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$192+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — SYD
4 May — 11 May1
1 adult

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 29 April 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$169 or less

Good one-way deal

$103 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,485).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 29 April 2025.

Thu 5/615:17ORD - SYD
2 stops32h 23mMultiple Airlines
Thu 12/617:45SYD - ORD
1 stop28h 06mMultiple Airlines
Deal found 29/4$1,816
Tue 14/1018:20ORD - CNS
2 stops26h 20mMultiple Airlines
Sat 25/1012:40CNS - ORD
2 stops25h 12mMultiple Airlines
Deal found 28/4$1,828
Tue 21/1017:45ORD - SYD
1 stop24h 40mANA
Fri 31/1012:25SYD - ORD
2 stops32h 38mANA
Deal found 28/4$1,846
Wed 10/917:50ORD - SYD
2 stops23h 55mAir New Zealand
Wed 24/909:55SYD - ORD
2 stops26h 29mAir New Zealand
Deal found 29/4$1,867
Sat 6/919:03ORD - SYD
2 stops25h 42mFiji Airways
Sat 20/913:45SYD - ORD
2 stops22h 17mFiji Airways
Deal found 28/4$1,911
Tue 2/914:25ORD - MEL
2 stops29h 25mAir New Zealand
Mon 15/912:05MEL - ORD
2 stops26h 10mAir New Zealand
Deal found 28/4$1,975
Wed 22/1023:45ORD - MEL
2 stops52h 40mTurkish Airlines
Wed 12/1120:40MEL - ORD
2 stops54h 30mTurkish Airlines
Deal found 28/4$2,045
Thu 15/511:45ORD - MEL
3 stops32h 45mMultiple Airlines
Fri 23/513:35MEL - ORD
2 stops32h 07mMultiple Airlines
Deal found 29/4$2,059
Tue 26/816:00ORD - SYD
1 stop27h 50mCathay Pacific
Sun 7/921:50SYD - ORD
1 stop31h 35mCathay Pacific
Deal found 28/4$2,059
Mon 19/518:59ORD - BNE
2 stops24h 36mMultiple Airlines
Thu 9/1011:40BNE - ORD
2 stops26h 51mMultiple Airlines
Deal found 28/4$2,069
Mon 4/808:50ORD - MEL
1 stop30h 55mQantas Airways
Wed 20/815:05MEL - ORD
1 stop20h 52mQantas Airways
Deal found 28/4$2,095
Wed 10/918:20ORD - SYD
1 stop21h 35mQantas Airways
Wed 24/909:10SYD - ORD
1 stop20h 07mQantas Airways
Deal found 29/4$2,106

Find flights from Chicago within your budget

Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 29 April 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 5/6

15:17-14:40

2 stops32h 23m

Sydney Kingsford Smith

Thu 12/6

17:45-06:51

1 stop28h 06m

$1,816

ChicagoCairns

ORD - CNS

ORDCNS

Chicago O'Hare Intl

Tue 14/10

18:20-11:40

2 stops26h 20m

Cairns

Sat 25/10

12:40-22:52

2 stops25h 12m

$1,828

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 21/10

17:45-10:25

1 stop24h 40m

Sydney Kingsford Smith

Fri 31/10

12:25-05:03

2 stops32h 38m

$1,846

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 10/9

17:50-08:45

2 stops23h 55m

Sydney Kingsford Smith

Wed 24/9

09:55-21:24

2 stops26h 29m

$1,867

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 6/9

19:03-11:45

2 stops25h 42m

Sydney Kingsford Smith

Sat 20/9

13:45-21:02

2 stops22h 17m

$1,911

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Tue 2/9

14:25-10:50

2 stops29h 25m

Melbourne

Mon 15/9

12:05-23:15

2 stops26h 10m

$1,975

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Wed 22/10

23:45-20:25

2 stops52h 40m

Melbourne

Wed 12/11

20:40-10:10

2 stops54h 30m

$2,045

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 26/8

16:00-10:50

1 stop27h 50m

Sydney Kingsford Smith

Sun 7/9

21:50-14:25

1 stop31h 35m

$2,059

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Thu 15/5

11:45-11:30

3 stops32h 45m

Melbourne

Fri 23/5

13:35-06:42

2 stops32h 07m

$2,059

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Mon 4/8

08:50-06:45

1 stop30h 55m

Melbourne

Wed 20/8

15:05-20:57

1 stop20h 52m

$2,095

Flights are sorted by cheapest return flights first.

Deals found on 27/4

Showing 1-10 of 60 results
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from 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 from Chicago

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

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

Use this chart to determine the optimal time to book a return flight from Chicago to Sydney. Price data was last updated on 25 April 2025.

The best time to book flights from Chicago is 2 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago?

Currently, March is the cheapest month in which you can book a flight from Chicago (average of $1,132). Flying from Chicago in December will prove the most costly (average of $1,346). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

When flying from Chicago check dates and pricing for the following: Qantas Airways, Air Canada, United Airlines. As they depart for the following popular destinations: Sydney.

Qantas Airways

Qantas Airways

From $854

Air Canada

Air Canada

From $1,092

Turkish Airlines

Turkish Airlines

From $823

United Airlines

United Airlines

From $1,203

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,717 flights per day), Detroit (1,278 flights per day) and Los Angeles (719 flights per day).

Los Angeles

Los Angeles

From $90

Dayton

Dayton

From $124

New York

New York

From $75

Seoul

Seoul

From $919

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Orlando, with prices starting at $70. Explore other affordable destinations below.

Orlando

Orlando

From $45

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From $66

New York

New York

From $75

Vancouver Intl

Vancouver Intl

From $77

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 647,157 searches.
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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.
Korean Air
8.4
Very Good
1,066 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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
1,459 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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
855 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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.
Fiji Airways
8.1
Very Good
190 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Crew

9.1

Boarding

8.7

Food

7.8

Entertainment

7.3

Comfort

8.1

Overall

8.8

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.

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Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Moline

Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 29 April 2025.

  • What are the most popular destinations to fly to from Chicago?

    For the current month, the most popular flights from Chicago are Atlanta, Boston, Barcelona-El Prat Airport. Atlanta, Boston, Mumbai are the most popular locations from Chicago year round.

  • What are the cheapest airlines flying from Chicago to anywhere?

    According to our data, users have found Spirit Airlines, Qantas Airways, and Air Canada to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to New York ($84). Qantas Airways flights from Chicago to Melbourne ($1,234). Air Canada flights from Chicago to Brisbane ($1,487).

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is March. The most expensive month for flights is December. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • Where are the cheapest places to fly to from Chicago?

    View the cheapest flight destinations from Chicago:
    Fly from Chicago to Melbourne from $1,519 round trip
    Fly from Chicago to Sydney from $1,588 round trip

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Yes! Cheapflights helps users easily find flights from Chicago with no change fees.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago?

Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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