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Chicago, Illinois: City Play List

Chicago: The Luxury Travel Atlas City Play List

Welcome to our curated guide to New York City, the world’s most dynamic and dazzling metropolis. For the luxury traveler, NYC is more than a destination—it’s a living canvas of opulence, culture, and exclusive experiences. From soaring skyscrapers to hidden speakeasies, the city offers a sophisticated escape like no other.

This City Playlist is your key to unlocking the very best of New York. We’ve handpicked the top luxury hotels in NYC, including iconic landmarks like The Waldorf Astoria and the ultra-exclusive Aman New York. Your perfect urban sanctuary awaits, with exclusive perks when you book with us.

Prepare to embark on a culinary journey with our selection of the best restaurants in New York City. Whether you’re craving a world-class steak, authentic Italian cuisine, or an unforgettable sushi experience, our list will guide you. We’ve also included the most chic rooftop bars, brunch spots, and speakeasies for a taste of the city’s vibrant nightlife and day-to-day glamour.

For those with limited time, our “Walk New York City in One Day” guide ensures you experience the most iconic sights in a single, exhilarating adventure. Get ready to explore, indulge, and fall in love with the city that never sleeps.

Best Luxury Hotels in Chicago

Booking with us on Classic Travel, you can get the following at no extra cost on most bookings: • Upgrade on arrival, subject to availability • Daily Full breakfast for up to two guests per bedroom • $100 USD equivalent Resort or Hotel credit • Early check-in/late check-out, subject to availability +More

Best Restaurants in Chicago

Best Brunch Spots in Chicago

Best Bars & Drinks in Chicago

Best Rooftops in Chicago

Speakeasies in Chicago

  • The Meadowlark – entrance is barely marked. It’s one of the best cocktail bars in the city.
  • Untitled Supper Club – Holy heck this place is gorgeous. Deep underground, behind a very inconspicuous sign. A doorman will wave you in
  • Scofflaw – for a similar aesthetic but less stuffy (probably because it has windows) and similar tier drinks.

  • Heavy Feather – for an even better, 70s aesthetic (great vintage-feel lighting) and non-innovative but solid cocktails.

  • Gilt Bar – ask to be seated down in “The Library” at the front of Gilt Bar, and you walk down the stairs, through a dramatic hallway with black and white photos (you can add your own too), and to the right behind a tiny, unassuming door you’ll find yourself there.

  •  The Drifter – The most speakeasy thing in Chicago. 

    It’s hidden underneath the Green Door Tavern, which is a very standard, casual, every day kind of bar – you sneak into the back down the stairs like you’re going to the restroom, and at the bottom of the stairs on the right there’s a hidden door that looks like a shelf. Behind that door, you’re transported back in time to the prohibition era.

Other City Play Lists

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