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Look for other cheap flights to Chicago Midway

$745 Cheap flights to Chicago Midway Airport

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago Midway Airport departing on 6/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Australia to Chicago Midway Airport

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
13:15 - 10:58
SYD
-
MDW
36h 43m
3 stops
Multiple Airlines Logo
07:25 - 11:50
MDW
-
SYD
37h 25m
3 stops
$1,318Multiple Airlines
Wed, 9 Sep - Sun, 13 Sep
Multiple Airlines Logo
13:15 - 09:51
SYD
-
MDW
35h 36m
3 stops
Multiple Airlines Logo
06:05 - 11:50
MDW
-
SYD
38h 45m
3 stops
$1,476Multiple Airlines
Thu, 6 Aug - Wed, 19 Aug
Multiple Airlines Logo
11:35 - 10:58
BNE
-
MDW
38h 23m
3 stops
Multiple Airlines Logo
07:25 - 10:35
MDW
-
BNE
36h 10m
3 stops
$1,882Multiple Airlines
Wed, 16 Sep - Mon, 28 Sep
Multiple Airlines Logo
09:10 - 20:32
SYD
-
MDW
26h 22m
2 stops
Multiple Airlines Logo
06:05 - 07:05
MDW
-
SYD
34h 00m
2 stops
$2,027Multiple Airlines
Thu, 6 Aug - Sun, 23 Aug
Multiple Airlines Logo
22:35 - 18:30
BNE
-
MDW
34h 55m
2 stops
Multiple Airlines Logo
18:25 - 20:20
MDW
-
BNE
33h 55m
2 stops
$2,258Multiple Airlines
Sat, 31 Oct - Sat, 7 Nov
Multiple Airlines Logo
12:00 - 16:51
SYD
-
MDW
19h 51m
1 stop
Multiple Airlines Logo
17:46 - 11:50
MDW
-
SYD
27h 04m
2 stops
$2,351Multiple Airlines
Tue, 4 Aug - Tue, 11 Aug
Delta Logo
09:15 - 18:19
SYD
-
MDW
24h 04m
2 stops
Delta Logo
13:00 - 06:50
MDW
-
SYD
26h 50m
2 stops
$2,442Delta
Thu, 10 Sep - Wed, 23 Sep
Delta Logo
09:15 - 18:19
SYD
-
MDW
24h 04m
2 stops
Delta Logo
09:59 - 07:50
MDW
-
SYD
29h 51m
2 stops
$2,517Delta
Thu, 1 Oct - Fri, 9 Oct
Delta Logo
12:00 - 18:37
MEL
-
MDW
23h 37m
2 stops
Delta Logo
13:00 - 09:50
MDW
-
MEL
27h 50m
2 stops
$2,524Delta
Tue, 8 Dec - Tue, 19 Jan
Delta Logo
10:40 - 19:05
SYD
-
MDW
24h 25m
2 stops
Delta Logo
12:28 - 08:30
MDW
-
SYD
27h 02m
2 stops
$2,555Delta
Sun, 1 Nov - Sun, 8 Nov

momondo Fare Finder

 
Locate flights to Chicago Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 78,305 searches and data was last updated on 23 July 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/9

13:15-10:58

3 stops36h 43m

Chicago Midway

Sun 13/9

07:25-11:50

3 stops37h 25m

$1,318

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

13:15-09:51

3 stops35h 36m

Chicago Midway

Wed 19/8

06:05-11:50

3 stops38h 45m

$1,476

BrisbaneChicago

BNE - MDW

BNEMDW

Brisbane

Wed 16/9

11:35-10:58

3 stops38h 23m

Chicago Midway

Mon 28/9

07:25-10:35

3 stops36h 10m

$1,882

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

09:10-20:32

2 stops26h 22m

Chicago Midway

Sun 23/8

06:05-07:05

2 stops34h 00m

$2,027

BrisbaneChicago

BNE - MDW

BNEMDW

Brisbane

Sat 31/10

22:35-18:30

2 stops34h 55m

Chicago Midway

Sat 7/11

18:25-20:20

2 stops33h 55m

$2,258
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 4/8

12:00-16:51

1 stop19h 51m

Chicago Midway

Tue 11/8

17:46-11:50

2 stops27h 04m

$2,351

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 23/9

13:00-06:50

2 stops26h 50m

$2,442

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 1/10

09:15-18:19

2 stops24h 04m

Chicago Midway

Fri 9/10

09:59-07:50

2 stops29h 51m

$2,517

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Tue 8/12

12:00-18:37

2 stops23h 37m

Chicago Midway

Tue 19/1

13:00-09:50

2 stops27h 50m

$2,524

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/11

10:40-19:05

2 stops24h 25m

Chicago Midway

Sun 8/11

12:28-08:30

2 stops27h 02m

$2,555

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago Midway Airport from

Flights to Chicago Midway Airport – Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago Midway Airport to help you craft the best travel plan.

How long does it take to fly to Chicago Midway Airport?

Flight times from Australia to Chicago Midway Airport vary, but if you’re flying out of Sydney Kingsford Smith and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 24h 35m on average. Another popular route from Australia to Chicago Midway Airport is flying from Melbourne to Chicago O'Hare Intl, which will take roughly 29h 48m. Keep in mind that layovers or delays could extend your travel time.

Cheapest flights to Chicago Midway

Find the cheapest flights to Chicago Midway from your nearest city or airport

Cheap Chicago Midway Airport flight deals and tips

Summary info about Chicago Midway Airport flight prices, duration and airlines

Best One-Way Price

$745

Best Round-Trip Price

$1,318

Fastest flight time

36h 35m
The best one-way flight price to Chicago from Australia in the last 5 days is $745 (Brisbane to Chicago Midway).
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The best return flight price to Chicago from Australia in the last 5 days is $1,318 (Sydney Kingsford Smith to Chicago Midway).
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The fastest flight to Chicago from Australia takes 36h 35m (Melbourne to Chicago Midway).
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Frequently asked questions about flying to Chicago Midway Airport

Is there an alternative airport near Chicago Midway Airport?

Finding an alternative and possibly cheaper destination airport near Chicago Midway Airport is possible. If you are planning a flight to Chicago Midway Airport, consider booking flights to Chicago O'Hare Intl Airport (26 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre).

Is there a cheaper alternative to flying into Chicago?

Chicago O'Hare Intl Airport has an average price of $911 per person and is typically the cheapest airport to fly into when visiting Chicago. This average price does vary based on departure city. Try momondo’s Airport-to-Airport Pricing Tool to find the cheapest flight.

What is the absolute cheapest flight to Chicago?

$294 is the cheapest deal found on momondo in the last two weeks for a flight to Chicago. This flight is from Los Angeles and is 68% cheaper than most flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

When did momondo last update prices for flights to Chicago Midway Airport?

Prices for flights to Chicago Midway Airport were last updated today.

How old do you have to be to fly to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's licence and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights to Chicago?

Once all potential Chicago flight options are in front of you momondo lets you sort and filter flights based on preferences such as airline, price and flight times, amongst many other options.

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert; this is where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway trip

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