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Lifestyle
Gray's Guides
Chicago

Chicago

There's plenty to explore in this cosmopolitan Midwestern city. Visit world class museums, vibrant parks, and renowned restaurants.

Stay

From family-run inns to world-renowned luxury resorts, find a welcoming home away from home.

The Langham

This stunning luxury hotel offers gorgeous views of the Chicago River and Lake Michigan.

The Peninsula

This luxury hotel is ideally located just a block away from the Museum of Contemporary Art and Water Tower Place.

Waldorf Astoria

This elegant hotel has large rooms and is found in a great location.

Park Hyatt Chicago

A refined luxury hotel just steps from the historic Water Tower and Michigan Avenue, offering serene rooms with sweeping views of Lake Michigan and an elegant, residential feel in the heart of downtown.

Thompson

Located in iconic Gold Coast, the Thompson is comfortable, modern, and sophisticated.

The Hoxton

A more trendy stay in the heart of Fulton Market District.

Eat

Dining out is an essential part of any travel experience. Explore our favorite restaurants, bars, and more.

Trivoli Tavern

A cozy West Loop restaurant tucked into a charming cobblestone courtyard.

Le Colonial

This gorgeous French-Vietnemese restaurant is housed in a Gold Coast row house.

Kasama

A Filipino restaurant and bakery that recently earned two Michelin stars.

Bavette's Bar & Boeuf

Chicago is known for its steak, and this lively, yet intimate spot is perhaps our favorite steakhouse in the city.

Daisies

A beloved Logan Square restaurant known for its handmade pastas, seasonal Midwestern ingredients, and warm, neighborhood atmosphere.

Lou Malnati's

What's a trip to Chicago without deep dish pizza? Opt for Lou Malnati's, a local favorite.

Monteverde

Known for its incredible Italian fare and impeccable service, Monteverde is a go-to choice for visitors and locals alike.

Drink

Dining out is an essential part of any travel experience. Explore our favorite restaurants, bars, and more.

RL Restaurant

Sip martinis at Ralph Lauren's iconic Chicago restaurant.

Artmitage Alehouse

A cozy, British-inspired tavern in Lincoln Park and a perfect spot to enjoy a classic cocktail alongside rich pub fare in an intimate, candlelit setting.

Kumiko

A Japanese dining bar known for its creative cocktails and hip atmosphere.

Three Dots and a Dash

An elevated tiki bar experience in River North.

Green Mill

At over 100 years old, this jazz and cocktail lounge is simply iconic. Note - they only accept cash.

The Allis

Soho House's public restaurant and bar is a terrific place to meet for drinks.

What to do

Immerse yourself in local activities — including world-class golf courses, beaches, spas, parks, and more.

Cubs Game

Visit Wrigley Field and experience iconic Chicago baseball.

Oak Street Beach

The perfect place to spend a summer day; relax in the sand with a view of the Chicago skyline.

Chicago Riverwalk

A 1.25 mile walk along the Chicago River; explore cafes, shops, restaurants, and more.

Chicago River Architecture Tour

Spend 90 minutes aboard a boat on the Chicago River and learn about the city's fascinating architecture.

Lincoln Park Zoo

A free 35-acre zoo founded in 1868, making it the fourth oldest zoo in North America.

The Second City

Watch a show at this iconic comedy club, comedy theater, and school of improvisation known for its many famous alums.

Culture

Discover local art museums, theaters, landmarks, festivals, and more.

The Art Institute of Chicago

One of the world’s great art museums, home to an extraordinary collection ranging from iconic Impressionist masterpieces to modern works.

Millennium Park

Explore public art, exhibitions, gardens, and more.

Barack Obama Presidential Library

A cultural campus dedicated to preserving the legacy of President Barack Obama through exhibits, community programs, and public spaces celebrating his presidency and civic leadership.

Field Museum

Chicago's natural history museum, found in 1893.

Museum of Science and Industry

Spend a day at the largest science center in the Western Hemisphere.

Explore Chicago Photography

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Boat Day, Chicago

Summer in Chicago

The Chicago Gal

The Crowd Goes Wild, Wrigley Field™, Chicago

Chicago River

Cubs Win, Wrigley Field™, Chicago

Chicago River II

Go Cubs Go, Wrigley Field™, Chicago

The Dog Beach, Chicago

The Sportscaster, Wrigley Field™, Chicago

Cheers to the Cubs, Wrigley Field™, Chicago

Welcome to Chicago

The Starting Lineup, Wrigley Field™, Chicago

Lake Forest Beach Day

Sailboat Regatta, Lake Michigan

Bleacher Bums, Wrigley Field™, Chicago

Wilmette Beach Day, Chicago

400 Club, Wrigley Field™, Chicago

Kenilworth Beach

Cubs Spirit, Wrigley Field™, Chicago

Chicago Bean II

Hats Off for the Cubs, Wrigley Field™, Chicago

Chicago Bean I

Sailboats of Lake Michigan

Take Me Out to the Ballgame, Wrigley Field™, Chicago

Wilmette Sailing Beach, Chicago

Game Day Tickets, Wrigley Field™, Chicago

North Avenue Beach, Chicago

The Dugout, Wrigley Field™, Chicago

Buckingham Fountain, Chicago

Oak Street Beach Diagonal, Chicago

Best Seats in the House, Wrigley Field™, Chicago

Wilmette Sailboat, Chicago

Let’s Play Ball, Wrigley Field™, Chicago

Tower Road Beach, Winnetka

Oak Street Beach Waves, Chicago

Home Run, Wrigley Field™, Chicago

Lake Michigan Boats, Chicago

Oak Street Beach Vertical, Chicago

Gloves in the Air, Wrigley Field™, Chicago

Wilmette Kayaks, Chicago

Cloud Gate, Chicago

Play Ball, Wrigley Field™, Chicago

Glencoe Beach, Chicago

The Wrigley Building, Chicago

The Playpen, Chicago

Cheers to the Wrigley Field™, Chicago

The Playpen Boats, Chicago

The Spectators, Wrigley Field™, Chicago

Wilmette Beach Day Vertical, Chicago