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Cheap Flights from Chicago†
Las Vegas from $87 ❯
Denver from $87 ❯
Miami from $91 ❯
Orlando from $97 ❯
Phoenix from $105 ❯
Tampa from $107 ❯
New York City from $117 ❯
Los Angeles from $124 ❯
Mexico City from $226 ❯
Honolulu from $662 ❯
Take a Break from Chicago’s Winter Weather

During winter months, warm-weather destinations are—not surprisingly—popular with Chicagoans.

Many families head to Orlando to visit Walt Disney World and other area amusement parks. Beach destinations such as Cancun, Fort Myers, Honolulu and San Juan are favorites of those who want to relax, soak up the sun’s rays or partake in outdoor sports such as fishing and surfing. Phoenix is also a hot destination, particularly among golfers.

Visit Another City

If you enjoy vibrant and bustling cities, consider taking a trip to New York City, Las Vegas, Los Angeles or Toronto. All are popular destinations for Chicagoans who want to enjoy fine restaurants, go to the theater, shop or simply have a romantic weekend getaway.

From Chicago, flying time to Toronto is about one hour. To cities such as New York and Washington DC, flying time is about two hours—perfect if you’re looking for a quick weekend out of town. Flying time to West Coast cities such as Los Angeles, San Diego, San Francisco and Seattle is about four hours. And because so many airlines fly these routes, cheap airfares to these destinations are often available.

Flying from Chicago

Thanks to its centralized location and two major airports, Chicagoans can fly non-stop to a host of business and vacation destinations in the United States, Canada, the Caribbean, South American, Europe and Asia.

Chicago O’Hare International Airport (ORD), located on the city’s northwest side, is one of the nation’s busiest airports. Dozens of domestic and international airlines service the airport, including American Airlines, Delta Air Lines, United Airlines and Spirit Airlines. Among the airport’s most-traveled routes: New York City, London, Los Angeles and San Francisco.

Because of the number of Southwest Airlines flights, Midway International Airport (MDW) is known for its cheap airfares. Located on the city’s southwest side, the airport has non-stop flights to dozens of destinations, including Atlanta, Denver, Minneapolis-St. Paul, Las Vegas and Orlando.

Looking for Low Fares? Consider Other Airports

Can’t find low airfares out of O’Hare or Midway? For cheap flights, consider expanding your flight search to other area airports.

General Mitchell International Airport (MKE) in Milwaukee is serviced by more than a dozen airlines (including American, Delta and Southwest). You may be able to find cheap flights to Atlanta, Dallas-Fort Worth, Denver, Phoenix and other destinations.

Allegiant Air and Apple Vacations flights operated by Frontier Airlines fly out of Chicago Rockford International Airport (RFD), which is located 68 miles northwest of Chicago in Rockford, Ill. Top destinations include Phoenix, Las Vegas, Orlando, St. Petersburg and Denver.

Cheap flights from Chicago, IL
  • Chicago, IL is the gateway for cheap flights to domestic and international destinations and it currently has non-stop flights to 251 cities.
  • Chicago, IL travelers take frequent flights to the following cities of Las Vegas, Nevada, Los Angeles, California and Orlando, Florida.
  • In 2016 London, United Kingdom was the favorite European destination for travelers flying from Chicago, IL and was followed by other cities like Dublin, Ireland, Rome, Italy and Athens, Greece.
  • San Juan, Puerto Rico and other favorite sunny locations like Montego Bay, Jamaica, Santo Domingo, Dominican Republic are also places visited by Chicago, IL travelers.
  • The Top Asia destinations like Mumbai (Bombay), India, New Delhi, India and Manila, Philippines are also some favorite places for Chicago, IL travelers.

Other popular flights from Chicago