The Most Instagrammable Spots in Chicago

May 8, 2017

Today’s society is so photo and social media driven, everyone wants to get that one great shot while they’re on vacation. I’m guilty you guys, I’m sure you are too and that’s ok! I love documenting all aspects of my life including vacations so when headed to Chicago I searched everything from things to do, see, eat and of course some of the must see spots to snap a photo at. No matter what neighborhood you’re in, Chicago has some of the most picturesque spots and I’m here to round them all up for you. Be sure to follow along on the adventures at @anniegpyle.

The Bean

Let’s start with the obvious. I think it’s impossible to go to Chicago without getting at least one picture at The Bean. Go early, I mean really early if you want a photo with no one around. The photo below was taken around 9am if that tells you anything. Tip: Head to Cindy’s Rooftop at the Chicago Athletic Association Hotel for an amazing view of The Bean and Millennium Park.

Thanks for a great weekend Chicago 👌🏼

A post shared by Annie • Discovering Your Happy (@anniegpyle) on


The Hampton Social

One of the top most instagrammed spots, the Hampton Social is the place to go to grab a few photos while also enjoying drinks and lunch.

Rosé all (brunch) day 🌹🥂💅🏼

A post shared by The Hampton Social (@thehamptonsocial) on



Inside the Willis Tower is the Skydeck. Another one of those places that first time visitors to Chicago automatically go to. It can get pretty busy so get there early if you can.

Jumping into the weekend like… 📷: @cmykchicago #SkyDeckChicago

A post shared by Skydeck Chicago (@skydeckchicago) on


Doughnut Vault

Not only are the doughnuts gigantic and delicious, but this place is screaming for a photo to be taken. The outside is so fun and the inside is nothing I’ve ever seen before, especially from a doughnut shop.

Don’t miss the newest blog post tomorrow, it’s a good one you guys! 📸

A post shared by Annie • Discovering Your Happy (@anniegpyle) on



Chicago and pizza. Two words that you’re bound to hear quite a bit on any trip to Chicago. Homeslice is a great little spot to relax and indulge in one of life’s greatest foods, pizza.

Where the happiest hours are had #🍕 #🍸 #🍹 #🍷 #🍻

A post shared by Homeslice Wheel House (@getsomehomie) on


3 Arts Cafe in Restoration Hardware

One of those hidden little treasures I would’ve never known about if a friend hadn’t recommended it. The wait to eat can get insanely long, but you can always opt to grab a drink from the bar and roam the 5 stories of dreamy home furniture.

Rosé + Restoration Hardware 🍷 A rainy afternoon spent exploring 5 levels of furniture that dreams are made of 😍

A post shared by Annie • Discovering Your Happy (@anniegpyle) on



Something I didn’t know Chicago had so many of, murals. And really great ones at that. There are so many, a few of my favorites are below. You can also search the #chicagomurals hashtag on Instagram to find more.

The Flamingo Wall is located on the outside of The Flamingo Rum Club building at 601 North Wells Street.


The moose photo can be found in the Wabash Art Corridor at 33 East Congress.


The Greetings From Chicago wall can be found at 2226 North Milwaukee Avenue.


Parlor Pizza

A delicious pizza spot that also has the cutest patio space? Count me in! Parlor Pizza Bar has two locations, one in West Loop and one in Wicker Park. You can’t go wrong with either.

You can’t beat Chicago pizza 🍕 and we were pretty impressed with Parlor Pizza Bar in Wicker Park last night 😋

A post shared by Annie • Discovering Your Happy (@anniegpyle) on


Soho House

The Allis at Soho House is the ultimate swoon-worthy spot. Cozy up in one of their vintage style chairs with a cup of coffee and snap a few great photos.

Love this photo @alexandra_wootla took of #theallis bar. #sohohouse

A post shared by The Allis Chicago (@theallischicago) on

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  • Reply Vanessa Sokic May 8, 2017 at 11:09 am

    You hit all the great spots!

    • Reply annie May 10, 2017 at 8:52 am

      So many more places to explore, I can’t wait to go back!

  • Reply Stefanie May 9, 2017 at 9:39 am

    What a fun place to visit! I need to plan a trip to Chicago!

    • Reply annie May 10, 2017 at 8:52 am

      Yes you do! There is so much to do and see. It’s such a great city!

  • Reply Silvia May 10, 2017 at 2:58 am

    Thanks for sharing these! I’m thinking of traveling to Chicago soon and this list totally helps!

    • Reply annie May 10, 2017 at 8:53 am

      Ahh yes you definitely should! It’s so fun and there’s so much to do, see and eat. I swear the list of things I wanted to do was endless!

  • Reply Erica @ Coming up Roses May 10, 2017 at 6:55 pm

    I need to visit that flamingo wall!!! The bean and Skydeck always look like fun too!

    • Reply annie May 10, 2017 at 10:00 pm

      Right!? The flamingo wall is everything. So many good murals I had no idea were in Chicago!

  • Reply Rachel May 10, 2017 at 10:45 pm

    Those are great places. There are some great places in Old Town and I feel like the lake and Navy Pier should somehow be in there.

    • Reply annie May 12, 2017 at 9:44 am

      I might just have to update my list! We loved the Old Town area, so much to do.

  • Reply Katie Sartz May 16, 2017 at 2:42 pm

    The Hampton Social is my favorite location. Definitely want to make it up to Chicago one day for maybe a weekend trip. But definitely during the summer–I can’t deal with snow haha. Thanks for sharing!

    • Reply annie May 16, 2017 at 8:00 pm

      Yes! The first time we went it snowed so much it was insane. Definitely make it a trip for summer!

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