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Cheap flights from Chicago Midway Airport to Sydney from $956

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 15/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
5 May — 12 May1
1 adult

Cheap flight deals from Midway to Sydney

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Sydney (SYD). 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 30 April 2025.

Round-trip from

$2,297

One-way from

$956

Popular in

December

Cheapest in

August

Average price

$1,369
Delta
  • Delta
  • 1/7-8/7
  • 4 total stops
  • 50h 05m total
  • Chicago to Sydney
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15/8
  • 15/8
  • 3 total stops
  • 47h 33m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($382 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease ($96 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Find flight deals from Midway to Sydney

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

Tue 1/712:44MDW - SYD
2 stops26h 51mDelta
Tue 8/709:25SYD - MDW
2 stops23h 14mDelta
Deal found 29/4$2,297
Mon 15/918:50MDW - SYD
2 stops44h 30mKorean Air
Tue 30/907:55SYD - MDW
2 stops43h 37mKorean Air
Deal found 29/4$3,877
Thu 19/609:21MDW - SYD
3 stops30h 59mMultiple Airlines
Sun 27/713:15SYD - MDW
3 stops34h 30mMultiple Airlines
Deal found 30/4$4,256
Sat 1/1115:40MDW - SYD
2 stops34h 00mLATAM Airlines
Mon 10/1111:45SYD - MDW
3 stops47h 13mLATAM Airlines
Deal found 29/4$6,070

Cheapflights Fare Finder

Customise your flight search to find flights from Midway to Sydney 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 647,157 searches. Data last updated 30 April 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sydney that are best for you.

Fly from

Midway

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 1/7

12:44-06:35

2 stops26h 51m

Sydney Kingsford Smith

Tue 8/7

09:25-17:39

2 stops23h 14m

$2,297

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 15/9

18:50-06:20

2 stops44h 30m

Sydney Kingsford Smith

Mon 29/9

07:55-12:32

2 stops43h 37m

$3,877

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 19/6

09:21-07:20

3 stops30h 59m

Sydney Kingsford Smith

Sun 27/7

13:15-08:45

3 stops34h 30m

$4,256

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 5/10

15:40-10:35

3 stops50h 55m

Sydney Kingsford Smith

Sat 18/10

12:50-09:51

3 stops37h 01m

$6,099

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 15/8

21:12-11:45

3 stops47h 33m

$956

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/9

09:30-06:35

2 stops30h 05m

$1,312

Flights are sorted by cheapest return flights first.

Deals found on 30/4

Best time to book a flight from Midway to Sydney

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

Rainfall in Sydney by month

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

In terms of precipitation, rainfall in Sydney ranges from 50.0 - 130.0 inches per month. March is typically the wettest month, when rainfall can reach 130.0 mm. September is typically the driest time to visit Sydney when rainfall is around 50.0 mm.

Temperature in Sydney by month

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

If weather is an important factor for your trip to Sydney, use this chart to help with planning. For those seeking warmer temperatures, January is the ideal time of year to visit, when temperatures reach an average of 22.0 C. Travellers hoping to avoid the cold should look outside of July, when temperatures are typically at their lowest (around 11.0 C).

Reviews of airlines servicing Sydney

Get insights into the airlines that provide service to Sydney. 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 Sydney. Reviews last updated 30 April 2025.
Korean Air
8.4
Very Good
1,068 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
Korean Air
8.4
Very Good
1,068 reviews
Korean Air
8.4
Very Good
1,068 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
Delta
8.0
Very Good
7,934 reviews
Korean Air
8.4
Very Good
1,068 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.
LATAM Airlines
7.5
Good
1,767 reviews
Korean Air
8.4
Very Good
1,068 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Food

8.1

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

Related info for your journey

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

    Sydney Kingsford Smith (SYD) is the airport you will fly into if you book a flight from Chicago Midway to Sydney. You should not have trouble finding flights to Kingsford Smith from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Sydney airport from Chicago Midway. It is only a 7.5 km journey from Kingsford Smith (SYD) to Sydney’s city centre.

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

    Flying on Delta is currently your cheapest option to Sydney, with prices starting at $2,297. Additional round-trip tickets that might be worth considering are offered by Korean Air and LATAM Airlines, with the lowest prices starting at $3,877 and $6,099, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Sydney 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 Chicago Midway Airport to Sydney?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Sydney (average of $129). Flying from Chicago Midway Airport to Sydney in October is currently the most expensive (average of $171). 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.

See more FAQs

Travelling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Parramatta
Wollongong
Katoomba
Manly
Penrith
Coogee
Randwick
Terrigal
Cronulla
Lithgow
Bondi Beach
Leura
Swansea

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Sydney

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Sydney flights

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

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