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$143+ 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
6 Feb — 13 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 7 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 $1,291).
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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

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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 7 January 2026.

Tue 27/118:40ORD - MEL
1 stop21h 50mQantas Airways
Wed 4/206:45MEL - ORD
2 stops26h 12mQantas Airways
Deal found 6/1$1,376
Wed 25/216:45ORD - MEL
2 stops31h 30mQantas Airways
Fri 6/312:00MEL - ORD
1 stop22h 46mQantas Airways
Deal found 6/1$1,378
Sun 18/118:40ORD - MEL
1 stop21h 50mQantas Airways
Sun 15/206:45MEL - ORD
2 stops25h 08mQantas Airways
Deal found 5/1$1,379
Fri 20/220:45ORD - MEL
1 stop43h 45mQantas Airways
Fri 27/206:45MEL - ORD
2 stops26h 52mQantas Airways
Deal found 5/1$1,385
Sat 24/119:40ORD - SYD
1 stop41h 30mQantas Airways
Sat 31/107:05SYD - ORD
2 stops25h 52mQantas Airways
Deal found 6/1$1,406
Sat 7/316:49ORD - MEL
2 stops36h 56mQantas Airways
Thu 12/312:00MEL - ORD
1 stop21h 46mQantas Airways
Deal found 6/1$1,411
Tue 10/218:40ORD - SYD
2 stops27h 10mQantas Airways
Thu 12/311:20SYD - ORD
1 stop19h 33mQantas Airways
Deal found 5/1$1,415
Sat 21/316:49ORD - MEL
2 stops37h 56mQantas Airways
Wed 8/409:45MEL - ORD
1 stop23h 01mQantas Airways
Deal found 5/1$1,418
Sun 1/218:40ORD - SYD
1 stop21h 20mQantas Airways
Wed 11/219:15SYD - ORD
2 stops38h 22mQantas Airways
Deal found 6/1$1,420
Thu 5/218:40ORD - SYD
2 stops43h 55mQantas Airways
Sat 21/211:20SYD - ORD
1 stop20h 33mQantas Airways
Deal found 6/1$1,421
Sat 31/108:50ORD - BNE
1 stop28h 10mQantas Airways
Tue 10/218:30BNE - ORD
2 stops36h 27mQantas Airways
Deal found 6/1$1,423
Sun 1/218:40ORD - SYD
1 stop21h 20mQantas Airways
Sat 7/219:15SYD - ORD
2 stops38h 34mQantas Airways
Deal found 5/1$1,424

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 7 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

Sat 31/1

14:15-05:00

1 stop22h 45m

Brisbane

Wed 11/2

18:30-17:45

2 stops39h 15m

$1,423

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 24/2

13:05-08:45

1 stop27h 40m

Brisbane

Wed 11/3

09:45-14:41

1 stop19h 56m

$1,424

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 10/2

08:45-08:45

2 stops32h 00m

Brisbane

Sun 22/2

10:45-14:41

1 stop19h 56m

$1,426

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 2/6

08:45-07:05

2 stops31h 20m

Brisbane

Tue 16/6

10:00-08:05

2 stops37h 05m

$1,434

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Wed 4/2

15:35-16:55

2 stops33h 20m

Brisbane

Tue 17/2

10:45-17:05

2 stops46h 20m

$1,475

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Thu 2/4

18:01-07:05

2 stops46h 04m

Brisbane

Sun 12/4

10:00-19:58

1 stop24h 58m

$1,492

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 1/2

18:40-09:00

1 stop21h 20m

Sydney Kingsford Smith

Sat 7/2

19:15-14:10

2 stops35h 55m

$1,495

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Thu 5/2

12:50-08:45

2 stops27h 55m

Brisbane

Mon 9/2

10:45-08:05

2 stops37h 20m

$1,498

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Mon 2/2

13:13-13:30

3 stops32h 17m

Brisbane

Mon 9/2

10:45-08:05

2 stops37h 20m

$1,570

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Tue 24/2

18:40-08:20

2 stops45h 40m

Brisbane

Wed 11/3

10:05-18:40

2 stops23h 35m

$1,753

Flights are sorted by cheapest return flights first.

Deals found on 5/1

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 2 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 $1,299

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,059 flights per day), Detroit (736 flights per day) and Toronto (734 flights per day).

Boston Logan Intl
Boston Logan Intl
From $353
Memphis
Memphis
From $173
Dublin
Dublin
From $798

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
Los Angeles
Los Angeles
From $119
Memphis
Memphis
From $173
San Diego
San Diego
From $194

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
967 reviews
Check prices

Crew

8.1

Comfort

7.5

Food

7.0

Entertainment

7.2

Boarding

7.7

Overall

7.5

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
967 reviews
Qantas Airways
7.5
Good
967 reviews
Check prices

Crew

8.1

Comfort

7.5

Food

7.0

Entertainment

7.2

Boarding

7.7

Overall

7.5

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 7 January 2026.

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

    For the current month, the most popular flights from Chicago are Ahmedabad, Atlanta, 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 ($1,198).

  • 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 $1,272 round trip
    Fly from Chicago to Melbourne from $1,379 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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