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Cheap flights from Sydney to Chicago Midway Airport from $613

SYD — MDW
2 Dec — 9 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Sydney to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Sydney to Midway

Mon 2/1110:40 -
2 stops28h 53m
Sun 15/1110:34 -
2 stops28h 56m
Deal found 31/10$1,051
Wed 2/1210:40 -
2 stops23h 10m
Wed 9/1213:02 -
2 stops26h 28m
Deal found 1/11$2,747
Thu 3/1210:40 -
2 stops24h 21m
Mon 7/1213:41 -
2 stops25h 49m
Deal found 1/11$2,898
Thu 12/1110:40 -
2 stops24h 24m
Sat 28/1112:30 -
2 stops27h 00m
Deal found 30/10$2,975
Wed 4/1122:20 -
2 stops54h 05m
Wed 11/1112:27 -
1 stop25h 28m
Deal found 2/11$3,007
Sat 28/1110:40 -
2 stops39h 10m
Thu 3/1213:41 -
2 stops25h 49m
Deal found 1/11$3,566
Mon 30/1122:00 -
2 stops52h 26m
Mon 7/1210:40 -
1 stop27h 15m
Deal found 2/11$3,569
Thu 3/1214:05 -
1 stop36h 41m
Mon 7/1210:40 -
1 stop27h 15m
Deal found 1/11$3,623
Thu 12/1106:00 -
3 stops34h 47m
Sat 28/1108:51 -
2 stops30h 14m
Deal found 31/10$3,657

Find flight deals from Sydney to Midway

Round-trip from

$1,052

One-way from

$613

Popular in

May

Cheapest in

November

Average price

$1,516
Delta
  • Delta
  • 20/1-31/1
  • 4 total stops
  • 51h 07m total
  • Sydney to Chicago
Search Deals
Delta
  • Delta
  • 2/2-31/12
  • 2 total stops
  • 27h 20m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($249 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($73 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2026
Search Deals

Cheapflights Fare Finder

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

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Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 5/3

14:00-12:13

3 stops39h 13m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$947

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 20/1

10:40-16:53

2 stops23h 13m

Chicago Midway

Sun 31/1

09:56-06:50

2 stops27h 54m

$1,052
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 14/4

09:15-18:37

2 stops24h 22m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,546

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 30/11

19:25-11:33

3 stops57h 08m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,679

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 28/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,920

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 21/12

21:40-12:10

3 stops31h 30m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,945

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

14:05-11:22

1 stop38h 17m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,254

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 3/3

12:15-05:55

2 stops34h 40m

Chicago Midway

Wed 10/3

15:50-17:55

2 stops33h 05m

$2,440

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 2/12

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 9/12

13:02-08:30

2 stops26h 28m

$2,747

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 12/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Sat 28/11

12:30-08:30

2 stops27h 00m

$2,975

Flights are sorted by cheapest return flights first.

Deals found on 31/10

Showing 1-10 of 15 resultsSorted by cheapest first
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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 return price

Related info for your journey

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

    For a flight from Sydney to Chicago Midway, 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 Midway per day. 0 airlines have flights to Chicago Midway from Sydney Kingsford Smith on a regular basis.

  • How long is the flight from Sydney to Chicago Midway Airport?

    A quick flight from Sydney to Chicago Midway Airport can take about 23h 13m. Delta provides one of the quickest options available for as low as $1,052. There are 14861 km between Sydney and Chicago Midway Airport. This flight may include one or multiple stops.

  • 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 holiday 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.

See more FAQs

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Alternative routes for Sydney to Midway

Sydney to O'Hare Intl flights

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When you search for this flight from Sydney to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

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