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$184+ 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 15/8. 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
8 Jul — 15 Jul1
1 adult

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 3 July 2025.

Cheapest airline

Spirit Airlines

Good round-trip deal

$88 or less

Good one-way deal

$80 or less
On average, Spirit Airlines currently has the cheapest one-way flight from Chicago (avg. price of $183).
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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

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 3 July 2025.

Wed 6/806:40ORD - SYD
2 stops48h 30mMultiple Airlines
Fri 22/813:15SYD - ORD
2 stops31h 25mMultiple Airlines
Deal found 30/6$1,340
Fri 15/807:05ORD - MEL
2 stops37h 55mMultiple Airlines
Fri 22/813:30MEL - ORD
2 stops31h 10mMultiple Airlines
Deal found 1/7$1,471
Sun 24/807:00ORD - SYD
2 stops33h 05mAlaska Airlines
Sat 6/909:10SYD - ORD
2 stops29h 54mAlaska Airlines
Deal found 1/7$1,523
Sat 16/819:09ORD - BNE
2 stops24h 16mMultiple Airlines
Sat 23/811:40BNE - ORD
2 stops33h 00mMultiple Airlines
Deal found 2/7$1,547
Sat 27/920:05ORD - SYD
2 stops32h 10mANA
Sun 12/1012:50SYD - ORD
1 stop35h 50mANA
Deal found 1/7$1,730
Thu 14/807:40MDW - MEL
2 stops37h 20mMultiple Airlines
Thu 21/813:30MEL - MDW
2 stops23h 21mMultiple Airlines
Deal found 30/6$1,766
Thu 14/807:05ORD - CBR
2 stops38h 15mMultiple Airlines
Thu 21/813:20CBR - ORD
2 stops31h 20mMultiple Airlines
Deal found 1/7$1,774
Thu 14/807:05ORD - ADL
2 stops38h 00mMultiple Airlines
Thu 21/812:35ADL - ORD
2 stops31h 35mMultiple Airlines
Deal found 1/7$1,774
Mon 22/919:01ORD - BNE
2 stops24h 34mFiji Airways
Sat 4/1011:40BNE - ORD
2 stops24h 44mFiji Airways
Deal found 1/7$1,883
Sat 16/807:05ORD - PER
2 stops35h 20mMultiple Airlines
Sat 23/808:45PER - ORD
2 stops46h 29mMultiple Airlines
Deal found 2/7$1,900
Sat 16/818:20ORD - CBR
2 stops27h 00mFiji Airways
Sat 23/813:20CBR - ORD
2 stops22h 37mFiji Airways
Deal found 2/7$1,902
Sun 19/1016:57ORD - MEL
1 stop44h 03mQantas Airways
Tue 28/1012:00MEL - ORD
1 stop24h 57mQantas Airways
Deal found 1/7$1,964

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 3 July 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 6/8

06:40-22:10

2 stops48h 30m

Sydney Kingsford Smith

Fri 22/8

13:15-05:40

2 stops31h 25m

$1,340

ChicagoMelbourne

ORD - MEL

ORDMEL

Chicago O'Hare Intl

Fri 15/8

07:05-12:00

2 stops37h 55m

Melbourne

Fri 22/8

13:30-05:40

2 stops31h 10m

$1,471

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sun 24/8

07:00-07:05

2 stops33h 05m

Sydney Kingsford Smith

Sat 6/9

09:10-00:04

2 stops29h 54m

$1,523

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Sat 16/8

19:09-10:25

2 stops24h 16m

Brisbane

Sat 23/8

11:40-05:40

2 stops33h 00m

$1,547

ChicagoSydney

ORD - SYD

ORDSYD

Chicago O'Hare Intl

Sat 27/9

20:05-19:15

2 stops32h 10m

Sydney Kingsford Smith

Sun 12/10

12:50-08:40

1 stop35h 50m

$1,730

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Thu 14/8

07:40-12:00

2 stops37h 20m

Melbourne

Thu 21/8

13:30-21:51

2 stops23h 21m

$1,766

ChicagoCanberra

ORD - CBR

ORDCBR

Chicago O'Hare Intl

Thu 14/8

07:05-12:20

2 stops38h 15m

Canberra

Thu 21/8

13:20-05:40

2 stops31h 20m

$1,774

ChicagoAdelaide

ORD - ADL

ORDADL

Chicago O'Hare Intl

Thu 14/8

07:05-11:35

2 stops38h 00m

Adelaide

Thu 21/8

12:35-05:40

2 stops31h 35m

$1,774

ChicagoBrisbane

ORD - BNE

ORDBNE

Chicago O'Hare Intl

Mon 22/9

19:01-10:35

2 stops24h 34m

Brisbane

Sat 4/10

11:40-21:24

2 stops24h 44m

$1,883

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 16/8

07:05-07:25

2 stops35h 20m

Perth

Sat 23/8

08:45-18:14

2 stops46h 29m

$1,900

Flights are sorted by cheapest return flights first.

Deals found on 1/7

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 27 June 2025.

The best time to book flights from Chicago is 2 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 $301). Flying from Chicago in December will prove the most costly (average of $1,311). 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, Air Canada. As they depart for the following popular destinations: Sydney.

Qantas Airways
Qantas Airways
From $854
Air Canada
Air Canada
From $1,092
American Airlines
American Airlines
From $140
Spirit Airlines
Spirit Airlines
From $59

What are popular destinations to fly to from Chicago?

Chicago offers frequent flights to New York (1,207 flights per day), Detroit (938 flights per day) and Los Angeles (546 flights per day).

Los Angeles
Los Angeles
From $78
New York
New York
From $43
Dayton
Dayton
From $124
Miami
Miami
From $64

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at $65. Explore other affordable destinations below.

New York
New York
From $43
Orlando
Orlando
From $45
Dallas/Fort Worth
Dallas/Fort Worth
From $58
Miami
Miami
From $64

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 ANA, Korean Air, andAlaska Airlines from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
ANA
8.4
Very Good
893 reviews
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Korean Air
8.4
Very Good
1,101 reviews
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Alaska Airlines
8.0
Very Good
10,000 reviews
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Fiji Airways
8.0
Very Good
202 reviews
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Delta
8.0
Very Good
7,983 reviews
ANA
8.4
Very Good
893 reviews
Check prices

Entertainment

7.9

Food

7.7

Boarding

8.5

Overall

8.4

Crew

8.7

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.

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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 3 July 2025.

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

    For the current month, the most popular flights from Chicago are Athens, Boston, Atlanta. Atlanta, Boston, Mumbai 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 $1,282. While Chicago Midway airport is usually cheaper if your destination is Sydney with prices starting at $1,632. 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, Qantas Airways, and Air Canada 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 ($82). Qantas Airways flights from Chicago to Melbourne ($1,203). Air Canada flights from Chicago to Brisbane ($1,449).

  • 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 $1,252 round trip
    Fly from Chicago to Melbourne from $1,471 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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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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