The cheapest times to fly from SYD to MDW are

  • January 22nd to March 11th
  • April 23rd to May 6th
  • May 21st to June 3rd
  • July 23rd to September 16th

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from SYD to MDW is mid October. Prices can be as high as $2453 for Friday flights during early January, or as low as $929 for Tuesday flights around mid October.


When to Fly to Chicago

Flying from Sydney (SYD) to Chicago, IL (MDW) will usually cost between $953 to $1842 per person if booking more than four weeks in advance. On average the very cheapest time to fly is mid October with an average ticket price of $955. Due to high demand the most expensive time to fly is early January, with an average price of $2263. Planning your trip to low-cost times can easily save you $1308 on economy flights and even more on first-class flights. Generally, any price below $1132 can be considered a good price for a round-trip SYD to MDW flight.

See below for a graph of average weekly prices for the SYD to MDW route. All prices are for round-trip tickets in USD.

SYD to MDW Flight Prices

Compared to other flights, the SYD to MDW flight is slightly more expensive than the average and costs slightly more than the average flight leaving from Sydney. The average price per mile (for a direct flight) is $0.08, which is far below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Fridays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $155 (10%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $1138. Return trip prices are from the MDW to SYD flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from SYD to MDW can generally find a 2-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 17 hour 37 minutes may not be realistic.


Alternative Nearby Airports

Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is not usually a nonstop flight from SYD to MDW while comparing.

Destination alternative #1: Chicago O’Hare International Airport (ORD) in Chicago, IL

  • 15 miles (24 km) away from MDW
  • Usually 15.59% less expensive than MDW
  • 1-layover flights available

See SYD to ORD flights

Destination alternative #2: General Mitchell International Airport (MKE) in Milwaukee, WI

  • 81 miles (130 km) away from MDW
  • Usually 14.66% less expensive than MDW
  • 1-layover flights available

See SYD to MKE flights


Flight Hacking SYD to MDW

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from SYD to MDW — but Champion Traveler does!

Hack #1: Los Angeles, CA (SYD > LAX > MDW)

  • Price for both tickets: $1013
  • Average savings: $120 (10.56%)

See SYD to SFO flights

Hack #2: San Francisco, CA (SYD > SFO > MDW)

  • Price for both tickets: $1121
  • Average savings: $11 (0.97%)

See SYD to LAX flights


Flight Questions Answered

Still have questions about flying from SYD to MDW? We’ve got answers.

Which airlines fly this route?

You can find 4 major airlines flying this route most often: Delta, United, Virgin Atlantic, Virgin Australia, and potentially more during busy seasons.

How far away is it from Chicago Midway International Airport to Sydney International Airport?

The distance between the two airports is roughly 9238 miles or 14867 kilometers.

How long does it take to fly from SYD to MDW?

The real-world flight time for a nonstop SYD to MDW flight is about 17 hour 37 minutes.

How many flights go between Sydney and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 32 available flights from SYD to MDW.


Airport Location Info


Departing Airport

Origination codeSYD
Origination airport nameSydney International Airport

Return Airport

Destination codeMDW
Destination airport nameChicago Midway International Airport
CityChicago, IL
Countrythe United States


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.