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$132+ 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 30/1. 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
19 Feb — 26 Feb1
1 adult
1 adult, Economy, 0 bags

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 20 January 2026.

Cheapest airline

Qantas Airways

Good round-trip deal

$259 or less

Good one-way deal

$101 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,290).
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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

Enter your travel dates to find the best prices.

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 20 January 2026.

Tue 24/215:35
ORD
-
BNE
1 stop25h 10m
Air Canada
Wed 11/309:45
BNE
-
ORD
1 stop19h 56m
Air Canada
Deal found 18/1$1,407
Wed 1/408:40
ORD
-
BNE
2 stops31h 25m
Air Canada
Wed 22/410:00
BNE
-
ORD
2 stops24h 50m
Air Canada
Deal found 18/1$1,417
Wed 25/212:50
ORD
-
BNE
2 stops27h 55m
Air Canada
Sun 8/310:45
BNE
-
ORD
2 stops24h 00m
Air Canada
Deal found 17/1$1,429
Tue 2/608:45
ORD
-
BNE
2 stops31h 20m
Air Canada
Tue 16/610:00
BNE
-
ORD
2 stops37h 05m
Air Canada
Deal found 19/1$1,433
Tue 7/708:45
ORD
-
BNE
2 stops31h 20m
Air New Zealand
Sun 19/710:00
BNE
-
ORD
1 stop19h 41m
Air New Zealand
Deal found 18/1$1,456
Tue 3/315:35
ORD
-
BNE
1 stop25h 10m
Air Canada
Tue 10/305:10
BNE
-
ORD
2 stops24h 31m
Air Canada
Deal found 18/1$1,457
Mon 11/513:01
ORD
-
BNE
3 stops31h 29m
Air Canada
Wed 20/510:00
BNE
-
ORD
2 stops41h 50m
Air Canada
Deal found 19/1$1,469
Sun 19/415:40
ORD
-
BNE
1 stop24h 25m
Air Canada
Thu 23/410:00
BNE
-
ORD
1 stop19h 43m
Air Canada
Deal found 20/1$1,471
Sun 15/215:35
ORD
-
BNE
1 stop25h 10m
Air Canada
Tue 3/310:45
BNE
-
ORD
2 stops46h 20m
Air Canada
Deal found 17/1$1,475
Tue 28/406:00
ORD
-
SYD
1 stop34h 30m
Multiple Airlines
Mon 4/513:15
SYD
-
ORD
2 stops32h 31m
Multiple Airlines
Deal found 20/1$1,545
Tue 12/506:00
ORD
-
SYD
1 stop34h 30m
Multiple Airlines
Tue 26/513:15
SYD
-
ORD
2 stops32h 31m
Multiple Airlines
Deal found 18/1$1,575
Wed 8/419:45
ORD
-
SYD
1 stop44h 45m
Multiple Airlines
Thu 30/413:15
SYD
-
ORD
2 stops32h 31m
Multiple Airlines
Deal found 20/1$1,589

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 20 January 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 2/6

15:40-07:05

1 stop24h 25m

Brisbane

Tue 16/6

10:00-14:45

1 stop19h 45m

$1,407

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 23/6

10:45-07:05

2 stops29h 20m

Brisbane

Tue 30/6

10:00-14:41

1 stop19h 41m

$1,413

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Thu 5/3

15:35-08:45

1 stop25h 10m

Brisbane

Thu 12/3

09:45-14:41

1 stop19h 56m

$1,533

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Fri 19/6

10:45-07:05

2 stops29h 20m

Brisbane

Fri 10/7

10:00-20:05

2 stops25h 05m

$1,543

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Wed 4/2

15:55-08:45

2 stops24h 50m

Brisbane

Sat 14/2

10:45-20:10

2 stops25h 25m

$1,582

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 10/2

15:35-08:45

1 stop25h 10m

Brisbane

Sun 22/2

10:45-14:41

1 stop19h 56m

$1,597

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sun 8/2

15:35-08:45

1 stop25h 10m

Brisbane

Thu 12/2

10:45-16:38

1 stop21h 53m

$1,631

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 10/3

14:40-05:00

1 stop23h 20m

Brisbane

Tue 17/3

19:40-23:47

1 stop19h 07m

$1,687

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 4/3

12:45-08:20

2 stops27h 35m

Brisbane

Wed 11/3

10:05-18:40

2 stops23h 35m

$1,730

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Tue 24/2

19:20-08:20

2 stops45h 00m

Brisbane

Wed 11/3

10:05-18:40

2 stops23h 35m

$1,751

Flights are sorted by cheapest return flights first.

Deals found on 19/1

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 16 January 2026.

The best time to book flights from Chicago is 20 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, August is the cheapest month in which you can book a flight from Chicago (average of $294). Flying from Chicago in December will prove the most costly (average of $1,269). 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. As it departs for the following popular destinations: Sydney.

Qantas Airways
Qantas Airways
From $1,298

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,556 flights per day), Toronto (820 flights per day) and Los Angeles (540 flights per day).

Boston Logan Intl
Boston Logan Intl
From $353
Memphis
Memphis
From $173
Dublin
Dublin
From $797

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $101. Explore other affordable destinations below.

Toronto
Toronto
From $101
Memphis
Memphis
From $173
San Diego
San Diego
From $194
Orlando
Orlando
From $216

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.
See what other customers who have flown with Qantas Airways from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
973 reviews
Check prices

Crew

8.2

Overall

7.5

Boarding

7.7

Comfort

7.5

Entertainment

7.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
Qantas Airways
7.5
Good
973 reviews
Qantas Airways
7.5
Good
973 reviews
Check prices

Crew

8.2

Overall

7.5

Boarding

7.7

Comfort

7.5

Entertainment

7.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.

Browse thousands of different options on Cheapflights for your next trip

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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 20 January 2026.

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

    For the current month, the most popular flights from Chicago are Atlanta, Ahmedabad, Mumbai. Atlanta, Boston, Ahmedabad 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, United Airlines, 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). United Airlines flights from Chicago to Sioux City Sioux Gateway ($319). Qantas Airways flights from Chicago to Melbourne ($695).

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is August. 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 $1,343 round trip
    Fly from Chicago to Melbourne from $1,389 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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