R1 805+ 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 5/3. 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
Feb 20 — Feb 271
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 21 January 2026.

Good one-way deal

R3 672 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 21 January 2026.

Mon 16/212:45
MDW
-
CPT
1 stop22h 30m
Virgin Atlantic
Tue 3/321:30
CPT
-
MDW
1 stop28h 15m
Virgin Atlantic
Deal found 19/1R20 136
Thu 5/310:49
MDW
-
CPT
1 stop24h 26m
Delta
Thu 19/321:30
CPT
-
MDW
1 stop26h 25m
Delta
Deal found 20/1R20 907
Tue 17/218:40
MDW
-
CPT
1 stop40h 35m
Virgin Atlantic
Tue 24/221:30
CPT
-
MDW
1 stop28h 15m
Virgin Atlantic
Deal found 20/1R21 006
Tue 3/312:45
MDW
-
CPT
2 stops25h 10m
Delta
Mon 23/321:30
CPT
-
MDW
1 stop21h 32m
Delta
Deal found 19/1R21 597
Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Wed 18/323:45
CPT
-
MDW
2 stops40h 08m
Delta
Deal found 20/1R21 679
Sat 28/216:13
MDW
-
CPT
1 stop19h 02m
Multiple Airlines
Sun 15/321:30
CPT
-
MDW
1 stop26h 25m
Multiple Airlines
Deal found 21/1R21 728
Fri 6/318:20
MDW
-
CPT
2 stops27h 30m
Delta
Wed 18/323:45
CPT
-
MDW
2 stops40h 08m
Delta
Deal found 20/1R22 368
Tue 17/212:45
MDW
-
CPT
2 stops26h 05m
Multiple Airlines
Tue 24/218:10
CPT
-
MDW
2 stops31h 35m
Multiple Airlines
Deal found 20/1R22 942
Sat 28/216:13
MDW
-
CPT
1 stop19h 02m
Delta
Sun 22/321:30
CPT
-
MDW
1 stop21h 32m
Delta
Deal found 20/1R23 205
Sun 8/39:35
MDW
-
CPT
2 stops26h 40m
Delta
Sun 22/321:30
CPT
-
MDW
1 stop21h 32m
Delta
Deal found 20/1R23 287
Thu 5/212:46
MDW
-
JNB
1 stop22h 14m
Delta
Sun 15/221:55
JNB
-
MDW
1 stop27h 50m
Delta
Deal found 20/1R23 861
Mon 23/29:34
MDW
-
JNB
2 stops28h 31m
Multiple Airlines
Tue 3/319:20
JNB
-
MDW
2 stops30h 25m
Multiple Airlines
Deal found 19/1R24 321

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 21 January 2026. 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

Mon 2/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Tue 24/3

21:30-16:55

1 stop26h 25m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 5/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Thu 19/3

21:30-16:55

1 stop26h 25m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Mon 23/3

21:30-12:02

1 stop21h 32m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/3

10:49-19:15

1 stop24h 26m

Cape Town Intl

Tue 17/3

21:30-12:02

1 stop21h 32m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 5/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Tue 24/3

21:30-16:55

1 stop26h 25m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 19/2

12:45-19:15

1 stop22h 30m

Cape Town Intl

Thu 26/2

21:30-17:45

1 stop28h 15m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 1/3

10:49-19:15

1 stop24h 26m

Cape Town Intl

Mon 23/3

21:30-12:02

1 stop21h 32m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 7/3

11:06-19:15

1 stop24h 09m

Cape Town Intl

Tue 24/3

21:30-12:02

1 stop21h 32m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 8/3

17:40-19:15

1 stop18h 35m

Cape Town Intl

Mon 16/3

21:30-16:55

1 stop26h 25m

R20 907

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

10:49-19:15

1 stop24h 26m

Cape Town Intl

Thu 19/3

21:30-16:55

1 stop26h 25m

R20 907

Flights are sorted by cheapest return flights first.

Deals found on 19/1

Showing 1-10 of 31 results
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 (181 flights per day) and Orlando (116 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696
Miami
Miami
From R3 672

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 672. Explore other affordable destinations below.

Miami
Miami
From R3 672
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 696

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 21 January 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 21 January 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 Cancún, Atlanta, Miami. 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 R3 672 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 421 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 796 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.