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Chicago, Illinois
Chicago is known as much for its food and speakeasies as it is for its architecture and Lake Shore Drive stretch of beaches. Venture into West Loop if you want to eat at the trendiest restaurants and sip on the finest craft cocktails; then head into Wicker Park and Bucktown for the speakeasies (like Velvet Hour and Bordel;) and pop into Logan Square for breweries (Hopewell is amazing,) dive bars (the Owl is a must,) and dance joints (Slippery Slope is a local favorite.)

Then, when you're feeling fancy, make your way back into downtown and sip on Rose at the adorable and classy Hampton Social, where you can take fun pictures underneath their pink neon lights.
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