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Cheap flights from Sydney to Chicago Midway Airport from $1,162

SYD — MDW
20 Oct — 27 Oct1
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

Thu 8/1010:30 -
2 stops29h 13m
Sat 24/1006:21 -
2 stops34h 19m
Deal found 19/9$1,933
Fri 9/1010:10 -
2 stops28h 12m
Sat 24/1006:21 -
2 stops32h 04m
Deal found 18/9$1,954
Thu 3/1210:40 -
2 stops29h 15m
Mon 11/109:30 -
2 stops30h 00m
Deal found 16/9$2,442
Tue 10/1110:40 -
2 stops24h 24m
Tue 17/1113:31 -
2 stops25h 59m
Deal found 18/9$2,444
Sun 22/1110:40 -
2 stops22h 59m
Sun 6/1212:39 -
2 stops26h 51m
Deal found 18/9$2,514
Sun 6/1210:40 -
2 stops24h 21m
Tue 12/113:00 -
2 stops24h 50m
Deal found 16/9$2,517
Fri 4/1210:40 -
2 stops24h 21m
Sun 13/1209:37 -
2 stops29h 53m
Deal found 19/9$2,518
Sun 22/1110:40 -
2 stops22h 59m
Sat 28/1113:31 -
2 stops25h 59m
Deal found 19/9$2,726
Mon 2/1110:40 -
2 stops23h 07m
Mon 9/1113:05 -
2 stops26h 25m
Deal found 18/9$2,738
Tue 27/1009:40 -
2 stops22h 34m
Wed 11/1113:31 -
2 stops25h 59m
Deal found 15/9$2,748

Find flight deals from Sydney to Midway

Round-trip from

$1,933

One-way from

$1,162

Popular in

May

Cheapest in

October

Average price

$1,770
8/10-24/10
  • 8/10-24/10
  • 4 total stops
  • 63h 32m total
  • Sydney to Chicago
Search Deals
10/11-31/12
  • 10/11-31/12
  • 3 total stops
  • 57h 00m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($216 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($68 potential savings vs. average return price).
Search Deals
Average for round-trip flights in September 2026
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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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Depart

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Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 10/11

19:25-11:25

3 stops57h 00m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,162

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 30/11

21:25-11:33

3 stops55h 08m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,256

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 2/12

12:45-14:55

3 stops43h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,344

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 22/10

21:35-23:43

2 stops42h 08m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,380

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 8/10

14:15-12:17

3 stops38h 02m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,518
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 6/12

10:40-18:01

2 stops24h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,640

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 22/9

20:45-11:59

2 stops54h 14m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,657

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 2/12

10:40-22:55

2 stops29h 15m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,831

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 3/12

10:40-22:55

2 stops29h 15m

Chicago Midway

Mon 11/1

09:30-08:30

2 stops30h 00m

$2,442

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 22/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Sun 6/12

12:39-08:30

2 stops26h 51m

$2,514

Flights are sorted by cheapest return flights first.

Deals found on 16/9

Showing 1-10 of 20 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 29h 15m. Delta provides one of the quickest options available for as low as $2,442. There are 14861 km between Sydney and Chicago Midway Airport.

  • 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.

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Cheapflights helps you find that perfect flight to Midway from Sydney by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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