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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 4/11. 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 Nov — 7 Dec1
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 31 October 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$539 or less

Good one-way deal

$104 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago (avg. price of $1,323).
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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 31 October 2025.

Tue 2/1215:40ORD - SYD
1 stop22h 15mAir Canada
Tue 16/1211:20SYD - ORD
2 stops34h 40mAir Canada
Deal found 30/10$1,290
Thu 11/1215:40ORD - SYD
1 stop24h 55mAir Canada
Thu 25/1216:00SYD - ORD
2 stops36h 18mAir Canada
Deal found 30/10$1,293
Tue 27/113:05ORD - SYD
2 stops32h 35mAir Canada
Tue 17/211:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 31/10$1,296
Sun 30/1115:40ORD - SYD
1 stop24h 55mAir Canada
Sun 14/1211:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 30/10$1,297
Sat 28/215:40ORD - SYD
1 stop24h 55mAir Canada
Thu 12/310:25SYD - ORD
1 stop20h 16mAir Canada
Deal found 29/10$1,300
Mon 17/1117:55ORD - SYD
3 stops46h 40mAir Canada
Tue 16/1211:20SYD - ORD
2 stops41h 09mAir Canada
Deal found 30/10$1,302
Sat 17/115:40ORD - SYD
2 stops30h 10mMultiple Airlines
Wed 28/111:20SYD - ORD
1 stop20h 21mMultiple Airlines
Deal found 30/10$1,305
Mon 1/1215:40ORD - SYD
2 stops33h 25mMultiple Airlines
Fri 5/1208:30SYD - ORD
2 stops23h 11mMultiple Airlines
Deal found 30/10$1,311
Sun 7/1215:40ORD - SYD
2 stops33h 25mAir Canada
Sun 14/1211:20SYD - ORD
1 stop20h 21mAir Canada
Deal found 30/10$1,313
Sat 17/115:40ORD - SYD
2 stops33h 00mMultiple Airlines
Tue 27/111:20SYD - ORD
2 stops27h 45mMultiple Airlines
Deal found 29/10$1,314
Mon 26/114:15ORD - MEL
1 stop26h 15mQantas Airways
Mon 16/206:45MEL - ORD
2 stops27h 56mQantas Airways
Deal found 30/10$1,590
Wed 21/118:40ORD - MEL
1 stop21h 50mQantas Airways
Mon 2/206:45MEL - ORD
2 stops25h 12mQantas Airways
Deal found 30/10$1,635

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

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Wed 25/3

15:40-12:40

2 stops29h 00m

Sydney Kingsford Smith

Mon 6/4

09:20-10:57

2 stops40h 37m

$1,409

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 25/11

08:45-08:45

2 stops32h 00m

Brisbane

Thu 25/12

10:45-14:41

1 stop19h 56m

$1,725

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Thu 2/4

15:45-07:05

2 stops48h 20m

Brisbane

Sun 12/4

10:00-08:05

2 stops37h 05m

$1,725

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Tue 17/3

13:00-07:45

1 stop27h 45m

Brisbane

Fri 20/3

09:45-19:53

1 stop25h 08m

$1,913

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Mon 8/12

18:35-07:30

1 stop20h 55m

Brisbane

Mon 15/12

11:40-14:48

1 stop19h 08m

$1,917

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sun 16/11

13:28-05:00

2 stops23h 32m

Brisbane

Sun 23/11

09:40-14:33

2 stops20h 53m

$1,917

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Mon 10/11

12:45-07:00

1 stop25h 15m

Sydney Kingsford Smith

Wed 19/11

12:10-14:50

1 stop19h 40m

$1,923

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 11/2

10:46-08:20

2 stops29h 34m

Brisbane

Sun 22/2

10:40-21:46

2 stops27h 06m

$1,925

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sun 7/12

16:50-06:30

2 stops21h 40m

Brisbane

Sun 21/12

12:10-18:29

2 stops22h 19m

$1,928

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 21/3

21:05-07:00

1 stop41h 55m

Sydney Kingsford Smith

Sun 29/3

11:20-12:08

1 stop40h 48m

$1,954

Flights are sorted by cheapest return flights first.

Deals found on 29/10

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.

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 $302). Flying from Chicago in January will prove the most costly (average of $1,307). 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, American Airlines. As they depart for the following popular destinations: Sydney.

Qantas Airways
Qantas Airways
From $1,322
American Airlines
American Airlines
From $1,305

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (711 flights per day), Detroit (432 flights per day) and Toronto (418 flights per day).

Los Angeles
Los Angeles
From $119
Vancouver Intl
Vancouver Intl
From $296
Memphis
Memphis
From $177

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Raleigh-Durham, with prices starting at $99. Explore other affordable destinations below.

Raleigh-Durham
Raleigh-Durham
From $99
Toronto
Toronto
From $104
Los Angeles
Los Angeles
From $119
Memphis
Memphis
From $177

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
925 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

7.0

Crew

8.2

Entertainment

7.2

Comfort

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
925 reviews
Qantas Airways
7.5
Good
925 reviews
Check prices

Overall

7.5

Boarding

7.7

Food

7.0

Crew

8.2

Entertainment

7.2

Comfort

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 31 October 2025.

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

    For the current month, the most popular flights from Chicago are Boston, Atlanta, Ahmedabad. 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 $1,235. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,431. 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 ($88). United Airlines flights from Chicago to Sioux City Sioux Gateway ($327). Qantas Airways flights from Chicago to Melbourne ($1,227).

  • 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 January. 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 $1,235 round trip
    Fly from Chicago to Melbourne from $1,590 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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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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