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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
Appleton, WI (ATW) $106 Chicago, IL (ORD) United
Birmingham, AL (BHM) $174 Chicago, IL (ORD) United
Bismarck, ND (BIS) $156 Chicago, IL (ORD) United

Editors' Picks: Chicago DealsSee All Chicago Travel Deals

  • $314 R/T Sale Fares to Canada From United*
    United's latest sale features travel to cities in Canada like Montreal, Calgary, Vancouver, Halifax, and others. However, carriers like US Airways, Delta, and Northwest, among others, offer significant savings over United's prices.
  • $18 R/T U.S. and Caribbean Winter Sale on Spirit*
    The ultra-low-cost carrier's latest sale features travel to many U.S. and Caribbean destinations including Chicago, Las Vegas, Nassau, and St. Thomas. Also look into fares from US Airways, who beats Spirit's already-low price on one route.
  • $116 R/T American Sale Matches Southwest, United, and Others*
    Why does American's latest sale look so familiar? Because it's nearly identical to competing promotions from Southwest, United, and Frontier. Add it all up and you've got a major fare war. And that's a huge win for bargain hunters.
  • $248 R/T Thanksgiving Day Sale From United*
    Just like Southwest, United has posted its own last-minute Thanksgiving holiday sale, and these prices are competitive. Also look into JetBlue for fair fares. Destinations include Los Angeles, Rock Springs, and Washington, D.C.
  • $75 O/W Last-Minute Thanksgiving Day Sale on Southwest*
    Just in time for that last-minute booking, Southwest has announced a Thanksgiving sale with dates encompassing the holiday period. Several carriers, including AirTran, Delta, Northwest, and US Airways, are also competing.
  • $51 O/W Seattle Winter Fares on Southwest*
    In time for the 2010 Winter Olympics, Southwest's latest sale features travel to Seattle. Promotional fares start at $51 one-way but we found that on most routes AirTran, American, JetBlue, among others, offer savings of about $100.
  • Extended Stay Hotels Offers Last-Minute Weekend Discounts
    Find last-minute weekend discounts on Extended Stay's website and save at least 20 percent off weekend rates. Plus, Extended Stay Hotels guarantees you'll find the best available rate when you book directly on its website.
  • $118 R/T United Matches Southwest Sale*
    United attempts to match Southwest's latest offer with sale fares to many domestic destinations this winter. The two airlines come head-to-head in the low-fare war, and Spirit also joins the competition.
  • Hawthorn Suites Offers Discounted Rates
    Hawthorn Suites offers discounts to members of groups like AAA and AARP in addition to offering senior, government, and military discounts. Plus, Hawthorn Suites offers special packages at select properties.
  • $59 O/W Southwest Sale on 2,500 Routes*
    Southwest's latest sale includes destinations like New York, Los Angeles, Chicago, and Las Vegas. Half of the researched routes offer savings, while the other half are beaten by carriers like JetBlue, AirTran, Continental, Delta, and Northwest.

Chicago Travel Advice See All Chicago Travel Advice

  • See the Country by Train and Save Big The Deal Detective helps a mom plan a getaway by train for her family. All aboard for ways to save and plan when riding the rails.
  • Car Rental Booking Test Yields Surprising Results Our series comparing online travel agencies with direct travel suppliers continues this month with a focus on rental cars. The results may be a real eye opener: Where you book is less important than previously thought.
  • Zoos, Aquariums a Good Bet in Cooler Weather Who needs an African safari when local zoos and aquariums have so much to offer? Eileen Ogintz highlights some of the special deals and programs being promoted this fall.
  • Tourist Taxes Add to Travel Budget If you thought taxation without representation was settled in 1763, think again. Ed Perkins explains which popular destinations tax tourists the most, and what you can do to avoid it.
  • Take Advantage of Fall Deals for Families The kids may have gone back to school, but with all the great travel deals out there, fall is the perfect time to travel. Eileen Ogintz reviews a few of the family specials available.

Find Chicago HotelsSee all

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