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$703+ 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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
3 Mar — 10 Mar1
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 26 February 2025.

Return from

$1,141

One-way from

$703

Popular in

December

Cheapest in

February

Average price

$1,282
Qantas Airways
  • Qantas Airways
  • 8/4-18/4
  • 2 total stops
  • 42h 31m total
  • Sydney to Chicago
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Qantas Airways
  • Qantas Airways
  • 17/5
  • 1 total stop
  • 28h 22m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($401 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease ($99 potential savings vs. average return price).
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Average for return flights in February 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 26 February 2025.

Tue 8/409:10SYD - ORD
1 stop21h 46mQantas Airways
Fri 18/419:20ORD - SYD
1 stop20h 45mQantas Airways
Deal found 24/2$1,141
Sun 2/311:15SYD - ORD
2 stops23h 21mAmerican Airlines
Sat 15/319:30ORD - SYD
1 stop21h 30mAmerican Airlines
Deal found 25/2$1,204
Fri 2/509:55SYD - ORD
2 stops28h 03mAir New Zealand
Thu 29/516:04ORD - SYD
2 stops34h 06mAir New Zealand
Deal found 25/2$1,767
Sat 7/611:50SYD - ORD
2 stops32h 01mANA
Mon 14/717:45ORD - SYD
1 stop34h 30mANA
Deal found 25/2$1,772
Mon 3/311:20SYD - ORD
2 stops37h 41mAir Canada
Sat 16/810:40ORD - SYD
3 stops29h 40mAir Canada
Deal found 24/2$1,810
Fri 13/609:10SYD - ORD
1 stop22h 46mMultiple Airlines
Sat 16/818:53ORD - SYD
2 stops25h 52mMultiple Airlines
Deal found 25/2$1,813
Mon 31/311:20SYD - ORD
1 stop34h 48mUnited Airlines
Tue 22/407:00ORD - SYD
1 stop33h 00mUnited Airlines
Deal found 25/2$1,832
Mon 3/311:05SYD - MDW
2 stops23h 38mDelta
Sat 16/814:00MDW - SYD
2 stops25h 35mDelta
Deal found 23/2$1,920
Wed 9/412:05SYD - ORD
2 stops41h 20mCathay Pacific
Tue 22/416:00ORD - SYD
1 stop27h 50mCathay Pacific
Deal found 25/2$2,317
Fri 11/420:55SYD - ORD
2 stops36h 00mTurkish Airlines
Fri 18/411:25ORD - SYD
2 stops40h 35mTurkish Airlines
Deal found 25/2$2,368
Tue 15/409:25SYD - ORD
2 stops29h 34mDelta
Tue 22/409:55ORD - SYD
2 stops29h 40mDelta
Deal found 25/2$2,415
Mon 4/808:55SYD - ORD
2 stops49h 39mJapan Airlines
Tue 9/901:05ORD - SYD
1 stop38h 15mJapan Airlines
Deal found 25/2$2,831

Find flights to Chicago within your budget

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 26 February 2025.

Fly from

Sydney

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 8/4

09:10-15:56

1 stop21h 46m

Chicago O'Hare Intl

Fri 18/4

19:20-07:05

1 stop20h 45m

$1,141

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 2/3

11:15-17:36

2 stops23h 21m

Chicago O'Hare Intl

Sat 15/3

19:30-09:00

1 stop21h 30m

$1,204

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 2/5

09:55-22:58

2 stops28h 03m

Chicago O'Hare Intl

Thu 29/5

16:04-17:10

2 stops34h 06m

$1,767

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 3/3

11:20-08:01

2 stops37h 41m

Chicago O'Hare Intl

Sat 16/8

10:40-07:20

3 stops29h 40m

$1,810

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 31/3

11:20-06:08

1 stop34h 48m

Chicago O'Hare Intl

Tue 22/4

07:00-07:00

1 stop33h 00m

$1,832

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 2/5

12:20-23:59

2 stops50h 39m

Chicago O'Hare Intl

Thu 29/5

15:15-07:05

1 stop24h 50m

$1,923

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 9/3

11:05-17:18

2 stops23h 13m

Chicago Midway

Thu 13/3

10:25-07:45

2 stops29h 20m

$1,997

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 9/4

12:05-14:25

2 stops41h 20m

Chicago O'Hare Intl

Tue 22/4

16:00-10:50

1 stop27h 50m

$2,317

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 11/4

20:55-17:55

2 stops36h 00m

Chicago O'Hare Intl

Fri 18/4

11:25-19:00

2 stops40h 35m

$2,368

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 15/4

09:25-23:59

2 stops29h 34m

Chicago O'Hare Intl

Tue 22/4

09:55-06:35

2 stops29h 40m

$2,415

Flights are sorted by cheapest return flights first.

Deals found on 25/2

Showing 1-10 of 32 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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 25 February 2025.

Booking 37 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 41 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 $665

Air Canada

Air Canada

From $989

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, ANA 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 26 February 2025.
Read through reviews of airlines servicing Chicago, such as Air Tahiti Nui, ANA and Korean Air. 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

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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
8.4
Very Good
836 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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.

Korean Air
8.4
Very Good
1,034 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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
1,438 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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.

Fiji Airways
8.0
Very Good
183 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Crew

9.1

Entertainment

7.2

Overall

8.7

Boarding

8.7

Food

7.8

Comfort

8.0

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.

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 $45, while return flights cost around $247.

  • 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 5 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).

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