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.

Cheap Tickets 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

A city of extremes, Chicago mingles sophisticated theatres with gritty jazz clubs, massive concrete structures with small patches of lush greenery, mild pastimes with a wild nightlife. Cheap flights to Chicago are relatively easy to find during the majority of the year, which is important, as you will want to spend your money on the city's vast dining menu, cultural sites, and fantastic accommodations.

Best time to go to Chicago

Peak Season:

The months of June through September make up the peak season in Chicago. Despite the high humidity, flights to Chicago tend to be pricey during this period, as visitors crowd the streets to enjoy the warmth, play on the lakefront, or go sightseeing on one of the many local tours.

Shoulder Season:

The shoulder season in Chicago falls in April and May, then again in October to December. The climate ranges from warm and pleasant, to crisp and cool. Although many visitors prefer to avoid the chill, these months are still great as the city sees vibrant flora during spring, romantic reds and oranges during autumn and clean, glimmering snow at the start of winter.

Off Season:

From January through March, Chicago sees its bitterest weather. Although many tourists flee the area in search of warmer climates, this is still a good time to go as you will be able to enjoy the New Years celebrations, take advantage of inexpensive flights and explore the city in solitude.

Chicago Airport and transfer information

Chicago O'Hare International Airport (ORD)

Distance: 27km northwest of city centre

The Go Airport Express shuttle bus is one of the most convenient methods of ground transport. This shuttle offers door-to-door service, is reasonably-priced, and relatively quick. Taxis and public buses are two other convenient methods. Both take around 25 minutes to an hour and half to arrive, depending upon your destination; however, taxis allow for more flexibility, but can be expensive, while the bus system is inexpensive, but is prone to delays. Alternatively, you can rent a car at a slightly higher rate.

Online resources for your travel to Chicago

The Chicago O'Hare International Airport website gives information on flights, transport, and available services. The Smartraveller website offers tips on travelling to America, such as entry and exit requirements, security issues, and important local contacts.

Top Flight Routes from Chicago

Top Flight Routes to Chicago (ORD)

Travel beyond your imagination, book your Chicago holidays (hotel+flight) with Expedia and save more!

    Reviews from verified customers

    Mar 19, 2019

    Travelling with my husband and we were allocated seat separately and at each end of the plan. Our tickets were purchased sometime ago so not like it was last minute.

    Jan 12, 2019

    Service was hit and miss. I asked for assistance to find my connecting flight three times and was told okay but in the end had to race with my three young children to make my flight on time. Some staff we great but others were rude and refused to assist. Although the flight was satisfactory I would choose another airline next time due to the inconsistency with your staff.

    Sep 8, 2018

    Basic economy but changed at gate to main cabin extra for free. They just relaxed the rules to allow one carry on in bins in basic economy, on time.

    Sep 3, 2018

    Cheese is wonderful

    Jun 14, 2018

    Landed early!!!

    May 31, 2018

    In flight entertainment was hard to hear conversations, sound not clear against lots of background noise. Love the Korean food.

    May 25, 2018

    Flight delayed but we were early to the airport and got on an earlier flight which was delayed too but handled well

    Apr 14, 2018

    Best view ever! It was great to see America from LA to Chicago from the air. Awesome!

    Mar 16, 2018

    One flight attendant wasn’t really friendly

    Nov 15, 2017

    Modern and funky, good communication

    *Based on averages savings on all package bookings made on in the period 1 Jan 2017 -30 Jun 2017. Rates & savings subject to selections made and not available on all packages.