Luxury Travel Chicago



The Wind City

Thinking about heading to Chicago for a long weekend? With its vibrant art scene, delectable food culture, pulsating nightlife and shimmering skyline, Chicago is the perfect weekend respite. American Excursionist can create your ultimate Windy City Getaway, seamlessly planning your trip from start to finish with punctual transfers, luxurious hotels and private tours with expert guides. See our experiences and partner hotels below.


Top Chicago Experiences



Architecture River Cruise

See the Windy City the way it should be. Hop aboard an antique yacht for a private sail with an expert guide! Cruise the Chicago River in elegance as Chicago’s impressive skyline, including some of its most iconic buildings, looms and glitters above you.



Chicago Crime Tour

Explore Chicago’s gritty history with a tour of its underworld! Learn about its most infamous criminals and gangsters like Al Capone and John Dillinger. Head to the most notorious sites in the city, including crime scenes, hideouts, escape routes and of course, hiding spots for alcohol during Prohibition! 



Chicago Art Tour

As one of the country’s leading art destinations, discover the city’s vibrant art scene with an exclusive tour through its world class museums and galleries. Whether you prefer photography, contemporary art, architecture, or a little of everything, your guide will customize your tour to fit your interests.



Chicago Food Tour

Explore Chicago’s tastiest neighborhoods! Start in the vibrant streets of Greek Town, stopping  for a traditional Greek appetizer. Next, it’s on to the colorful streets of Chinatown, where you will munch on delicious Chinese dishes. For dessert, sample fresh cannoli or a creamy scoop of gelato in Little Italy!



Art Institute After Hours

The Art Institute of Chicago is one of the oldest and largest museums in the USA. What better way to see it than after-hours! Your expert guide will lead you through the museum after it has been closed to the public to visit America’s greatest collection of Impressionist  and Contemporary paintings.



Chicago Lakefront Bike Tour

Enjoy the spectacular Chicago Lakefront like a local on a privately guided bike tour! Your expert guide will lead you leisurely past some of the city’s most iconic landmarks. Go off the beaten path to explore the quiet neighborhood streets, beautiful city parks, and packed beaches of the North Side.



Art Insider: Modern and Contemporary Art

Enjoy a privately guided insider’s tour of modern and contemporary art, starting with the Modern and Contemporary Art Wing at the Art Institute of Chicago. Wander through streets and parks full of public sculptures and one-of-a-kind architecture. Head in and out of some of the most cutting edge galleries to conclude your tour.



Evolution of Blues and Jazz

Chicago’s roots in Jazz, Blues and African American culture run deep. With your expert local guide, explore the Blues Trail, visit historic lounges and enjoy some delicious soul food! From former President Obama’s home to the famous Velvet Lounge, from Chess Records to Hyde Park’s newest jazz venues, your guide won’t miss a beat.



Private Pizza Making Class

Where better to learn the tricks of the pizza trade than in Chicago, home of the delicious deep-dish?! Arrive to one of the city’s most beloved pizza shops, where a seasoned chef will teach you to professionally toss dough, mix sauce and properly bake a mouthwatering pizza.


Featured Luxury Hotels & Resorts in Chicago
  • Enjoy the legendary service of the 5-star Langham in Chicago

    Offering incredible views of Chicago's river,this five-star luxury hotel is located in the heart of Chicago's city.

  • Best Available Nightly Rates

    Located along the Magnificent Mile, The Peninsula Chicago combines Asian inspiration with the charm of the city of Chicago.

  • Best Available Nightly Rates

    Located near the famed Magnificent Mile & the glamorous North Michigan Avenue shopping, lies the Four Seasons Chicago.

  • Best Available Nightly Rates

    8 minutes from the beach & boasting a world-renowned spa & restaurant this luxury hotel is across from the historic Water Tower.

  • Best Available Nightly Rates

    Waldorf Astoria Chicago offers Parisian-inspired elegance in downtown's prestigious Gold Coast neighborhood.


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