Cheap flights from Sydney to Chicago Midway Airport

SYD — MDW
17 Aug — 24 Aug1
Return
1 adult
Economy
From?
To?
Wed 17/8
Wed 24/8

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How far in advance should I book a flight from Sydney to Chicago Midway Airport?

To save on the cost of your flight from Sydney to Chicago Midway Airport, book at least 61 days before your planned departure. Booking around this time can save you about 16% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $2,591 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $2,591.

What is the cheapest month to fly from Sydney to Chicago Midway Airport?

Flights from Sydney to Chicago Midway Airport lean towards being more expensive in August. Prices are generally better when you fly from Sydney to Chicago Midway Airport in May, with the cheapest ticket starting at $1,619.

When is the cheapest time to fly from Sydney to Chicago Midway Airport (SYD - MDW)?

When flying from Sydney to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Sydney to Midway in August, September 2022

The best prices found for SYD to MDW flights in August, September
30 Sep. - 28 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

45h 34m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

45h 35m
$2,302

Virgin Atlantic

Pick Dates

Deal found 10/8/22

7 Sep. - 14 Sep.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

25h 25m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

26h 06m
$2,730

Multiple Airlines

Pick Dates

Deal found 10/8/22

30 Sep. - 28 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

1 stop

40h 46m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

1 stop

21h 56m
$4,622

Multiple Airlines

Pick Dates

Deal found 10/8/22

Sydney to Midway 2022 flight deals

Cheap flights to Midway from Sydney found for this year
4 Oct. - 31 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 05m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

30h 04m
$2,186

Delta

Pick Dates

Deal found 10/8/22

4 Oct. - 25 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 05m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

26h 05m
$2,200

Delta

Pick Dates

Deal found 11/8/22

4 Oct. - 27 Nov.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 05m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

26h 25m
$2,260

Delta

Pick Dates

Deal found 10/8/22

Cheap Delta flights from Sydney to Midway

4 Oct. - 31 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 05m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

30h 04m
$2,186

Delta

Pick Dates

Deal found 10/8/22

4 Oct. - 25 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 05m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

26h 05m
$2,200

Delta

Pick Dates

Deal found 11/8/22

19 Oct. - 31 Oct.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

2 stops

26h 12m
MDW

Chicago Midway

SYD

Sydney Kingsford Smith

2 stops

30h 04m
$2,224

Delta

Pick Dates

Deal found 12/8/22

One-way flights to Midway from Sydney

The cheapest one-way flights from Sydney to Midway
7 Sep.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

3 stops

40h 44m
$937

Multiple Airlines

Pick Dates

Deal found 11/8/22

9 Sep.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

3 stops

40h 14m
$962

Multiple Airlines

Pick Dates

Deal found 11/8/22

11 Sep.
SYD

Sydney Kingsford Smith

MDW

Chicago Midway

3 stops

40h 14m
$1,047

Multiple Airlines

Pick Dates

Deal found 11/8/22

Related info for your journey

Useful info, stats and facts about Sydney to Midway flights.

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. 1 airline has flights to Chicago Midway from Sydney Kingsford Smith on a regular basis.

Which airlines flying from Sydney Kingsford Smith to Chicago Midway have flexible changes due to COVID-19?

Virgin Atlantic is one of the carriers that may have flexible change policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Sydney to Chicago Midway Airport for under $2,200 on Cheapflights?

Yes, there are multiple flights from Sydney to Chicago Midway Airport for under $2,200. The cheapest flight booked recently is on Delta for just $2,186, but on average you can expect to pay $2,667.

Other flights from Sydney

Alternative routes for Sydney to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Sydney to O'Hare Intlfrom $1,249 pp