R2 531+ 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 21/4. 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 — CPT
Mrz 22 — Mrz 291
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 20 Februar 2026.

Good one-way deal

R4 613 or less
Price to beat on a one-way flight from Chicago Midway.
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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 20 Februar 2026.

Do 19/312:47
MDW
-
CPT
1 stop23h 28m
Virgin Atlantic
So 29/320:05
CPT
-
MDW
1 stop28h 17m
Virgin Atlantic
Deal found 16/2R25 195
Do 19/39:35
MDW
-
CPT
2 stops26h 40m
Delta
So 29/320:05
CPT
-
MDW
1 stop28h 17m
Delta
Deal found 16/2R25 420
Sa 21/316:30
MDW
-
CPT
1 stop19h 45m
Delta
So 5/420:05
CPT
-
MDW
1 stop22h 57m
Delta
Deal found 18/2R25 743
Sa 21/39:35
MDW
-
CPT
2 stops26h 40m
Delta
Fr 3/420:05
CPT
-
MDW
1 stop20h 51m
Delta
Deal found 18/2R25 807
Mo 9/318:07
MDW
-
CPT
1 stop18h 08m
Delta
So 12/420:05
CPT
-
MDW
1 stop33h 23m
Delta
Deal found 19/2R25 823
Sa 21/316:30
MDW
-
CPT
1 stop19h 45m
Delta
Di 7/423:15
CPT
-
MDW
2 stops30h 16m
Delta
Deal found 18/2R26 404
Di 24/312:47
MDW
-
CPT
2 stops26h 08m
Delta
Fr 3/420:05
CPT
-
MDW
1 stop20h 51m
Delta
Deal found 18/2R26 420
Sa 11/416:30
MDW
-
JNB
1 stop20h 10m
Delta
Mo 20/421:55
JNB
-
MDW
1 stop21h 12m
Delta
Deal found 19/2R28 402
So 3/517:21
MDW
-
JNB
1 stop19h 19m
Delta
Di 19/521:55
JNB
-
MDW
1 stop21h 01m
Delta
Deal found 16/2R28 418
Sa 7/316:13
MDW
-
JNB
1 stop18h 47m
Delta
Di 7/421:55
JNB
-
MDW
1 stop21h 07m
Delta
Deal found 16/2R28 483
Mo 16/310:45
MDW
-
CPT
1 stop25h 30m
Multiple Airlines
Do 9/49:55
CPT
-
MDW
2 stops38h 27m
Multiple Airlines
Deal found 18/2R28 628
Sa 11/413:10
MDW
-
JNB
2 stops25h 10m
KLM
Mo 20/423:15
JNB
-
MDW
2 stops26h 21m
KLM
Deal found 19/2R28 854

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 20 Februar 2026. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

Cape Town

Route

Depart

Return

Price

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Do 19/3

9:35-19:15

2 stops26h 40m

Cape Town Intl

So 29/3

20:05-17:22

1 stop28h 17m

R25 420

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mo 23/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Fr 3/4

20:05-9:56

1 stop20h 51m

R25 743

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mi 25/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Fr 3/4

20:05-9:56

1 stop20h 51m

R25 743

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sa 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

So 5/4

20:05-12:02

1 stop22h 57m

R25 743

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mi 25/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

So 5/4

20:05-9:56

1 stop20h 51m

R25 743

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sa 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

Fr 3/4

20:05-9:56

1 stop20h 51m

R25 743

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

So 22/3

14:05-19:15

2 stops22h 10m

Cape Town Intl

So 5/4

20:05-9:56

1 stop20h 51m

R25 807

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mo 9/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

So 12/4

20:05-22:28

1 stop33h 23m

R25 823

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sa 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

Di 7/4

23:15-22:31

2 stops30h 16m

R26 404

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sa 11/4

10:45-19:40

1 stop25h 55m

Johannesburg OR Tambo

So 19/4

21:55-16:26

1 stop25h 31m

R28 402

Flights are sorted by cheapest return flights first.

Deals found on 17/2

Showing 1-10 of 38 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?

From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (186 flights per day), Atlanta (169 flights per day) and Orlando (114 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 613

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

The cheapest city to fly to from Chicago Midway Airport is Atlanta Hartsfield-Jackson, with prices starting at R4 613. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 613

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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 20 Februar 2026.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
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 20 Februar 2026.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    The most selected flight destinations from Chicago Midway Airport for the current month are Atlanta, Phoenix Sky Harbor Intl Airport, Orlando Airport. While Atlanta, Las Vegas, Orlando Airport are the top choices made by travellers 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 R4 613 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 613 to fly from Chicago Midway Airport.

  • What is the cheapest first class flight from Chicago Midway Airport?

    If you’re looking to fly first-class from Chicago Midway Airport to anywhere, put Minneapolis on your list as prices start at R8 640 for this destination.

  • 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 helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Midway with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Midway flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Not ready to book yet? You can track prices for flights from Midway on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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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 helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Not ready to book yet? You can track prices for flights from Midway on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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