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
- Trump International Hotel & Tower Chicago
- The Peninsula Chicago
- The Ritz-Carlton Chicago
- Waldorf Astoria Chicago
- The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
- JW Marriott Chicago
- The Blackstone Autograph Collection
- InterContinental Hotels CHICAGO MAGNIFICENT MILE
- The St Regis 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
- Maple & Ash – Chicago
- Gibsons Bar & Steakhouse – Chicago
- LUXBAR
- Sophia Steak Chicago
- Chicago Cut Steakhouse
- Le Colonial
- Prime & Provisions Steakhouse (River North)
- Beatnik (West Town)
- The Alston (River North)
- Elske (West Loop)
- Lýra (West Loop)
- 3 Arts Club Cafe at RH Chicago (Gold Coast)
- Aba (West Loop)
- Tre Dita (River North)
- Duck Duck Goat (West Loop)
- Boka (Lincoln Park)
- avec (West Loop)
- El Che Steakhouse & Bar (West Loop)
- Moody Tongue Brewing Company (South Loop)
- Lula Cafe is the original farm-to-table New American spot in Chicago. The food and drinks are excellent, and the split dining room creates a cozier atmosphere. It earns bonus points for being great for any meal and being open on Mondays.
- Mi Tocaya Antojería is the perfect fancier and cooler spot for elevated Mexican food, standing out even in a city packed with incredible Mexican options (like Birrieria Zaragoza, Carnitas Uruapán, etc).
- The Loyalist is home to the perfect burger, but even without it, the restaurant would make the list due to its amazing French food and moody bar vibes.
- Cellar Door is small and cozy, with a menu that changes all the time. The staff is amazing and incredibly passionate about their work. I still miss the Cellar Door quiche, which was the best I’ve ever eaten (tied with Warda Patisserie in Detroit).
Best Brunch Spots in Chicago
Best Bars & Drinks in Chicago
Best Rooftops in Chicago
- The London House Rooftop Bar
- The Robey
- the Rooftop at Nobu Hotel
- CloudBar at 360 CHICAGO (94th story of the John Handcock Building)
- The Gwen: A Luxury Collection Hotel, Michigan Avenue Chicago
- Z Bar
- Raised
- Aba restaurant
- Cerise Rooftop
- Cindy’s Rooftop
- Gibson’s Italia
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
Dack Patrick
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I travel for a living, a Delta 1 Million Miler 1MM, 10 years Diamond Medallion, 7 years straight Marriott Ambassador Elite, and oddly still Hilton Diamond (lame!). It’s the stories I collect along the way that truly fuel me.
From high-rise hotels in buzzing metropolises to quiet beachside cafés tucked between palm trees, my career takes me across the United States and beyond—and I take every opportunity to explore, taste, and soak up the local vibe. Whether I'm grabbing late-night bites in Belgium, sipping wine in Napa, or discovering rooftop gems in New York City, I always keep an eye out for the places and moments worth sharing.
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This site is my travel log and guidebook rolled into one—a place where you’ll find detailed insights into the restaurants, hotels, rooftops, beach spots, bars, and other hidden treasures that define each city. Whether you're chasing your next adventure or planning a weekend escape, I hope my posts help you travel smarter, eat better, and find magic in every stop.