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$158+ 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 1/4. 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
26 Feb — 5 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 21 February 2025.

Cheapest airline

Qantas Airways
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,634).
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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 21 February 2025.

Wed 30/415:02MDW - SYD
2 stops24h 33mDelta
Sun 11/509:25SYD - MDW
2 stops24h 05mDelta
Deal found 21/2$1,450
Mon 7/411:15MDW - MEL
3 stops33h 40mMultiple Airlines
Mon 14/413:45MEL - MDW
3 stops35h 35mMultiple Airlines
Deal found 20/2$3,448
Sun 6/409:23MDW - BNE
2 stops30h 22mKorean Air
Tue 22/408:40BNE - MDW
2 stops42h 55mKorean Air
Deal found 20/2$3,507
Thu 3/409:23MDW - BNE
2 stops30h 22mMultiple Airlines
Sat 19/408:40BNE - MDW
2 stops42h 55mMultiple Airlines
Deal found 20/2$3,509
Sat 8/305:30MDW - SYD
2 stops32h 55mMultiple Airlines
Mon 17/311:50SYD - MDW
1 stop42h 09mMultiple Airlines
Deal found 21/2$3,639
Sat 7/615:45MDW - SYD
2 stops34h 30mLATAM Airlines
Fri 20/612:10SYD - MDW
2 stops36h 08mLATAM Airlines
Deal found 20/2$5,574
Sat 15/316:00MDW - MEL
2 stops45h 25mLATAM Airlines
Mon 31/313:00MEL - MDW
2 stops36h 09mLATAM Airlines
Deal found 20/2$5,832

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 21 February 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

Wed 30/4

15:02-06:35

2 stops24h 33m

Sydney Kingsford Smith

Sun 11/5

09:25-18:30

2 stops24h 05m

$1,450

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 7/4

11:15-11:55

3 stops33h 40m

Melbourne

Mon 14/4

13:45-10:20

3 stops35h 35m

$3,448

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sun 6/4

09:23-06:45

2 stops30h 22m

Brisbane

Tue 22/4

08:40-12:35

2 stops42h 55m

$3,507

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Thu 3/4

09:23-06:45

2 stops30h 22m

Brisbane

Sat 19/4

08:40-12:35

2 stops42h 55m

$3,509

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 8/3

05:30-07:25

2 stops32h 55m

Sydney Kingsford Smith

Mon 17/3

11:50-13:59

1 stop42h 09m

$3,639

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 7/6

15:45-17:15

2 stops34h 30m

Sydney Kingsford Smith

Fri 20/6

12:10-09:18

2 stops36h 08m

$5,574

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Sat 15/3

16:00-05:25

2 stops45h 25m

Melbourne

Mon 31/3

13:00-09:09

2 stops36h 09m

$5,832

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sat 29/3

06:40-21:35

3 stops47h 55m

$886

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 28/5

09:20-06:35

2 stops30h 15m

$1,315

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 28/2

20:14-19:45

2 stops30h 31m

$1,356

Flights are sorted by cheapest return flights first.

Deals found on 19/2

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.
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.
Delta
8.0
Very Good
8,217 reviews
Check prices

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very Good
8,217 reviews
Delta
8.0
Very Good
8,217 reviews
Check prices

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

LATAM Airlines
7.5
Good
1,794 reviews
Delta
8.0
Very Good
8,217 reviews
Check prices

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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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 21 February 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 21 February 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 Las Vegas, Atlanta, Miami. 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 $1,469 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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