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Chicago Travel Guide

The Chicago Theatre's marqueeAbout Chicago

Though it's only the third largest city in the U.S., Chicago is nothing short of a world hub. There are so many things to do, most people find one visit isn't enough. The city delivers architecture, art, shopping, nature, and one giant dinosaur. read more

When to Visit Chicago

Chicago is a big, bustling city that's popular all year long. Deciding when to visit, and when to book, will determine how much you spend on accommodations and airfare. read more

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Chicago Trip du JourSee all Trips du Jour

Chicago girl relaxing in Grant Park, Chicago, Illinois (Photo: iStockphoto/Jim Jurica)Chicago makes 'green' fashionable, but not spendy

The Windy City offers goods made from recycled materials, cocktails with a purpose, and organic pizza. Plus, you can make green choices without turning blue from high prices. read more

Last-Minute Airfares to ChicagoSee all

Departure City Price Arrival City Airline
La Crosse, WI (LSE) $200 Chicago, IL (ORD) American
Milwaukee, WI (MKE) $180 Chicago, IL (ORD) American
Minneapolis, MN (MSP) $98 Chicago, IL (ORD) American

Editors' Picks: Chicago DealsSee All Chicago Travel Deals

  • $18 R/T U.S. and Caribbean Sale From Spirit*
    Spirit's latest sale features U.S. and Caribbean destinations including Chicago, Las Vegas, the Bahamas, and Puerto Rico. Travel is valid on select dates through April, but hurry because this promotion will only be around until February 10.
  • Through Thursday: $80 O/W Southwest Sale - More Than 1,300 Routes*
    Southwest's recently announced promotion offers more than 1,300 on sale for winter and spring getaways. The low-cost king's fares start at $80 one-way, but AirTran, Continental, Frontier, Midwest, United, and US Airways also offer savings.
  • Wow! $39 O/W Southwest Sale - Save 64% on Flights*
    Stop, drop, and book these sale fares! Southwest has just announced a short-haul promotion, but there's nothing short about the savings. Our research shows that the competitors are not coming even close to touching the low-cost king's rates.
  • $530 R/T Hawaii Sale Fares From American*
    Thaw out on a Kona, Lihue, or Kahului beach while gazing at a serene sunset with American's latest sale. Our research shows that the fares are comparable to those offered by Delta, United, and US Airways, with the exception of travel from a key city.
  • $678 R/T Honolulu Sale From US Airways*
    Boston, Chicago, and New York, are but a few of the East Coast or Midwest cities from where you'll find departures to sunny Honolulu. US Airways' sale fares start at $678 round-trip, and travel is valid through March.
  • $390 R/T United Features Sale Fares to Canada*
    United's latest sale features travel to Canadian destinations such as Montreal, Quebec City, Toronto, Vancouver, and others. This sale doesn't list a book-by date, but the sooner you book, the more likely you'll find the lowest fares.
  • $260 R/T Canada Sale Fares From American*
    Scenic landscapes, vast wildlife, exciting metropolises, plus the Vancouver Olympics to boot! It might be time to visit the neighbors up north, and American's latest sale helps out by offering fares from $260 round-trip.
  • $248 R/T American Sale to Ski Destinations*
    Grind some Colorado or Wyoming snow with American's ski sale. Destinations include Gunnison, Jackson Hole, Montrose, Steamboat Springs, and Vail. Competing carriers, Continental, Delta, and United, challenge American's low fares.
  • February Weekend Getaways From $55 per Night
    February is the perfect month to get out of town for a weekend and celebrate or rekindle romance with a significant other. And, for those who detest the month of love, several packages offer great ways to defeat those winter blues.
  • $98 R/T American Sale Fares - Lots of Competition*
    American Airlines' newly-announced sale, with starting prices of $98 round-trip, includes Boston, Dallas, Miami, and Orlando, among several other destinations. Competing carriers Southwest, United, Delta, AirTran, and more, get involved.

Chicago Travel Advice See All Chicago Travel Advice

Find Chicago HotelsSee all

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