$194+ Cheap flights from Chicago Midway Airport

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/9. 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.
MDW — SYD
21 ago — 28 ago1
1 adult

What to know about flights from Midway

Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 16 agosto 2025.

Cheapest airline

Qantas Airways

Good one-way deal

$172 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,471).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 16 agosto 2025.

dom 28/906:20MDW - SYD
2 stops33h 45mMultiple Airlines
sáb 11/1013:10SYD - MDW
2 stops26h 15mMultiple Airlines
Deal found 15/8$1,684
dom 28/906:20MDW - SYD
2 stops33h 45mMultiple Airlines
dom 5/1013:10SYD - MDW
2 stops26h 10mMultiple Airlines
Deal found 13/8$1,699
sáb 11/1017:20MDW - BNE
2 stops26h 05mMultiple Airlines
sáb 25/1011:40BNE - MDW
2 stops26h 40mMultiple Airlines
Deal found 15/8$2,053
seg 24/1110:35MDW - SYD
2 stops28h 55mDelta
dom 7/1210:40SYD - MDW
2 stops24h 27mDelta
Deal found 14/8$2,251
dom 2/1113:48MDW - SYD
2 stops25h 42mDelta
ter 18/1110:40SYD - MDW
2 stops24h 27mDelta
Deal found 12/8$2,252
qua 11/213:00MDW - SYD
2 stops26h 30mDelta
sex 27/210:40SYD - MDW
2 stops24h 54mDelta
Deal found 14/8$2,328
sex 7/1113:08MDW - SYD
2 stops26h 22mDelta
qua 19/1110:40SYD - MDW
2 stops24h 56mDelta
Deal found 12/8$2,329
seg 6/1013:08MDW - SYD
2 stops26h 27mDelta
dom 19/1010:25SYD - MDW
2 stops27h 49mDelta
Deal found 14/8$2,366
qui 1/110:08MDW - SYD
2 stops27h 42mDelta
sáb 17/110:40SYD - MDW
2 stops24h 54mDelta
Deal found 13/8$2,405
sex 7/1113:08MDW - SYD
2 stops26h 22mDelta
sex 21/1110:40SYD - MDW
2 stops24h 56mDelta
Deal found 12/8$2,406
seg 15/913:43MDW - SYD
2 stops25h 52mDelta
seg 6/1010:25SYD - MDW
2 stops23h 18mDelta
Deal found 13/8$2,481
qua 1/1012:43MDW - SYD
2 stops26h 52mDelta
qua 1/410:25SYD - MDW
2 stops23h 43mDelta
Deal found 15/8$2,483

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 16 agosto 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

dom 28/9

06:20-07:05

2 stops33h 45m

Sydney Kingsford Smith

sáb 11/10

13:10-23:25

2 stops26h 15m

$1,684

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

dom 28/9

06:20-07:05

2 stops33h 45m

Sydney Kingsford Smith

dom 5/10

13:10-23:20

2 stops26h 10m

$1,699

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

sáb 11/10

17:20-10:25

2 stops26h 05m

Brisbane

sáb 25/10

11:40-23:20

2 stops26h 40m

$2,053

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 26/1

13:05-08:30

2 stops26h 25m

Sydney Kingsford Smith

dom 8/2

10:40-18:08

2 stops24h 28m

$2,251

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 19/1

09:30-08:30

2 stops30h 00m

Sydney Kingsford Smith

dom 1/2

10:40-18:08

2 stops24h 28m

$2,251

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 9/2

09:30-08:30

2 stops30h 00m

Sydney Kingsford Smith

dom 22/2

10:40-18:08

2 stops24h 28m

$2,251

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 2/2

10:35-08:30

2 stops28h 55m

Sydney Kingsford Smith

dom 15/2

10:40-18:08

2 stops24h 28m

$2,251

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 24/11

13:05-08:30

2 stops26h 25m

Sydney Kingsford Smith

seg 15/12

10:40-21:44

2 stops28h 04m

$2,251

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 3/11

13:08-08:30

2 stops26h 22m

Sydney Kingsford Smith

dom 16/11

10:40-18:07

2 stops24h 27m

$2,251

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

seg 25/8

15:25-05:00

1 stop22h 35m

Melbourne

seg 8/9

15:05-20:52

1 stop20h 47m

$2,609

Flights are sorted by cheapest return flights first.

Deals found on 13/8

Showing 1-10 of 34 results
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Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

What are popular destinations to fly to from Chicago Midway Airport?

Chicago Midway Airport offers frequent flights to Detroit (230 flights per day), Atlanta (171 flights per day) and Orlando (92 flights per day).

Tucson
Tucson
From $112

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Tucson, with prices starting at $172. Explore other affordable destinations below.

Tucson
Tucson
From $112

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Alternate flight departure points to Midway

Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 16 agosto 2025.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
Flights from Bloomington
Flights from Peoria
Flights from Moline
Flights from Springfield

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 16 agosto 2025.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    For the current month, the most popular flights from Chicago Midway Airport are Atlanta, Las Vegas, Orlando Airport. Atlanta, Las Vegas, Cancún are the most popular locations from Chicago Midway Airport year round.

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

    Users have flown out of Chicago Midway Airport for as low as $172 to Tucson (prices may vary depending on the airline and departure time). On average, users have booked flights for $172 to fly from Chicago Midway Airport.

  • How does Cheapflights help users find flights from Midway?

    Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

  • Why should you use Cheapflights to find cheap flight tickets from Midway?

    Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway for you. Better yet — we are completely free to use.

  • Can Cheapflights find flights from Midway with no change fees?

    Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway, users can toggle the no change fees filter when performing a flight search.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Of course! You can now track prices for flights from Midway and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Midway?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Midway with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Of course! You can now track prices for flights from Midway and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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