flights-to-chicago

Flight deals to Chicago

Find cheap flights and special deals to Chicago from Australia.

Chicago, affectionately as The Windy City, 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 and the weather is much more enjoyable for city river cruises cycling opportunities, and park and harbour visits. It’s still possible to find flight deals to Chicago during these months too.

45% off Water Country USA

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Valid for travel on select dates. Includes admission tickets. T&C's apply.

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USA flights from $447 return

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Valid for travel on select dates. Sample fare is Sydney-Honolulu. Destinations include Los Angeles, San Francisco, New York, Las Vegas, Washington and Dallas.

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Up to 49% off early bird trips Book now and save up to 49% off on tour packages booked through TourRadar. Valid for travel on select dates in May 2018. Destinations include Vietnam, Thailand, USA, Egypt, Burma, Alaska and more. T&C's apply.

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$120 off first class seats

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Valid for travel on select dates. Destinations include San Francisco, Chicago, London, Dubai, Venice and more. T&C's apply.

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Up to 15% off select USA trips

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Valid for travel from 1 March 2018 - 31 March 2019. Destinations include New York City, New Orleans and more. T&C's apply.

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Up to 25% on Sofitel stays Valid for stays until 30 April 2018 at across USA, Canada, Mexico, Bermuda, and the Caribbean. Book a stay three nights or longer and save up to 25% on the regular price. T&C's apply.

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Up to 30% off Chicago stays

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Valid for stays at all Chicago Crown Plaza Hotels on select dates until 30 April 2018. T&C's apply.

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Up to 10% off USA and Canada tours

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Valid on select dates and tours. Destinations include New York City, Texas, Florida, San Francisco and more. T&C's apply.

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$999 flights to USA or Canada with tour bookings

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Valid for travel on select dates with Virgin Australia and Delta. Destinations Toronto, Ottawa, Quebec, New England, Boston, Grand Canyon, Las Vegas and more. T&C's apply.

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Up to 25% off Pullman stays Valid for stays until 30 April 2018 at across USA, Canada, Mexico, Bermuda, and the Caribbean. Book a stay three nights or longer and save up to 25% on the regular price. T&C's apply.

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Chicago flight time

  • From Sydney: 19 hrs 20 mins +
  • From Melbourne: 20 hrs 40 mins +
  • From Perth: 25 hrs +
  • From Brisbane: 20 hrs 25 mins +

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 more than 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.

Sarah Neate

Sarah is our shopping & lifestyle publisher here at finder.com.au. She'll help you find the perfect gift, an unbeatable flight deal, the hottest fashion sales and pretty much anything else you're looking for - all at a discount, naturally.

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