Our Top Chicago Photo Spots

If you follow us on Instagram, you know that we love to post photos of Chicago on our insta feed. We may be a little biased, but we think the Windy City is drop-dead GORGEOUS. To highlight some of these photo worthy spots, we thought we would compile a go-to guide for visitors (or even locals playing tourists for the day!) that outlines some of our favorite Photo Spots in Chicago. In no specific order, here’s our all-star line up:


chicago park(the view from above the bean)

Specific Location: Millennium Park (nearest to intersection of Michigan Avenue & Madison)

Tips: The bean (official name “Cloud Gate”) is something like we’ve never seen before and offers tons of silly, fun, creative photo-ops. Whether you hit up this iconic spot to take a selfie in its reflection or enjoy the skyline’s lights in the background, we promise you won’t be disappointed. If you’re visiting in the winter, you can skate on the ice rink right below it for some gorgeous views OR in the summer, you can enjoy a delicious lunch in that same spot.


Chicago fountain night(Buckingham Fountain at Night… note the Air Jordan in the lights of the buildings in the background. Details below)

Specific Location: Grant Park (Between Columbus & Lake Shore Drive, near Congress Parkway)

Tips: Before you go to see this huge and beautiful fountain, make sure you check the dates to make sure it is still spouting water! This was news to us when we went to take pics for this post and there wasn’t water running anymore! Cold weather = No water. On a brighter note (literally), if you notice in the back of one of our old photos… the skyline behind the fountain often coordinates to spell out something special going on in the city. Whether it’s a sports accomplishment, cancer awareness month, honoring veterans, these buildings turn on their lights at night to literally highlight something meaningful and important within the windy city. <– pretty awesome if you ask us!


View More: http://ginacristine.pass.us/casey--mike-1(Casey’s gorgeous wedding photos in Olive Park)

Chicago Skyline(The view of the skyline from the park)

Specific Location: 1 block Northeast of Navy Pier.

Tips: This hidden gem has a beach, a tree-filled path, and some  breathtaking views of the Gold Coast. This park is so gorgeous that it’s where Casey & Finn took their wedding photos last fall.  <– If you want to see more photos of Olive Park, definitely check out those photos.


Chicago-walk-blackhawks(The lions are seen here dressed up for the Blackhawks’ Stanley Cup win in 2015. These famous lions wear helmets, jerseys, even scarves/ear muffs too!)

 Specific Location: Intersection of Michigan Avenue & Adams Street

Tips: These charming lions stand outside of the Art Institute of Chicago. They dress up depending on the season and are definitely a Chicago symbol you want to check out. We would suggest checking these bad boys out at the same time you check out the bean & Buckingham Fountain because all three are in the same general area.


View More: http://ginacristine.pass.us/casey--mike-1chicago-skylineChicago flag river summer(View from the bridge around 4th of July)chicago st. patricks day green(A view from the Michigan Avenue Bridge looking West after the river was dyed green for St. Patrick’s Day!) 

Specific Location: Anywhere along the Chicago River.

Tips: If you’re in the heart of the city, there is no way you’re going to miss the Chicago River because it runs right there. Standing on any of the bridges and looking down the river (both directions) is pretty incredible. And if you’re looking to take an architectural boat tour  (highly recommended!), you can pick up the boat tour (or water taxi) right below the bridge on Michigan Avenue and the River. <– Plus, the photo ops on the boat tour are AH-MAZING!!!   



(Frigid temperatures and still water at Museum Campus’ path along the lake)Chicago Skyline

Insta-Chicago-Skyline-rookiesSpecific Location: Museum Campus (from the “heart of Chicago” take Lakeshore Drive South about 2-3 miles and exit at McFetridge Drive by the Field Museum) OR water taxi from Navy Pier for a few bucks.

Tips: This is hands down the best place to photograph the skyline (because you can get the entire skyline in 1 picture), plus it’s super peaceful and a place you can park and enjoy walking (or running) the lake front. If you’re in this area, you can also visit the three museums right there (Shedd Aquarium, Adler Planetarium and the Field Museum) or the Chicago Bears’ Stadium (aka Soldier’s Field).


chicago macy'sSpecific Location: Intersection of State Street & Lake Street

Tips: The Chicago Theater sign is pretty magical, especially when it’s lit up at night. It’s a block away from the original Marshall Field’s (which is now Macy’s) and is surrounded by even more shopping and theaters. If you’re in the area and looking for a sweet treat, you have to stop at Garrett’s popcorn right there (a Chicago staple) and we promise you’ll be hooked… and full!

Now onto a few of the “less-touristy” photo op spots. These ones all feature local artists and some gorgeous graffiti…



Specific Location: Along Damen near Moffat Street.

Tips: Honestly we don’t know the story behind this wall art, but we certainly LOVE it. Seeing these happy words can instantly make your day a little brighter. Plus this sign is near the new 606 (which is a walking/running/cycling trail you can check out on a nice day in the city!)


IMG_2825Specific Location: Outside the Bucktown Nike Store; Damen & Concord Place.

Tips: A local artist was commissioned to create these little running guys on the side of the Nike store in Bucktown. Even if you’re not a runner, it’s a fun spot to stop and take a pic. Plus you can explore the awesome Bucktown/Wicker Park neighborhood while you’re in the area.


IMG_2759Specific Location: Milwaukee Avenue & Prindiville Street. You can take the blue line and get off at the California stop. It’s right there.

Tips: You may not realize it from this photo, but this uber creative wall mural is actually in a large parking lot! We love the color and Chicago culture mixed into each letter and had fun going on a Saturday adventure to snap this photo. If you’re looking to create your very own SUPERSIZED postcard-like memory, you have to check out this street art. Oh and while you’re in the area…. keep your eyes peeled for lots of wall art.


IMG_2836(When in Chicago, eat a donut…. or 5! You can DO IT!)

Specific Location: Damen & Milwaukee. If on the blue line, get off at the Damen stop.

Tips: Okay, maybe this isn’t an iconic Chicago mural (even though Chicagoans do love their donuts), but we just couldn’t resist sharing.  And if you do love donuts as much as us & you eventually make your way to take a picture with this delicious work of art…. you have to check out the donut shop directly next door orrrrr across the street. Yup, you will find not one but two equally delicious and trendy donut shops just steps away from here. #yourewelcome

chicago guide graphicAnd just because you have no reason to take these gorgeous photos until you’re actually here in CHICAGO, here’s a weekend guide (and a whole LIST of reasons why you need to visit ASAP!!) to the our favorite city.

Bridget and Casey Signature

PS. Are we missing your favorite iconic or just plain fun photo op in Chicago?! We’d love, love, LOVE to hear! (And maybe add it to the Round 2 to-do list…..)


  • Heather

    Aww how cool! You made me homesick for about .06 seconds….then I realized how COOOLLLDD it is there in the winter and I am much better down south! 🙂

    • Hahahaha we completely understand!! Wish we were enjoying some warmer weather right about now. 😉

  • Taylor

    This is so dangerous!! Makes me want to come back! Bummed we missed the Love sign & donuts 🙂

  • I loved this!! I haven’t been in forever and really need to make the trip. Saving this for when we do!

  • LOVE this! As a Chicago native and current WI transplant I miss Chicago so much! These are some great spots! We tried to have photos done in Olive Park for our wedding but it was too windy! We ended up getting some great ones though by the LP Zoo. So many wonderful parts of Chicago!

    Annie- All Things Big And Small

    • Thanks so much Annie! Where do you now live in WI? We lived there for a few years and loved it.


  • I’m visiting this weekend, and can’t wait to check some of these out! Thanks!