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$184+ 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 12/8. 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
18 Jun — 25 Jun1
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 13 June 2025.

Cheapest airline

Spirit Airlines

Good round-trip deal

$89 or less

Good one-way deal

$126 or less
On average, Spirit Airlines currently has the cheapest one-way flight from Chicago (avg. price of $185).
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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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Find flights from Chicago

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 13 June 2025.

Sat 6/915:21ORD - SYD
3 stops29h 24mMultiple Airlines
Thu 11/913:15SYD - ORD
2 stops25h 16mMultiple Airlines
Deal found 12/6$1,572
Tue 12/818:20ORD - BNE
2 stops25h 05mFiji Airways
Tue 19/811:35BNE - ORD
2 stops24h 22mFiji Airways
Deal found 11/6$1,747
Mon 28/706:40ORD - MEL
2 stops37h 10mMultiple Airlines
Mon 4/812:05MEL - ORD
2 stops32h 20mMultiple Airlines
Deal found 13/6$1,785
Sat 15/1115:40ORD - BNE
1 stop25h 00mAir Canada
Fri 21/1110:45BNE - ORD
1 stop21h 53mAir Canada
Deal found 11/6$1,798
Sun 27/706:40ORD - BNE
2 stops37h 20mMultiple Airlines
Sun 3/812:15BNE - ORD
2 stops32h 10mMultiple Airlines
Deal found 12/6$1,834
Sun 27/706:40ORD - OOL
2 stops34h 10mMultiple Airlines
Sun 3/809:00OOL - ORD
2 stops35h 25mMultiple Airlines
Deal found 12/6$1,862
Tue 2/920:20ORD - SYD
2 stops31h 55mANA
Tue 14/1012:50SYD - ORD
1 stop35h 50mANA
Deal found 12/6$1,864
Tue 2/918:20ORD - SYD
2 stops26h 25mFiji Airways
Tue 14/1014:15SYD - ORD
2 stops22h 47mFiji Airways
Deal found 11/6$1,894
Sun 27/717:45ORD - PER
2 stops45h 45mMultiple Airlines
Sun 3/805:10PER - ORD
2 stops46h 45mMultiple Airlines
Deal found 12/6$1,913
Wed 22/1006:00ORD - SYD
2 stops33h 30mAlaska Airlines
Wed 29/1017:25SYD - ORD
2 stops27h 36mAlaska Airlines
Deal found 11/6$1,922
Mon 20/1015:40ORD - MEL
2 stops27h 10mAir New Zealand
Tue 28/1008:35MEL - ORD
2 stops27h 50mAir New Zealand
Deal found 12/6$1,954
Wed 22/1016:40ORD - BNE
2 stops26h 20mAir New Zealand
Wed 12/1111:10BNE - ORD
2 stops24h 20mAir New Zealand
Deal found 12/6$1,996

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 13 June 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

Sat 6/9

15:21-11:45

3 stops29h 24m

Sydney Kingsford Smith

Thu 11/9

13:15-23:31

2 stops25h 16m

$1,572

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 12/8

18:20-10:25

2 stops25h 05m

Brisbane

Tue 19/8

11:35-20:57

2 stops24h 22m

$1,747

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Mon 28/7

06:40-10:50

2 stops37h 10m

Melbourne

Mon 4/8

12:05-05:25

2 stops32h 20m

$1,785

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sat 15/11

15:40-08:40

1 stop25h 00m

Brisbane

Fri 21/11

10:45-16:38

1 stop21h 53m

$1,798

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sun 27/7

06:40-11:00

2 stops37h 20m

Brisbane

Sun 3/8

12:15-05:25

2 stops32h 10m

$1,834

ChicagoCoolangatta

ORD - OOL

ORDOOL

Chicago O'Hare Intl

Sun 27/7

06:40-07:50

2 stops34h 10m

Coolangatta Gold Coast

Sun 3/8

09:00-05:25

2 stops35h 25m

$1,862

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/9

20:20-19:15

2 stops31h 55m

Sydney Kingsford Smith

Tue 14/10

12:50-08:40

1 stop35h 50m

$1,864

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 2/9

18:20-11:45

2 stops26h 25m

Sydney Kingsford Smith

Tue 14/10

14:15-21:02

2 stops22h 47m

$1,894

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 22/10

06:00-07:30

2 stops33h 30m

Sydney Kingsford Smith

Wed 29/10

17:25-05:01

2 stops27h 36m

$1,922

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Mon 20/10

15:40-10:50

2 stops27h 10m

Melbourne

Tue 28/10

08:35-20:25

2 stops27h 50m

$1,954

Flights are sorted by cheapest return flights first.

Deals found on 11/6

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 9 June 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 $1,048). Flying from Chicago in December will prove the most costly (average of $1,323). 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. 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
American Airlines
American Airlines
From $140

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to Detroit (1,226 flights per day), New York (985 flights per day) and Los Angeles (762 flights per day).

Los Angeles
Los Angeles
From $57
New York
New York
From $43
Dayton
Dayton
From $124
Hong Kong Intl
Hong Kong Intl
From $1,126

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at $65. Explore other affordable destinations below.

New York
New York
From $43
Orlando
Orlando
From $45
Los Angeles
Los Angeles
From $57
Miami
Miami
From $64

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
8.7
Very Good
64 reviews
Check prices

Food

7.8

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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.
Fiji Airways
8.1
Very Good
194 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Food

7.8

Overall

8.7

Comfort

8.1

Entertainment

7.3

Boarding

8.7

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.

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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 13 June 2025.

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

    For the current month, the most popular flights from Chicago are Athens, Boston, Amman. Atlanta, Boston, Mumbai are the most popular locations from Chicago year round.

  • Which is the cheapest airport to catch a flight from Chicago?

    The cheapest routes to Melbourne can be found at Chicago O'Hare Intl airport from $1,328. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,604. Reference our flight search to find the best deals in real time.

  • 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 ($83). Qantas Airways flights from Chicago to Melbourne ($1,214). Air Canada flights from Chicago to Brisbane ($1,462).

  • 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 Sydney from $1,328 round trip
    Fly from Chicago to Melbourne from $1,489 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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