R2 844+ 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 29/4. 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 2 — May 91
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 2 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

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 6/9

10:35-19:40

1 stop26h 05m

Johannesburg OR Tambo

Sun 20/9

21:55-16:27

1 stop25h 32m

R33 325

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 6/9

14:00-19:40

2 stops22h 40m

Johannesburg OR Tambo

Sun 20/9

21:55-18:31

2 stops27h 36m

R33 409

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 4/6

13:22-21:20

2 stops24h 58m

Johannesburg OR Tambo

Thu 18/6

20:25-18:31

2 stops29h 06m

R38 509

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 25/6

11:05-19:40

1 stop25h 35m

Johannesburg OR Tambo

Sun 19/7

21:55-16:15

1 stop25h 20m

R38 728

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 25/6

13:49-19:40

2 stops22h 51m

Johannesburg OR Tambo

Sun 19/7

21:55-18:25

2 stops27h 30m

R38 812

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 25/6

11:05-19:40

1 stop25h 35m

Johannesburg OR Tambo

Mon 20/7

21:55-16:15

1 stop25h 20m

R38 980

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 13/8

13:05-22:25

2 stops26h 20m

Johannesburg OR Tambo

Fri 28/8

16:20-21:46

2 stops36h 26m

R39 536
Fastest return journey

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 3/5

13:24-21:25

2 stops25h 01m

Cape Town Intl

Tue 19/5

20:05-12:42

2 stops23h 37m

R39 637

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 4/6

12:53-19:40

1 stop23h 47m

Johannesburg OR Tambo

Thu 18/6

20:25-22:17

2 stops32h 52m

R39 973

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 8/8

10:55-19:40

1 stop25h 45m

Johannesburg OR Tambo

Tue 18/8

21:55-16:27

1 stop25h 32m

R40 057

Flights are sorted by cheapest return flights first.

Deals found on 28/3

Showing 1-10 of 33 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 (228 flights per day), Atlanta (164 flights per day) and Minneapolis (94 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 816

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 816. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 816

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 2 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 2 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 Atlanta, Las Vegas, Los Angeles. 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 816 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 816 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.

See more FAQs

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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