Find flights
Airlines

$150+ 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 14/8. 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
6 Jul — 13 Jul1
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 1 July 2025.

Cheapest airline

Spirit Airlines
On average, Spirit Airlines currently has the cheapest one-way flight from Chicago Midway (avg. price of $184).
Search Deals

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 1 July 2025.

Thu 14/807:40MDW - BNE
2 stops35h 45mMultiple Airlines
Thu 21/811:40BNE - MDW
2 stops25h 11mMultiple Airlines
Deal found 30/6$1,720
Thu 14/807:40MDW - MEL
2 stops37h 20mMultiple Airlines
Thu 21/813:30MEL - MDW
2 stops23h 21mMultiple Airlines
Deal found 30/6$1,772
Mon 8/1210:35MDW - MEL
2 stops28h 25mDelta
Sun 21/1210:10MEL - MDW
2 stops24h 27mDelta
Deal found 30/6$2,212
Wed 10/913:43MDW - SYD
2 stops25h 52mDelta
Tue 23/909:25SYD - MDW
2 stops23h 10mDelta
Deal found 30/6$2,237
Tue 21/1006:00MDW - BNE
2 stops33h 45mKorean Air
Tue 28/1008:40BNE - MDW
2 stops52h 04mKorean Air
Deal found 30/6$3,324
Thu 14/820:38MDW - SYD
2 stops32h 07mMultiple Airlines
Thu 21/812:10SYD - MDW
1 stop24h 41mMultiple Airlines
Deal found 30/6$3,338
Mon 27/1017:25MDW - SYD
2 stops45h 30mKorean Air
Thu 20/1109:10SYD - MDW
2 stops43h 45mKorean Air
Deal found 29/6$3,419

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 1 July 2025. 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

Thu 14/8

07:40-10:25

2 stops35h 45m

Brisbane

Thu 21/8

11:40-21:51

2 stops25h 11m

$1,720

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Thu 14/8

07:40-12:00

2 stops37h 20m

Melbourne

Thu 21/8

13:30-21:51

2 stops23h 21m

$1,772

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 8/12

09:30-08:00

2 stops29h 30m

Melbourne

Sun 21/12

10:10-17:37

2 stops24h 27m

$2,212

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 10/9

13:43-06:35

2 stops25h 52m

Sydney Kingsford Smith

Tue 23/9

09:25-17:35

2 stops23h 10m

$2,237

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Tue 21/10

06:00-06:45

2 stops33h 45m

Brisbane

Tue 28/10

08:40-21:44

2 stops52h 04m

$3,324

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 14/8

20:38-19:45

2 stops32h 07m

Sydney Kingsford Smith

Thu 21/8

12:10-21:51

1 stop24h 41m

$3,338

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 27/10

17:25-06:55

2 stops45h 30m

Sydney Kingsford Smith

Thu 20/11

09:10-11:55

2 stops43h 45m

$3,419

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 28/7

16:01-09:25

2 stops50h 24m

$865

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Fri 15/8

16:00-06:45

2 stops47h 45m

$1,212

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/9

09:30-06:35

2 stops30h 05m

$1,451

Flights are sorted by cheapest return flights first.

Deals found on 29/6

Showing 1-10 of 16 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.
See what other customers who have flown with Korean Air and Delta from Chicago Midway Airport have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Korean Air
8.4
Very Good
1,101 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.4

Food

8.1

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
1,101 reviews
Korean Air
8.4
Very Good
1,101 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.4

Food

8.1

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
7,973 reviews
Korean Air
8.4
Very Good
1,101 reviews
Check prices

Comfort

8.3

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.4

Food

8.1

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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 1 July 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 1 July 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 Punta Cana, Las Vegas, Atlanta. Atlanta, Las Vegas, Cancún 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 $1,468 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.

See more FAQs

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights