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$138+ 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 2/3. 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
14 Feb — 21 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 15 January 2026.

Cheapest airline

Qantas Airways

Good round-trip deal

$260 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 $1,298).
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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 15 January 2026.

Mon 26/118:40
ORD
-
MEL
1 stop21h 50m
Qantas Airways
Sat 31/106:45
MEL
-
ORD
2 stops25h 12m
Qantas Airways
Deal found 13/1$1,361
Wed 11/216:10
ORD
-
MEL
1 stop24h 20m
Qantas Airways
Wed 18/206:45
MEL
-
ORD
2 stops25h 08m
Qantas Airways
Deal found 13/1$1,390
Tue 3/218:40
ORD
-
MEL
2 stops27h 55m
Qantas Airways
Fri 27/212:00
MEL
-
ORD
1 stop22h 46m
Qantas Airways
Deal found 14/1$1,391
Wed 25/214:05
ORD
-
MEL
2 stops34h 10m
Qantas Airways
Fri 6/312:00
MEL
-
ORD
1 stop22h 46m
Qantas Airways
Deal found 14/1$1,393
Tue 24/209:25
ORD
-
BNE
2 stops54h 05m
Qantas Airways
Wed 11/319:40
BNE
-
ORD
1 stop37h 06m
Qantas Airways
Deal found 14/1$1,399
Tue 24/215:35
ORD
-
BNE
1 stop25h 10m
Air Canada
Wed 11/309:45
BNE
-
ORD
1 stop19h 56m
Air Canada
Deal found 14/1$1,415
Wed 18/215:35
ORD
-
BNE
1 stop25h 10m
Air Canada
Wed 25/210:45
BNE
-
ORD
1 stop19h 56m
Air Canada
Deal found 14/1$1,417
Tue 2/608:45
ORD
-
BNE
2 stops31h 20m
Air Canada
Tue 16/610:00
BNE
-
ORD
1 stop19h 45m
Air Canada
Deal found 13/1$1,421
Wed 25/318:49
ORD
-
MEL
2 stops30h 26m
Qantas Airways
Mon 6/409:45
MEL
-
ORD
1 stop26h 56m
Qantas Airways
Deal found 13/1$1,424
Sat 14/216:49
ORD
-
MEL
2 stops36h 56m
Qantas Airways
Sat 28/212:00
MEL
-
ORD
1 stop22h 46m
Qantas Airways
Deal found 14/1$1,426
Mon 27/412:50
ORD
-
BNE
2 stops27h 15m
Air Canada
Wed 6/510:00
BNE
-
ORD
2 stops25h 08m
Air Canada
Deal found 14/1$1,426
Sat 21/316:49
ORD
-
MEL
2 stops37h 56m
Qantas Airways
Wed 8/409:45
MEL
-
ORD
1 stop23h 01m
Qantas Airways
Deal found 14/1$1,427

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

Fly to

Sydney

Route

Depart

Return

Price

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Tue 27/1

15:10-17:15

2 stops33h 05m

Melbourne

Mon 9/2

12:00-21:23

1 stop26h 23m

$1,361

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Fri 27/2

16:45-07:30

2 stops46h 45m

Brisbane

Fri 6/3

19:40-14:53

1 stop35h 13m

$1,399

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 24/2

09:25-07:30

2 stops54h 05m

Brisbane

Wed 11/3

19:40-17:46

1 stop37h 06m

$1,399

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 2/6

08:45-07:05

2 stops31h 20m

Brisbane

Tue 16/6

10:00-14:45

1 stop19h 45m

$1,421

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Mon 27/4

15:40-07:05

1 stop24h 25m

Brisbane

Fri 8/5

10:00-20:08

2 stops25h 08m

$1,486

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 1/3

16:49-07:35

2 stops45h 46m

Sydney Kingsford Smith

Tue 31/3

18:50-23:47

1 stop20h 57m

$1,515

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sat 28/2

07:15-08:45

2 stops33h 30m

Brisbane

Sat 7/3

10:45-14:41

1 stop19h 56m

$1,548

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Fri 27/3

15:35-07:05

1 stop24h 30m

Brisbane

Mon 6/4

10:00-14:43

1 stop19h 43m

$1,574

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Thu 2/4

15:45-07:05

2 stops48h 20m

Brisbane

Sun 12/4

10:00-14:43

1 stop19h 43m

$1,580

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

$1,608

Flights are sorted by cheapest return flights first.

Deals found on 13/1

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 9 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 $296). Flying from Chicago in December will prove the most costly (average of $1,276). 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 $1,306

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,406 flights per day), Detroit (892 flights per day) and Toronto (790 flights per day).

Boston Logan Intl
Boston Logan Intl
From $355
Memphis
Memphis
From $174
Dublin
Dublin
From $802

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Toronto, with prices starting at $102. Explore other affordable destinations below.

Toronto
Toronto
From $102
Memphis
Memphis
From $174
San Diego
San Diego
From $195
Orlando
Orlando
From $218

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
971 reviews
Check prices

Comfort

7.5

Boarding

7.7

Crew

8.2

Entertainment

7.2

Food

7.0

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
971 reviews
Qantas Airways
7.5
Good
971 reviews
Check prices

Comfort

7.5

Boarding

7.7

Crew

8.2

Entertainment

7.2

Food

7.0

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.

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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 15 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.

  • 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 $1,312. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,357. 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, 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 ($321). Qantas Airways flights from Chicago to Melbourne ($1,204).

  • 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 $1,312 round trip
    Fly from Chicago to Melbourne from $1,378 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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