Flights to Chicago

Best Anytime fares to Chicago

Cheap round-trip flights to Chicago

Boston

Thu, Mar 3 Wed, Mar 9
jetBlue

$99

Newark

Thu, Mar 3 Sat, Mar 5
United Airlines

$252

Portland

Sat, Mar 5 Sat, Mar 12
Frontier Airlines

$238

Philadelphia

Sun, Mar 13 Wed, Mar 16
Spirit Airlines

$81

Denver

Thu, Mar 10 Mon, Mar 14
Spirit Airlines

$99

Portland

Sat, Mar 12 Mon, Mar 14
Frontier Airlines

$258

Atlanta

Fri, Feb 26 Sat, Feb 27
Spirit Airlines

$107

Washington DC

Thu, Mar 3 Mon, Mar 7
United Airlines

$201

Seattle

Wed, Mar 9 Tue, Mar 15
Frontier Airlines

$238

Philadelphia

Fri, Apr 8 Mon, Apr 11
Spirit Airlines

$81

Los Angeles

Tue, Mar 8 Wed, Mar 9
Spirit Airlines

$117

Denver

Wed, Mar 2 Tue, Mar 8
Spirit Airlines

$89

New York

Mon, Mar 7 Wed, Mar 9
Spirit Airlines

$81

San Francisco

Thu, Mar 3 Sun, Mar 6
American Airlines

$137

Minneapolis

Thu, Apr 7 Sat, Apr 9
Spirit Airlines

$81

Boston

Sat, Feb 27 Mon, Feb 29
American Airlines

$131

Newark

Wed, Mar 23 Wed, Mar 30
jetBlue

$225

Washington DC

Tue, Mar 8 Thu, Mar 17
American Airlines

$189

Atlanta

Wed, Mar 16 Tue, Mar 22
United Airlines

$81

New York

Thu, Mar 10 Sat, Mar 12
Spirit Airlines

$81

Seattle

Sat, Mar 12 Mon, Mar 14
Frontier Airlines

$258

Minneapolis

Thu, Apr 7 Fri, Apr 8
Spirit Airlines

$81

Los Angeles

Fri, Feb 26 Mon, Feb 29
Spirit Airlines

$147

San Francisco

Tue, Mar 1 Mon, Mar 7
American Airlines

$132

Best weekend fares to Chicago

Best weekend fares to Chicago

Newark

Thu, Mar 3 Sat, Mar 5
United Airlines

$252

Boston

Sat, Feb 27 Mon, Feb 29
American Airlines

$131

Denver

Thu, Mar 10 Mon, Mar 14
Spirit Airlines

$99

Portland

Sat, Mar 12 Mon, Mar 14
Frontier Airlines

$258

Atlanta

Fri, Feb 26 Sat, Feb 27
Spirit Airlines

$107

New York

Thu, Mar 10 Sat, Mar 12
Spirit Airlines

$81

Washington DC

Thu, Mar 3 Mon, Mar 7
United Airlines

$201

Seattle

Sat, Mar 12 Mon, Mar 14
Frontier Airlines

$258

Philadelphia

Fri, Apr 8 Mon, Apr 11
Spirit Airlines

$81

Los Angeles

Fri, Feb 26 Mon, Feb 29
Spirit Airlines

$147

Minneapolis

Thu, Apr 7 Sat, Apr 9
Spirit Airlines

$81

San Francisco

Thu, Mar 3 Sun, Mar 6
American Airlines

$137

Fly to Chicago

When you fly to Chicago Illinois, you can choose between flying into the smaller Midway Airport (MDW), which is a little closer to downtown, or O'Hare International Airport (ORD), which is serviced by most domestic and international carriers. The Windy City hosts a cornucopia of entertainment, sporting and cultural events.

Attractions

You can experience your own Ferris Bueller s Day Off when you fly to Chicago Illinois by visiting iconic Chicago landmarks such as The Art Institute of Chicago, where you can view the vast collection of Impressionist works, or by scaling the Willis Tower to get a bird s eye view of this magnificent city. Chicago is home to teams from all major league sports, including the Cubs that play at the famous Wrigley field. Chicago is also a notable culinary city, with its own style of hot dogs, pizza and fine dining opportunities downtown. Additionally, a trip to Chicago should include an evening of jazz at one of the city s many clubs.

Hints and tips

When you fly into Midway Airport (MDW), you can reach the city of Chicago by car rental, taxi, a variety of shared-ride van services or use the Chicago Transit Authority (CTA) Orange Line train. When you fly into Chicago O Hare (ORD) you can reach the city of Chicago by car rental, taxi, bus or use Chicago Transit Authority Blue Line train. Annual events include the Jazz Festival, NFL Draft, Architecture Biennial and ITU World Triathlon.

  • Chicago When to Go

    Come summer, Chicagoans head to the beaches, parks, and festivals along Lake Michigan. A chill often lingers in the air in early summer, while late summer can be muggy. Regardless of the season, pack layers, as weather can fluctuate greatly. Summer also brings spikes in hotel rates.

    Fall is pleasant until mid-November, when temperatures plunge, and spring doesn’t get reliably comfortable until late April. Anytime between May and November, you’ll be able to combine season-less indoor attractions with the convivial appeal of the outdoors at the lakefront, on Chicago River boats, and milling around Millennium Park.

    Weather and prices are tradeoffs in Chicago. In January and February, the “hawk” (a local term for the harsh wind off Lake Michigan) sweeps down Michigan Avenue, and snow buries the streets. But hotel rates are bargain basement and attractions uncrowded.

Airports in Chicago IL, US

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Carriers