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$772+ 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 23/8. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
18 Jun — 25 Jun1
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 13 June 2025.

Return from

$1,606

One-way from

$772

Popular in

December

Cheapest in

March

Average price

$1,669
14/8-4/9
  • 14/8-4/9
  • 4 total stops
  • 63h 26m total
  • Sydney to Chicago
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23/8
  • 23/8
  • 2 total stops
  • 24h 21m total
  • Sydney to Chicago
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Highest demand for flights based on searches. 19% potential increase in price ($588 potential increase over avg. return price).
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Cheapest flight prices on average. 5% potential price decrease ($123 potential savings vs. average return price).
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Average for return flights in June 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 13 June 2025.

Thu 14/813:15SYD - ORD
2 stops24h 31mMultiple Airlines
Thu 4/906:20ORD - SYD
2 stops38h 55mMultiple Airlines
Deal found 12/6$1,606
Mon 21/709:25SYD - MDW
2 stops23h 37mDelta
Sun 17/810:11MDW - SYD
2 stops29h 24mDelta
Deal found 12/6$1,678
Mon 21/709:25SYD - ORD
2 stops25h 02mDelta
Sun 17/815:50ORD - SYD
2 stops23h 45mDelta
Deal found 12/6$1,678
Fri 13/620:55SYD - ORD
1 stop26h 45mANA
Thu 31/709:05ORD - SYD
2 stops43h 10mANA
Deal found 12/6$1,686
Mon 4/809:10SYD - ORD
1 stop23h 32mAmerican Airlines
Mon 25/806:00ORD - SYD
1 stop34h 05mAmerican Airlines
Deal found 12/6$1,733
Wed 23/708:55SYD - ORD
2 stops29h 48mJapan Airlines
Tue 19/801:30ORD - SYD
1 stop37h 50mJapan Airlines
Deal found 12/6$1,868
Thu 17/709:10SYD - ORD
1 stop21h 34mBritish Airways
Mon 28/722:17ORD - SYD
1 stop41h 48mBritish Airways
Deal found 9/6$1,891
Wed 8/1010:20SYD - ORD
2 stops27h 47mAir Canada
Thu 16/1008:55ORD - SYD
2 stops31h 25mAir Canada
Deal found 10/6$1,957
Thu 12/607:40SYD - ORD
1 stop45h 45mCathay Pacific
Wed 25/616:00ORD - SYD
1 stop27h 50mCathay Pacific
Deal found 11/6$2,109
Thu 25/1211:20SYD - ORD
1 stop26h 02mUnited Airlines
Fri 23/112:45ORD - SYD
1 stop24h 35mUnited Airlines
Deal found 10/6$2,165
Sat 19/721:40SYD - ORD
2 stops47h 00mAlaska Airlines
Wed 30/706:00ORD - SYD
2 stops46h 45mAlaska Airlines
Deal found 11/6$2,244
Sat 19/720:30SYD - MDW
2 stops28h 15mWestJet
Mon 28/709:24MDW - SYD
2 stops30h 11mWestJet
Deal found 12/6$11,777

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 13 June 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 14/8

13:15-22:46

2 stops24h 31m

Chicago O'Hare Intl

Thu 4/9

06:20-12:15

2 stops38h 55m

$1,606

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 21/7

09:25-18:02

2 stops23h 37m

Chicago Midway

Sun 17/8

10:11-06:35

2 stops29h 24m

$1,678

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 21/7

09:25-19:27

2 stops25h 02m

Chicago O'Hare Intl

Sun 17/8

15:50-06:35

2 stops23h 45m

$1,678

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/8

20:55-08:40

1 stop26h 45m

Chicago O'Hare Intl

Mon 25/8

20:20-19:15

2 stops31h 55m

$1,712

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/8

09:10-17:42

1 stop23h 32m

Chicago O'Hare Intl

Mon 25/8

06:00-07:05

1 stop34h 05m

$1,733

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 23/7

08:55-23:43

2 stops29h 48m

Chicago O'Hare Intl

Tue 19/8

01:30-06:20

1 stop37h 50m

$1,868

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 31/7

09:20-07:59

2 stops37h 39m

Chicago O'Hare Intl

Thu 7/8

08:45-07:20

2 stops31h 35m

$1,970

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 19/7

14:05-14:25

1 stop39h 20m

Chicago O'Hare Intl

Wed 30/7

16:00-10:50

1 stop27h 50m

$2,088

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 19/7

21:40-05:40

2 stops47h 00m

Chicago O'Hare Intl

Wed 30/7

06:00-19:45

2 stops46h 45m

$2,244

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 25/6

09:30-04:51

1 stop34h 21m

Chicago O'Hare Intl

Mon 4/8

07:10-07:00

1 stop32h 50m

$2,541

Flights are sorted by cheapest return flights first.

Deals found on 11/6

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 9 June 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 22 hours 55 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 $662
Air Canada
Air Canada
From $832
United Airlines
United Airlines
From $1,104
American Airlines
American Airlines
From $780

What are the cheapest airlines that fly to Chicago?

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

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 13 June 2025.
Read through reviews of airlines servicing Chicago, such as Air Tahiti Nui, Korean Air and Japan Airlines. 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
64 reviews
Check prices

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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
1,091 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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
1,490 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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
8.3
Very Good
882 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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.
Delta
8.0
Very Good
7,950 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Food

7.8

Entertainment

7.3

Overall

8.7

Boarding

8.7

Comfort

8.1

Crew

9.0

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.

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, Qantas Airways 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 $50, while return flights cost around $153.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $101, however they can be found for as little as $100.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Melbourne offers the quickest one-way flight (21 hours 19 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

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