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Cheap flights from Sydney to Chicago from $431

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Sydney to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:40 am - 4:53 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
23h 13m2 stops Los Angeles Minneapolis St Paul
Delta Logo
9:56 am - 6:50 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 54m2 stops Minneapolis St Paul Los Angeles
$740Delta
Wed, Jan 20 - Sun, Jan 31
Singapore Airlines Logo
12:15 pm - 5:55 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
34h 40m2 stops Singapore Changi Los Angeles
Singapore Airlines Logo
3:50 pm - 5:55 pmMDW  Chicago Midway-SYD Sydney Kingsford Smith
33h 05m2 stops Los Angeles Singapore Changi
$1,716Singapore Airlines
Wed, Mar 3 - Wed, Mar 10
Delta Logo
10:40 am - 4:50 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
23h 10m2 stops Los Angeles Minneapolis St Paul
Delta Logo
1:02 pm - 8:30 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
26h 28m2 stops Atlanta Hartsfield-Jackson Los Angeles
$1,932Delta
Wed, Dec 2 - Wed, Dec 9
Delta Logo
10:40 am - 6:01 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
24h 21m2 stops Los Angeles Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 8:30 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
25h 49m2 stops Detroit Metropolitan Wayne County Los Angeles
$2,038Delta
Thu, Dec 3 - Mon, Dec 7
Delta Logo
10:40 am - 8:50 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
39h 10m2 stops Los Angeles Minneapolis St Paul
Delta Logo
1:41 pm - 8:30 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
25h 49m2 stops Detroit Metropolitan Wayne County Los Angeles
$2,508Delta
Sat, Nov 28 - Thu, Dec 3
Multiple Airlines Logo
10:00 pm - 9:26 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
52h 26m2 stops Melbourne Dallas/Fort Worth
Multiple Airlines Logo
10:40 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 15m1 stop Dallas/Fort Worth
$2,510Multiple Airlines
Mon, Nov 30 - Mon, Dec 7
Multiple Airlines Logo
2:05 pm - 9:46 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
36h 41m1 stop Dallas/Fort Worth
Multiple Airlines Logo
10:40 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
27h 15m1 stop Dallas/Fort Worth
$2,548Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
2:05 pm - 12:03 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
38h 58m1 stop Dallas/Fort Worth
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$3,181Multiple Airlines
Fri, Dec 18 - Fri, Dec 25
Multiple Airlines Logo
9:45 am - 12:03 pmSYD  Sydney Kingsford Smith-MDW Chicago Midway
43h 18m3 stops Nadi San Francisco Dallas/Fort Worth
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$3,257Multiple Airlines
Fri, Dec 18 - Fri, Dec 25
Multiple Airlines Logo
2:05 pm - 12:01 amSYD  Sydney Kingsford Smith-MDW Chicago Midway
26h 56m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:01 am - 6:55 amMDW  Chicago Midway-SYD Sydney Kingsford Smith
31h 54m1 stop Dallas/Fort Worth
$4,065Multiple Airlines
Fri, Dec 18 - Fri, Dec 25

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WestJet flights from Sydney to Chicago Midway Airport

Our best WestJet deals on Sydney to Chicago Midway Airport flight tickets
WestJet
Dec 17
SYD8:30 pmSydney Kingsford Smith
61h 54m
2 stops
MDW5:24 pmChicago Midway
Dec 24
MDW6:30 pmChicago Midway
43h 05m
2 stops
SYD6:35 amSydney Kingsford Smith
$7,044
WestJet
Dec 21
SYD8:30 pmSydney Kingsford Smith
61h 54m
2 stops
MDW5:24 pmChicago Midway
Jan 4
MDW9:56 amChicago Midway
51h 39m
2 stops
SYD6:35 amSydney Kingsford Smith
$7,866

Singapore Airlines flights from Sydney to Chicago Midway Airport

Our best Singapore Airlines deals on Sydney to Chicago Midway Airport flight tickets
Singapore Airlines
Mar 3
SYD12:15 pmSydney Kingsford Smith
34h 40m
2 stops
MDW5:55 amChicago Midway
Mar 10
MDW3:50 pmChicago Midway
33h 05m
2 stops
SYD5:55 pmSydney Kingsford Smith
$1,716
Singapore Airlines
Dec 23
SYD12:15 pmSydney Kingsford Smith
34h 40m
2 stops
MDW5:55 amChicago Midway
Jan 8
MDW3:50 pmChicago Midway
33h 05m
2 stops
SYD5:55 pmSydney Kingsford Smith
$4,467
Singapore Airlines
Dec 18
SYD12:15 pmSydney Kingsford Smith
34h 40m
2 stops
MDW5:55 amChicago Midway
Dec 25
MDW3:45 pmChicago Midway
33h 10m
2 stops
SYD5:55 pmSydney Kingsford Smith
$6,640

momondo 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 round-trip

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 1/20

10:40 am-4:53 pm

2 stops23h 13m

Chicago Midway

Sun 1/31

9:56 am-6:50 am

2 stops27h 54m

$740

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 3/3

12:15 pm-5:55 am

2 stops34h 40m

Chicago Midway

Wed 3/10

3:50 pm-5:55 pm

2 stops33h 05m

$1,716
Quickest round-trip

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 12/2

10:40 am-4:50 pm

2 stops23h 10m

Chicago Midway

Wed 12/9

1:02 pm-8:30 am

2 stops26h 28m

$1,932

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 12/3

10:40 am-6:01 pm

2 stops24h 21m

Chicago Midway

Mon 12/7

1:41 pm-8:30 am

2 stops25h 49m

$2,038

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 11/28

10:40 am-8:50 am

2 stops39h 10m

Chicago Midway

Thu 12/3

1:41 pm-8:30 am

2 stops25h 49m

$2,508

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 11/30

10:00 pm-9:26 am

2 stops52h 26m

Chicago Midway

Mon 12/7

10:40 am-6:55 am

1 stop27h 15m

$2,510

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 12/3

2:05 pm-9:46 am

1 stop36h 41m

Chicago Midway

Mon 12/7

10:40 am-6:55 am

1 stop27h 15m

$2,548

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 12/18

2:05 pm-12:03 pm

1 stop38h 58m

Chicago Midway

Fri 12/25

6:01 am-6:55 am

1 stop31h 54m

$3,181

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 12/18

9:45 am-12:03 pm

3 stops43h 18m

Chicago Midway

Fri 12/25

6:01 am-6:55 am

1 stop31h 54m

$3,257

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 12/18

2:05 pm-12:01 am

2 stops26h 56m

Chicago Midway

Fri 12/25

6:01 am-6:55 am

1 stop31h 54m

$4,065

Flights are sorted by cheapest round-trip flights first.

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

How to get the cheapest flight ticket from Sydney to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Sydney Kingsford Smith to Chicago Midway?

Delta is the most popular carrier operating from Sydney Kingsford Smith to Chicago Midway

When to book flights from Sydney to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sydney to Chicago Midway Airport (SYD to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago Midway Airport

Best Price Found

$431

Fastest flight time

24h 21m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $431. The best round-trip flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $740.
The fastest flight from Sydney to Chicago Midway Airport takes 24h 21m
There are no direct flights from Sydney to Chicago Midway Airport. There are no popular flight routes from Sydney to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Sydney to Chicago Midway Airport

  • How far is Sydney Kingsford Smith to Chicago Midway by plane?

    Chicago Midway is 9230.4 mi away from Sydney Kingsford Smith. A reasonable flight in good conditions will take 24h 21m.

  • When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago Midway Airport?

    Prices for flights from Sydney Kingsford Smith Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Sydney Kingsford Smith Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sydney to Chicago for you.

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

Yes. momondo allows you to filter the results for Sydney to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Sydney to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Sydney to Chicago.

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

Price alerts on flights to Chicago from Sydney are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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