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$786+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
22 Apr — 29 Apr1
1 adult

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 17 April 2025.

Return from

$1,436

One-way from

$786

Popular in

December

Cheapest in

March

Average price

$1,321
8/5-15/5
  • 8/5-15/5
  • 4 total stops
  • 71h 45m total
  • Sydney to Chicago
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29/5
  • 29/5
  • 3 total stops
  • 46h 36m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($512 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($112 potential savings vs. average return price).
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Average for return flights in April 2025
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Find flight deals to Chicago

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 17 April 2025.

Thu 8/513:15SYD - ORD
2 stops33h 30mMultiple Airlines
Thu 15/507:00ORD - SYD
2 stops38h 15mMultiple Airlines
Deal found 16/4$1,436
Tue 5/809:55SYD - ORD
2 stops26h 23mAir New Zealand
Tue 12/816:50ORD - SYD
2 stops24h 55mAir New Zealand
Deal found 16/4$1,611
Fri 13/615:00SYD - ORD
2 stops38h 15mQantas Airways
Mon 23/609:59ORD - SYD
2 stops32h 46mQantas Airways
Deal found 16/4$1,711
Mon 16/611:50SYD - ORD
2 stops32h 01mANA
Mon 14/717:45ORD - SYD
1 stop34h 30mANA
Deal found 16/4$1,928
Fri 10/1010:20SYD - ORD
1 stop20h 35mAir Canada
Mon 20/1015:40ORD - SYD
1 stop24h 40mAir Canada
Deal found 16/4$2,022
Mon 9/610:20SYD - ORD
1 stop19h 35mUnited Airlines
Sun 22/606:48ORD - SYD
1 stop33h 07mUnited Airlines
Deal found 15/4$2,069
Thu 9/1010:25SYD - MDW
2 stops23h 42mDelta
Tue 21/1014:00MDW - SYD
2 stops25h 35mDelta
Deal found 16/4$2,104
Mon 16/609:25SYD - ORD
2 stops26h 59mDelta
Mon 14/709:30ORD - SYD
2 stops30h 05mDelta
Deal found 16/4$2,104
Thu 5/614:05SYD - ORD
1 stop39h 20mCathay Pacific
Tue 17/616:00ORD - SYD
1 stop27h 50mCathay Pacific
Deal found 17/4$2,135
Mon 9/608:55SYD - ORD
2 stops49h 34mJapan Airlines
Sat 21/601:30ORD - SYD
1 stop37h 50mJapan Airlines
Deal found 15/4$2,139
Fri 6/609:10SYD - ORD
2 stops23h 01mAmerican Airlines
Tue 17/616:56ORD - SYD
2 stops23h 09mAmerican Airlines
Deal found 16/4$2,291
Thu 15/510:25SYD - MDW
1 stop25h 08mMultiple Airlines
Thu 22/507:45MDW - SYD
1 stop32h 10mMultiple Airlines
Deal found 16/4$3,719

Cheapflights Fare Finder

Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 17 April 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Sydney

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 8/5

13:15-07:45

2 stops33h 30m

Chicago O'Hare Intl

Thu 15/5

07:00-12:15

2 stops38h 15m

$1,436

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 5/8

09:55-21:18

2 stops26h 23m

Chicago O'Hare Intl

Tue 12/8

16:50-08:45

2 stops24h 55m

$1,611

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 13/6

15:00-14:15

2 stops38h 15m

Chicago O'Hare Intl

Mon 23/6

09:59-09:45

2 stops32h 46m

$1,711

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 16/6

11:50-04:51

2 stops32h 01m

Chicago O'Hare Intl

Mon 14/7

17:45-19:15

1 stop34h 30m

$1,928

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 10/10

10:20-14:55

1 stop20h 35m

Chicago O'Hare Intl

Mon 20/10

15:40-08:20

1 stop24h 40m

$2,022

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 9/6

10:20-14:55

1 stop19h 35m

Chicago O'Hare Intl

Sun 22/6

06:48-06:55

1 stop33h 07m

$2,069

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 9/10

10:25-18:07

2 stops23h 42m

Chicago Midway

Tue 21/10

14:00-07:35

2 stops25h 35m

$2,104

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 16/6

09:25-21:24

2 stops26h 59m

Chicago O'Hare Intl

Mon 14/7

09:30-06:35

2 stops30h 05m

$2,104

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/6

14:05-14:25

1 stop39h 20m

Chicago O'Hare Intl

Tue 17/6

16:00-10:50

1 stop27h 50m

$2,135

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 9/6

08:55-19:29

2 stops49h 34m

Chicago O'Hare Intl

Sat 21/6

01:30-06:20

1 stop37h 50m

$2,139

Flights are sorted by cheapest return flights first.

Deals found on 16/4

Showing 1-10 of 22 results
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Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Sydney to Chicago. Price data was last updated on 11 April 2025.

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 21 hours 33 minutes. Flights to Chicago from other popular cities in Australia will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 13 October 2024.

Users looking for the lowest fares to Chicago should consider flying on Monday at midday, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday evenings, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Sydney to Chicago are Qantas Airways, Air Canada and United Airlines.

Qantas Airways

Qantas Airways

From $664

Air Canada

Air Canada

From $832

United Airlines

United Airlines

From $1,015

American Airlines

American Airlines

From $986

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Sydney to Chicago are Qantas Airways, Air Canada and American Airlines.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 17 April 2025.
Read through reviews of airlines servicing Chicago, such as Air Tahiti Nui, Japan Airlines and ANA. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air Tahiti Nui
8.8
Very Good
62 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Japan Airlines
8.3
Very Good
1,440 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
ANA
8.3
Very Good
844 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Singapore Airlines
8.1
Very Good
1,288 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Delta
8.0
Very Good
7,916 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Entertainment

7.3

Overall

8.8

Crew

9.1

Comfort

8.1

Boarding

8.7

Food

7.8

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

FAQs about flying to Chicago

Getting around Chicago

Chicago’s regular, grid-like layout makes navigation straightforward, but the “City With Big Shoulders” can be a little too large to get around easily on foot. Fortunately, the city’s public transportation system, including the famous “L” (short for “elevated train tracks”), is efficient, with especially good coverage in the city centre area. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Cycling is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.

Getting downtown from the airport

Chicago’s major airport is O’Hare International Airport (ORD) located in the city’s northwest corner, about 27 km away from the Loop. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available.

Travel Tips

One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water.

  • Can I find cheaper flights to Chicago if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, American Airlines is rated the highest out of the airlines that fly to Chicago.

  • What is the cheapest airport to fly to in Chicago?

    Chicago O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost $66, while return flights cost around $246.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $784, however they can be found for as little as $157.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Sydney Kingsford Smith offers the quickest one-way flight (20 hours 12 minutes).

  • Does Chicago O'Hare Intl have car hire?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Airports serving Chicago

Book a flight to or from one of these Chicago airports.
Flights to Midway
Flights to O'Hare Intl
Flights from Midway
Flights from O'Hare Intl

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Certainly. Search results for flights to Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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