R2 576+ 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 25/2. 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
Feb 13 — Feb 201
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 14 January 2026.

Good one-way deal

R3 672 or less
Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Enter your travel dates to find the best prices.

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 14 January 2026.

Thu 29/112:48
MDW
-
JNB
1 stop22h 12m
Virgin Atlantic
Wed 11/221:55
JNB
-
MDW
1 stop32h 36m
Virgin Atlantic
Deal found 14/1R12 176
Mon 26/112:48
MDW
-
CPT
1 stop22h 27m
Virgin Atlantic
Sun 8/221:30
CPT
-
MDW
1 stop27h 59m
Virgin Atlantic
Deal found 12/1R12 307
Tue 27/112:48
MDW
-
JNB
1 stop22h 12m
Delta
Sun 8/221:55
JNB
-
MDW
1 stop27h 34m
Delta
Deal found 13/1R12 537
Wed 28/112:48
MDW
-
CPT
1 stop22h 27m
Delta
Fri 13/221:30
CPT
-
MDW
1 stop25h 51m
Delta
Deal found 13/1R12 537
Thu 29/113:49
MDW
-
CPT
2 stops21h 26m
Delta
Thu 12/221:30
CPT
-
MDW
2 stops23h 35m
Delta
Deal found 13/1R12 619
Wed 28/118:14
MDW
-
JNB
1 stop40h 46m
Delta
Wed 11/221:55
JNB
-
MDW
1 stop22h 04m
Delta
Deal found 13/1R12 636
Wed 28/118:14
MDW
-
JNB
1 stop40h 46m
Delta
Sun 8/221:55
JNB
-
MDW
2 stops28h 00m
Delta
Deal found 13/1R12 701
Mon 2/212:46
MDW
-
CPT
1 stop22h 29m
Multiple Airlines
Sun 15/221:30
CPT
-
MDW
1 stop28h 15m
Multiple Airlines
Deal found 12/1R12 701
Tue 27/113:29
MDW
-
JNB
2 stops21h 31m
Kenya Airways
Tue 10/221:55
JNB
-
MDW
1 stop22h 04m
Kenya Airways
Deal found 13/1R12 783
Tue 27/118:35
MDW
-
CPT
2 stops40h 40m
Delta
Thu 12/221:30
CPT
-
MDW
2 stops23h 35m
Delta
Deal found 13/1R12 783
Wed 18/213:28
MDW
-
JNB
2 stops24h 37m
Multiple Airlines
Mon 16/319:20
JNB
-
MDW
2 stops28h 35m
Multiple Airlines
Deal found 13/1R12 997
Tue 27/113:49
MDW
-
JNB
2 stops24h 16m
KLM
Mon 9/223:59
JNB
-
MDW
2 stops26h 37m
KLM
Deal found 13/1R13 013

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

Fly to

Cape Town

Route

Depart

Return

Price

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 29/1

12:48-19:00

1 stop22h 12m

Johannesburg OR Tambo

Wed 11/2

21:55-22:31

1 stop32h 36m

R12 176

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 30/1

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Wed 11/2

21:55-11:59

1 stop22h 04m

R12 537

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 3/2

10:48-19:00

1 stop24h 12m

Johannesburg OR Tambo

Wed 11/2

21:55-17:45

1 stop27h 50m

R12 537

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 29/1

9:33-19:00

2 stops25h 27m

Johannesburg OR Tambo

Wed 11/2

21:55-11:59

1 stop22h 04m

R12 619

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 30/1

9:33-19:00

2 stops25h 27m

Johannesburg OR Tambo

Sun 8/2

21:55-11:59

1 stop22h 04m

R12 619

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 26/1

13:26-19:15

2 stops21h 49m

Cape Town Intl

Sun 8/2

21:30-12:46

2 stops23h 16m

R12 619

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 8/2

11:45-19:15

2 stops23h 30m

Cape Town Intl

Mon 16/2

21:30-17:45

1 stop28h 15m

R12 619

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 19/3

10:45-19:15

1 stop25h 30m

Cape Town Intl

Fri 27/3

21:30-15:25

1 stop24h 55m

R12 701

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 4/3

13:49-22:05

2 stops24h 16m

Johannesburg OR Tambo

Mon 16/3

19:20-16:55

2 stops28h 35m

R12 997

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 23/2

6:00-22:05

2 stops32h 05m

Johannesburg OR Tambo

Tue 3/3

19:20-22:31

2 stops35h 11m

R12 997

Flights are sorted by cheapest return flights first.

Deals found on 12/1

Showing 1-10 of 35 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 (174 flights per day), Atlanta (170 flights per day) and Orlando (138 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696
Miami
Miami
From R3 672

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

The cheapest city to fly to from Chicago Midway Airport is Miami, with prices starting at R3 672. Explore other affordable destinations below.

Miami
Miami
From R3 672
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696

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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 14 January 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 14 January 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 Cancún, Atlanta, Miami. 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 R3 672 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 421 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 795 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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