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$824+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
1 Apr — 8 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 27 March 2025.

Return from

$1,513

One-way from

$824

Popular in

December

Cheapest in

February

Average price

$1,438
Air Canada
  • Air Canada
  • 21/5-25/5
  • 4 total stops
  • 84h 03m total
  • Sydney to Chicago
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5/6
  • 5/6
  • 2 total stops
  • 31h 50m total
  • Sydney to Chicago
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Highest demand for flights based on searches. 14% potential increase in price ($459 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease ($104 potential savings vs. average return price).
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Average for return flights in March 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 27 March 2025.

Thu 7/809:20SYD - ORD
1 stop20h 29mAir Canada
Mon 25/815:35ORD - SYD
1 stop24h 45mAir Canada
Deal found 26/3$1,365
Wed 21/509:10SYD - ORD
1 stop21h 45mQantas Airways
Sun 25/519:13ORD - SYD
1 stop20h 52mQantas Airways
Deal found 26/3$1,613
Thu 1/521:30SYD - ORD
1 stop28h 53mMultiple Airlines
Mon 19/515:17ORD - SYD
2 stops25h 13mMultiple Airlines
Deal found 26/3$1,674
Thu 27/311:15SYD - ORD
2 stops34h 05mAmerican Airlines
Tue 22/417:30ORD - SYD
1 stop22h 35mAmerican Airlines
Deal found 26/3$1,704
Tue 22/410:20SYD - ORD
2 stops23h 35mUnited Airlines
Tue 29/408:45ORD - SYD
1 stop31h 10mUnited Airlines
Deal found 26/3$1,724
Wed 21/509:25SYD - MDW
2 stops23h 20mDelta
Sun 25/509:20MDW - SYD
2 stops30h 15mDelta
Deal found 26/3$1,743
Mon 31/311:20SYD - ORD
1 stop23h 35mLufthansa
Wed 16/414:20ORD - SYD
1 stop25h 40mLufthansa
Deal found 27/3$1,839
Sat 28/609:25SYD - ORD
2 stops27h 45mDelta
Fri 11/710:35ORD - SYD
2 stops29h 00mDelta
Deal found 26/3$1,892
Fri 2/520:55SYD - ORD
1 stop26h 45mANA
Tue 20/519:45ORD - SYD
2 stops46h 40mANA
Deal found 27/3$1,923
Wed 26/322:20SYD - ORD
1 stop31h 40mCathay Pacific
Mon 21/416:00ORD - SYD
1 stop27h 50mCathay Pacific
Deal found 26/3$2,033
Mon 14/409:30SYD - ORD
1 stop29h 11mVirgin Australia
Wed 30/406:30ORD - SYD
1 stop33h 25mVirgin Australia
Deal found 26/3$2,112
Sun 11/510:25SYD - MDW
1 stop25h 08mMultiple Airlines
Sun 18/514:45MDW - SYD
1 stop25h 10mMultiple Airlines
Deal found 26/3$2,267

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 27 March 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 7/8

09:20-14:49

1 stop20h 29m

Chicago O'Hare Intl

Mon 25/8

15:35-07:20

1 stop24h 45m

$1,365

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 21/5

09:10-15:55

1 stop21h 45m

Chicago O'Hare Intl

Sun 25/5

19:13-07:05

1 stop20h 52m

$1,613

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/5

21:30-11:23

1 stop28h 53m

Chicago O'Hare Intl

Mon 19/5

15:17-07:30

2 stops25h 13m

$1,674

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 22/4

09:30-18:55

1 stop24h 25m

Chicago O'Hare Intl

Tue 29/4

16:09-06:55

1 stop23h 46m

$1,724

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 21/5

09:25-17:45

2 stops23h 20m

Chicago Midway

Sun 25/5

09:20-06:35

2 stops30h 15m

$1,743

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 25/4

09:10-15:56

1 stop21h 46m

Chicago O'Hare Intl

Fri 2/5

17:02-07:05

2 stops23h 03m

$1,871

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 28/6

09:25-22:10

2 stops27h 45m

Chicago O'Hare Intl

Fri 11/7

10:35-06:35

2 stops29h 00m

$1,892

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 2/5

20:55-08:40

1 stop26h 45m

Chicago O'Hare Intl

Tue 20/5

19:45-09:25

2 stops46h 40m

$1,923

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 14/4

09:30-23:41

1 stop29h 11m

Chicago O'Hare Intl

Wed 30/4

06:30-06:55

1 stop33h 25m

$2,112

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 11/5

21:50-14:25

1 stop31h 35m

Chicago O'Hare Intl

Sun 18/5

16:00-20:10

1 stop37h 10m

$2,206

Flights are sorted by cheapest return flights first.

Deals found on 26/3

Showing 1-10 of 24 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 21 March 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 20 hours 50 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, United Airlines and Air Canada.

Qantas Airways

Qantas Airways

From $665

United Airlines

United Airlines

From $1,015

Air Canada

Air Canada

From $889

ANA

ANA

From $978

What are the cheapest airlines that fly to Chicago?

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

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 27 March 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
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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
8.7
Very Good
61 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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
829 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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
1,285 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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
7,895 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Crew

9.1

Overall

8.7

Food

7.8

Boarding

8.7

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 $65, while return flights cost around $249.

  • 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 9 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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How does Cheapflights help users find flights to Chicago?

Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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Cheapflights helps you find that perfect flight to Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights to Chicago with no change fees?

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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Of course! You can track prices for flights to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals to set up your price alerts.

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