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Chicago, Illinois

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Unexpected adventures in Illinois

Adventure is calling you to Illinois. In Chicago, you'll experience world-class culture, luxury shopping and ocean-like beaches. Venture to Galena, and you'll find small town charm and breathtaking landscapes along the Galena River. Or Kickstart your journey with a legendary Route 66 road trip, featuring over 100 unique roadside attractions that make for an unforgettable 484km tour of Americana.

City

Explore the world-class cuisine, luxury shopping and stunning architecture that makes Chicago a must-see city.

Adventure

Take America's most legendary road trip, Route 66 – a nearly 500km Illinois adventure featuring over 100 iconic roadside attraction.

Outdoors

Illinois boasts over 70 stunning state parks, 2,900 lakes and 7 scenic drives, making it a premier destination for outdoor enthusiasts.

Start your great American adventure in Illinois

Chicago City trip

Explore one of the world's greatest cities, where a magnificent lakefront skyline provides a stunning backdrop to experience world-class art, architecture, museums, luxury shopping on the Magnificent Mile and more.

World-class gastronomy

Beyond Chicago’s famous deep-dish pizza is indulgent, award-winning, world-class dining. From the innovative, three-Michelin-starred Smyth, to Indian cuisine re-invented at Michelin-starred Indienne, to Camp Aramoni’s farm-to-table retreat in Tonica.

Art and culture

From the world-famous museums, art and architecture of Chicago to the rich American presidential history of Springfield and the historic towns and cultural sites throughout Illinois, history comes alive. 

Architecture

Embark on award-winning architecture tours to discover Chicago's iconic buildings, then explore Frank Lloyd Wright masterpieces in Oak Park – Illinois has breathtaking world-class architecture to explore throughout the state.

Outdoor adventure

From stunning Starved Rock State Park to the awe-inspiring Shawnee National Forest, Illinois boasts over 70 lush state parks, 2,900 lakes and 7 scenic drives, making it a premier destination for outdoor enthusiasts.

Illinois Made

Discover locally crafted, one-of-a-kind goods from handmade treasures to innovative creations, each carrying the heart and soul of the Illinois artisans who made them. Meet the makers, and discover Illinois' rich spirit of kindness, creativity and craftsmanship.

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Flights to Chicago, Illinois

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Terms and Conditions

Expedia's usual booking terms and conditions apply. Special offers are only available at participating hotels. Minimum stay may be required. Offers are subject to availability and may be discontinued without notice. Additional restrictions and blackout dates may apply.