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Today, Chicago mixes innovative architecture with green spaces, cutting-edge cuisine with hot dogs and pizza, and world-class shopping with independent boutiques. Its cultural scene boasts great museums, celebrated blues joints, and a superb theater scene that includes Steppenwolf, Second City, and the Goodman—all of this in a prime location on the shores of shimmering (and often windy) Lake Michigan.

Our Picks

8 Hotels 9 Restaurants 26 Activities

Destinations: Chicago · Wilmette · Gold Coast · Lincoln Park · The Loop · Magnificent Mile · Near North · Old Town · Ravenswood · River North · South Loop · Wicker Park/Bucktown · Logan Square · West Loop

Themes: Arts + Culture · Food + Drink · Hotels + Resorts · Shopping

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Hotels (8)

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1 - 8 of 8 Results

Hotel Blake

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South Loop | U.S. and Canada | U.S. | Illinois | Chicago

Fusing boutique-hotel modern with the historic architecture of the Printers Row neighborhood, the Blake’s 19th-century Morton Salt building façade
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Hotel Indigo, Chicago

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Gold Coast | U.S. and Canada | U.S. | Illinois | Chicago

Finding what looks like the interior of a seaside resort in the middle of this swanky Gold Coast neighborhood can be a little disorienting, but as
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The Beldon-Stratford Hotel

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Lincoln Park | U.S. and Canada | U.S. | Illinois | Chicago

Built in 1923 and featuring a grand, hushed lobby topped with a ceiling mural of clouds in the sky, the Belden-Stratford offers the “Eloise at the
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The James, Chicago

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River North | U.S. and Canada | U.S. | Illinois | Chicago

Opened in April 2006, The James marries a residential vibe to a hotel setting. To evoke an apartment style, all of the 297 contemporary rooms have
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The Drake

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Near North | U.S. and Canada | U.S. | Illinois | Chicago

As the preferred stop for visiting heads of state, the Drake is the grande dame of Chicago hotels, with a prime location, storied history, white-gl
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Hotel Burnham

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The Loop | U.S. and Canada | U.S. | Illinois | Chicago

Perhaps no other hotel showcases Chicago’s impressive architectural history like the Burnham. The historic 1894 Reliance Building was lavishly rest
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The Peninsula, Chicago

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River North | U.S. and Canada | U.S. | Illinois | Chicago

As you walk into the Peninsula, the concierge and receptionist greet you by name; classical music plays when you enter one of the 339 rooms; and yo
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Sofitel Chicago Water Tower

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Gold Coast | U.S. and Canada | U.S. | Illinois | Chicago

Paris flirts with the Midwest at Sofitel’s North American flagship property. The 32-floor glass prism, Parisian-inspired restaurant (Café des Archi
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1 - 8 of 8 Results

Restaurants (9)

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1 - 9 of 9 Results

Billy Goat Tavern

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River North | U.S. and Canada | U.S. | Illinois | Chicago

Immortalized by the 1970’s Saturday Night Live skit in which a short-order cook (John Belushi) screamed “Cheezborger! Cheezborger! No fries, cheeps
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Wishbone

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West Loop | U.S. and Canada | U.S. | Illinois | Chicago

Just steps away from Oprah’s Harpo Studios, the unfussy Wishbone is a favorite among staffers for southern-inspired fare that tends toward the ligh
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Podhalanka Polksa Restauracja

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Wicker Park/Bucktown | U.S. and Canada | U.S. | Illinois | Chicago

Unless you knew to look for it, you’d probably never notice the dingy storefront of this local secret—and that would be a shame. The interior, remi
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Gene & Georgetti

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River North | U.S. and Canada | U.S. | Illinois | Chicago

Aside from the absence of cigarette smoke, it’s hard to imagine that this classic steak-and-seafood place has changed much since it first opened in
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Spacca Napoli

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Ravenswood | U.S. and Canada | U.S. | Illinois | Chicago

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Lula Cafe

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Logan Square | U.S. and Canada | U.S. | Illinois | Chicago

<p>A regular spot among locals and a destination for foodies, Lula is an ambitious restaurant disguised as a low-key hipster hangout. The regular m
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Avec

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Chicago | U.S. and Canada | U.S. | Illinois

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Alinea

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Lincoln Park | U.S. and Canada | U.S. | Illinois | Chicago

At the forefront of the groundbreaking molecular gastronomy movement, Alinea offers meals that are quite simply unlike any others. Dedicated follow
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Irazu

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Wicker Park/Bucktown | U.S. and Canada | U.S. | Illinois | Chicago

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1 - 9 of 9 Results

Activities (26)

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1 - 10 of 26 Results

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Le Bar at The Sofitel

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Gold Coast | U.S. and Canada | U.S. | Illinois | Chicago

With overstuffed royal-purple chairs, a French oil painting, and architectural books scattered throughout, Sofitel’s Le Bar feels like a nobleman’s
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The Bar at The Peninsula

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River North | U.S. and Canada | U.S. | Illinois | Chicago

This cigar bar-turned-cocktail lounge is a popular after-work hangout for locals—and tourists in the know. The friendly waitstaff, roaring fireplac
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The Signature Lounge

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Magnificent Mile | U.S. and Canada | U.S. | Illinois | Chicago

Instead of visiting the John Hancock Center’s zenith during daylight hours, opt for an evening cocktail in the building’s high-flying lounge. Locat
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Garrett Popcorn

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Magnificent Mile | U.S. and Canada | U.S. | Illinois | Chicago

Stroll down the Magnificent Mile and stop at Garrett Popcorn. Although the company now has stores throughout Chicago and New York City, the first o
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Gem

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Wicker Park/Bucktown | U.S. and Canada | U.S. | Illinois | Chicago

From a wood and amethyst ring to white gold and blue topaz earrings, Gem showcases one-of-a-kind handmade accessories. In 2004, Laura Kitsos opened
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Alternatives

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Gold Coast | U.S. and Canada | U.S. | Illinois | Chicago

Located in the 900 Shops of North Michigan Avenue, Alternatives not only stays ahead of current trends but also inspires them. Its Florentine owner
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Guise | Chic

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Lincoln Park | U.S. and Canada | U.S. | Illinois | Chicago

Get a haircut, shop for new outfits, and watch TV—all at the recently opened Guise|Chic. Owners Brad Habansky, Heidi Taylor, and Jodi Immel transfo
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Veruca Salt Fun

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Chicago | U.S. and Canada | U.S. | Illinois

Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grass
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Veruca Salt Fancy

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Chicago | U.S. and Canada | U.S. | Illinois

Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grass
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Robin Richman

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Chicago | U.S. and Canada | U.S. | Illinois

From her own clothing line to the commissioned skirt-form sculpture hanging from the ceiling, owner Robin Richman displays her touch everywhere in
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1 - 10 of 26 Results

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Similar Trips (7)

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1 - 7 of 7 Results

Green Travel in Chicago

Chicago, The Loop, Near North

Blessed with a crop of sustainably-minded restaurants, energy-efficient public transportation, and the wide green oasis of Milennium Park, Chi-Town is a green traveler's haven.
Mini Trip: Performing Arts in Washington, D.C.

Penn Quarter, Dupont Circle, Gold Coast, Chinatown/Convention Center, Foggy Bottom

Catch a performance at the Kennedy Center's free Open House Arts Festival, wine and dine, and go undercover at the International Spy Museum.
Driving Trip: Chicago to Harbor Country

Chicago, Union Pier, Sawyer, Lakeside, Indiana

Harbor Country, Michigan, a cluster of eight lakefront communities connected by windy, tree-lined back roads, is the weekend getaway of choice for Windy City residents (including Oprah!).
Mini Trip: Chicago's North Avenue Beach

Chicago, Lincoln Park, River North

A short drive from downtown, you'll see everyone from lobster-red Ditka fans to bronzed, buff young professionals swimming, sunning, and spiking volleyballs.
Chicago's Best Hot Dogs

Chicago, Lincoln Park, River North, Lakeview, Avondale

Ever since Austro-Hungarian immigrants introduced them at the 1893 World’s Fair, hot dogs—and the stands that sell them—have become central to Chicago's food infrastructure. Chicago hot dogs aren’t...
The Midwest: An Architecture Buff's Tour

Milwaukee & Lake Michigan Area, Minneapolis/St. Paul, Spring Green, Toledo, Downtown Minneapolis

It's no secret anymore: The Midwest is home to some of the most innovative contemporary architecture in America. Our five day self-guided tour includes stops in Toledo, Milwaukee, Minneapolis, and
...
Touring Chicago's Hottest Tables

Western Springs, Lincoln Park, River North, South Loop, Wicker Park/Bucktown

Though chefs like Charlie Trotter and Rick Bayless long ago helped Chicago shed its "Hog Butcher for the World" image, the city hasn't quite been able to edge past the dining capitals on the coasts...