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 thriving. Best of all, you can count on an exceptionally warm welcome and friendly service wherever you go.

Cheat Sheet

  • Sleep…in a suite at The Peninsula, the most visually stunning hotel in the city
  • Experience…the city’s steely skyscrapers from the water on an Architecture Cruise
  • Splurge…on a tasting menu at Alinea, headed by celebrated chef Grant Achatz
  • Drink…fantastically inventive cocktails at The Aviary
  • See…impressionist and post-impressionist paintings at the Art Institute of Chicago
  • Visit…the spectacular Shedd Aquarium with the kids
  • Shop…at the Midwest’s high temple of fashion, Ikram
  • Know…that as an Indagare member you can contact our Bookings Team for customized recommendations and itineraries.

Lay of the Land

“Chicago is a city of contradictions, of private visions haphazardly overlaid and linked together. If the city was unhappy with itself yesterday — and invariably it was — it will reinvent itself today.”
~Pat Colander

Located on Lake Michigan in Illinois, Chicago is the third largest city in the U.S. The city’s downtown, encircled by the L (elevated train), which runs around its perimeter, is the Loop; it encompasses the financial district and a variety of cultural offerings, including the Art Institute, the Chicago Cultural Center and Millennium Park. Don’t miss the amazing array of public sculpture by such artists as Picasso and Calder.

The Magnificent Mile, the eight blocks of North Michigan Avenue from East Oak Street south to the river, is home to Chicago’s finest hotels and shopping. It’s just south of the aptly named Gold Coast, a posh neighborhood that extends from Rush Street east to Lake Shore Drive.

North of the river and west of the Magnificent Mile, the North River area is full of Chicago mainstay eateries, like Topolobampo. The West Loop is one of the city’s fastest growing neighborhoods; you’ll find an incredible concentration of Chicago’s hottest restaurants, including Paul Kahan’s Blackbird and Avec, Grace, and Monteverde in this once-industrial neighborhood.

Located northwest of the Loop, the artsy areas of Bucktown and Wicker Park have a number of chic boutiques and casual eateries. It’s a 15-minute cab ride from the Magnificent Mile.

For a taste of how the locals live, head to Lincoln Park; the name refers not only to the massive green space, crisscrossed with paths for walking and biking, that hugs the lakefront, but also to the residential neighborhood that borders it. Head here for a café scene that’s populated less by tourists, and more by laid-back local families. At the center of the park is the Lincoln Park Zoo, a hit with kids.

Getting Around

The city has two airports: O’Hare International Airport is larger and busier, while Midway Airport handles mainly domestic services plus some flights to Canada and Mexico. A cab takes 30 to 60 minutes to get to the Loop from O’Hare, and about half that from Midway. Cabs are plentiful downtown, especially around the Magnificent Mile and the Loop; to save money, take Ubers, which are about half the cost of cabs. The subway is wide-reaching but slow. But it’s fun to ride the L (elevated train) around the Loop at least once during your trip.

When to Go

The frequent gusts off Lake Michigan bestowed the city with its “Windy City” moniker, and the wind chill make the winter months extremely cold. The best time to visit is summer (chilly temperatures can last through the spring) when it is warm enough to swim in the lake and enjoy outdoor activities or early fall.

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