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$189+ 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 19/4. 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
11 Mar — 18 Mar1
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 6 March 2025.

Cheapest airline

Qantas Airways
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,533).
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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 6 March 2025.

Thu 3/416:31MDW - MEL
2 stops27h 59mMultiple Airlines
Thu 10/412:55MEL - MDW
2 stops24h 32mMultiple Airlines
Deal found 6/3$1,365
Wed 20/814:00MDW - SYD
2 stops25h 35mDelta
Wed 3/909:25SYD - MDW
2 stops23h 38mDelta
Deal found 6/3$1,507
Thu 17/410:19MDW - SYD
2 stops29h 46mMultiple Airlines
Thu 24/409:10SYD - MDW
2 stops24h 56mMultiple Airlines
Deal found 5/3$1,992
Sat 5/416:00MDW - BNE
2 stops47h 45mKorean Air
Sat 19/408:40BNE - MDW
2 stops42h 55mKorean Air
Deal found 6/3$3,583
Thu 3/409:23MDW - BNE
2 stops30h 22mMultiple Airlines
Sat 19/408:40BNE - MDW
2 stops28h 42mMultiple Airlines
Deal found 5/3$3,643
Tue 25/316:59MDW - SYD
2 stops45h 56mKorean Air
Sun 30/309:10SYD - MDW
2 stops43h 26mKorean Air
Deal found 5/3$4,340
Sat 12/416:00MDW - SYD
2 stops47h 45mLATAM Airlines
Sat 26/411:50SYD - MDW
3 stops36h 17mLATAM Airlines
Deal found 6/3$5,910
Fri 25/410:20MDW - SYD
2 stops53h 10mWestJet
Sat 3/520:30SYD - MDW
2 stops27h 37mWestJet
Deal found 5/3$10,018

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 6 March 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Thu 3/4

16:31-12:30

2 stops27h 59m

Melbourne

Thu 10/4

12:55-22:27

2 stops24h 32m

$1,365

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 20/8

14:00-06:35

2 stops25h 35m

Sydney Kingsford Smith

Wed 3/9

09:25-18:03

2 stops23h 38m

$1,507

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 17/4

10:19-07:05

2 stops29h 46m

Sydney Kingsford Smith

Thu 24/4

09:10-19:06

2 stops24h 56m

$1,992

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sat 5/4

16:00-06:45

2 stops47h 45m

Brisbane

Sat 19/4

08:40-12:35

2 stops42h 55m

$3,583

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Thu 3/4

09:23-06:45

2 stops30h 22m

Brisbane

Sat 19/4

08:40-22:22

2 stops28h 42m

$3,643

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 25/3

16:59-06:55

2 stops45h 56m

Sydney Kingsford Smith

Sun 30/3

09:10-12:36

2 stops43h 26m

$4,340

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 12/4

16:00-06:45

2 stops47h 45m

Sydney Kingsford Smith

Sat 26/4

11:50-09:07

3 stops36h 17m

$5,910

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 25/4

10:20-06:30

2 stops53h 10m

Sydney Kingsford Smith

Sat 3/5

20:30-09:07

2 stops27h 37m

$10,018

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Tue 15/4

07:50-11:30

2 stops36h 40m

$687

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 5/4

06:00-12:45

2 stops38h 45m

$773

Flights are sorted by cheapest return flights first.

Deals found on 5/3

Showing 1-10 of 15 results
1
2

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.
No data available for this route at this time. Please check back soon.

Airline reviews for flights from Midway

Get insights into the airlines that provide service from Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Midway. In the last 7 days, Cheapflights users made a total of 647,157 searches.
Korean Air
8.4
Very Good
1,034 reviews
Check prices

Entertainment

8.2

Overall

8.4

Crew

8.7

Food

8.1

Comfort

8.3

Boarding

8.5

Reviews

1 / 20

10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

Korean Air
8.4
Very Good
1,034 reviews
Korean Air
8.4
Very Good
1,034 reviews
Check prices

Entertainment

8.2

Overall

8.4

Crew

8.7

Food

8.1

Comfort

8.3

Boarding

8.5

Reviews

1 / 20

10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

Delta
8.0
Very Good
8,036 reviews
Korean Air
8.4
Very Good
1,034 reviews
Check prices

Entertainment

8.2

Overall

8.4

Crew

8.7

Food

8.1

Comfort

8.3

Boarding

8.5

Reviews

1 / 20

10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

LATAM Airlines
7.5
Good
1,762 reviews
Korean Air
8.4
Very Good
1,034 reviews
Check prices

Entertainment

8.2

Overall

8.4

Crew

8.7

Food

8.1

Comfort

8.3

Boarding

8.5

Reviews

1 / 20

10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

WestJet
7.2
Good
2,785 reviews
Korean Air
8.4
Very Good
1,034 reviews
Check prices

Entertainment

8.2

Overall

8.4

Crew

8.7

Food

8.1

Comfort

8.3

Boarding

8.5

Reviews

1 / 20

10.0
Excellent

Chris,Mar 2025

SEA - ICN

Was told the flight was overbooked so they selected only a few people to weight their bags and we were forced to check our luggage. We Once we got seated on the flight there were many seats vacant and our overhead bin was completely open. Both our luggage and our carryon were small. We had booked our tickets months in advance and we watched people carry two small suitcases on without one word to them. Am I upset?? Yes it was disappointing.

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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 6 March 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 6 March 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 Orlando Airport, Las Vegas, Phoenix Sky Harbor Intl Airport. Las Vegas, Atlanta, Orlando Airport are the most popular locations from Chicago Midway Airport year round.

  • 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 $1,539 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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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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