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Top 30 Destinations by Personality Type
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Chicago, Illinois

Great Destination:

Value for Money:

Total Stars:

Personality Types that Like it Best

Did You Know…?

  • Route 66 starts in Chicago.
  • The city’s first known settler was Jean Baptiste Point du Sable, a black man.
  • Chicago is the Windy City because of Chicagoan bragging about the 1893 Columbian Exposition.
  • The world’s first skyscraper was built in Chicago (1885).
  • Engineers reversed the flow of the Chicago River in 1900.

Great city, Great Lake

Chicago is a great metropolis set, literally, on a Great Lake. Tourists come for top museums, leading-edge theater, jazz and blues; strolls within sight of Lake Michigan, and shopping in Marshall Field’s and other spots.

The city is noted for an eclectic collection of other things, too: the stockyards, grain markets, Al Capone and Elliott Ness, elevated trains, two mayors named Richard Daley, a president named Obama, a cow and a very big fire, the Palmer House, skyscrapers including the Sears Tower, cold winters and wind (meaning Mother Nature’s, in this case) and a version of its past regularly reprised on stage in “Chicago.”

The Midwest’s largest city knows a thing or two about living with a checkered history, but Prohibition-era murder and mayhem are well into the past. Today, such doings are merely background color for a businesslike 21st century city dramatically situated on Lake Michigan.

The need to rebuild after the Great Fire in 1871 attracted top architects who created the Chicago School of architecture and, ultimately, the skyscraper. In the 1880s, Frank Lloyd Wright came to town with his Prairie School of architecture. In the 1940s, the German architect Ludwig Mies van der Rohe reinvented the Chicago School.  No wonder engineers and designers come from around the globe to have a look and tourists walk downtown streets with eyes directed upwards.

By night, Chicago offers plenty of jazz and blues and, as host to one-of-a-kind theater companies, it is the source of original comedy and drama.

By day, Chicago is a place to do business. Long known for its stockyards, It also has the world’s largest grain market. The city’s location in the center of the U.S. and the vast McCormick Place convention and exhibition complex bring in numerous conventions and other events. Visitors may come to do business, but they stay around long enough to relish the dining, the nightlife, the streetscape, not to mention the shopping in a city also known for its huge department stores.

Visitors come in winter if they must, but the other seasons are more comfortable.

Things to do for Venturers

  • Enter one of the area’s paddle races, the Mid-American Canoe & Kayak Race on the Fox River or the Chicago River Flatwater Classic.
  • Go ice skating in town at the Michigan Avenue rink at Millennium Park. Warm up with hot chocolate or more at the Park Grill. Alternatively, skate on the Navy Pier during the LaSalle Bank Winter WonderFest.
  • Hear blues in the city that calls itself the Blues Capital of the World. Choose the House of Blues, or a smaller trendy spot, or seek out something grittier, such as the legendary B.L.U.E.S., on North Halsted.
  • Join hundreds of others in the annual Chicago Polar Plunge — in March into Lake Michigan. You can plunge as much or as little of yourself as you wish; the goal is raising funds for Special Olympics Chicago.
  • Cycle the city’s bike paths.
  • Compete in the Chicago Marathon. Or, compete in the Chicago Speed Skating Classic, which is open to skaters of all ages and skill levels.

Things to do for Centrics

  • Attend a baseball game (two teams to choose from, the Cubs or White Sox), a basketball game or other professional sport, depending on your schedule.
  • Come to town in late summer for the Chicago Jazz Festival, staged in Grant Park. Events are free.
  • Zero in on architecture, a key attraction in the Windy City. Take a self-guided Early Skyscrapers Tour to learn how builders developed the first tall buildings and see examples of their work. See for details.
  • Get on the water. Canoe or kayak on the Chicago River. Rent a boat in Clark Park. Choose a moonlight dinner journey, which involves paddling to a disembarkation point for a riverside dinner, followed by the return journey under the moon. Alternatively, take a sightseeing or dinner cruise from Chicago’s Navy Pier.
  • Come to Chicago for theater. It is the home to the well-known Second City, Lookingglass and Steppenwolf theater companies, among other options.
  • Step out for some late-night jazz at the Green Mill Jazz Club. If your schedule permits, come to town for the Winter Delights Jazz Fair.

Things to do for Authentics

  • Take an architecture boat tour aboard Chicago’s First Lady with a Chicago Architecture Foundation guide pointing out more than 50 of the city’s important buildings.
  • Do a little Christmas shopping and drink warm spiced wine at Christkindlmarket Chicago, an annual Christmas market inspired by a traditional Christmas in Nuremberg, Germany. The market lasts about four weeks.  Or, in any season, shop Chicago’s Magnificent Mile, i.e., North Michigan Avenue, one of the world’s ritziest shopping streets.
  • Plan a tour that takes in places in the city that are relevant to the life of President Barack Obama.
  • Explore an early version of a model town, the Pullman Historic District on the South Side, created in the late 1800s to house workers for the Pullman Palace Car Company.
  • Take the free Saturday afternoon Loop Tour Train, a unique way to sightsee in the historic downtown Loop. Chicago Architecture Foundation docents narrate the tour, providing history plus information on the city’s architecture and elevated trains.
  • Find the 57-acre lakefront Museum Campus, then visit one or more of the three great museums it connects: the Adler Planetarium and Astronomy Museum, the Field Museum and the John G. Shedd Aquarium.

Additional Resources

For more information, consult Choose Chicago at