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Travel Blog Posts

5 Most Instagrammable Spots in Chicago

Are you planning a trip to Chicago sometime soon? Do you live in the Chicago area? Have you wanted to take unique photos for posting to your instagram? If so, this is the blog post for you! I spent a short weekend in Chicago and hit up the hottest instagrammable spots in the city. Follow this guide on your next trip! Before booking your Chicago flights, follow my Secret Tips and Tricks So YOU Can Buy Cheap Flights!


Happy Place is a pop-up interactive museum that tours major cities around the country. If you want to see it in Chicago, then buy your tickets soon (they usually sell out), because they will only be in Chicago until September 3, 2018!

We had so much fun touring Happy Place. Some rooms are definitely better than others, but you are guaranteed to leave with a ton of fun, colorful pictures! Bring your camera of course and wear something that will pop against the bright and colorful backgrounds. I recommend either solid, bold colors or something more neutral like black and white. No busy patterns! We spent just over an hour in Happy Place, which I felt was the perfect amount of time. It was enough that I felt I got my money’s worth ($35 per ticket), but I was definitely ready to go by the time we reached the end.

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2. Goddess and the Baker

Goddess and the Baker is a café with 2 Chicago locations. The décor is super cute with black and white patterned tile floors, brass light fixtures, minty colored walls, and a giant neon sign along one wall that says “Eat Now Caffeinate”. The location alone will give you ample opportunities for pictures. You have to order some food and beverages too while you are there. Not only was everything I tried delicious, but it was all presented beautifully, perfect insta-worthy options. They do latte art in the foam when you order coffee drinks, and their baked goods are almost too pretty to eat. Perfect for those food bloggers out there!

3. The Chicago Riverwalk

I feel like this one goes without saying, but you cannot visit Chicago without stopping at the Riverwalk. During the summer is an especially fun time because you can relax with a glass of wine from City Winery at the Riverwalk, watch the boats go by on the water, and admire all the adorable dogs passing by. Selfies in front of the water are always a good idea, no matter where the location!

4. Cindy’s Rooftop

I don’t know about you, but I will not visit a major city without visiting at least one rooftop. Cindy’s Rooftop in Chicago has some of the best views in the city. From the deck, you can see the iconic bean and the blue waters of Lake Michigan. Not only are the views stunning, but their food and cocktails are made for documenting in pictures! The cocktails are colorful with beautiful garnishes, and the meals are plated with obvious attention to detail. Just like at Goddess and the Baker, the food is not just pretty, but also delicious. The entire ambiance at Cindy’s Rooftop is trendy and attractive and perfect for instagram pics.

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5. Yuzu Sushi & Robata Grill

My final recommendation for hot instragrammable spots is Yuzu Sushi. You must order at least one item from their Jumbo Rolls menu. The rolls are incredibly elaborate and colorful. These rolls are served on wooden planks with art on the side! Some of the art includes the Chicago Skyline, dragons, crabs, and trippy designs. This restaurant is BYOB, which is always fun for those of us from the suburbs without this option. You can bring along your own bottle wine and they will open it for you (usually for a corkage fee, $5 on average) and provide an ice bucket for keeping it chilled.

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I hope this list was helpful, and I would love to see your pics from these places! Tag me in your photos on instagram (@leah_little_travel) or post a comment to this blog post with your pics!


cropped-me flowers Leah Little has a full time job as a social worker, and has managed to travel the world while wearing beautiful clothes by knowing how to score deals in travel and fashion. Learn more about her journey here.  Join the Leah Little Travel and Fashion tribe by entering your email to subscribe to be the first to learn new ways to enjoy the best in travel and fashion for less. Say hi and send her a message! Contact

Related Links:

Choose Chicago

Chicago on Trip Advisor

Happy Place


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  1. I love your recommendations for 5 most instragrammable spots, they all look really beautiful, and so colourful😊😍❤️

    1. Thank you Lenka! Glad you liked it!

  2. I haven’t been to Chicago in years. I need to go check out some of these spots. Thanks for the recommendations. 🙂

    1. wanderlustleah13 says:

      You’re welcome! Let me know if you check any out!

  3. Lincoln Park and Grant park are also gorgeous, and Navy Pier is super touristy but it looks good in pictures

    1. wanderlustleah13 says:

      Yes! I love navy pier. I wanted to try some lesser known spots for this post!

  4. Wow! I have lived so close to Chicago my whole life but have only been downtown 4 times. Out of the 5, I’ve only been to the Riverwalk! I must try the other 4!!

    1. wanderlustleah13 says:

      Definitely! Let me know if you do! Where do you live? I am a 3.5 hour drive from Chicago

  5. Omg I love this idea – what a handy list to have in your head for a traveling blogger! 😉 I’ve never been to Chicago but will actually be planning a trip there soon, hopefully I can check out some of these spots!

    1. wanderlustleah13 says:

      Oh good! Let me know when you go!

  6. […] no secret that Chicago is one of the most Instagrammable cities in the United States. If you want to get some awesome pics while observing the city and all of its […]

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