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$526+ Cheap flights from Sydney (SYD) to Midway (MDW)

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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Sydney to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,434
(Delta)

One-way from

$526
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$857
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago (CHI) flights.
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From Sydney Kingsford Smith to Chicago Midway
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One-way flight from Sydney Kingsford Smith to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($141 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Sydney to Midway

Cheapest flights from Sydney to Midway
Explore the most affordable flight options available from Sydney to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2910:05 amSYD - MDW
2 stops24h 23mDelta
Wed 11/51:05 pmMDW - SYD
2 stops26h 30mDelta
Deal found 2/20$1,339
This Kiwi.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1010:25 amSYD - MDW
1 stop27h 02mMultiple Airlines
Fri 5/22:45 pmMDW - SYD
1 stop25h 10mMultiple Airlines
Deal found 2/20$2,974
This BYOjet deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:45 amSYD - MDW
3 stops46h 18mLATAM Airlines
Mon 11/33:40 pmMDW - SYD
2 stops33h 00mLATAM Airlines
Deal found 2/20$3,266
This Korean Air deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/69:10 amSYD - MDW
2 stops44h 55mKorean Air
Thu 3/139:25 amMDW - SYD
2 stops29h 30mKorean Air
Deal found 2/20$5,082

Find flights from Sydney to Midway within your budget

Customize your flight search to find flights from Sydney to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Sydney

Fly to

Midway

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 4/20

9:25 am-6:20 pm

2 stops23h 55m

Chicago Midway

Thu 5/8

9:20 am-6:35 am

2 stops30h 15m

$1,434

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/10

10:25 am-10:27 pm

1 stop27h 02m

Chicago Midway

Fri 5/2

2:45 pm-6:55 am

1 stop25h 10m

$2,974

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/6

9:10 am-1:05 pm

2 stops44h 55m

Chicago Midway

Thu 3/13

9:25 am-6:55 am

2 stops29h 30m

$5,082

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/25

6:15 am-10:09 pm

2 stops32h 54m

$526

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 6/1

9:25 am-9:46 pm

2 stops27h 21m

$909

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 6/1

11:50 am-6:00 pm

3 stops45h 10m

$1,493

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/6

9:10 am-1:05 pm

2 stops44h 55m

$3,045

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Best time to book a flight from Sydney to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sydney with our price prediction graph.
Estimated round-trip 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 Sydney to Midway

Get recent, data-driven insights about flights from Sydney to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated February 20, 2025.
Korean Air
8.4
Very good
1,037 reviews

Entertainment

8.2

Boarding

8.5

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Korean Air
8.4
Very good
1,037 reviews
Korean Air
8.4
Very good
1,037 reviews

Entertainment

8.2

Boarding

8.5

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Delta
8.0
Very good
8,219 reviews
Korean Air
8.4
Very good
1,037 reviews

Entertainment

8.2

Boarding

8.5

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

LATAM Airlines
7.5
Good
1,795 reviews
Korean Air
8.4
Very good
1,037 reviews

Entertainment

8.2

Boarding

8.5

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Anonymous,Feb 2025

ATL - SBN

Regional jets are small and uncomfortable. When flying in or out of South Bend airport, that's usually what I'm on. It's the price one pays for the great convenience of using a small airport (cheap parking, no lines). The CRJ900 has engines attached to the fuselage near the rear of the plane. So, very loud in the back of the plane, and I happened to have the far back corner that also had no window. Oh well, a short flight and pleasant neighbor and cheerful attendant.

Related info for your journey

Find useful and relevant information for your journey from Sydney to Midway. 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 Midway?

    Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Sydney airport to Chicago Midway. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $909. However, be on the lookout for offers from LATAM Airlines and Korean Air, as they are both options that can get you from Sydney to Chicago Midway Airport for a low price.

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

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

  • How can I find direct flights from Sydney to Midway?

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

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

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

  • What is the cheapest month to book a flight from Sydney to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Sydney to Chicago Midway Airport (average of $160). Flying from Sydney to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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