Cheap flights to Chicago for 2021

Chicago is famous for its skyscraper skyline, Lake Michigan, and deep dish pizzas. The chilly winters offer plenty to keep visitors entertained indoors, with great food, world-class museums, theatres and art galleries. If you can brave the cold then this is the season to find the best flight deals to Chicago.

On the other hand, Chicago is arguably at its best in the spring, summer and even early autumn months. There are a larger number of tours available in spring, summer and early and the weather is much more enjoyable for city river cruises, cycling opportunities, and park and harbour visits.

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Last verified 7 Sep 2020

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How much you can expect to pay for cheap flights to Chicago

A flight from Australia to Chicago will take less than 24 hours of travel time from Sydney, Melbourne and Brisbane. Here's what's considered to be a good deal compared to the average cost of a flight from Australia to Chicago.

Chicago flight time

• From Sydney: Approximately 20 hrs + with a stopover, landing at Chicago O'Hare International Airport
• From Melbourne: Approximately 22 hrs + with a stopover, landing at Chicago O'Hare International Airport
• From Brisbane: Approximately 20 hrs 25 mins + with a stopover, landing at Chicago O'Hare International Airport
• From Perth: Approximately 26 hrs + with two stopovers, landing at Chicago O'Hare International Airport

Airlines that fly to Chicago

• Air Canada
• Delta Airlines
• Qantas
• United Airlines
• Virgin Australia

Chicago insider flight tips

• One-stop flights are available to Chicago. The quickest are via Los Angeles International airport (LAX) – but you can normally save a lot by stopping twice. Most flights from Australia get to Chicago via LAX, San Francisco or Dallas – so if you were planning on visiting places outside of Chicago, it could be worth booking your return flights to one of these major cities and arranging internal flights to Chicago.
• From Chicago you can fly cheaply and direct to other US cities including Vegas, New York, Boston and to Canada (Toronto and Montreal). Low-cost airlines such as Frontier Airlines, Spirit Airlines operate on these routes.
• Cheap flights to Chicago from Sydney and Melbourne can almost always be found with China Eastern. These flights however do extend total journey time to around 40 hours due to a stopover of around 16 hours in Shanghai. This is fine if you aren’t in a rush and like the idea of breaking up the long journey to stretch your legs. This layover also gives you time to explore some of Shanghai and there is a 72-Hour Visa Free Transit policy which you should be able to arrange when checking into your flight in Australia.

How to get from the airport

Chicago O'Hare International Airport (ORD) is 25 kilometres from the city and tourists are spoilt for choice with Chicago’s wonderfully efficient public transport system. The easiest way to reach the city is the Blue Line on the subway which runs 24 hours a day from the lower level of terminal 2.

O’Hare Airport’s Airport Transit System (ATS) moves passengers between the 4 terminals and the car parks 24 hours a day. You can take this to Economy Parking for the shuttle bus to O’Hare Transfer Station. From here, trains run to downtown areas of Chicago and beyond. The 250 and 330 buses also connect to Chicago’s central areas and shopping centres. Taxis are available from the lower level of each terminal outside the baggage claim areas, and there are designated ride-sharing pickup areas too. Major car rental companies can be booked in advance.