off-roading.

For Sam and Jake’s engagement session, Jake requested that we take a few photos by his truck. The photos of these two snuggling in the back of his pickup are some of my favorites from their Chicago engagement session.

21. Embrace your inner foodie.

If you two are foodies who are always looking for the next new restaurant to try then why not celebrate that in your Chicago engagement photos.

Do you love ice cream, pizza, tacos, or something else? Let’s incorporate your favorite foodie spot into your engagement session.

Alexandra and Grant chose the perfect way to end their engagement session – grilled cheese! We stopped at Everdine’s Grilled Cheese Co and they even had a gluten free option for Alexandra. Also, these photos of them chowing down on grilled cheese are some of my favorites from their engagement session.

22. Exchange letters with your partner. 

An engagement session might seem like something else to check off your wedding to-do list, but I encourage you to make it a truly fun and memorable experience. Exchanging letters during your session will make it that much more special.

23. Show off your wedding vibe. 

It’s also a great idea to consider what the vibe of your wedding is when deciding where to take your engagement photos.

Is your wedding going to be artsy, outdoorsy, rustic, modern, or something else? For example, if your wedding is going to be at a barn venue then maybe you want your engagement photos to take place at a rustic or nature location.

Or some couples prefer to do something completely different for their engagement photos. For example, if you’re having your wedding in the country maybe you want to do your engagement photos in Chicago. That way you get two completely different backgrounds and vibes for your engagement photos.

24. Take Chicago engagement photos at home.

There is something extra special about the simplicity of an at home engagement session. The place you feel most comfortable is often at home and it truly does bring a personal and intimate feeling to your photos.

25. Do your favorite activity together.

If you’re worried about feeling awkward or not knowing what to do for your session, then an activity can be a great idea. It’s also a special way to personalize your session and have even more fun taking photos.

Jill and Mike love the outdoors so they decided to go canoeing during their engagement session. There are so many fun activities to choose from, but just make sure the activity you choose is something you both enjoy and reflects who you are as a couple.

Some ideas are paddle boarding, kayaking, swimming, biking, sailing/boating, reading, baking, cooking, hiking, and more.

Let’s work together!

Are you getting married and looking for a photographer to capture your Chicago engagement photos, proposal or wedding? I’d love to hear from you. Click here to contact me today.