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With top-of-the-line hotels and shopping, gorgeous architecture and a world-famous skyline, plus one of the most exciting dining scenes in the country, the Windy City is one of America’s most exciting cities. Best of all, you can count on an exceptionally warm welcome and friendly service wherever you go.
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
The best Chicago itineraries include customized, special access and private guided touring. Here is just one example of what our destination experts can create for you.
After lunch at a legendary Chicago diner, jump in a cab to North Avenue Beach to admire the views of Lake Michigan. Take a cruise along the Chicago River to learn about the Windy City and its architecture. You may also opt to visit the pier and landmark Ferris Wheel. Board one of the 40 gondolas that soar 150 feet into the air to take your love of Chicago’s beauty to new heights.
Begin today with a trip to the Art Institute of Chicago, which is full of treasures (including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks). Particularly impressive is its collection of more than 2,000 European paintings and sculptures, among them Impressionist and Postimpressionist works by such artists as Monet, Degas, van Gogh and Seurat. Make your way to the Lincoln Park neighborhood to recharge your batteries with a relaxing lunch (al fresco dining is the quintessential Chicago experience).
Today, head to Millennium Park, a gorgeous outdoor venue complete with a Frank Gehry–designed music pavilion, iconic Cloud Gate sculpture and Lurie Garden. Later, wander up to the rooftop to the chilled out J. Parker bar that attracts a good crowd and offers magnificent views of the city, the park and Lake Michigan just beyond it. Enjoy dinner tonight at a foodie-approved, Michelin-starred restaurant.
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special perks, including upgrades, early check-in, spa credits, and more. Look for the Indagare Plus logo in the reviews.
This hip hideaway, housed in a restored Venetian Gothic building originally constructed in the 1890s, is Chicago’s newest and trendiest property.
Being the closest luxury hotel to Lake Michigan, the Four Seasons offers magnificent views of the water, plus dependably excellent service and amenities.
A quiet property despite its location just off the Magnificent Mile, the Park Hyatt is sleek with a simple, contemporary vibe.
Like its Hong Kong and Paris sister properties, the Peninsula is a top-notch property with fresh rooms and high-tech amenities, making it one of Chicago’s top luxury picks.
The Art Institute is full of treasures (including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks) but small enough to manage in an afternoon. Particularly impressive is its collection of more than 2,000 European paintings and sculptures, among them Impressionist...
The Asian Art Museum boasts one of the largest collections of Asian art outside of Asia. Housed in a 1917 Beaux Arts building (the city’s former Main Library), the Asian Art Museum was designed by Gae Aulenti, an Italian architect...
Fans of the great architect may feel the need to make a pilgrimage to Wright’s home and studio, where he lived and worked from 1889 to 1909. You can take a guided tour of the buildings, which were renovated by...
One of the most appealing attributes of the Lincoln Park Zoo is that it’s free, so you don’t have to deal with tickets or lines but can simply stroll in and out at any of several entrances at your leisure....
One of Chicago’s most beloved assets is its phenomenal public art, of which there’s a surprising amount. In the course of a twenty-minute stroll through the Loop, you can ogle more than a dozen enormous outdoor sculptures by the likes...
Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.
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The Windy City, Chi-Town, The City That Works—call it what you will, but Chicago is a veritable powerhouse. As the third most populous city in the United States, Chicago feels quintessentially new, with towering, reflective skyscrapers and impressive urban planning. Add its...
Indagare member April Paffrath recently traveled to Chicago. Here are her impressions from the trip.
Chicago is a fantastic place to stay with kids, and the Ritz-Carlton, Peninsula and Four Seasons compete to offer the most memorable children’s amenities and the most thoughtful service. Here are a few highlights:
For teenagers, heading off to college means freedom and fun and all the glory that entails (e.g., sleeping on dorm room futons and eating dining hall rations). But on college visits—and later, when visiting collegiate children—parents need not accept sub-par...
A trip here can easily be combined with these amazing destinations and more. Contact our team to craft the perfect itinerary.
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