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.

Trafalgar Tours Trafalgar Tours

$200 off tours per couple

Valid fro 2019 tours. Destinations include Europe, USA, Canada, South America and Asia. Minimum of 15-day tour. T&Cs apply.

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MyBali MyBali

Up to $5,000 free in extras with Bali packages

Valid for travel from August - December 2018 and January - March 2019. Resorts are Peppers Seminyak, The Westin Resort Nusa Dua Bali, The Royal Santrian Luxury Beach Villas and more. T&Cs apply.

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Budget Car Rental Budget Car Rental

10% off USA car hire + 30% off Legoland tickets

Valid until 31 October 2018. T&Cs apply.

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STA Travel STA Travel

20% Contiki USA tours

Valid for travel from September 2018 - August 2019. Destinations include New York, Los Angeles and more. T&Cs apply.

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Trafalgar Tours Trafalgar Tours

$100 off tours per couple

Valid fro 2019 tours. Destinations include Europe, USA, Canada, South America and Asia. Minimum of 15-day tour. T&Cs apply.

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Air New Zealand - Longhaul Air New Zealand - Longhaul

North America flights from $929 return + extra bag for $1

Valid for travel from 1 September - 20 November 2018 and 1 February - 27 June 2019. Destinations include Los Angeles, San Francisco, Houston and Chicago. Sample fare is Melbourne-Los Angeles.

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LookUpFare LookUpFare

US$36 off on flights

Valid for travel from September - November 2018 on select USA flights. Minimum of 3 passengers. T&Cs apply.

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LookUpFare LookUpFare

US$100 off on business class flights

Valid for travel from September - November 2018 on select USA flights. Minimum of 4 passengers. T&Cs apply.

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LookUpFare LookUpFare

US$120 off on first class flights

Valid for travel from September - November 2018 on select USA flights. Minimum of 4 passenger. T&Cs apply.

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Avis Avis

Up to 15% off USA car hire

Valid until 28 February 2019 and get up to 65% off voucher at any Simon Shopping destination. T&Cs apply.

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Travel Online Travel Online

Bali: Beachfront family holiday + flights from $955

Valid for travel between 1–23 September and 28 October – 20 December 2018. Package includes 5 nights accommodation at Westin Resort Nusa Dua, daily breakfast, kids stay for free, return flights from Perth and more. T&Cs apply.

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Dusit Hotels Dusit Hotels

Up to 20% off luxury hotels worldwide

Valid for stays until 31 December 2018. Includes free WiFi and welcome drinks upon arrival. Destinations include China, Kenya, Maldives, Philippines, Thailand, UAE, USA and more. T&Cs apply.

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Veltra Veltra

Up to 50% off Korea tours

Valid on all dates. Destinations include Seoul, Busan, Jeju and more. T&Cs apply.

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Millennium & Copthorne Hotels Millennium & Copthorne Hotels

Up to 15% off USA hotels

Valid for stays until 3 September 2018. Includes $15 food and beverage credit, free breakfast and more. T&Cs apply.

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Skiddoo Skiddoo

Business class fare to Korea from $2,425 return

Valid for travel between October - November 2018 with Asiana Airlines. Sample fare is Sydney-Seoul. Destinations include Jeju Island and Busan.

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Travel Insurance Saver Travel Insurance Saver

Get up to 30% discount on travel insurance

Save on policies to Bali, New Zealand, USA, Europe, Thailand, Fiji and more when you purchase cover online. Terms and conditions apply.

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Budget Air Budget Air

$20 off USA flights

Valid on all dates. Destinations include Los Angeles, San Francisco, New York, Chicago, Honolulu, Las Vegas and more. T&Cs apply.

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Hertz Hertz

10% off USA car hire

Valid until 31 December 2018 at select USA locations. Minimum of 5 days rental.

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Cathay Pacific Cathay Pacific

Premium economy flights from $1,905 return

Valid for travel until 30 June 2019. Sample fare is Perth-Tokyo. Booking must be made 50 days in advance. Destinations include New York, Chicago, Boston, Los Angeles, San Francisco, Washington D.C., Vancouver, Toronto, China, Taiwan, Japan, Philippines, Vietnam, Thailand, India, Amsterdam, Barcelona and more.

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Hertz Hertz

15% off USA premium car hire

Valid until 31 December 2018 at select USA locations. Minimum of 5 days rental.

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Trafalgar Tours Trafalgar Tours

10% off USA and Canada tours

Enjoy 10% off on your USA and Canada trips when you book in advance. Head now to Trafalgar Tours to book. T&Cs apply.

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TourRadar TourRadar

12% off 2018 Busabout passes

Valid on select passes including the unlimited pass, 15-stop pass, six-stop pass and two-week pass. Destinations include France, Spain, Portugal, Italy, Croatia, Germany, Netherlands, Belgium, Switzerland, Austria and more.

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TourRadar TourRadar

10% off Croatia sailing tours

Valid on select 2018 Croatia sailing trips with Busabout.

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Go Airport Shuttle Go Airport Shuttle

5% off airport transfers and car hire

Valid on select dates and locations worldwide. Destinations include USA, Canada, Europe, Mexico, the Caribbean, Sydney, and the Czech Republic. T&C's apply.

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LookUpFare LookUpFare

$120 off first class seats

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

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Sofitel Sofitel

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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Pullman Pullman

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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Smart Destinations Smart Destinations

Up to 5% off any Boston, Chicago, Miami, San Francisco, Washington, Orlando, Go-Card All-Inclusive and Explorer Pass

Get 5% off any Boston, Chicago, Miami, San Francisco, Washington, Orlando, Go-Card All-Inclusive and Explorer Pass. Sign up for the Smart Destinations newsletter to receive the discount.

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Big Bus Tours Big Bus Tours

Up to 10% off Big Bus tours

Valid on select tours in Abu Dhabi, Chicago, Darwin, Dubai, Hong Kong, Las Vegas, London, Miami, Muscat, New York, Paris, Philadelphia, Rome, San Francisco, Sydney, Vienna and Washington DC.

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Design Hotels Design Hotels

Up to 30% off if you book in advance

Valid for bookings made at least 30 days in advance at hotels around the world. Destinations include France, USA, Bali, Germany, Greece, Italy, Spain, UK, Singapore, Japan and more.

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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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