R1 715+ 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 9/1. 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
Dec 27 — Jan 31
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 27 November 2025.

Good one-way deal

R3 837 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 27 November 2025.

Mon 19/110:46MDW - CPT
1 stop24h 29mDelta
Tue 3/221:30CPT - MDW
1 stop22h 29mDelta
Deal found 25/11R23 507
Mon 2/212:48MDW - CPT
1 stop22h 27mDelta
Sun 15/221:30CPT - MDW
1 stop28h 15mDelta
Deal found 26/11R23 525
Mon 8/1210:49MDW - CPT
2 stops27h 06mDelta
Thu 11/1223:45CPT - MDW
2 stops26h 33mDelta
Deal found 25/11R24 245
Sat 7/26:00MDW - JNB
1 stop29h 00mVirgin Atlantic
Wed 25/221:55JNB - MDW
1 stop27h 50mVirgin Atlantic
Deal found 25/11R26 594
Thu 12/312:47MDW - JNB
1 stop23h 13mDelta
Wed 25/321:55JNB - MDW
1 stop25h 58mDelta
Deal found 26/11R26 611
Mon 30/310:49MDW - CPT
1 stop24h 01mDelta
Fri 10/420:05CPT - MDW
1 stop20h 50mDelta
Deal found 25/11R27 022
Sat 21/316:30MDW - JNB
1 stop19h 30mDelta
Mon 6/421:55JNB - MDW
1 stop25h 58mDelta
Deal found 27/11R27 040
Fri 6/213:49MDW - JNB
2 stops24h 16mMultiple Airlines
Sat 14/219:20JNB - MDW
2 stops28h 03mMultiple Airlines
Deal found 25/11R27 074
Tue 20/113:31MDW - JNB
2 stops24h 34mKLM
Thu 5/223:59JNB - MDW
2 stops26h 37mKLM
Deal found 27/11R27 091
Mon 30/36:30MDW - CPT
1 stop28h 20mDelta
Sun 12/420:05CPT - MDW
1 stop32h 40mDelta
Deal found 25/11R27 160
Tue 20/112:48MDW - JNB
1 stop22h 12mDelta
Thu 5/219:20JNB - MDW
2 stops30h 35mDelta
Deal found 27/11R27 314
Sun 29/318:35MDW - CPT
2 stops40h 15mDelta
Fri 10/420:05CPT - MDW
1 stop26h 20mDelta
Deal found 25/11R27 331

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 27 November 2025. 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

Mon 19/1

10:46-19:15

1 stop24h 29m

Cape Town Intl

Tue 3/2

21:30-11:59

1 stop22h 29m

R23 507

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/2

10:46-19:15

1 stop24h 29m

Cape Town Intl

Sun 15/2

21:30-22:42

1 stop33h 12m

R23 610

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 7/2

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Wed 25/2

21:55-17:45

1 stop27h 50m

R26 594

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 12/3

10:49-19:00

1 stop25h 11m

Johannesburg OR Tambo

Wed 25/3

21:55-12:02

1 stop21h 07m

R26 594

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 30/3

10:49-17:50

1 stop24h 01m

Cape Town Intl

Fri 10/4

20:05-9:55

1 stop20h 50m

R27 022

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 21/3

16:30-19:00

1 stop19h 30m

Johannesburg OR Tambo

Mon 6/4

21:55-16:53

1 stop25h 58m

R27 040

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 7/2

13:26-22:05

2 stops24h 39m

Johannesburg OR Tambo

Wed 25/2

23:59-17:37

2 stops25h 38m

R27 074

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 13/2

13:49-22:05

2 stops24h 16m

Johannesburg OR Tambo

Sun 1/3

23:59-18:37

2 stops26h 38m

R27 091

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 20/1

13:31-22:05

2 stops24h 34m

Johannesburg OR Tambo

Thu 5/2

23:59-18:36

2 stops26h 37m

R27 091

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/2

13:26-21:55

2 stops24h 29m

Cape Town Intl

Sun 15/2

23:45-18:37

2 stops26h 52m

R27 417

Flights are sorted by cheapest return flights first.

Deals found on 25/11

Showing 1-10 of 28 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 (170 flights per day), Orlando (132 flights per day) and Detroit (128 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 907
Miami
Miami
From R3 837

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 837. Explore other affordable destinations below.

Miami
Miami
From R3 837
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 907

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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 27 November 2025.
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 27 November 2025.

  • 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, Orlando Airport, Denver. While Atlanta, Las Vegas, Cancún 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 837 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 620 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 R9 190 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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