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In this series, we explore what it takes to land—and work—the world’s coolest travel jobs. Previous installments featured interviews with a doctor without borders, a social media influencer, and a professional ghost hunter. Up next: a designer of extreme obstacle courses.

Is Chicago the Coolest Hotel City in America?

The Best Cities in America for Football Fanatics

The 50 Best Things to Do This Summer in All 50 States: The Midwest

‘National Parks Adventure’ director Greg MacGillivray talks filming, preservation, and the beauty of our nation’s untouched land

Overview

Founder’s Note: The Roots of Experiential Travel

Musicians Aimee Mann, Joe Henry, and Loudon Wainwright III gather in Louisville to indulge in raw oysters, dry martinis, and unscripted conversation.

These are worth taking the long way.

John T. Edge lands in Kazakhstan, determined to get to know the country’s largest city through its food.

The suburbs of southeast Michigan, outside of Detroit, are a destination worthy of any traveler’s time. Don’t limit yourself only to the city if you find yourself in this area of the Midwest.

This hotel is on our list of The 11 Best Hotels in Chicago.

Often rated the best hotel in Chicago since it first opened in 2001, the Peninsula Chicago keeps its reputation by offering the finest high-end Chinese cuisine in the city and easily one of the top hotel spas in the Midwest. The Magnificent Mile mainstay has 339 spacious guest rooms and suites, outfitted in an understated style with floral motifs by artist David Qian. Thoughtful details include soaking tubs with hands-free televisions, a table for two set beside a window with a view, and linens custom created by Pratesi.

No stay would be complete without a meal at the Shanghai Terrace, where chef de cuisine Elmo Han earns accolades for his modern interpretations of Shanghainese, Cantonese, and Sichuanese classics. During the warmer months, you can dine (or just have a mocktail) on the actual terrace, the whole of Chicago displayed before you. Also required: an afternoon at the 15,000-square-foot Peninsula Spa, with its floor-to-ceiling windows, facials using Biologique Recherche products, and an Olympic-size pool and sun deck.

Twenty-four hours before check-in, be sure to request “Peninsula Time,” which allows guests to access their rooms as early as 6 a.m. and stay as late as 10 p.m.—a lifesaver for international or early-bird travelers. And eco-conscious travelers take note: The Pen recently received Gold Status from EarthCheck, its second consecutive Gold Status award.

This particular area of the Gold Coast is jokingly nicknamed the Viagra Triangle, but the Thompson Chicago doesn’t discriminate by age. The 247-room hotel is dark and moody, drawing artists of every generation to its swanky lobby bar at the back, peppered with colorful canvases and couples sneaking a snuggle in a booth. The whole town is awaiting the opening of Tavern on Rush, a reboot of the beloved steak house that used to reside just up the block. Rumors say this hangout will become a dining destination, what with its cocktail lounge, main dining room, patio, and private rooms spread across 16,000 square feet and multiple levels.


Set among all the best shopping in the Midwest, the Thompson’s midcentury-style guest rooms with hardwood floors provide the perfect minimalist location to unbox those favorite finds from Michigan Avenue around the corner. Digital nomads can book their work meetings in one of the rooms named after the Chicago Seven: countercultural anti-war protesters charged by the U.S. federal government with conspiracy and intent to incite a riot to stop the Vietnam War. The Abbie Hoffman room is a favorite.

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

This hotel is on our list of The 11 Best Hotels in Chicago.

Following a much-needed $60 million makeover in July 2022, the Park Hyatt Chicago is once again a contender for one of the best hotels in town. Located in the bustling Magnificent Mile neighborhood at 800 N. Michigan Avenue, the storied property has been a landmark destination since it opened in 1980 as the first property to bear the Park designation. The renewed sanctuary now delivers a true sense of place, with a refreshed lobby design that’s more of an urban living room, an updated Library, and a vibrant new art program spotlighting some of Chicago’s most talented creatives. Critically, the hotel’s signature restaurant NoMI (named for the location on North Michigan Avenue) now has three different concepts: NoMI Kitchen, which emphasizes American cuisine with French techniques, NoMI Garden, a terrace space that’s ideal for lunch, and NoMI Lounge, which includes a six-seat sushi bar.

The Park Hyatt Chicago, facing ever stiffer competition from newer luxury hotel entries in the Magnificent Mile orbit, nevertheless remains a great choice for families because of the central location optimizing sightseeing and kid-heaven treats. Budding geologists will love the geodes, minerals, and marine fossils in the lobby alcove. Chefs at the seventh-floor NoMI restaurant, known for fine wines, city views, and standout American contemporary cuisine, take young foodies to the open kitchen’s soft-serve ice cream dispenser. The 7,000 square foot fitness center includes a 25 yard lap pool with skyline views, or borrow a complimentary Jamis commuter bike to ride the scenic Lakefront Trail four blocks east on the beach side of Lake Shore Drive. Guestrooms have notable design flourishes such as padded window seats, Eames chairs, and Mies van der Rohe–designed Brno desks from which to view the city’s famous architecture. Pets are welcome, and the hotel donates 100% of its standard pet fee to one of the city’s largest animal shelters.