Courtesy Adam Alexander Photography

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.

  • Perfect for
    Art Lovers | Families | Intellectuals | Foodies
  • When to go
    March-May | June-August | September-November
  • Ideal length of stay
    1-2 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.

  • 3 Days: Essential Chicago-LP
    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.

Indagare's Shoshana Balistierri
"Chicago is the heartbeat of the Midwest. It's a city of architecture, of soulful music and amazing food. But the star of Chicago isn't the shores of Lake Michigan, the deep-dish pizza, the art scene or the world-class museums, but the incredibly welcoming locals who make you feel at home."
Ready to go and in need of expert trip planning? Contact us today.

What To Read

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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