R1 641+ 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 19/1. 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
Oca 1 — Oca 81
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 2 Aralık 2025.

Good one-way deal

R3 826 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 2 Aralık 2025.

Pzt 2/210:46MDW - CPT
1 stop24h 29mDelta
Paz 15/221:30CPT - MDW
1 stop33h 12mDelta
Deal found 30/11R23 540
Cum 23/113:26MDW - CPT
2 stops32h 24mDelta
Paz 1/221:30CPT - MDW
1 stop20h 23mDelta
Deal found 2/12R24 155
Cmt 31/110:46MDW - CPT
1 stop24h 29mDelta
Cmt 14/27:55CPT - MDW
2 stops40h 19mDelta
Deal found 1/12R24 377
Pzt 23/212:46MDW - CPT
1 stop22h 29mDelta
Çar 4/37:55CPT - MDW
2 stops41h 42mDelta
Deal found 29/11R25 916
Sal 27/110:48MDW - JNB
1 stop24h 12mVirgin Atlantic
Sal 17/221:55JNB - MDW
1 stop27h 50mVirgin Atlantic
Deal found 1/12R26 531
Sal 27/19:50MDW - JNB
2 stops25h 10mDelta
Sal 17/221:55JNB - MDW
2 stops27h 42mDelta
Deal found 1/12R26 600
Pzt 23/210:53MDW - CPT
2 stops27h 57mMultiple Airlines
Çar 4/320:50CPT - MDW
2 stops28h 55mMultiple Airlines
Deal found 29/11R26 839
Pzt 12/117:31MDW - CPT
1 stop17h 44mDelta
Sal 27/121:30CPT - MDW
1 stop27h 59mDelta
Deal found 29/11R26 959
Cum 30/113:49MDW - JNB
2 stops24h 16mKLM
Cmt 14/219:20JNB - MDW
2 stops28h 54mKLM
Deal found 1/12R27 010
Cmt 3/16:00MDW - CPT
1 stop29h 15mVirgin Atlantic
Pzt 19/121:30CPT - MDW
1 stop27h 59mVirgin Atlantic
Deal found 30/11R27 044
Cmt 3/16:00MDW - CPT
1 stop29h 15mDelta
Pzt 19/121:30CPT - MDW
2 stops28h 25mDelta
Deal found 30/11R27 130
Cum 30/112:48MDW - JNB
1 stop22h 12mDelta
Cmt 14/219:20JNB - MDW
2 stops28h 54mDelta
Deal found 1/12R27 232

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 2 Aralık 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

Pzt 2/2

10:46-19:15

1 stop24h 29m

Cape Town Intl

Paz 15/2

21:30-22:42

1 stop33h 12m

R23 540

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Cmt 31/1

10:46-19:15

1 stop24h 29m

Cape Town Intl

Cmt 14/2

7:55-16:14

2 stops40h 19m

R24 377

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Pzt 23/2

12:46-19:15

1 stop22h 29m

Cape Town Intl

Çar 4/3

7:55-17:37

2 stops41h 42m

R25 916

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sal 27/1

10:48-19:00

1 stop24h 12m

Johannesburg OR Tambo

Sal 17/2

21:55-17:45

1 stop27h 50m

R26 531

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Cmt 28/2

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Çar 11/3

21:55-12:02

1 stop21h 07m

R26 531

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sal 27/1

9:50-19:00

2 stops25h 10m

Johannesburg OR Tambo

Sal 17/2

21:55-17:37

2 stops27h 42m

R26 600

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Pzt 12/1

17:31-19:15

1 stop17h 44m

Cape Town Intl

Sal 27/1

21:30-17:29

1 stop27h 59m

R26 959

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Cmt 17/1

13:28-22:05

2 stops24h 37m

Johannesburg OR Tambo

Cmt 31/1

23:59-18:36

2 stops26h 37m

R27 010

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Cmt 28/2

11:45-22:05

2 stops26h 20m

Johannesburg OR Tambo

Çar 11/3

19:20-16:53

2 stops28h 33m

R27 010

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Cum 30/1

13:49-22:05

2 stops24h 16m

Johannesburg OR Tambo

Cmt 14/2

19:20-16:14

2 stops28h 54m

R27 010

Flights are sorted by cheapest return flights first.

Deals found on 1/12

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 (158 flights per day), Atlanta (148 flights per day) and Minneapolis (99 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 892
Miami
Miami
From R3 826

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 826. Explore other affordable destinations below.

Miami
Miami
From R3 826
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 892

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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 2 Aralık 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 2 Aralık 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, Miami. 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 826 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 606 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 163 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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