Creative ideas and favorite locations for your engagement photo session in the Windy City.

All Photos by Artistrie Co.

You’re engaged, living in Chicago, and starting to plan your engagement session. Where do you begin? Chicago is a beautiful city with unlimited possibilities for your engagement photos, and I’m here to help! I have loaded this blog post with content to help you find a way to personalize your photo experience and find the perfect city backdrop. Plus, you can check out my Engagement Session Guide here!

Before planning your engagement session, here are a few key tips:

Location

Where do you feel most at home together? I like to ask my clients this question because it’s important for you to feel comfortable to let your personalities shine in your photos. Some love the bustle — walking downtown on Michigan Avenue or having a drink at their favorite West Loop bar is how you spend your free time. Others prefer the peace and quiet found along the lakefront or in their favorite park.

Are there sentimental places you’d like to revisit? Perhaps the place where you celebrated your engagement or shared your first date together. And while the city of Chicago offers so many beautiful photo locations, don’t forget about places beyond the city limits. Nature lovers can take advantage of forest preserves and arboretums (a wide open field and the glow of sunset is sometimes all you need). And if you like to travel or have a home-away-from-home, think about your favorite place to be together. There’s no limit to what you can do for your engagement photos.

Related: Chic Indoor Chicago Engagement Photo Locations

Related: Five Fabulous Chicago Engagement Photo Locations

Related: Artistrie Co. Engagement Photo Portfolio

Wardrobe

Your outfits should complement one another, but not match exactly. For example: If one of you wears a bolder color, then the other could wear something more neutral to create harmony and balance. Keep in mind the locations you have selected for your portrait session. Avoid wearing colors that will blend in or clash with your surroundings. You want to be the focal point of your photographs. Consider colors that flatter your skin tone and hair best. What hues make you feel the most beautiful? Lastly, if you are bringing props and accessories to your shoot, be sure to coordinate the colors of these details with your outfits so everything flows together.

Lighting

The best times of day for outdoor portraits are sunrise and sunset. Because of this, I recommend that my clients schedule their photos around these times for optimal results. Sunset is the most popular time because it gives my clients the entire day to get ready for their shoot.

Depending on the finalized plan, we’ll usually start taking photos about 2 hours before the sun sets. If you will be visiting popular tourist and photo locations, sunrise can be a great way to get the city all to yourself. In Chicago, sunrise is the easiest during fall and winter where it comes up around 7:00-8:00am.

Hair & Makeup

I always recommend to hire a professional makeup artist and hair stylist for your engagement session. One of my favorite Chicago area makeup artists, Joanna of Joanna B Artistry, says it best:

“When being professionally photographed, you need to be sure you are wearing the proper amount of makeup in order for it to actually be visible on camera. Your everyday application may not be enough. A professional makeup artist knows how to achieve this look using specific techniques to enhance your natural beauty and create a flawless look that will show up beautifully on camera.”

With that in mind, here are my 62 ideas to inspire your Chicago engagement photo session!

Creative Ideas for Your Chicago Engagement Photos

No. 1: Toast to the Occassion 

Call ahead to your favorite bar and ask if you can order a few drinks at take photos in their bar. The answer will almost always be yes! Try to go at a time where the bar isn’t too crowded so you have your first pick at seats. This particular photo was taken at the Kennison in Lincoln Park.

No. 2: Twirl

Movement in engagement photos is everything! I don’t want you standing like statues. Move, dance, twirl. Have fun with it!

No. 3: Get Cozy

A cozy blanket is a cozy and practical accessory to a Chicago engagement photo shoot, especially on a chilly fall evening.

No. 4: Visit the Bean

I know, I know. The Bean is so touristy. But if you plan it right and go at a less busy time of year, the view can be pretty epic. This particular shot was taken in the winter when the foot traffic is way less.

No. 5: Coffee Date

Do you and your fiance drink coffee by the gallon? Consider visiting your favorite coffee shop or pick up a pair of lattes to go for your engagement photos.

No. 6: Make Bold Color Choices

Don’t be afraid of color! For some reason, a lot of brides think they have to dress in white for their engagement photos. While there’s nothing wrong with that, if you are wearing a white dress on the wedding day, spice it up for your engagement session. The bolder, the better in photos.

No. 7: Feel the Heat at Garfield Park Conservatory

This is one of my favorite retreats for winter engagement photo shoots. You can read more about my go-to indoor Chicago locations here. Garfield Park Conservatory is always warm and fully of greenery. I especially love the Desert House, pictured above. If you love greenhouses, this place is perfect for Chicago engagement photos at any time of the year.

No. 8: Bring the Drama

You cannot overdress for your engagement session. And if you dress to the nines, everyone walking around Chicago will be left wondering if you are a celebrity.

No. 9: Puppy Love

I love your fur babies (especially dogs), so bring them along for a few photos. To keep it as easy and stress-free as possible, I recommend bringing a friend or family member along to help with your pup and take him home when we’re done. Plus, it’s great to have the extra set of hands to hold toys and dog treats over my head. 😉

No. 10: Sunset Chicago Skyline Views

I’ve never seen the same sunset in Chicago twice. Every sunset is different and beautiful in its own way. My Chicago engagement photo clients especially love the views from North Avenue Beach, where we can take in the whole city with the golden sunlight pouring through.

No. 11: Find Unique Architectural Details

Keep your eyes peeled. Chicago is filled with surprising pops of architectural detail, fancy doorways, grand staircases and beyond.

No. 12: Relive Your Proposal

I love when my couples do this! If you love the location of your proposal, let’s return to the scene of the crime to capture the moment all over again.

No. 13: Find Fall Foliage

Fall is the most popular time of year for engagement photos and its obvious why. Chicagoans love their fall colors and cozy sweaters!

No. 14: Visit Your Favorite Paintings at the Art Institute

If you don’t mind buying a pair of tickets, the Art Institute is a beautiful place for engagement photos, inside and out. Week day mornings are the best time to go (when it’s as quiet as possible). This location is perfect for the cultural couple who love art and museums.

No. 15: Go Glam

Again for those in the back: you cannot overdress for your engagement photos. And sparkles are always okay.

And speaking of glam, if you are getting married and are considering a bridal boudoir session, it’s one of my most popular services! You can read more about boudoir and all that great reasons to do a boudoir session here.

No. 16: Recreate a First Date

Go down memory lane by reliving a sentimental date. It will help your photos tell a story and you’ll feel right at home in front of the camera (especially in a restaurant as pretty as the Warbler).

No. 17: Find Quiet at the North Pond

I know everyone is all about the South Pond, but I’m team North Pond. It’s quiet, peaceful and filled with beautiful nature.

No. 18: Hit a Home Run at Wrigley Field

You have to play for or work for the Cubs organization to pull this one off, but I’ll say that taking photos on Wrigley Field is still a highlight of my life. Thank you to my client Alex for letting me wear his World Series ring. 😉

No. 19: Drink Champagne

Champagne is the perfect accessory to any engagement session! Sip it or spray it, the choice is yours. 😉

No. 20: Visit the Chicago Bridges

There’s an endless supply of bridges in Chicago and I love them all for different reasons. Pictured above is the Wells Street Bridge caught at a very rare split second during rush hour where no one else was in frame.

No. 21: Vintage Finds at Salvage One

If you have a Wicker Park soul and love antiques and vintage warehouses, Salvage One could be a perfect spot for your photos. Artifact Events in Ravenswood is another great option!

No. 23: Take in Your Favorite View of Chicago

Do you have a favorite view of the city? With Chicago’s entire lakefront being open to the public, there’s no shortage of stunning views. Consider this for your photos!

No. 24: Ride in Style

Capture photos in motion as you ride off into the sunset together…or in this case, under the L tracks.

No. 25: Get out of the City

Just beyond the city limits, there’s a multitude of forest preserves and arboretums that are beautiful options for the couple who loves the calm of nature. Honestly, I love the simplicity of an open field and golden sunshine. It’s all you need.

No. 26: Travel to Your Favorite Destination

No one said you HAVE to take photos in Chicago. Even if you live here and are getting married here, if your heart belongs somewhere else, consider a destination engagement session. Sedona (pictured above) is my personal favorite place and I consider it heaven on earth.

No. 27: Visit State Street (that great street)

The Chicago Theater sign on State Street is ICONIC. This is for the couple who want the quintessential Chicago engagement photo.

No. 28: Find Street Art

Street art in Chicago is everywhere. Keep your eyes peeled for fun graffiti or wall murals that speak to your style.

No. 29: Wake up for the Sunrise

Sunrise is magic. There’s nothing quite as beautiful as watching the sunrise over Lake Michigan as Chicago wakes up.

No. 30: Carry a Bouquet

Not sure what to do with your hands? A simple bouquet can be a beautiful accessory to your engagement photos.

No. 31: Dip Your Toes Into Lake Michigan

Love the water? Go for it! Summer only lasts for so long around here.

No. 32: Picnic at Oak Street Beach

Oak Street Beach in the fall is quiet and offers stunning scenery of the Gold Coast.

No. 33: Play in the Snow

This photo is social proof that Chicago winter doesn’t always have to be dreary and drab.

Related: Five Festive Chicago Holiday Engagement Photo Ideas

No. 34: Kiss in the Rain

While you can easily reschedule your session due to rain, you can also grab an umbrella and embrace it!

No. 35: Explore the Beauty of Hyde Park

Hyde Park has so many hidden gems worth exploring! The University of Chicago campus is the perfect place to start and I highly recommend paying a visit to the historic Museum of Science and Industry.

No. 36: Watch the City Glow

I know I’ve already told you I love sunset lighting for engagement photos, but if time allows, hang back just a few extra minutes until dusk and all the city lights start to glitter in the distance. We did just that for this evening shot and it’s easily one of my favorite Chicago engagement photos I’ve taken yet.

No. 37: Visit Pure Michigan

Considering a day trip for your engagement session? I’m all about the Pure Michigan love!

No. 38: Get Musical

Does you significant other serenade you with the tunes of a guitar? Incorporate that into your photos.

No. 39: Wear a Floral Crown

Floral crowns are perfect for the bride with the bohemian soul.

No. 40: Pose by Your Favorite West Loop Bar

West Loop is the best loop, amiright?

No. 41: Tour the River Walk

The bridges, the architecture, the water. What’s not to love?

No. 42: Dance on the Kinzie Street Bridge

One of my favorite bridges in Chicago so it deserved it’s own post. If you are one of my clients, you probably have memories of twirling and dancing in the middle of this iconic bridge.

No. 43: Steal Kisses Inside Union Station

Inside and out, Union Station is a Chicago gem.

No. 44: Explore Chicago’s’ Beautiful Gardens

When people think about Chicago downtown gardens, they usually think about Millennium Park and the Art Institute and it ends there. Michigan Avenue offers miles of city gardens. Explore them!

No. 45: Take a Neighborhood Stroll

Want to make it personal? Take a stroll with your love around your neighborhood and take in the sights. This makes your Chicago engagement photos feel more personal and true to you.

No. 46: Watch the Sunset at Promontory Point

I love love love Promontory Point.

No. 47: Sip Cocktails on a Patio

It’s every Chicagoan’s favorite summer activity for a reason.

No. 48: Go Ice Skating at Millennium Park

This one takes a lot of planning and time commitment (given how busy it can be), but if you love winter activities, ice skating downtown is a fun and unique way to approach your engagement session.

No. 49: Take a Leap

I call these aerials. Engagement sessions aren’t all play, they are work too!

No. 50: Visit the Morton Arboretum

I spend a big chunk of my time at the Morton Arboretum and I know the grounds like the back of my hand. It’s one of my favorite places to take photos at all times of the year.

No. 51: Enjoy Your Rooftop Views

Sometimes the simplest solution is the homiest. If your apartment building has a rooftop deck with a view, consider using it for your session. It’s a view no one else will be able to get.

No. 52: Walk the Nature Boardwalk

The Nature Boardwalk in Lincoln Park is always everyone’s favorite. Consider it as an option for your Chicago engagement photos, especially if you love nature.

No. 53: Scenery at Olive Park

For an alternate view of Chicago’s iconic skyline views, visit Olive Park. It’s one of a kind.

No. 54: Toss Confetti

But make sure it’s biodegradable.

No. 55: Wear Custom Design Sweaters

You have my permission to be as cute and adorable as possible.

No. 56: Perfect Your First Dance Dip

Engagement sessions are a great time to work on that photo worthy dip.

No. 57: Get Silly

It’s all about having fun! Don’t take it too seriously. We’ll laugh a lot.

No. 58: Take a Long Walk Down North Avenue Beach

Ditch the shoes and walk along the shore.

No. 59: Find Romantic City Gardens

This is one of the most romantic gardens in the city.

No. 60: Walk Where City Meets Nature at Montrose Harbor

My personal favorite location in Chicago. I love how you can get the lake, nature and the city skyline together in one shot.

No. 61: Pose in Front of Chicago Signage

If you really want people to know where you are taking your photos…

No. 62: Pop Bottles

Champagne isn’t just there for sipping, it can be so much fun in pictures…especially if you shake up that bottle! And if you like this snowy session, be sure to read more about taking beautiful engagement photos in the winter.

Like what you see?

If you like my Chicago engagement photos, I’d love to hear from you and answer your questions about working together. Please view my Engagement Photo Portfolio here. To get more info, please contact me through my contact form or email me directly at ashley@artistrieco.com or call at 630.674.8001.

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