R2 397+ 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 22/4. 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
Apr 11 — Apr 181
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 12 March 2026.

Good one-way deal

R4 764 or less
Price to beat on a one-way flight from Chicago Midway.
Search Deals

Find flights from Midway

Enter your travel dates to find the best prices.

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 12 March 2026.

Fri 24/410:41
MDW
-
JNB
1 stop25h 59m
Virgin Atlantic
Sat 2/521:55
JNB
-
MDW
1 stop25h 31m
Virgin Atlantic
Deal found 7/3R30 482
Fri 24/414:12
MDW
-
JNB
2 stops22h 28m
Delta
Sat 2/521:55
JNB
-
MDW
2 stops27h 03m
Delta
Deal found 7/3R30 565
Thu 9/418:07
MDW
-
JNB
1 stop18h 33m
Virgin Atlantic
Wed 22/421:55
JNB
-
MDW
1 stop31h 33m
Virgin Atlantic
Deal found 9/3R30 582
Thu 9/413:10
MDW
-
JNB
2 stops23h 30m
Delta
Wed 22/421:55
JNB
-
MDW
1 stop31h 33m
Delta
Deal found 9/3R30 648
Sun 19/417:21
MDW
-
JNB
1 stop19h 19m
Virgin Atlantic
Tue 5/521:55
JNB
-
MDW
1 stop25h 31m
Virgin Atlantic
Deal found 10/3R30 898
Sat 2/513:24
MDW
-
JNB
2 stops24h 56m
KLM
Sun 17/523:15
JNB
-
MDW
2 stops25h 41m
KLM
Deal found 7/3R30 931
Mon 20/417:21
MDW
-
JNB
1 stop19h 19m
Delta
Mon 27/423:15
JNB
-
MDW
2 stops26h 21m
Delta
Deal found 7/3R31 164
Thu 16/49:27
MDW
-
JNB
2 stops27h 13m
Delta
Thu 23/418:00
JNB
-
MDW
2 stops29h 26m
Delta
Deal found 7/3R31 248
Thu 16/417:21
MDW
-
CPT
1 stop17h 29m
Delta
Tue 12/520:05
CPT
-
MDW
1 stop20h 55m
Delta
Deal found 9/3R31 381
Sun 19/413:24
MDW
-
JNB
2 stops23h 16m
Delta
Tue 5/521:55
JNB
-
MDW
1 stop25h 31m
Delta
Deal found 10/3R31 398
Mon 6/414:05
MDW
-
CPT
2 stops20h 45m
Delta
Sun 19/420:05
CPT
-
MDW
1 stop27h 21m
Delta
Deal found 9/3R31 464
Thu 23/413:24
MDW
-
CPT
2 stops25h 21m
Multiple Airlines
Wed 6/523:15
CPT
-
MDW
2 stops26h 18m
Multiple Airlines
Deal found 8/3R31 847

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 12 March 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

Fri 24/4

9:27-19:40

2 stops27h 13m

Johannesburg OR Tambo

Sat 2/5

21:55-12:07

1 stop21h 12m

R30 565

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 9/4

13:10-19:40

2 stops23h 30m

Johannesburg OR Tambo

Wed 22/4

21:55-22:28

1 stop31h 33m

R30 648

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 2/5

13:24-21:20

2 stops24h 56m

Johannesburg OR Tambo

Sun 17/5

23:15-17:56

2 stops25h 41m

R30 931
Fastest return journey

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 20/4

17:21-19:40

1 stop19h 19m

Johannesburg OR Tambo

Mon 27/4

23:15-18:36

2 stops26h 21m

R31 164

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 6/4

10:45-17:50

1 stop24h 05m

Cape Town Intl

Sun 19/4

20:05-16:26

1 stop27h 21m

R31 381

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 9/4

12:47-19:40

1 stop23h 53m

Johannesburg OR Tambo

Wed 22/4

21:55-22:28

1 stop31h 33m

R31 414

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 25/4

10:41-19:40

1 stop25h 59m

Johannesburg OR Tambo

Sat 2/5

18:00-17:58

2 stops30h 58m

R32 014

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 16/5

9:22-21:25

2 stops29h 03m

Cape Town Intl

Sun 24/5

20:05-10:00

1 stop20h 55m

R32 063

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 14/5

10:55-19:40

1 stop25h 45m

Johannesburg OR Tambo

Fri 29/5

21:55-16:12

1 stop25h 17m

R32 280

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 17/4

12:52-19:40

1 stop23h 48m

Johannesburg OR Tambo

Fri 24/4

18:00-17:58

2 stops30h 58m

R32 630

Flights are sorted by cheapest return flights first.

Deals found on 11/3

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

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 (186 flights per day), Atlanta (164 flights per day) and Orlando (98 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 764

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 764. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 764

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 12 March 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 12 March 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 Orlando Airport, Las Vegas, Phoenix Sky Harbor Intl Airport. 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 764 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 764 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 R8 923 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.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.