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8 Insta-Worthy Spots in Chicago

The windy city is known for many things- music, food, baseball, and more, but little did you know that Chicago has some of the best photo ops to really up your Instagram feed. From coffee shops to the architecture, there is really an Instagram worthy photo around every turn.

So check out my top 8 Insta-Worthy Spots for Chicago below! I conveniently linked their Instagram’s for even more inspo. These are all winter friendly and in the heart of the city. (Think River North & West Loop.) Explore surrounding neighborhoods of the city and you will find even more hidden gems.

The Allis @ Soho House

Come for the interior, stay for the food, and the people watching… If you visit in the winter see how many Canada Goose jackets you can spot.  The Allis offers all-day dining with a relaxed vibe and is all sorts of IG worthy with its millennial pink sofas, exposed ceilings, and exquisite chandeliers. Grab a sofa by a large table for a bigger group or steal away a quaint table for 2 in a cozy corner. Make sure to grab a specialty cocktail so it’s really worth the $15+ price tag. We ended up splurging and doing tableside Manhattans because why not? All of the food was amazing as well.

Head to the end of the bar and follow the stairs up to their second restaurant Chicken Shop for another cozy cute upstairs corner of this place.

The Hampton Social

Walk in and feel immediately transported to the East Coast. Think shiplap walls and all white everything. Pineapple drinks and delectable seafood dishes. Don’t forget the “Rosé All Day” wall. It’s usually always packed in there so try to get there early or during the week for a prime snap of the wall. They have live music on the weekends typically, so belly up to the bar and enjoy!


Can any list not include the bean? Yes, it’s cliché, but hey it’s pretty darn cool if you’ve never seen it! Plus there are so many cool angles and photos you can get from this. Get Creative!

Chicago Theatre Sign

When you’re walking along State Street area, snap a pic of the iconic Chicago Theatre sign. Another slight cliché photo op, but this marquee is definitely a city landmark that’s worthy to be posted on your IG. And if you’re in town for a while, make sure to catch a show!

Bombo Bar

Mosey down the street from The Allis to warm up with the most over-the-top hot chocolate ever.  Visiting in the Summer? Cool off with a teetering cone of gelato. This fast- casual, walk-up eatery is known for their extravagant hot chocolate or gelatos to go. Don’t forget to actually try a Bombolino which is where the Bombo Bar name came from. It is an Italian holeless donut that can be infused with Nutella, salted caramel, or raspberry filling and is super delicious.


Latte art, fun churros, and tacos. Sounds like a dream right? This shop in River North is TINY but a quick little pop in is all you need to brighten your day. Get a fun surprise message on your latte and instantly gram that while you wait for your decadent churro!

Stans Donuts or Doughnut Vault

Stans donuts. Iconic, on everyone’s list, & so instagrammable. Easy choice, right? BUT.. don’t forget about the Doughnut Vault. Blink and you honestly might miss this little hole in the wall. (Especially in the winter when they don’t have an outdoor patio.) Located over by the Hampton Social, snag an old fashioned on your walk there. (Or grab one for dessert!) Do get their early as their selections sell out pretty fast.



Flamingo Wall

Chicago has PLENTY of cool and colorful walls, but I think this flamingo wall is my favorite that I’ve actually seen in person. Although, I may be biased because I love pink so much! This wall wraps around the Flaming Rum Club which is a private event venue.  I will say this wall is perfect for spring and summer when the sun is out, but it’ll still put a smile on your face all year round.

Honorable Mentions:

Broken English Taco Pub – Come for the margs but stay for the wall art and décor. Fun little spot to escape the cold or heat when you’re by the Bean!

Goddess and the Baker – Multilocation with fun floors, catchy wall signs, and glitter lattes. Their cookies are yummy too.

The Signature Room – Did you really go to Chicago if you didn’t take a pic of the skyline from a rooftop bar?

Firecakes Donuts – Tiny hole in the wall shop in River North. The name says it all…these donuts are fire.

Three Dots and a Dash – The alley to get here is pretty IG worthy itself. Walk on through and head down to this tiki speakeasy. It is dark so if you’re willing to whip out your flash, these drinks are exotic and beautifully handcrafted. Oh, and I hope you like rum because every single drink is made with it!

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