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$156+ 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 5/5. 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
27 Mar — 3 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 22 March 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$172 or less

Good one-way deal

$102 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,535).
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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 22 March 2025.

Mon 5/508:40ORD - YUL
Nonstop2h 15mAir Canada
Mon 12/518:40YUL - ORD
Nonstop2h 32mAir Canada
Deal found 21/3$406
Sun 20/413:55ORD - YUL
Nonstop2h 31mMultiple Airlines
Tue 22/409:45YUL - ORD
Nonstop2h 47mMultiple Airlines
Deal found 21/3$442
Wed 16/419:35ORD - YUL
1 stop11h 13mUnited Airlines
Fri 18/416:31YUL - ORD
Nonstop2h 51mUnited Airlines
Deal found 21/3$469
Sun 4/518:15ORD - YUL
1 stop4h 13mDelta
Sun 11/506:15YUL - ORD
1 stop6h 32mDelta
Deal found 21/3$473
Wed 20/806:00ORD - YUL
1 stop6h 58mWestJet
Wed 20/816:55YUL - ORD
1 stop26h 45mWestJet
Deal found 21/3$582
Sat 3/511:53ORD - SYD
2 stops32h 52mMultiple Airlines
Sat 10/513:45SYD - ORD
3 stops31h 57mMultiple Airlines
Deal found 19/3$1,548
Sat 3/511:53ORD - MEL
2 stops33h 22mMultiple Airlines
Sat 10/512:55MEL - ORD
2 stops32h 47mMultiple Airlines
Deal found 21/3$1,550
Thu 1/511:53ORD - CNS
2 stops32h 32mMultiple Airlines
Thu 8/512:25CNS - ORD
2 stops33h 17mMultiple Airlines
Deal found 20/3$1,604
Sat 3/511:53ORD - ADL
2 stops33h 12mMultiple Airlines
Sat 10/512:35ADL - ORD
2 stops32h 37mMultiple Airlines
Deal found 21/3$1,640
Sun 4/508:40ORD - SYD
2 stops31h 40mAir Canada
Sun 11/509:20SYD - ORD
2 stops37h 42mAir Canada
Deal found 19/3$1,648
Sun 31/801:55ORD - YUL
1 stop28h 34mAeromexico
Wed 10/911:05YUL - ORD
1 stop14h 24mAeromexico
Deal found 21/3$1,768
Sat 23/818:53ORD - BNE
2 stops24h 32mFiji Airways
Sat 1/1111:25BNE - ORD
2 stops24h 24mFiji Airways
Deal found 21/3$1,870

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

Fly to

Sydney

Route

Depart

Return

Price

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Mon 5/5

09:35-15:21

1 stop4h 46m

Montreal Pierre Elliott Trudeau Intl

Mon 12/5

13:00-18:54

1 stop6h 54m

$422

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sun 20/4

13:55-17:26

Nonstop2h 31m

Montreal Pierre Elliott Trudeau Intl

Tue 22/4

09:45-11:32

Nonstop2h 47m

$442

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Wed 16/4

19:35-07:48

1 stop11h 13m

Montreal Pierre Elliott Trudeau Intl

Fri 18/4

16:31-18:22

Nonstop2h 51m

$469

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sun 4/5

18:15-23:28

1 stop4h 13m

Montreal Pierre Elliott Trudeau Intl

Sun 11/5

06:15-11:47

1 stop6h 32m

$473

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Wed 20/8

06:00-13:58

1 stop6h 58m

Montreal Pierre Elliott Trudeau Intl

Wed 20/8

16:55-18:40

1 stop26h 45m

$582

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 3/5

11:53-11:45

2 stops32h 52m

Sydney Kingsford Smith

Sat 10/5

13:45-06:42

3 stops31h 57m

$1,548

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Sat 3/5

11:53-12:15

2 stops33h 22m

Melbourne

Sat 10/5

12:55-06:42

2 stops32h 47m

$1,550

ChicagoCairns

ORD - CNS

ORDCNS

Chicago O'Hare Intl

Thu 1/5

11:53-11:25

2 stops32h 32m

Cairns

Thu 8/5

12:25-06:42

2 stops33h 17m

$1,604

ChicagoAdelaide

ORD - ADL

ORDADL

Chicago O'Hare Intl

Sat 3/5

11:53-11:35

2 stops33h 12m

Adelaide

Sat 10/5

12:35-06:42

2 stops32h 37m

$1,640

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 4/5

08:40-07:20

2 stops31h 40m

Sydney Kingsford Smith

Sun 11/5

09:20-08:02

2 stops37h 42m

$1,648

Flights are sorted by cheapest return flights first.

Deals found on 21/3

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 14 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 $1,209). Flying from Chicago in December will prove the most costly (average of $1,372). 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 (1,535 flights per day), Detroit (1,116 flights per day) and Orlando (795 flights per day).

Los Angeles

Los Angeles

From $38

New York

New York

From $38

New Delhi Indira Gandhi Intl

New Delhi Indira Gandhi Intl

From $780

Dayton

Dayton

From $124

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

Los Angeles

Los Angeles

From $38

Toronto

Toronto

From $96

Dayton

Dayton

From $124

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

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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
1,046 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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
1,437 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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.
Singapore Airlines
8.1
Very Good
1,282 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Entertainment

7.2

Overall

8.7

Crew

9.1

Boarding

8.7

Food

7.8

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 22 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 Melbourne from $1,550 round trip
    Fly from Chicago to Sydney from $1,553 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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