After devouring a deep-dish pizza, go outside the tourist loop to discover the fun and unusual spots that make Chicago, well, Chicago! From the unique neon sculpture in the airport to the local Pilsen art walls there are so many reasons to get off the beaten path to these beautiful and unusual spots. Flock to the Flamingo Wall for rum and one of the best murals in the city or sip Rosé in front of the neon sign at Hampton Social. Here is our Chicago Instagram photo bucket list!

title on flamingo pink feathered pattern of the mural at Flamingo Rum Club

  1. Chicago O’Hare International Airport: What better place to start than the airport, home of the longest neon sculpture in the world! Perfectly titled, “Sky’s the Limit,” the piece is 744 feet long.
  2. Flamingo Wall: One of the best murals in Chicago can be found at The Flamingo Rum Club. Though many photograph the longer side wall, we had fun photographing the less-popular front mural which frames two black doors.
  3. The Allis in Soho House: Though technically house rules forbid photography, who can resist sneaking a photo of afternoon tea at The Allis? Check out our photo review of The Allis.
  4. Pilsen art walls: Explore a long street of urban murals on 16th street before or after trying some of the best Mexican food in Chicago!
  5. 3 Arts Club Café: Located inside Restoration Hardware, 3 Arts Club Café offers a classy indoor oasis with floor-to-ceiling windows complete with glittering chandeliers.
  6. Chicago Union Station: This is the busiest train station outside of NYC, Washington, D.C. and Philadelphia. The beautiful Great Hall was once the “Women’s Lounge” where ladies traveling could wait for their train near a beauty parlor.
  7. The Hampton Social: In a city that has subfreezing temperature days 1/3rd of the year, it is refreshing to see the “Rosé all day” neon sign.
  8. Wabash arts corridor:Visit Wabash Avenue to see the “living urban canvas” of art installations.
  9. Parsons Chicken & Fish: From the red striped umbrellas to the wood tables, this spot is a fun photographer’s playground.
  10. Cindy’s Rooftop Bar in the Chicago Athletic Association: The best view of the “bean” or “Cloud Gate” in Millennium Park is from Cindy’s Rooftop. Go before 6 to snag a spot along the railing overlooking the park, and order the Grey Garden drink complete with orchid.
  11. Barrel Run: Tour local distilleries and breweries or take a gangster tour to learn about famous mobsters like Al Capone in this one-of-a-kind barrel-shaped bus.

For more, read our Ultimate Guide to Chicago!

Have you been to these spots? Any favorite spots we missed?

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