Cheap round-trip flights to Chicago

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.


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.


Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

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Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.