$614+ Cheap flights to Midway

— MDW
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Midway Airport

Thu 26/1110:40 -
2 stops29h 14m
Thu 3/1213:41 -
2 stops25h 49m
Deal found 26/10$2,823
Thu 29/1009:40 -
2 stops22h 34m
Wed 11/1113:05 -
2 stops26h 25m
Deal found 27/10$2,891
Mon 9/1110:40 -
2 stops29h 14m
Thu 12/1112:30 -
2 stops27h 00m
Deal found 26/10$2,972
Mon 2/1108:45 -
2 stops43h 37m
Mon 16/1112:20 -
1 stop25h 35m
Deal found 28/10$3,157
Mon 2/1108:45 -
2 stops43h 37m
Mon 9/1112:20 -
1 stop25h 35m
Deal found 26/10$3,282
Thu 29/1011:50 -
2 stops39h 35m
Wed 11/1112:27 -
1 stop25h 28m
Deal found 27/10$3,317
Mon 2/1111:15 -
2 stops29h 32m
Sun 15/1112:30 -
1 stop25h 25m
Deal found 28/10$3,457
Mon 9/1114:05 -
1 stop38h 17m
Thu 12/1112:20 -
1 stop25h 35m
Deal found 26/10$3,547

Find flight deals to Midway Airport

Return from

$1,043

One-way from

$614

Popular in

May

Cheapest in

October

Average price

$1,540
American Airlines
  • American Airlines
  • 17/11-2/12
  • 2 total stops
  • 48h 25m total
  • Sydney to Chicago
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Delta
  • Delta
  • 9/11-31/12
  • 2 total stops
  • 24h 24m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($148 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($49 potential savings vs. average return price).
Search Deals
Average for return flights in October 2026
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Cheapflights Fare Finder

 
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 Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 22/1

08:45-12:13

2 stops44h 28m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,246

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 5/3

14:00-11:41

3 stops38h 41m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,250

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 6/12

21:40-16:06

3 stops35h 26m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,397

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 27/1

10:40-23:55

2 stops30h 15m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,544

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 14/4

09:15-18:37

2 stops24h 22m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,544

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 10/12

22:20-09:45

2 stops52h 25m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,614
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 5/12

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,786

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 10/2

14:05-23:46

2 stops26h 41m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,814

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 19/1

10:40-16:54

2 stops23h 14m

Chicago Midway

Tue 26/1

09:56-06:50

2 stops27h 54m

$2,448

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 28/1

10:40-16:53

2 stops23h 13m

Chicago Midway

Tue 9/2

12:44-08:30

2 stops26h 46m

$2,448

Flights are sorted by cheapest return flights first.

Deals found on 25/10

Showing 1-10 of 20 resultsSorted by cheapest first
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Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

Rainfall in Midway by month

In terms of precipitation, rainfall in Midway ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Midway when rainfall is around 43.0 mm.

Temperature in Midway by month

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

How long is the flight to Midway?

On average, a flight from Sydney to Midway takes 22 hours 34 minutes. Flights to Midway from other popular cities in Australia will vary in length. Below are a few examples of popular routes and their flight times.

FAQs about flying to Midway

  • Can I find cheaper flights to Midway if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost $310, while return flights cost around $230.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $244, however they can be found for as little as $230.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Sydney Kingsford Smith offers the quickest one-way flight (22 hours 34 minutes).

  • Does Chicago Midway have car hire?

    Yes. Those touching down at Chicago Midway can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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Certainly. Search results for flights to Midway shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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