
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.
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Perfect forArt Lovers | Families | Intellectuals | Foodies
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When to goMarch-May | June-August | September-November
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Ideal length of stay1-2 Nights
Designing Your Journey
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.
- Courtesy City of Chicago
3 Days: Essential Chicago
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.
Day One: Sightseeing on the Water
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.
Day Two: Art Exploration and Millennium Park
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).
Day Three: Millennium Park
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.
Where To Stay
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.
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Chicago Athletic Association Hotel
This hip hideaway, housed in a restored Venetian Gothic building originally constructed in the 1890s, is Chicago’s newest and trendiest property.
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Four Seasons Hotel Chicago
Being the closest luxury hotel to Lake Michigan, the Four Seasons offers magnificent views of the water, plus dependably excellent service and amenities.
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Park Hyatt Chicago
A quiet property despite its location just off the Magnificent Mile, the Park Hyatt is sleek with a simple, contemporary vibe.
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Peninsula Chicago
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.