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$161+ 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 6/5. 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
30 Mar — 6 Apr1
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 25 March 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$172 or less

Good one-way deal

$61 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,534).
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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 25 March 2025.

Tue 6/506:15ORD - JFK
Nonstop2h 15mJetBlue
Tue 6/512:00JFK - ORD
1 stop7h 36mJetBlue
Deal found 25/3$161
Thu 17/407:10ORD - JFK
Nonstop2h 19mDelta
Sun 20/408:00JFK - ORD
Nonstop2h 55mDelta
Deal found 25/3$227
Mon 12/520:05ORD - JFK
1 stop12h 55mSun Country Air
Thu 22/511:28JFK - ORD
1 stop6h 53mSun Country Air
Deal found 24/3$406
Tue 8/411:36ORD - JFK
Nonstop2h 22mAmerican Airlines
Thu 10/407:40JFK - ORD
1 stop6h 25mAmerican Airlines
Deal found 24/3$442
Sun 25/515:15ORD - SYD
1 stop25h 15mQantas Airways
Wed 18/609:10SYD - ORD
1 stop23h 07mQantas Airways
Deal found 24/3$1,311
Thu 1/511:53ORD - SYD
2 stops33h 22mMultiple Airlines
Fri 9/513:15SYD - ORD
2 stops32h 27mMultiple Airlines
Deal found 24/3$1,532
Tue 6/511:53ORD - MEL
2 stops32h 37mMultiple Airlines
Tue 13/512:55MEL - ORD
2 stops32h 47mMultiple Airlines
Deal found 23/3$1,549
Tue 13/517:38ORD - OOL
2 stops37h 27mMultiple Airlines
Sat 24/518:35OOL - ORD
2 stops37h 51mMultiple Airlines
Deal found 24/3$1,588
Sun 25/519:13ORD - AVV
2 stops27h 57mMultiple Airlines
Wed 18/606:00AVV - ORD
2 stops32h 55mMultiple Airlines
Deal found 24/3$1,608
Thu 8/505:51ORD - CNS
3 stops38h 34mMultiple Airlines
Thu 15/512:25CNS - ORD
2 stops33h 17mMultiple Airlines
Deal found 24/3$1,632
Tue 3/619:13ORD - BNE
2 stops26h 22mQantas Airways
Wed 11/614:15BNE - ORD
2 stops24h 20mQantas Airways
Deal found 24/3$1,635
Wed 10/915:40ORD - SYD
1 stop24h 40mAir Canada
Wed 24/909:20SYD - ORD
2 stops25h 51mAir Canada
Deal found 25/3$1,648

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 25 March 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sun 13/7

07:00-10:22

Nonstop2h 22m

New York John F Kennedy Intl

Fri 15/8

12:59-18:40

1 stop6h 41m

$399

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Mon 12/5

20:05-10:00

1 stop12h 55m

New York John F Kennedy Intl

Thu 22/5

11:28-17:21

1 stop6h 53m

$406

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 10/7

06:00-09:12

Nonstop2h 12m

New York John F Kennedy Intl

Sun 13/7

21:30-23:25

Nonstop2h 55m

$410

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 8/4

11:36-14:58

Nonstop2h 22m

New York John F Kennedy Intl

Thu 10/4

07:40-13:05

1 stop6h 25m

$442

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 25/5

15:15-07:30

1 stop25h 15m

Sydney Kingsford Smith

Wed 18/6

09:10-17:17

1 stop23h 07m

$1,311

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Thu 1/5

11:53-12:15

2 stops33h 22m

Sydney Kingsford Smith

Fri 9/5

13:15-06:42

2 stops32h 27m

$1,532

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Tue 6/5

11:53-11:30

2 stops32h 37m

Melbourne

Tue 13/5

12:55-06:42

2 stops32h 47m

$1,549

ChicagoCoolangatta

ORD - OOL

ORDOOL

Chicago O'Hare Intl

Tue 13/5

17:38-22:05

2 stops37h 27m

Coolangatta Gold Coast

Sat 24/5

18:35-17:26

2 stops37h 51m

$1,588

ChicagoMelbourne

ORD - AVV

ORDAVV

Chicago O'Hare Intl

Sun 25/5

19:13-14:10

2 stops27h 57m

Melbourne Avalon

Wed 18/6

06:00-23:55

2 stops32h 55m

$1,608

ChicagoCairns

ORD - CNS

ORDCNS

Chicago O'Hare Intl

Thu 8/5

05:51-11:25

3 stops38h 34m

Cairns

Thu 15/5

12:25-06:42

2 stops33h 17m

$1,632

Flights are sorted by cheapest return flights first.

Deals found on 24/3

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 21 March 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, October is the cheapest month in which you can book a flight from Chicago (average of $1,214). Flying from Chicago in December will prove the most costly (average of $1,371). 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: Air Canada, Qantas Airways, United Airlines. As they depart for the following popular destinations: Sydney.

Air Canada

Air Canada

From $1,131

Qantas Airways

Qantas Airways

From $854

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 (1,234 flights per day), Detroit (904 flights per day) and Los Angeles (493 flights per day).

Los Angeles

Los Angeles

From $85

Seattle/Tacoma Intl

Seattle/Tacoma Intl

From $84

New York

New York

From $38

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From $780

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 $60. Explore other affordable destinations below.

New York

New York

From $38

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From $66

Seattle/Tacoma Intl

Seattle/Tacoma Intl

From $84

Los Angeles

Los Angeles

From $85

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
61 reviews
Check prices

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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
1,284 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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

Boarding

8.7

Overall

8.7

Food

7.8

Crew

9.1

Comfort

8.0

Entertainment

7.2

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 25 March 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, Athens 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, Air New Zealand, and Qantas Airways 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 ($86). Air New Zealand flights from Chicago to Melbourne ($1,184). Qantas Airways flights from Chicago to Melbourne ($1,258).

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is October. 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 $1,311 round trip
    Fly from Chicago to Melbourne from $1,626 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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