Chicago is a city with a rich history that today boasts a diverse, thriving scene for arts, eats, shopping, and more. With more than 70 neighborhoods spanning its city limits, the Windy City always offers something new to explore.
Flights to and from Chicago are offered seasonally. Dates may vary.
Why Go To Chicago
For foodies, art lovers, sports fanatics, and shoppers (or all of the above), few cities have more to offer than Chicago. There are more than 200 theaters, miles of shop-lined streets, Michelin-star restaurants, countless museum treasures, and lakefront views to boot. There’s something for everyone, and when you add in a dash of Midwestern hospitality, it’s no wonder visitors to Chicago quickly claim it feels like a home away from home.
Buckingham Fountain in Grant Park
What To Do
When you think about Chicago, it’s hard not to picture the towering buildings that dot its iconic skyline from staples like the Willis (or formerly Sears) Tower to more modern additions like the Aqua. If heights aren’t your thing, stay a little closer to the ground and check out the resilient Chicago Water Tower (one of the only buildings to survive the Great Chicago Fire of 1871) or Frank Lloyd Wright's Robie House.
The city’s proximity to Lake Michigan gives it a unique identity as a sprawling metropolis with plenty of nature to enjoy, too. In fact, there are more than 7,600 acres of parkland within the Chicago city limits. Millennium Park is a crowd favorite for its Cloud Gate sculpture (more commonly called the “Bean”) and its pavilion that frequently hosts music festivals. Other parks like Grant, Humboldt, Lincoln, and Jackson Parks also have their own landmarks well worth visiting.
Get your fill of a wide range of treasured paintings, sculptures and more at the Art Institute of Chicago, walk among Warhols at the Museum of Contemporary Art, revel in natural history at the Field Museum, stare at the stars at the Alder Planetarium, or stroll the 14 acres of exhibit space at the largest science museum in the western hemisphere (and the last remaining building from the 1893 World’s Columbian Exposition, or World’s Fair) at the Museum of Science and Industry.
Trendy boutiques, high-end designer brands, and quirky locally made goods are all just around the corner from most of the city’s streets, but Michigan Avenue’s famous Magnificent Mile is by far the most popular. State Street is another great choice, and neighborhood shopping areas like Lincoln Park, Lakeview, Wicker Park, and Bucktown are great spots for more independent shops.
The reputation for Chicago’s dining scene is strong, and for good reason. While it may be most famous for deep dish pizza, hot dogs, and steaks, it’s also nestled in America’s heartland. That means the access to farm fresh ingredients benefits everyone from acclaimed chefs, to mom and pop shops, smaller vendors and, of course, their patrons. Head to the Loop or North Side for fine dining and steak houses, or try something new in the ethnic neighborhoods of Greektown, Little Italy, or Chinatown. Not sure what you’re feeling? Stoll around Lakeview or Lincoln Park for a variety of options or just grab a classic Chicago dog on Navy Pier.
Not unlike its culinary scene, the libation game is strong in the Windy City. Mixologist and bartenders abound, but so do classic neighborhood dive bars and breweries around the city for those travelers looking for something more casual. If clubbing is what you’re after, you’ll find the largest ones in River North and West Loop and the casual ones in Wicker Park. Wrigleyville and Boystown have good middle-ground options as well.