$223+ 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 3/3. 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
1 мар. — 8 мар.1
1 adult
1 adult, Economy, 0 bags

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 30 января 2026.

Cheapest airline

Qantas Airways

Good one-way deal

$97 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,232).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Enter your travel dates to find the best prices.

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 30 января 2026.

вт. 24/218:40
MDW
-
BNE
2 stops45h 40m
Delta
ср. 11/310:05
BNE
-
MDW
2 stops22h 17m
Delta
Deal found 28/1$1,677
ср. 11/312:47
MDW
-
MEL
2 stops26h 13m
Delta
вс. 22/309:10
MEL
-
MDW
2 stops29h 21m
Delta
Deal found 28/1$1,966
вт. 24/213:26
MDW
-
SYD
2 stops26h 04m
Delta
вс. 8/310:40
SYD
-
MDW
2 stops22h 42m
Delta
Deal found 28/1$1,966
вс. 12/714:00
MDW
-
SYD
2 stops25h 50m
Delta
ср. 22/709:15
SYD
-
MDW
2 stops23h 50m
Delta
Deal found 29/1$1,968
сб. 14/209:15
MDW
-
SYD
2 stops29h 10m
Multiple Airlines
пт. 20/211:20
SYD
-
MDW
2 stops29h 21m
Multiple Airlines
Deal found 29/1$2,036
пт. 13/310:45
MDW
-
MEL
2 stops28h 15m
Delta
вс. 22/309:10
MEL
-
MDW
2 stops24h 44m
Delta
Deal found 29/1$2,037
вс. 22/212:45
MDW
-
SYD
2 stops25h 05m
Delta
пт. 6/310:40
SYD
-
MDW
2 stops23h 57m
Delta
Deal found 28/1$2,037
пн. 23/208:15
MDW
-
SYD
1 stop29h 40m
Multiple Airlines
сб. 7/314:00
SYD
-
MDW
2 stops23h 21m
Multiple Airlines
Deal found 28/1$2,039
пт. 27/207:45
MDW
-
SYD
2 stops30h 40m
Multiple Airlines
пт. 6/311:20
SYD
-
MDW
2 stops42h 48m
Multiple Airlines
Deal found 28/1$2,043
сб. 14/321:16
MDW
-
SYD
1 stop41h 39m
Multiple Airlines
сб. 21/314:00
SYD
-
MDW
2 stops22h 21m
Multiple Airlines
Deal found 28/1$2,087
вт. 10/212:46
MDW
-
SYD
2 stops25h 04m
Delta
вт. 17/313:15
SYD
-
MDW
2 stops25h 16m
Delta
Deal found 28/1$2,090
пт. 17/413:23
MDW
-
SYD
2 stops26h 27m
Delta
сб. 25/409:15
SYD
-
MDW
2 stops28h 13m
Delta
Deal found 28/1$2,108

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 30 января 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

вт. 24/2

18:40-08:20

2 stops45h 40m

Brisbane

ср. 11/3

10:05-17:22

2 stops22h 17m

$1,677

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

ср. 11/3

12:47-07:00

2 stops26h 13m

Melbourne

вс. 22/3

09:10-22:31

2 stops29h 21m

$1,966

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

пн. 16/3

10:45-07:00

2 stops28h 15m

Melbourne

ср. 25/3

09:10-17:22

2 stops24h 12m

$1,966

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

вс. 15/3

18:07-07:00

2 stops44h 53m

Melbourne

вс. 22/3

09:10-18:40

2 stops25h 30m

$1,966

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

ср. 29/4

12:53-07:50

2 stops27h 57m

Melbourne

вс. 31/5

10:00-18:31

2 stops23h 31m

$1,966

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

вс. 1/3

19:20-08:00

2 stops43h 40m

Melbourne

вс. 8/3

10:10-17:40

2 stops24h 30m

$1,966

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

вт. 26/5

13:05-06:50

2 stops26h 45m

Sydney Kingsford Smith

ср. 10/6

09:15-18:31

2 stops24h 16m

$1,966

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

пн. 16/3

12:47-07:25

2 stops26h 38m

Sydney Kingsford Smith

ср. 25/3

09:40-17:54

2 stops24h 14m

$1,968

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

пн. 22/6

13:00-06:50

2 stops26h 50m

Sydney Kingsford Smith

пн. 6/7

09:15-18:31

2 stops24h 16m

$1,968

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

пн. 23/2

12:45-08:30

2 stops26h 45m

Sydney Kingsford Smith

вс. 8/3

10:40-17:40

2 stops24h 00m

$1,968

Flights are sorted by cheapest return flights first.

Deals found on 28/1

Showing 1-10 of 42 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 (178 flights per day), Atlanta (176 flights per day) and Orlando (80 flights per day).

New York
New York
From $241
Toronto
Toronto
From $97

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

The cheapest city to fly to from Chicago Midway Airport is Toronto, with prices starting at $97. Explore other affordable destinations below.

Toronto
Toronto
From $97
New York
New York
From $241

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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 30 января 2026.
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 30 января 2026.

  • 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 Cancún, Atlanta, Miami. Atlanta, Las Vegas, Orlando Airport 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 $97 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $169 to fly from Chicago Midway Airport.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    View the cheapest flight destinations from Chicago Midway Airport:
    Fly from Chicago to Sydney from $1,404 round trip

  • 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

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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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