Tips for Chicago Engagement Sessions: A Guide for Out-of-Towners

Featuring Danielle & Jake’s North Beach Engagement Session

Planning an engagement session in a big city can be exciting, especially if you’re not from the area. Chicago, with its stunning urban landscapes, iconic landmarks, and picturesque natural spots, offers a perfect backdrop for capturing your love story. Whether you're visiting from a small town or another city, here are some tips to make the most of your big city engagement session, featuring popular locations like North Beach, Garfield Park Conservatory, Lincoln Park Zoo, and more.

1. Plan Ahead and Scout Locations

Before your session, spend some time researching and scouting potential locations. Some locations might require a permit for formal photography, which can be an additional expense. For the actual location of your session, Chicago is full of beautiful spots, each offering a unique vibe. Popular locations include:

• North Beach: Ideal for romantic sunset shots on the lakefront with the city skyline in the background

  • This is where Danielle and Jake chose to have their engagement session!

• Garfield Park Conservatory: Perfect for nature lovers with its lush, vibrant plant displays.

• Lincoln Park Zoo: Offers a mix of charming animal exhibits and scenic gardens.

• Millennium Park: Known for the iconic Cloud Gate (The Bean) and its modern architectural features. Get a mix of urban and nature by visiting Lurie Gardens.

• Riverwalk: Get some of the most iconic city views and bridges up close along the river.

• Wrigleyville: Home of the Chicago Cubs and a perfect spot for sports fans

• Chicago Botanical Garden: 385 acre nature garden full of flowers and unique greenery.

• Buckingham Fountain Flower Gardens: One of the world’s largest rococo fountain with a view of the city skyline. Also has easy access to the lakefront as a second location.

• Navy Pier: An old Navy training center turned tourist attraction with a ferris wheel, views of the city, and unique activities.

2. Timing is Everything

Timing your engagement session is crucial to get the best lighting and avoid crowds. Early mornings or late afternoons are ideal for softer, more flattering light. If you’re planning to shoot at popular spots like Millennium Park or North Beach, visiting during off-peak hours will help you avoid large crowds and give you more flexibility. Make sure to check community calendars to make sure there are no big events scheduled where you plan to take photos. It is important to check traffic and be aware of where to park so you are on time. 

3. Dress for the Occasion

Choose outfits that reflect your personality and complement the urban setting. Consider bringing multiple outfits for variety. For a chic city look, opt for sleek, stylish attire that stands out against the city backdrop. For a more relaxed vibe, casual wear works well, especially in natural settings like Garfield Park Conservatory or North Beach. Don't forget comfortable shoes for walking between locations.

4. Embrace the Urban Vibe

Big cities like Chicago offer a unique blend of modern architecture and historical charm. Use this to your advantage by incorporating city elements into your photos. Posing near iconic landmarks, strolling down bustling streets, or capturing candid moments in local cafes can add a dynamic and authentic feel to your session. Feel free to include locations that are special to your relationship, like your favorite bar or where you had your first date.

5. Incorporate Personal Touches

Make your engagement session uniquely yours by incorporating personal elements. Bring props that are meaningful to you, like a favorite book, a picnic setup, or even your pet. Personal touches make your photos more special and tell your love story more vividly. Keep in mind that larger displays or props may not be allowed at certain locations and must follow Leave No Trace guidelines.

6. Be Prepared for the Weather

Chicago's weather can be unpredictable, so it’s essential to be prepared. Check the forecast before your session and plan accordingly. Bring umbrellas, jackets, or extra layers if needed. Embracing the weather, whether it’s a sunny day or a bit of rain, can lead to some unexpectedly beautiful shots.

7. Hire a Photographer That Knows the City

Working with an experienced photographer who knows the city well can be a game-changer: they can recommend the best locations, timing, and angles for your shots. Plus, they can help you navigate the city efficiently, making the most of your time and ensuring a smooth experience.

8. Explore Lesser-Known Spots

While iconic locations are a must, exploring lesser-known spots can add a unique touch to your engagement photos. Consider visiting local parks, hidden alleyways with street art, or charming neighborhoods like Wicker Park or Logan Square. These areas often provide a more intimate and personal backdrop.

9. Be Authentically You

While posed shots are great, don't forget that your engagement session is a time to show off your relationship and love for each other! Don’t be afraid to be playful, give little kisses on the cheek, make jokes at each other, and interact how you normally do together. This allows you to get photos that feel natural and more relaxed. If you’re feeling nervous, just keep your attention to each other and remember you’re celebrating your love!

Engagement sessions in big cities like Chicago offer endless possibilities for stunning and memorable photos. By planning ahead, embracing the urban vibe, and adding personal touches, you can create a beautiful collection of images that capture your love story. Whether you’re posing at North Beach, exploring Garfield Park Conservatory, or strolling through Lincoln Park Zoo, these tips will help you make the most of your big city engagement session.

FAQ’s

1. What time of day is best for an engagement session in Chicago?

   Early mornings or around sunset are the best times for outdoor photos for the most flattering lighting. The best time for indoor locations is usually midday or early afternoon.

2. What should we wear for our engagement photos?

   Choosing items that reflect your personal style and you feel comfortable in are the most important factors when picking your engagement photo outfits. Neutral, or lightly patterned clothing will compliment your skin tones and limit colored reflections that can come from bright colors. If you are unsure about which outfits you like best, feel free to bring multiple options and we can choose what looks best at the location you choose.

3. How can we make our photos unique?

   Incorporate personal touches and props that are meaningful to you. Explore lesser-known spots for a unique backdrop. Including your pets, going to your first date spot, or doing an activity you enjoy doing together like riding bikes along the riverfront can be fun ways to show off special parts of your relationship.

4. Is there anything I should check about my venue beforehand?

   It is always important to contact the venue you are wanting to take photos at to confirm if a photography permit is required, check if there are any events or other photoshoots that are taking place that could interfere with your photoshoot, and make sure you are allowed to take photos in that area. Most parks in Chicago, like the Nature Boardwalk at Lincoln Park Zoo and North Beach, require a photography permit that can range from $80-100.

5. What if the weather is bad?

   Be prepared for all weather conditions and embrace them! Sometimes, unexpected weather can lead to beautiful and unique photos. In the case of severe weather, if an indoor location cannot be found we will reschedule your session to a new date. Please note that permits may be nonrefundable and you could be required to purchase a permit for your new date.

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Ready to book your Chicago engagement session? Contact me below to learn about pricing and availability!

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Hey there! I’m Reagan - an Indianapolis wedding and elopement photographer documenting candid and colorful love all over Indiana & Michigan.

I’m a Muncie native but currently live on the east side of Indy with my partner, Will, and our two dogs, Winston & Poppy. When I’m not out documenting wedding days, you can find me at a concert, building legos, watching Star Wars, eating Thai food, or exploring a new city.