Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Cheapest Flights to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago Flights

Although this city is filled with all of the usual hustle and bustle, it still manages to maintain its laid-back, Midwestern American charm.
Travellers gather to this destination to soak up some culture at the Chicago Cultural Centre, see the water show at the Buckingham Fountain, or get a view of the city from the Hancock Observatory.
Food enthusiasts delight in a plethora of dining options downtown, while nature lovers enjoy the Grant Park Rose Gardens. With no shortage of things to do, tourists abound in this city. Despite this, cheap flights to Chicago are easy to find most of the year.

Best time to go to Chicago

Peak Season:

Flights to Chicago are at their most expensive from June through September. Although it’s humid, the temperature is warm and beautiful, making it a great time to discover Lake Michigan, or stroll through Humboldt Park.

Shoulder Season:

April and May, and October to December make up the shoulder season in Chicago. Crowds thin out during these cooler months, so this is a fantastic time to either take the Hop On Hop Off city tour, visit the Museum of Science and Industry, or peacefully wander through the Navy Pier.

Off Season:

Due to the bitter weather from January through March, flights are inexpensive and tourists are few. Although it can be chilly, this is one of the best times to indulge in one of the many indoor activities, like seeing a performance at The Second City comedy theatre or the Lyric Opera, dancing at Enclave, or exploring the Shedd Aquarium.

Chicago Airport and transfer information

Chicago O'Hare International Airport (ORD)
Distance: 27km northwest of city centre
Offering door-to-door service at a reasonable price, the Go Airport Express shuttle bus is one of the most convenient methods of ground transport. Alternatively, you can take a taxi or a public bus. Both take around 25 - 90 minutes to arrive at your destination.
Taxis can be expensive, but are one of the more flexible options. Buses buses are inexpensive, but are sometimes delayed. Car rentals are also available at a higher price.

Online resources for your travel to Chicago

http://www.safetravel.govt.nz/destinations/unitedstates.shtml
The Safetravel website provides details on travel safety, as well as information on entry requirements and important local contacts.
http://www.flychicago.com/About/OHare/Default.aspx
The Chicago O'Hare International Airport website offers details on flights, services, and ground transport.