The Most Instagrammable Places in Chicago!

the bean cloud gate chicago

In this article you will find locations for the most Instagrammable places in Chicago as well as a one day travel itinerary.

Think the windy city is no more than a concrete jungle? Think again! With miles of beautiful lakeshore beaches, stunning river walks, parks with unique architecture and an incredible skyline, Chicago is a paradise for anyone who enjoys taking photos! Now, instead of just giving you a list of the most Instagrammable places in Chicago and leaving you to fend for yourself, I have carefully crafted (and tried and tested!) this itinerary, including the order to visit places, and timings to ensure you get your photos with as few people in them as possible! Along with the 10 awesome Instagrammable shots in Chicago (all geo-tagged on Google maps!) is a map with all the locations numbered at the end. Come along with me on my 24 hours Instagrammable route of Chicago!

24 hours instagrammable route of chicago


1. Cloud Gate at Millennium Park

the bean cloud gate chicago the bean cloud gate chicago

the bean cloud gate chicago

Head to Millennium Park first thing in the morning to get to Cloud Gate when there are no crowds. Cloud Gate is this beautiful stainless-steel sculpture, more affectionately known as “The Bean” as it is shaped like a kidney-bean. The sculpture is mirrored so you can see the reflection of Chicago’s skyline in it. During the day this place is absolutely packed, and the reflection of everyone will be in the giant mirrored sculpture, which is why it is important to get here early. I was here at 7am and there were only a few people around which was perfect, so make sure to visit The Bean as early as you can! It is an impressive piece of art and to see it is the highlight of many people’s trip to Chicago!

Click here for the Google maps location of The Bean.

2. Chicago “L” Railway

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You’ll notice as you walk around Chicago city centre that trains don’t run underground: rather they run overground on railway systems above the road. This is known as The Chicago “L” (short for “elevated”) – the elevated railway system that runs through Chicago. The elevated rail system makes for some amazing photos and there are literally so many locations where you can get great shots under the arches!

As I mentioned, the elevated rail system runs above the road so I advise to get pictures here straight after you have visited Cloud Gate as you want to get these shots where there are as few cars on the road as possible so as not to disrupt the traffic (or get run over!). Sunday mornings are the best morning to go, when there is the least traffic around but if that’s not possible for you, any morning before 8am is ok. I really don’t advise you to shoot alone with a tripod, but rather with someone so you can both get out of the road quickly if needed. Be advised that the drivers can understandably get a little impatient if you are shooting in the middle of the road so be quick here.

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Click here for the Google maps location of the photo above, shot at the corner of Washington and Wabash (near the Washington/Wabash stop on the Chicago “L”), just a couple minutes walk from Cloud Gate.

3. Chicago Theatre

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A short walk from the previous 2 spots is The Chicago Theatre: be sure to visit this place – another one of Chicago’s landmarks! Standing at almost 100 years old it was America’s first lavish movie palace and is one of the only ones that still remains and runs to this day! There aren’t crowds here so it is quite easy to get a photo here, you just need to wait for the traffic to be clear before you get your shot!

Click here for the Google maps location of The Chicago Theatre.

4. Willis Tower OR John Hancock Centre

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After visiting The Chicago Theatre it’s time to see Chicago from above! Both The Willis Tower and The John Hancock Centre are some of Chicago’s tallest skyscrapers that offer incredible views of Chicago. The Willis Tower is close to Union Station whereas The John Hancock Centre is on Michigan Avenue (The Magnificent Mile). Chances are you’ll only get to visit one of them, so it’s up to you which one you visit: The Willis Centre has glass panels that you can stand on and look down at the city below, whereas The John Hancock Centre has TILT boxes: enclosed boxes that tilt you towards Michigan Avenue (far too scary for me!) and a bar as well offering perfect views over the lake. Whichever one you choose, both have big queues so do your best to get there before 10am to beat the crowds.

Click here for the Google maps location of The Willis Tower, and click here for the Google maps location of The John Hancock Centre.

5. Boat ride on Lake Michigan

river cruise chicago Michigan lake river cruise chicago Michigan lake

If you are in Chicago between March and November take a boat ride out onto Lake Michigan and enjoy some fabulous views of the skyline. I went with Shoreline Sightseeing and had a really enjoyable time. The tour departed from Michigan Avenue dock, went along the Chicago River and out into the lake. Click here for the boat schedule and to book tickets. The area where the boat docks is lovely, so before or after your boat trip take time to enjoy the area around the river.

Click here for the Google maps location of Michigan Avenue dock.

6. Flamingo Rum Club wall mural

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This flamingo wall mural is quickly becoming an Instagram hot-spot! Located on the side of The Flamingo Rum Club, a Cuban restaurant located on North Wells Street just a few blocks up from the Chicago riverwalk. The restaurant itself is pretty exclusive, but you’re free to take pictures outside without anyone bothering you! Like at The Chicago Theatre, you won’t have to compete with crowds here, only the passing traffic.

Click here for the Google maps location of Flamingo Rum Club.

7. North Avenue Beach Hook Pier

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To get a stunning view of the Chicago skyline, walk north of The Magnificent Mile (Chicago’s main shopping street) to North Avenue Beach. Just before you get to the main beaches however, you will find a pier called North Avenue beach hook pier (as the pier curves around like a hook). It is a great place to enjoy the skyline without all the crowds on the beach, however as the pier sticks out quite a bit it can get very windy here (as you can see from my picture!) so be careful if you use a tripod here.

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Click here for the Google maps location of North Avenue beach hook pier. Now Google Maps doesn’t actually recognise hook pier as a place as it is so small: if you click on the link, you’ll see it links just to North Avenue Beach. However, if you look on the map you’ll see below the beaches a thin part of the land hooking round (just to the right of where it says Chicago SUP). This is hook pier.

8. North Avenue Beach

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I love how just a short walk away from Chicago’s skyscrapers you will find miles of beaches along the shores of Lake Michigan! I love coming up here during the summer, seeing the beach full of students playing volleyball and enjoying Chicago’s beautiful summer weather.

Click here for the Google maps location of North Avenue beach

9. Nature Boardwalk at Lincoln Park Zoo

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A beautiful urban oasis just across from the beaches is the Nature Boardwalk at Lincoln Park Zoo. Again from here you can get a beautiful view of the skyline, and it is not too busy here. Entrance to the boardwalk is free as it is not actually in the zoo: it is between the zoo and Lincoln Park, you just walk around the zoo to reach this area. It is very peaceful here and the lush ecosystem is home to a variety of wildlife. I enjoy taking some time out from the city and relaxing here for a while.

Click here for the Google maps location of the Nature Boardwalk at Lincoln Park Zoo.

10. Cindy’s rooftop bar

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After a long day of sightseeing, relax in one of the best rooftop bars in Chicago! Cindy’s Bar has the perfect view of Chicago: go on the outdoor terrace to see great views of Lake Michigan and the legendary Chicago Bean. The atmosphere in this place is great, the place is always buzzing and the cocktails are pretty yummy too!

Click here for the Google maps location of Cindy’s rooftop bar.

Stay here until it gets dark and you’ll see Chicago is also a beautiful city at night time. If you still have energy you can head back to The Chicago Theatre to see it fabulously lit up at night, or stroll around near the riverwalk or even go back to see The Bean. There is a great energy in this city and even after dark you’ll feel the buzz of the city.


Below is a map of Chicago and I have marked and numbered all the above spots for you so you can easily see the route you need to take to enjoy 24 hours in Chicago. Of course feel free to alter the itinerary, I am just writing it as a guide. This map was from “Where maps Chicago” and you can pick up the same map in many locations across Chicago.

best photo spots in chicago map

  1. Cloud Gate at Millennium Park
  2. Chicago “L” railway
  3. Chicago Theatre
  4. Willis Tower OR John Hancock centre (choose)
  5. Boat ride
  6. Flamingo Rum Club
  7. North Avenue Beach hook pier
  8. North Avenue Beach
  9. Nature Boardwalk at Lincoln Park Zoo
  10. Cindy’s rooftop bar
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Chicago is one of my favourite cities in the US, how about you? If you are looking for more inspiration on itineraries for US cities, check out my post “24 Hours in New Orleans, Louisiana” here!

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