What are the cheapest airlines flying from Sydney to Chicago round-trip?

Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,849. Other airlines that can offer you cheap pricing are American Airlines, from $1,866, and Japan Airlines, from $1,917. Find deals

What are the cheapest airlines to fly from Sydney to Chicago one-way?

To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $1,084. Cathay Pacific flights start at $1,294 while deals on Delta start at $1,332 one-way. Find deals

What are the most popular airlines that fly from Sydney to Chicago?

When booking a flight from Sydney to Chicago, you may want to consider flying on American Airlines, Air Canada or Delta as they are the most popular for this route.

What is the cheapest day to fly return from Sydney to Chicago?

Flying to your destination on a Friday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Sydney to Chicago?

Travellers have found it’s best to book a flight 38 days in advance to save up to 56% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Sydney to Chicago 1-2 weeks in advance for as low as $1,735, or $2,059 for flights within the next 24 hours.

What is the cheapest month to fly from Sydney to Chicago?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, March can be a great choice for travel to Chicago. Flights to Chicago from Sydney in March are about $1,660 on average during March, but can be found for as low as $1,038.

What airport do you fly from for flights from Sydney to Chicago?

For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 7 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.

Can I find deals for flights from Sydney to Chicago that include hotel bookings?

Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

How can I find direct flights from Sydney to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.

Can I find deals for business class flights from Sydney to Chicago?

Yes. Cheapflights offers flight deals from Sydney to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$753+ Flights from Sydney to Chicago

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 87 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Sydney to Chicago

Round-trip from	$1,611
One-way from	$753
Popular in	December
Cheapest in	March
Average price	$1,326

13/6-20/6
4 total stops
70h 25m total
Sydney to Chicago

Search Deals

21/5
2 total stops
39h 20m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 16% potential increase in price ($504 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($111 potential savings vs. average return price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Find flight deals from Sydney to Chicago

Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Thu 5/613:15SYD - ORD

2 stops24h 40mMultiple Airlines

Mon 23/606:10ORD - SYD

2 stops38h 35mMultiple Airlines

Deal found 29/4$1,557

Thu 11/911:50SYD - ORD

1 stop35h 50mANA

Mon 15/920:20ORD - SYD

2 stops31h 55mANA

Deal found 29/4$1,707

Tue 24/609:10SYD - ORD

2 stops24h 25mAmerican Airlines

Tue 29/716:39ORD - SYD

2 stops23h 26mAmerican Airlines

Deal found 29/4$1,866

Wed 1/1007:45SYD - ORD

2 stops29h 56mAir New Zealand

Fri 10/1014:20ORD - SYD

2 stops26h 25mAir New Zealand

Deal found 29/4$1,895

Wed 4/608:55SYD - ORD

1 stop39h 20mJapan Airlines

Sun 22/609:12ORD - SYD

2 stops30h 08mJapan Airlines

Deal found 28/4$1,955

Wed 3/1211:15SYD - ORD

1 stop23h 13mQantas Airways

Thu 11/1216:45ORD - SYD

2 stops36h 40mQantas Airways

Deal found 29/4$1,967

Thu 4/1216:00SYD - ORD

2 stops33h 57mAir Canada

Thu 11/1213:00ORD - SYD

2 stops24h 55mAir Canada

Deal found 29/4$2,033

Thu 19/610:10SYD - ORD

1 stop43h 15mCathay Pacific

Sat 28/616:00ORD - SYD

1 stop27h 50mCathay Pacific

Deal found 30/4$2,070

Mon 1/1211:20SYD - ORD

1 stop20h 17mUnited Airlines

Tue 9/1212:49ORD - SYD

1 stop25h 11mUnited Airlines

Deal found 29/4$2,092

Thu 7/809:25SYD - MDW

2 stops23h 14mDelta

Mon 25/809:30MDW - SYD

2 stops30h 05mDelta

Deal found 30/4$2,106

Sun 10/809:25SYD - ORD

2 stops38h 06mDelta

Sun 24/807:00ORD - SYD

2 stops32h 35mDelta

Deal found 29/4$2,183

Fri 5/1209:10SYD - ORD

1 stop40h 20mKorean Air

Sun 7/1211:05ORD - SYD

1 stop26h 50mKorean Air

Deal found 29/4$2,356

Best flights from Sydney to Chicago
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 30 April 2025.

Fri 13/606:15SYD - ORD

2 stops31h 50mMultiple Airlines

Fri 20/606:10ORD - SYD

2 stops38h 35mMultiple Airlines

Deal found 29/4$1,611

Tue 24/611:50SYD - ORD

2 stops47h 35mANA

Tue 29/717:45ORD - SYD

1 stop34h 30mANA

Deal found 29/4$1,849

Tue 24/609:10SYD - ORD

2 stops24h 25mAmerican Airlines

Tue 29/716:39ORD - SYD

2 stops23h 26mAmerican Airlines

Deal found 29/4$1,866

Thu 12/608:55SYD - ORD

1 stop39h 20mJapan Airlines

Wed 18/601:30ORD - SYD

1 stop37h 50mJapan Airlines

Deal found 28/4$1,917

Tue 10/609:20SYD - ORD

2 stops37h 39mAir Canada

Tue 24/615:35ORD - SYD

1 stop24h 45mAir Canada

Deal found 28/4$2,044

Thu 17/710:10SYD - ORD

1 stop43h 15mCathay Pacific

Tue 22/716:00ORD - SYD

1 stop27h 50mCathay Pacific

Deal found 29/4$2,072

Mon 14/709:30SYD - ORD

1 stop24h 25mUnited Airlines

Wed 27/816:10ORD - SYD

1 stop23h 50mUnited Airlines

Deal found 27/4$2,092

Mon 7/709:25SYD - MDW

2 stops23h 37mDelta

Tue 15/713:46MDW - SYD

2 stops25h 49mDelta

Deal found 28/4$2,106

Wed 16/709:55SYD - ORD

2 stops26h 23mAir New Zealand

Mon 21/715:35ORD - SYD

2 stops26h 10mAir New Zealand

Deal found 29/4$2,122

Fri 4/717:45SYD - ORD

1 stop20h 50mQantas Airways

Thu 24/708:50ORD - SYD

1 stop31h 15mQantas Airways

Deal found 28/4$2,234

Sun 13/721:40SYD - ORD

2 stops47h 00mAlaska Airlines

Wed 27/814:07ORD - SYD

2 stops38h 38mAlaska Airlines

Deal found 27/4$2,351

Sun 13/720:55SYD - ORD

2 stops51h 45mTurkish Airlines

Mon 25/823:45ORD - SYD

2 stops52h 15mTurkish Airlines

Deal found 27/4$2,564

Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated 30 April 2025 and is based on user searches.

Tue 29/418:30SYD - ORD

2 stops34h 55mMultiple Airlines

Thu 8/516:00ORD - SYD

1 stop47h 10mMultiple Airlines

Deal found 29/4$2,369

Wed 30/411:50SYD - ORD

2 stops32h 14mANA

Wed 7/517:45ORD - SYD

1 stop34h 30mANA

Deal found 29/4$1,922

Wed 30/408:55SYD - ORD

2 stops30h 04mJapan Airlines

Wed 7/507:25ORD - SYD

2 stops31h 55mJapan Airlines

Deal found 29/4$2,092

Wed 30/414:05SYD - ORD

1 stop39h 20mCathay Pacific

Wed 7/516:00ORD - SYD

1 stop27h 50mCathay Pacific

Deal found 29/4$2,133

Wed 30/421:45SYD - ORD

3 stops47h 32mChina Southern

Wed 7/517:38ORD - SYD

2 stops35h 02mChina Southern

Deal found 29/4$4,564

Sat 17/510:20SYD - ORD

2 stops46h 30mFinnair

Thu 22/521:30ORD - SYD

2 stops65h 55mFinnair

Deal found 29/4$8,644

Sun 25/507:55SYD - MDW

2 stops43h 33mMultiple Airlines

Thu 5/609:16MDW - SYD

2 stops30h 04mMultiple Airlines

Deal found 29/4$17,813

One-way flights from Sydney to Chicago
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated 30 April 2025.

Wed 21/513:15SYD - ORD

2 stops39h 20mMultiple Airlines

Deal found 29/4$753

Mon 26/516:20SYD - MDW

3 stops55h 25mMultiple Airlines

Deal found 28/4$831

Sun 1/609:10SYD - ORD

1 stop19h 46mAmerican Airlines

Deal found 29/4$1,084

Thu 29/514:05SYD - ORD

1 stop39h 20mCathay Pacific

Deal found 28/4$1,294

Tue 15/709:25SYD - MDW

2 stops27h 16mDelta

Deal found 27/4$1,332

Sat 21/610:20SYD - ORD

1 stop34h 09mUnited Airlines

Deal found 29/4$1,424

Thu 29/508:55SYD - ORD

3 stops25h 43mAir Tahiti Nui

Deal found 28/4$1,636

Sat 17/509:10SYD - ORD

1 stop21h 45mQantas Airways

Deal found 28/4$1,713

Sat 17/509:25SYD - ORD

2 stops24h 23mDelta

Deal found 28/4$1,722

Sun 1/621:45SYD - ORD

3 stops47h 22mChina Southern

Deal found 29/4$1,894

Tue 17/609:20SYD - ORD

3 stops37h 39mAir Canada

Deal found 29/4$2,134

Fri 30/515:00SYD - ORD

3 stops45h 54mSingapore Airlines

Deal found 28/4$2,217

Cheapflights Fare Finder

Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 5/6

13:15-22:55

2 stops24h 40m

Chicago O'Hare Intl

Mon 23/6

06:10-11:45

2 stops38h 35m

$1,557

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 11/9

11:50-08:40

1 stop35h 50m

Chicago O'Hare Intl

Mon 15/9

20:20-19:15

2 stops31h 55m

$1,707

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 24/6

09:10-18:35

2 stops24h 25m

Chicago O'Hare Intl

Tue 29/7

16:39-07:05

2 stops23h 26m

$1,866

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 1/10

07:45-22:41

2 stops29h 56m

Chicago O'Hare Intl

Fri 10/10

14:20-08:45

2 stops26h 25m

$1,895

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 4/6

08:55-09:15

1 stop39h 20m

Chicago O'Hare Intl

Sun 22/6

09:12-06:20

2 stops30h 08m

$1,955

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 11/9

09:20-07:59

2 stops37h 39m

Chicago O'Hare Intl

Mon 15/9

20:25-07:20

2 stops43h 55m

$2,044

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 19/6

10:10-14:25

1 stop43h 15m

Chicago O'Hare Intl

Sat 28/6

16:00-10:50

1 stop27h 50m

$2,070

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 18/6

09:30-14:39

1 stop20h 09m

Chicago O'Hare Intl

Wed 25/6

19:40-07:00

1 stop20h 20m

$2,092

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 7/8

09:25-17:39

2 stops23h 14m

Chicago Midway

Mon 25/8

09:30-06:35

2 stops30h 05m

$2,106

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/8

09:25-19:27

2 stops25h 02m

Chicago O'Hare Intl

Mon 25/8

10:35-06:35

2 stops29h 00m

$2,108

Flights are sorted by cheapest return flights first.

Deals found on 29/4

Showing 1-10 of 29 results

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney 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.

Cheapflights Insights

Everything you need to know about your flight from Sydney to Chicago

How far ahead should I book a flight from Sydney to Chicago?

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest time of day to fly from SYD to CHI?

Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Sydney to Chicago by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Sydney to Chicago?

Travellers seeking maximum savings on their Sydney to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday at midday flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

Air Tahiti Nui

8.8

Very Good

62 reviews

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

Korean Air

8.4

Very Good

1,066 reviews

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

Japan Airlines

8.3

Very Good

1,459 reviews

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

ANA

8.3

Very Good

852 reviews

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

Singapore Airlines

8.1

Very Good

1,292 reviews

Air Tahiti Nui

8.8

Very Good

62 reviews

Check prices

Reviews

1 / 2

10.0

Excellent

Isabelle,Apr 2023

AKL - PPT

Related info for your journey

What airport do you fly from for flights from Sydney to Chicago?
For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 7 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.
What are the cheapest airlines flying from Sydney to Chicago round-trip?
Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,849. Other airlines that can offer you cheap pricing are American Airlines, from $1,866, and Japan Airlines, from $1,917.
What are the cheapest airlines to fly from Sydney to Chicago one-way?
To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $1,084. Cathay Pacific flights start at $1,294 while deals on Delta start at $1,332 one-way.
Can I find deals for flights from Sydney to Chicago that include hotel bookings?
Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from Sydney to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.
Can I find deals for business class flights from Sydney to Chicago?
Yes. Cheapflights offers flight deals from Sydney to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Fly from Sydney to Chicago on these airlines

Qantas Airways flights from Sydney Kingsford Smith to Chicago

Air Canada flights from Sydney Kingsford Smith to Chicago

ANA flights from Sydney Kingsford Smith to Chicago

Top 7 airlines flying from Sydney to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Qantas Airways	Cheapest$1,035	Average$1,412	FlexibilityNo cancel fee	On-time74%	Search Qantas Airways flights
Air Canada	Cheapest$1,299	Average$1,745	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
American Airlines	Cheapest$1,546	Average$1,716	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
United Airlines	Cheapest$1,585	Average$2,394	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
ANA	Cheapest$1,714	Average$2,244	FlexibilityNo cancel fee	On-time80%	Search ANA flights
Virgin Australia	Cheapest$1,733	Average$2,845	FlexibilityNo cancel fee	On-time80%	Search Virgin Australia flights
Delta	Cheapest$1,825	Average$1,957	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights

Fly with Cheapflights

How does Cheapflights help users find flights from Sydney to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Sydney to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Sydney to 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 to Chicago from Sydney.

Can Cheapflights find flights from Sydney to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Sydney to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?

Of course! You can now track prices for flights from Sydney to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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Cheap flights from Sydney to Chicago from $753

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/5. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or February, booked 87 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Sydney to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Sydney to Chicago

Cheapest flights from Sydney to ChicagoExplore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Sydney to Chicago that are best for you.

Best time to book a flight from Sydney to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Sydney to Chicago

How far ahead should I book a flight from Sydney to Chicago?

Use this chart to determine the optimal time to book a return flight from Sydney to Chicago. Price data was last updated on 25 April 2025.

What is the cheapest time of day to fly from SYD to CHI?

Find hourly flight availability from Sydney to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 April 2025.

What is the cheapest day to fly from Sydney to Chicago?

Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 13 October 2024.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Related info for your journey

Find useful and relevant information for your journey from Sydney to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Sydney to Chicago?

What are the cheapest airlines flying from Sydney to Chicago round-trip?

What are the cheapest airlines to fly from Sydney to Chicago one-way?

Can I find deals for flights from Sydney to Chicago that include hotel bookings?

How can I find direct flights from Sydney to Chicago?

Can I find deals for business class flights from Sydney to Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Sydney to Chicago on these airlines

Choose from the following airlines for your flight from Sydney to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 30 April 2025.

Top 7 airlines flying from Sydney to Chicago

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 Sydney to Chicago?

Why should you use Cheapflights to find cheap flight tickets from Sydney to Chicago?

Can Cheapflights find flights from Sydney to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?

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Cheapest flights from Sydney to Chicago
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.