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Best of Chicago

America's first skyscraper city owes its dramatic lakefront skyline to a tragedy. The 1871 Great Chicago Fire destroyed the business district of this nineteenth-century rail and inland trading hub but enabled Chicago to make a sudden, shocking leap from the Victorian period into the modern era—thanks to battalions of immigrant laborers and a handful of visionary builders such as Frank Lloyd Wright, Louis Sullivan, and Daniel Burnham.

The Windy City got its moniker not from the freezing winter blasts off Lake Michigan but from the lengthy, impassioned speeches of politicians who won Chicago the right to host the 1893 Columbian Exposition, a world's fair that showcased the physical and cultural rebirth of America's second-largest city. Mild temperatures and street festivals make June and early July the best time to visit this architectural treasure-house, which became an urban design studio for the likes of Mies van der Rohe and, lately, Frank Gehry, who deems Chicago America's most visually exciting metropolis.

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Explore Chicago
Use this interactive map to explore the sights that await you in Chicago. Click on a camera to see a 360° view. Click on a hotel to see the hotels in that area.
Lincoln Park OHare Airport hotels Oak Street Beach Magnificent Mile River North/Magnificent Mile hotels Sears Tower The Loop hotels Navy Pier Adler Planetarium Museum of Natural History
What to expect
When to go
For the best weather conditions and non-stop activities, plan your travel dates during the summer or fall months. To avoid the crowds and hot weather, travel during the fall. If you like to snuggle up indoors, visit the city during the winter months and enjoy the cheapest hotel rates.
Are we there yet?
Flight times
2 hours from Dallas, 2.5 hours from New York City, 4 hours from San Francisco
Drive times
  • From O’Hare International Airport to downtown: 30 minutes
  • From Detroit, Michigan: 4 hours
  • From Cincinnati, Ohio: 5 hours
  • From Minneapolis, Minnesota: 6 hours
  • Must-see sights
  • Take a walk on the Magnificent Mile, a stretch of North Michigan Avenue providing upscale shopping unmatched anywhere else.
  • Explore The Loop: The Art Institute of Chicago, the Chicago Symphony Orchestra, the financial district, and multiple theaters.
  • Sears Tower Sky Deck: Enjoy views atop one of the world's tallest buildings.
  • Wrigley Field: See a game at one of the country's most famous ballparks.
  • Insider tips
  • From late spring to fall, the city is brimming with festivals and fairs.
  • The best way to see Chicago is by walking, but during the slushy winter months, a good alternative is the El (Chicago’s rapid transit system).

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