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$151+ 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 5/12. 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 Dec — 21 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 14 November 2025.

Cheapest airline

Qantas Airways

Good round-trip deal

$540 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 $1,326).
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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 14 November 2025.

Thu 4/1218:17ORD - SYD
1 stop21h 43mQantas Airways
Fri 27/207:05SYD - ORD
2 stops26h 34mQantas Airways
Deal found 13/11$1,347
Wed 25/219:39ORD - MEL
2 stops28h 36mQantas Airways
Sat 7/312:00MEL - ORD
1 stop22h 41mQantas Airways
Deal found 13/11$1,437
Wed 11/218:40ORD - SYD
1 stop21h 20mQantas Airways
Sat 28/207:05SYD - ORD
2 stops31h 28mQantas Airways
Deal found 12/11$1,450
Thu 4/1220:46ORD - MEL
1 stop39h 29mQantas Airways
Thu 11/1206:45MEL - ORD
2 stops28h 07mQantas Airways
Deal found 13/11$1,453
Thu 29/118:40ORD - BNE
2 stops30h 30mQantas Airways
Thu 12/219:40BNE - ORD
1 stop20h 01mQantas Airways
Deal found 13/11$1,477
Tue 10/218:40ORD - MEL
2 stops29h 35mQantas Airways
Sat 21/212:00MEL - ORD
1 stop28h 49mQantas Airways
Deal found 13/11$1,483
Sun 1/218:40ORD - SYD
2 stops30h 00mQantas Airways
Thu 12/211:20SYD - ORD
1 stop29h 21mQantas Airways
Deal found 12/11$1,483
Thu 4/1220:46ORD - MEL
1 stop39h 29mQantas Airways
Wed 14/118:30MEL - ORD
2 stops37h 27mQantas Airways
Deal found 12/11$1,485
Sun 30/1118:23ORD - SYD
1 stop21h 37mQantas Airways
Wed 10/1207:05SYD - ORD
2 stops25h 57mQantas Airways
Deal found 12/11$1,495
Fri 13/219:47ORD - SYD
2 stops42h 48mQantas Airways
Fri 27/211:20SYD - ORD
1 stop19h 45mQantas Airways
Deal found 13/11$1,497
Mon 2/314:00ORD - SYD
2 stops37h 50mQantas Airways
Sun 8/321:25SYD - ORD
1 stop29h 40mQantas Airways
Deal found 12/11$1,509
Tue 10/215:10ORD - SYD
2 stops33h 30mQantas Airways
Sun 28/609:10SYD - ORD
1 stop24h 40mQantas Airways
Deal found 13/11$1,534

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 14 November 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

Mon 2/3

14:00-20:50

2 stops37h 50m

Sydney Kingsford Smith

Sat 14/3

11:20-15:55

1 stop20h 35m

$1,483

ChicagoAdelaide

ORD - ADL

ORDADL

Chicago O'Hare Intl

Sat 28/2

15:40-16:20

2 stops32h 10m

Adelaide

Mon 9/3

06:00-19:53

2 stops29h 23m

$1,711

ChicagoAdelaide

ORD - ADL

ORDADL

Chicago O'Hare Intl

Wed 25/2

15:40-18:10

2 stops34h 00m

Adelaide

Tue 31/3

18:55-14:43

2 stops35h 18m

$1,711

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 8/2

13:10-17:50

2 stops38h 40m

Perth

Sun 22/2

20:25-07:35

2 stops49h 10m

$1,781

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Fri 13/2

11:16-14:25

2 stops34h 09m

Sydney Kingsford Smith

Wed 25/2

07:05-17:36

2 stops27h 31m

$1,799

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 1/2

06:20-07:25

2 stops32h 05m

Sydney Kingsford Smith

Thu 12/2

11:20-23:25

2 stops29h 05m

$1,885

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 10/2

18:40-17:40

2 stops30h 00m

Sydney Kingsford Smith

Wed 25/2

07:05-16:39

2 stops26h 34m

$1,889

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 8/2

18:40-17:40

2 stops30h 00m

Sydney Kingsford Smith

Sun 1/3

06:20-21:31

2 stops32h 11m

$1,889

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Tue 10/2

18:40-17:40

2 stops30h 00m

Sydney Kingsford Smith

Fri 27/2

07:05-17:41

2 stops27h 36m

$1,889

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Wed 11/2

18:40-17:10

2 stops30h 30m

Brisbane

Sun 1/3

18:30-17:41

2 stops39h 11m

$1,906

Flights are sorted by cheapest return flights first.

Deals found on 12/11

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 $1,297). 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 $1,324
American Airlines
American Airlines
From $1,307

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,565 flights per day), Detroit (1,104 flights per day) and Los Angeles (686 flights per day).

Los Angeles
Los Angeles
From $120
Vancouver Intl
Vancouver Intl
From $297
Memphis
Memphis
From $178

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 $120
Memphis
Memphis
From $178

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
934 reviews
Check prices

Boarding

7.7

Comfort

7.5

Food

7.0

Overall

7.5

Crew

8.2

Entertainment

7.2

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
934 reviews
Qantas Airways
7.5
Good
934 reviews
Check prices

Boarding

7.7

Comfort

7.5

Food

7.0

Overall

7.5

Crew

8.2

Entertainment

7.2

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 14 November 2025.

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

    For the current month, the most popular flights from Chicago are Mumbai, Atlanta, Ahmedabad. 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 ($88). United Airlines flights from Chicago to Sioux City Sioux Gateway ($328). Qantas Airways flights from Chicago to Melbourne ($1,230).

  • 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 $1,347 round trip
    Fly from Chicago to Melbourne from $1,437 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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