R2 018+ 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 5/11. 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
Nov 25 — Dec 21
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 26 October 2025.

Good one-way deal

R3 860 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 26 October 2025.

Thu 6/1110:40MDW - CPT
1 stop24h 35mDelta
Sun 9/1121:30CPT - MDW
1 stop27h 09mDelta
Deal found 24/10R21 235
Mon 8/1210:36MDW - CPT
1 stop24h 39mDelta
Mon 15/1221:30CPT - MDW
1 stop27h 14mDelta
Deal found 24/10R22 960
Fri 28/1117:34MDW - CPT
2 stops28h 16mDelta
Sun 14/1221:30CPT - MDW
1 stop20h 11mDelta
Deal found 24/10R23 684
Fri 23/113:00MDW - CPT
2 stops24h 55mDelta
Sun 1/221:30CPT - MDW
1 stop26h 55mDelta
Deal found 24/10R24 375
Sun 1/210:35MDW - CPT
1 stop24h 40mDelta
Wed 25/27:55CPT - MDW
2 stops40h 30mDelta
Deal found 23/10R24 599
Mon 2/217:25MDW - CPT
1 stop17h 50mDelta
Sun 15/221:30CPT - MDW
1 stop22h 31mDelta
Deal found 24/10R26 755
Sun 4/19:50MDW - CPT
1 stop25h 25mDelta
Sun 18/121:30CPT - MDW
1 stop20h 26mDelta
Deal found 24/10R27 186
Thu 26/310:35MDW - CPT
1 stop25h 40mDelta
Fri 3/420:05CPT - MDW
1 stop26h 20mDelta
Deal found 23/10R27 204
Fri 30/113:28MDW - JNB
2 stops24h 37mKLM
Sat 14/223:59JNB - MDW
2 stops26h 09mKLM
Deal found 25/10R27 255
Fri 30/112:48MDW - JNB
1 stop22h 12mDelta
Sat 14/219:20JNB - MDW
2 stops31h 14mDelta
Deal found 25/10R27 480
Thu 12/29:30MDW - JNB
2 stops25h 30mDelta
Thu 19/223:59JNB - MDW
2 stops26h 09mDelta
Deal found 24/10R27 549
Mon 10/116:00MDW - JNB
1 stop29h 00mDelta
Wed 24/1221:55JNB - MDW
1 stop24h 49mDelta
Deal found 24/10R27 635

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 26 October 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

Fri 28/11

17:34-5:50

2 stops28h 16m

Cape Town Intl

Sun 14/12

21:30-9:41

1 stop20h 11m

R23 684

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Fri 23/1

13:00-21:55

2 stops24h 55m

Cape Town Intl

Sun 1/2

21:30-16:25

1 stop26h 55m

R24 375

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 1/2

10:35-19:15

1 stop24h 40m

Cape Town Intl

Wed 25/2

7:55-16:25

2 stops40h 30m

R24 599

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/2

12:48-19:15

1 stop22h 27m

Cape Town Intl

Sun 15/2

21:30-12:01

1 stop22h 31m

R26 755

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 4/1

17:05-19:15

1 stop18h 10m

Cape Town Intl

Sun 18/1

21:30-12:01

1 stop22h 31m

R27 186

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 26/3

10:35-19:15

1 stop25h 40m

Cape Town Intl

Fri 3/4

20:05-15:25

1 stop26h 20m

R27 204

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 19/2

13:05-19:15

1 stop22h 10m

Cape Town Intl

Thu 26/2

23:45-18:08

2 stops26h 23m

R27 480

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 27/2

9:20-22:05

2 stops28h 45m

Johannesburg OR Tambo

Sat 7/3

21:55-17:34

2 stops27h 39m

R27 549

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 10/11

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Wed 24/12

21:55-14:44

1 stop24h 49m

R27 635

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 12/3

13:05-19:00

1 stop22h 55m

Johannesburg OR Tambo

Wed 25/3

22:00-18:08

2 stops27h 08m

R27 669

Flights are sorted by cheapest return flights first.

Deals found on 24/10

Showing 1-10 of 26 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 (160 flights per day), Atlanta (131 flights per day) and Orlando (108 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 936
Miami
Miami
From R3 860

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 860. Explore other affordable destinations below.

Miami
Miami
From R3 860
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 936

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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 26 October 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 26 October 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, Las Vegas, Dallas/Fort Worth Airport. 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 860 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 648 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 246 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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