R1 428+ 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 25/5. 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
May 10 — May 171
1 adult
1 adult, Economy, 0 bags

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

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 12/5

19:13-17:50

2 stops63h 37m

Cape Town Intl

Fri 22/5

20:05-18:33

2 stops29h 28m

R33 721

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 25/4

17:21-17:50

1 stop17h 29m

Cape Town Intl

Tue 5/5

20:05-16:26

1 stop27h 21m

R34 197
Fastest return journey

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 25/4

17:21-17:50

1 stop17h 29m

Cape Town Intl

Sun 3/5

20:05-9:56

1 stop20h 51m

R34 197

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 1/5

13:24-19:40

2 stops23h 16m

Johannesburg OR Tambo

Sat 9/5

21:55-11:56

1 stop21h 01m

R35 625

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 10/5

12:53-21:25

2 stops25h 32m

Cape Town Intl

Fri 22/5

20:05-13:19

2 stops24h 14m

R37 659

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 12/5

13:22-21:25

2 stops25h 03m

Cape Town Intl

Sun 24/5

20:05-13:19

2 stops24h 14m

R37 659

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 26/4

13:24-21:25

2 stops25h 01m

Cape Town Intl

Thu 7/5

23:15-18:33

2 stops26h 18m

R37 938

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 1/5

13:24-19:40

2 stops23h 16m

Johannesburg OR Tambo

Sun 31/5

23:15-17:56

2 stops25h 41m

R38 234

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 27/4

17:21-19:40

1 stop19h 19m

Johannesburg OR Tambo

Fri 29/5

15:05-16:12

2 stops32h 07m

R38 660

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 10/5

13:22-21:20

2 stops24h 58m

Johannesburg OR Tambo

Wed 20/5

23:15-18:33

2 stops26h 18m

R38 808

Flights are sorted by cheapest return flights first.

Deals found on 9/4

Showing 1-10 of 39 resultsSorted by cheapest first
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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 (220 flights per day), Atlanta (162 flights per day) and Minneapolis (94 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696

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 696. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696

Browse thousands of different options on Cheapflights for your next trip

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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 10 April 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 10 April 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 Los Angeles, 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 696 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 696 to fly from Chicago Midway Airport.

  • 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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Fly with Cheapflights

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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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