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  • Kate Bek

Where To Go: Your Downtown Chicago Engagement Session

Updated: Apr 14, 2018


To many of us, “engagement photos” used to mean Dad haphazardly snapping head shots to send to the newspaper column. That’s right. You took it on your front porch, got it developed (wut?) and then physically mailed it off to the local press. Et voila. You were on your way to happily-ever-after via the analog social media of yesteryear.


Not everyone takes engagement photos, and that's absolutely fine.


Mind you, this was was in ye olden days (circa 1950 - 2008). Times change; and whether you do it professionally, employ Dad (who probably has a drone by now), or grab a smartphone and selfie stick, documenting the decision to spend your lives together doesn’t have to be slapdash or basic. If you choose to do it, just make it flat out YOU - as in “you two” the pair who somehow found each other and have agreed to forever share coffee and toothbrushes and leftovers. The two of you who will (lovingly) battle over music playlists and blanket hogging and dog poop duties. The team who will band together to navigate the complicated stuff like Netflix and mortgage applications and your inlaws’ food preferences. There may or may not be a garden or babies or college funds. There may or may not be vacations, dream jobs or 401ks. There may or may not be a lot of things, but you’re preparing for those maybes together. And this is your start - the photographic calm before all of the adventures that lie ahead. Today there are so many creative ways to capture the “here and now," it's gotten much easier to fall in love with the idea of modern couples and engagement photos.


After all, this is your first family photo session, right? However you do it, approach it in a way that feels right and organic and uniquely "you two."


As a practice, I include a complimentary mini-session for engagement photos as part of my wedding package. It’s special, it's great practice, and it's one of many genuine ways to bond with the couple on the journey towards the wedding day. But aside from that, I also often also get requests for engagement sessions, couples portrait sessions and mini-couple sessions in Chicago. For all of it, I come prepared both for couples who know where they want to shoot and for those who are up for suggestions. Your photographer should have a handful of ideas, so when discussing your preferred location, don’t be afraid to say, “We are hoping you could help with that.” Trust me, your photographer will have preferred locations and ideas ready for brainstorming.


So, if you happen to be a couple who wants to capture the essence of togetherness in Chicago, these quick suggestions are for you. These are great ideas for those who want to document yourselves under an iconic Chicago environment. While I do have many favorites, I’ll start this series with a few locations in the heart of downtown Chicago. All of these locations can capture a little bit of nature, a side of skyline and the genuine heart of this city.


Here are a few of my favorite location suggestions for romantic couples and engagement sessions in downtown Chicago:


Lakeshore + Downtown + Riverwalk

If you have a full 1-2 hours for your shoot, this is an absolutely lovely tour through the heart of Chicago’s downtown and Lakeshore. I really think it captures the essence of the city. My preferred progression is:

  • North Avenue Beach (Start)

  • El Steps of Choice

  • Chicago Theater

  • Marina Harbor / Wacker Drive

  • Riverwalk

  • Lasalle Bridge (end)

Plan a nice dinner or cocktail hour you can walk to after the shoot, and you have an incredibly fun, romantic evening. For this tour, I suggest bringing walking shoes to throw on between shoots and take an Uber from the beach into downtown. You may also choose to change into a new outfits at the beach before you head into downtown. And obviously, each of these locations is good as a briefer, stand-alone Chicago mini session.






(Never underestimate the timeless joy in a completely air-balled high five.)



Milton Lee Olive Park

This is one of my absolute favorite spots in the city. It’s perfect for catching a gorgeous Chicago backdrop with a side of Lake Michigan and a treeline. Plus, you can always add a quick walk to extend your engagement session at Navy Pier.


MLO Park is located near Navy Pier. Get Directions.












Millennium Park

Seriously, what’s not to love about this downtown gem? Millennium Park is full of creative spaces and backdrops year round. From the busy summer to bristling winter, I've shot it all, and it’s perfect for a shorter session any time of year. From Cloud Gate (The Bean) to the gorgeous walkway to the Art Institute, this is one of my favorite selections for mini-shoots. Particularly for out-of-town visitors, as it's usually close to your hotel! Typically you can get 3 different backdrops in 20-30 minutes.


Tip: Sometimes public trans is tough for everyone involved in a shoot. I have a lot of clients who come in from nearby areas, neighborhood and suburbs with parking concerns. True, sometimes we just want to drive and parking can get tricky (not to mention expensive!) in the Millennium Garages. If you prepay, you'll save up to 50%! I do this for every shoot.





Lincoln Park Zoo to Peggy Notebaert Nature Museum

Tucked just north of the skyline, this is a fantastically quiet Chicago location. The stretch from the Lincoln Park Zoo to the Honeycomb (aka the People's Gas Education Pavilion...call it what you will) to the PNNM is one of my favorites. It's a gorgeous private walk and the whole shoot can easily be covered in 40-60 minutes. I find this walk particularly great for fall, as it captures the city skyline with a gorgeous wave of maples and fall colors.





On Second Thought...

Maybe these vibes aren't for you, or maybe you want to get a little hyper-local creative in your own neighborhood? Think about making your shoot unique to your own Chicago life or getaway in the city. It's hard to narrow it down, because there are so many places in the city that can be perceived as busy and urban, but truly photograph in a surprisingly intimate way. Here are a few more of my favorite suggestions for local Chicago engagement and couple's shoots:

  • A Chicago sunset sail or Architecture Tour

  • The Adler Planetarium

  • Jackson Park & The Japanese Garden

  • Your beloved Chicago hot dog, taco or pizza spot

  • A cafe or brewery you frequent

  • Your favorite nearby Chicago park

  • Your home <3