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$164+ 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 8/7. 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
18 jun — 25 jun1
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 13 junho 2025.

Cheapest airline

Spirit Airlines

Good one-way deal

$197 or less
On average, Spirit Airlines currently has the cheapest one-way flight from Chicago Midway (avg. price of $185).
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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 13 junho 2025.

dom 3/813:46MDW - SYD
2 stops25h 49mDelta
ter 19/809:25SYD - MDW
2 stops24h 12mDelta
Deal found 12/6$2,249
qui 9/1009:30MDW - BNE
2 stops30h 15mMultiple Airlines
dom 19/1008:30BNE - MDW
2 stops28h 14mMultiple Airlines
Deal found 12/6$3,726
qui 9/1009:30MDW - BNE
2 stops30h 15mKorean Air
dom 19/1008:30BNE - MDW
2 stops28h 14mKorean Air
Deal found 11/6$3,727
sáb 15/1116:25MDW - SYD
2 stops45h 30mKorean Air
seg 1/1209:10SYD - MDW
2 stops53h 34mKorean Air
Deal found 12/6$3,892
seg 20/1009:30MDW - SYD
2 stops29h 50mMultiple Airlines
qua 5/1109:10SYD - MDW
2 stops29h 34mMultiple Airlines
Deal found 12/6$4,197
qua 9/711:39MDW - MEL
2 stops52h 06mMultiple Airlines
qua 16/715:05MEL - MDW
1 stop37h 24mMultiple Airlines
Deal found 11/6$4,214
qui 25/913:05MDW - SYD
2 stops37h 10mLATAM Airlines
seg 6/1012:50SYD - MDW
3 stops37h 01mLATAM Airlines
Deal found 12/6$5,239
qua 25/609:21MDW - SYD
2 stops30h 14mWestJet
sáb 28/620:30SYD - MDW
2 stops36h 10mWestJet
Deal found 11/6$15,136

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 13 junho 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

qua 10/9

13:08-06:35

2 stops26h 27m

Sydney Kingsford Smith

qua 24/9

09:25-21:44

2 stops27h 19m

$2,249

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

qui 9/10

09:30-06:45

2 stops30h 15m

Brisbane

dom 19/10

08:30-21:44

2 stops28h 14m

$3,726

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

qui 9/10

09:30-06:45

2 stops30h 15m

Brisbane

dom 19/10

08:30-21:44

2 stops28h 14m

$3,727

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

sáb 15/11

16:25-06:55

2 stops45h 30m

Sydney Kingsford Smith

seg 1/12

09:10-21:44

2 stops53h 34m

$3,892

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

seg 20/10

09:30-07:20

2 stops29h 50m

Sydney Kingsford Smith

qua 5/11

09:10-21:44

2 stops29h 34m

$4,197

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

qua 9/7

11:39-06:45

2 stops52h 06m

Melbourne

qua 16/7

15:05-13:29

1 stop37h 24m

$4,214

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

qui 25/9

13:05-17:15

2 stops37h 10m

Sydney Kingsford Smith

seg 6/10

12:50-09:51

3 stops37h 01m

$5,239

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

qua 25/6

09:21-06:35

2 stops30h 14m

Sydney Kingsford Smith

sáb 28/6

20:30-17:40

2 stops36h 10m

$15,136

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

qui 28/8

11:00-07:30

2 stops29h 30m

$966

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

ter 8/7

18:02-22:45

3 stops37h 43m

$1,059

Flights are sorted by cheapest return flights first.

Deals found on 11/6

Showing 1-10 of 13 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.

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

Chicago Midway Airport offers frequent flights to Detroit (216 flights per day), Atlanta (200 flights per day) and Minneapolis (112 flights per day).

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From $128

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

The cheapest city to fly to from Chicago Midway Airport is Las Vegas Harry Reid Intl, with prices starting at $197. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From $128

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
1,091 reviews
Check prices

Overall

8.4

Entertainment

8.2

Food

8.1

Boarding

8.5

Comfort

8.3

Crew

8.7

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
1,091 reviews
Korean Air
8.4
Very Good
1,091 reviews
Check prices

Overall

8.4

Entertainment

8.2

Food

8.1

Boarding

8.5

Comfort

8.3

Crew

8.7

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
7,950 reviews
Korean Air
8.4
Very Good
1,091 reviews
Check prices

Overall

8.4

Entertainment

8.2

Food

8.1

Boarding

8.5

Comfort

8.3

Crew

8.7

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
1,785 reviews
Korean Air
8.4
Very Good
1,091 reviews
Check prices

Overall

8.4

Entertainment

8.2

Food

8.1

Boarding

8.5

Comfort

8.3

Crew

8.7

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
2,869 reviews
Korean Air
8.4
Very Good
1,091 reviews
Check prices

Overall

8.4

Entertainment

8.2

Food

8.1

Boarding

8.5

Comfort

8.3

Crew

8.7

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 13 junho 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 13 junho 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 Cancún, 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 $197 to Las Vegas (prices may vary depending on the airline and departure time). On average, users have booked flights for $197 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 $1,604 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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