R1 983+ 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 25/4. 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 — JNB
Mar 6 — Mar 131
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 4 February 2026.

Good one-way deal

R4 577 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 4 February 2026.

Thu 19/210:49
MDW
-
CPT
1 stop24h 26m
Delta
Thu 26/221:30
CPT
-
MDW
1 stop20h 24m
Delta
Deal found 3/2R21 992
Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Fri 13/321:30
CPT
-
MDW
1 stop24h 55m
Delta
Deal found 2/2R22 008
Sun 22/318:07
MDW
-
CPT
1 stop18h 08m
Delta
Thu 2/420:25
CPT
-
MDW
2 stops28h 29m
Delta
Deal found 2/2R26 390
Mon 9/312:47
MDW
-
CPT
1 stop23h 28m
Delta
Thu 26/321:30
CPT
-
MDW
1 stop21h 32m
Delta
Deal found 2/2R27 734
Thu 2/410:45
MDW
-
JNB
1 stop25h 55m
Virgin Atlantic
Sat 18/421:55
JNB
-
MDW
1 stop25h 34m
Virgin Atlantic
Deal found 3/2R28 182
Thu 2/418:07
MDW
-
JNB
1 stop18h 33m
Virgin Atlantic
Fri 17/421:55
JNB
-
MDW
1 stop25h 30m
Virgin Atlantic
Deal found 2/2R28 198
Thu 2/413:10
MDW
-
JNB
2 stops23h 30m
Delta
Sat 18/421:55
JNB
-
MDW
2 stops27h 03m
Delta
Deal found 3/2R28 262
Wed 8/49:30
MDW
-
JNB
2 stops27h 10m
Delta
Fri 17/421:55
JNB
-
MDW
1 stop25h 30m
Delta
Deal found 2/2R28 278
Mon 16/212:45
MDW
-
JNB
1 stop22h 15m
Delta
Wed 4/321:55
JNB
-
MDW
1 stop27h 50m
Delta
Deal found 2/2R28 310
Tue 17/213:28
MDW
-
JNB
2 stops21h 32m
Delta
Sun 1/321:55
JNB
-
MDW
1 stop27h 50m
Delta
Deal found 2/2R28 374
Wed 18/218:40
MDW
-
JNB
1 stop40h 20m
Delta
Wed 4/321:55
JNB
-
MDW
1 stop27h 50m
Delta
Deal found 2/2R28 438
Sun 1/318:40
MDW
-
JNB
1 stop40h 20m
Delta
Tue 17/321:55
JNB
-
MDW
2 stops26h 59m
Delta
Deal found 2/2R28 502

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

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Fri 13/3

21:30-15:25

1 stop24h 55m

R22 008

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 19/2

9:50-19:15

2 stops25h 25m

Cape Town Intl

Thu 26/2

21:30-17:37

2 stops28h 07m

R22 056

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 22/3

13:10-19:15

2 stops23h 05m

Cape Town Intl

Thu 2/4

20:25-17:54

2 stops28h 29m

R26 470

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 9/3

9:30-19:15

2 stops26h 45m

Cape Town Intl

Thu 26/3

21:30-17:54

2 stops27h 24m

R27 798

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 2/4

10:45-19:40

1 stop25h 55m

Johannesburg OR Tambo

Sat 18/4

21:55-16:29

1 stop25h 34m

R28 182

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 2/4

18:07-19:40

1 stop18h 33m

Johannesburg OR Tambo

Fri 17/4

21:55-16:25

1 stop25h 30m

R28 198

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 2/4

13:10-19:40

2 stops23h 30m

Johannesburg OR Tambo

Sat 18/4

21:55-17:58

2 stops27h 03m

R28 262

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 8/4

9:30-19:40

2 stops27h 10m

Johannesburg OR Tambo

Fri 17/4

21:55-16:25

1 stop25h 30m

R28 278

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 20/2

12:45-19:00

1 stop22h 15m

Johannesburg OR Tambo

Tue 3/3

21:55-17:45

1 stop27h 50m

R28 310

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 1/3

18:40-19:00

1 stop40h 20m

Johannesburg OR Tambo

Tue 17/3

21:55-17:22

1 stop26h 27m

R28 438

Flights are sorted by cheapest return flights first.

Deals found on 3/2

Showing 1-10 of 36 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: Atlanta (188 flights per day), Detroit (184 flights per day) and Orlando (126 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 577

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 577. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 577

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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 4 February 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 4 February 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 Tampa, Atlanta, Las Vegas. 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 577 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 577 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 573 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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