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Wandering Chef: Jose Garces in Ecuador

Like Locals Do: Explore a City With a Greeter Guide

On a luxurious journey from Singapore to Bangkok, writer Chris Colin lifts the veil on the magic—and mystery—of rail travel.

AFAR chose a destination at random—by literally spinning a globe—and sent writer Jonathan Gold on a spontaneous journey to Prague with just 24 hours’ notice.

A writer travels to the Horn of Africa to find the source of a global obsession.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

Chris Walker and Morgan Hartley spent three months cycling through central Asia as part of an 18-month bike trip. Here is part one of five of their account, in which their trip is almost thwarted from the start.

Receiving rave reviews over the years from the Chicago Tribune, Zagat, the Chicago Sun Times and Fra Noi (Chicagoland’s Italian American Voice), DeMarco’s is a well-known authentic Italian eatery in the truest sense of the word. The team at DeMarco’s focuses on fine pasta dishes, incorporating veal, fish, chicken and steak into their foodie masterpieces. All pastas are made right at home, and patrons can customize their delicious meal any way they like. DeMarco’s also sources fresh ingredients to keep all their customers happy, and as you can guess, constantly coming back for more.

Far above the plains where lions roam, there’s another Kenya, where life moves slowly and the people run fast. Writer Matt Gross tries to keep up.

Itasca is a lovely town located in the suburbs of Chicago. With a quaint historical downtown to explore, and the surrounding areas featuring activities for everyone, it’s a great place to come and get away from the hustle and bustle of the big city. Come to Itasca, there are adventures waiting just for you!

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.

The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of Chicago in 1967 and it caused a big ruckus because, well, it’s weird looking and no one knew what it was supposed to be. A woman? A chimera? A face? Hard telling. We do know that it was the first modern sculpture installed in the downtown area and it’s now the pride and joy of Chicagoans and photographed almost as much as the Bean. On sunny days you’ll see kids sliding down that sloping steel base and I love that the city still allows those jungle gym antics on such famous real estate.

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

The world has been waiting years for the St. Regis Chicago, located in the city’s 101-floor skyscraper designed by Jeanne Gang, to welcome guests and owners; in 2023, it finally made its stunning debut. The triple-tower building’s architecture was based on the frustrum shape, which is basically a pyramid with its top chopped off. (Think of a popcorn box.) That form is replicated subtly throughout the hotel, from the exoskeleton to the marble tiles in the inviting lobby on the Chicago River. Each of the 192 guest rooms comes with floor-to-ceiling windows and panoramic city views, a dedicated butler, one of four soaking tubs, brass detailing, and curvilinear furnishings from a collaboration between architectural powerhouse Gensler and boutique firm Simeone Deary Design Group.


Rounding out the amenities: the Miru all-day-dining restaurant that is anything but casual, a new Tuscan steakhouse concept, a truly cossetting seven-room spa, an indoor pool with an outdoor patio, and the finest urban hotel gym probably anywhere. Was the wait worth it? Indeed it was.

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

Designers Lisa Simeone and Gina Deary of KTGY Simeone Deary Design Group oversaw the original design of the Parisian-inspired Waldorf-Astoria Chicago in 2009, and the pair was once again brought in to breathe new life into this 215-room Gold Coast gem. Rooms are now bright white, well-lit, and include pops of uplifting magenta. Before you hit any of them, however, there’s much to entice at street level. Enter from the circular driveway and marvel at the Swarovski chandelier, modeled after a vintage brooch, along with the herringbone wood floors and black-and-white pinstriped stone. Don’t miss the Peacock Lounge and its secret sister, Bernard’s Bar, an intimate craft cocktail and champagne boîte, which is virtually unknown even by city denizens (which means you can always find a seat). Its Scottish and equestrian themes are almost as anachronistic as the Mansard roof and circular driveway, which just adds charm to this newly beloved Chicago hotel.

The guest rooms feature oversize headboards and abstract floral bedspreads, while bathrooms are a marvel of marble. For something more, splurge on either the new 1,800-square-foot Astoria Suite or the redesigned 2,400-square-foot Presidential Suite, both of which will have you feeling you’ve been transported to a Parisian pied-à-terre (the latter’s primary bedroom features a fireplace).

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.