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SYD - MDW

Find cheap flights from Sydney to Chicago Midway Airport from $625

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Sydney to Midway departing on 5/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sydney to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

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Cheap flight deals from Sydney to Midway (SYD-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Sydney to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:25 am - 5:58 pmSYD-MDW
23h 33m2 stops
1:24 pm - 6:35 amMDW-SYD
26h 11m2 stops
$1,504Delta
Find Deal
Thu, May 30 - Wed, Jun 12
9:25 am - 5:58 pmSYD-MDW
23h 33m2 stops
12:45 pm - 6:35 amMDW-SYD
26h 50m2 stops
$1,536Delta
Find Deal
Thu, May 30 - Fri, Jun 7
9:25 am - 5:58 pmSYD-MDW
23h 33m2 stops
1:21 pm - 6:35 amMDW-SYD
26h 14m2 stops
$1,646Delta
Find Deal
Thu, May 23 - Fri, May 31
9:25 am - 5:58 pmSYD-MDW
23h 33m2 stops
12:42 pm - 6:35 amMDW-SYD
26h 53m2 stops
$1,661Delta
Find Deal
Thu, May 23 - Fri, May 31
9:25 am - 5:59 pmSYD-MDW
23h 34m2 stops
3:45 pm - 6:35 amMDW-SYD
23h 50m2 stops
$1,737Delta
Find Deal
Mon, Jul 22 - Mon, Jul 29
9:25 am - 5:59 pmSYD-MDW
23h 34m2 stops
1:24 pm - 6:35 amMDW-SYD
26h 11m2 stops
$1,786Delta
Find Deal
Fri, Jul 12 - Sun, Jul 21
9:25 am - 5:14 pmSYD-MDW
22h 49m2 stops
9:20 am - 6:35 amMDW-SYD
30h 15m2 stops
$1,800Delta
Find Deal
Mon, Aug 26 - Fri, Sep 13
9:25 am - 6:06 pmSYD-MDW
23h 41m2 stops
10:11 am - 6:35 amMDW-SYD
29h 24m2 stops
$1,801Delta
Find Deal
Sun, Sep 1 - Tue, Oct 1
9:40 pm - 5:50 amSYD-MDW
47h 10m2 stops
5:54 am - 6:15 amMDW-SYD
33h 21m1 stop
$2,252
Find Deal
Sun, Jun 2 - Sun, Jun 9
7:55 am - 12:43 pmSYD-MDW
43h 48m2 stops
6:00 am - 6:20 amMDW-SYD
33h 20m2 stops
$4,460Korean Air
Find Deal
Thu, Jun 13 - Sat, Jun 22

Flights from Sydney to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Sydney to Midway to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Sydney to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($1,201) and LATAM Airlines ($1,488). The cheapest round-trip tickets were found on Delta ($1,504) and Korean Air ($4,460).

Good to know

Cheapest flight

$625
Flight from Sydney to Chicago Midway Airport

When to book flights from Sydney to Midway

Are your dates flexible? Find out the best times to travel from Sydney to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Sydney to Chicago Midway Airport flights

  • What is the cheapest flight from Sydney to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Sydney to Chicago Midway Airport was $625 for a one-way ticket and $1,504 for a round-trip.

  • Do I need a passport to fly between Sydney and Chicago Midway Airport?

    Yes

  • Which aircraft models fly most regularly from Sydney to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Sydney to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Sydney and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Sydney to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Sydney to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Sydney to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Sydney is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Sydney to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Sydney with another airline. Booking your flights between Sydney and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Sydney to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Sydney up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Sydney to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Sydney to Chicago found on KAYAK in the last 72 hours.
5/24Fri
3 stops
48h 13mSYD-MDW
$625
5/24Fri
2 stops
32h 43mSYD-MDW
$638
6/18Tue
3 stops
40h 19mSYD-MDW
$743
6/18Tue
2 stops
41h 05mSYD-MDW
$786
9/16Mon
2 stopsDelta
38h 20mSYD-MDW
$1,201
5/31Fri
2 stopsDelta
27h 36mSYD-MDW
$1,222
10/13Sun
3 stopsLATAM Airlines
39h 23mSYD-MDW
$1,488
10/13Sun
1 stop
20h 12mSYD-MDW
$1,499
9/16Mon
3 stopsLATAM Airlines
39h 23mSYD-MDW
$1,790
10/13Sun
2 stopsKorean Air
43h 36mSYD-MDW
$3,037

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Last minute flights from Sydney to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Sydney to Chicago that are departing in the next 10 days.
5/6Mon
multi-stopDelta
22h 39mSYD-MDW
9/10Tue
multi-stopDelta
26h 25mMDW-SYD
$1,948
5/5Sun
multi-stopDelta
22h 39mSYD-MDW
9/18Wed
multi-stopDelta
26h 25mMDW-SYD
$1,997
5/5Sun
multi-stopDelta
23h 34mSYD-MDW
8/23Fri
multi-stopDelta
26h 25mMDW-SYD
$2,029
5/5Sun
multi-stop
28h 56mSYD-MDW
9/18Wed
multi-stop
42h 21mMDW-SYD
$2,349
5/6Mon
multi-stop
32h 01mSYD-MDW
8/20Tue
multi-stop
30h 45mMDW-SYD
$2,359
5/6Mon
multi-stop
32h 01mSYD-MDW
9/3Tue
multi-stop
41h 13mMDW-SYD
$2,392
5/5Sun
multi-stop
28h 56mSYD-MDW
8/23Fri
multi-stop
42h 21mMDW-SYD
$2,458

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Sydney - Chicago Midway Airport Flights

Departure:

Sydney (SYD)Australia

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Sydney

Cabin classes: