R2 516+ 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 14/4. 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 — CPT
Mar 24 — Mar 311
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 22 February 2026.

Good one-way deal

R4 586 or less
Price to beat on a one-way flight from Chicago Midway.
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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 22 February 2026.

Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Mon 9/321:30
CPT
-
MDW
1 stop26h 52m
Delta
Deal found 20/2R22 035
Wed 4/313:49
MDW
-
CPT
2 stops21h 26m
Delta
Fri 13/321:30
CPT
-
MDW
1 stop24h 55m
Delta
Deal found 20/2R22 115
Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Sun 8/321:30
CPT
-
MDW
1 stop32h 01m
Delta
Deal found 20/2R22 147
Thu 5/313:29
MDW
-
CPT
2 stops24h 26m
Delta
Tue 10/321:30
CPT
-
MDW
1 stop21h 32m
Delta
Deal found 20/2R22 708
Thu 5/313:29
MDW
-
CPT
2 stops24h 26m
Delta
Thu 12/321:30
CPT
-
MDW
1 stop32h 01m
Delta
Deal found 20/2R22 820
Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Wed 11/37:55
CPT
-
MDW
2 stops40h 59m
Delta
Deal found 20/2R22 916
Thu 5/313:29
MDW
-
CPT
2 stops24h 26m
Delta
Wed 11/37:55
CPT
-
MDW
2 stops45h 36m
Delta
Deal found 20/2R23 589
Sat 21/316:30
MDW
-
CPT
1 stop19h 45m
Delta
Sun 5/420:05
CPT
-
MDW
1 stop22h 57m
Delta
Deal found 18/2R25 592
Sat 21/39:35
MDW
-
CPT
2 stops26h 40m
Delta
Fri 3/420:05
CPT
-
MDW
1 stop20h 51m
Delta
Deal found 18/2R25 656
Mon 9/318:07
MDW
-
CPT
1 stop18h 08m
Delta
Sun 12/420:05
CPT
-
MDW
1 stop33h 23m
Delta
Deal found 19/2R25 672
Sat 21/316:30
MDW
-
CPT
1 stop19h 45m
Delta
Tue 7/423:15
CPT
-
MDW
2 stops30h 16m
Delta
Deal found 18/2R26 249
Sat 11/416:30
MDW
-
JNB
1 stop20h 10m
Delta
Mon 20/421:55
JNB
-
MDW
1 stop21h 12m
Delta
Deal found 19/2R28 236

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

Fly to

Cape Town

Route

Depart

Return

Price

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 22/3

12:47-19:15

1 stop23h 28m

Cape Town Intl

Sun 5/4

20:05-12:02

1 stop22h 57m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 23/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Fri 3/4

20:05-9:56

1 stop20h 51m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 25/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Fri 3/4

20:05-9:56

1 stop20h 51m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

Sun 5/4

20:05-12:02

1 stop22h 57m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 25/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Sun 5/4

20:05-9:56

1 stop20h 51m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

Fri 3/4

20:05-9:56

1 stop20h 51m

R25 592

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 9/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Sun 12/4

20:05-22:28

1 stop33h 23m

R25 672

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 21/3

16:30-19:15

1 stop19h 45m

Cape Town Intl

Tue 7/4

23:15-22:31

2 stops30h 16m

R26 249

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 23/4

17:21-19:40

1 stop19h 19m

Johannesburg OR Tambo

Wed 6/5

21:55-21:09

1 stop30h 14m

R28 236

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 5/4

10:45-19:40

1 stop25h 55m

Johannesburg OR Tambo

Thu 23/4

21:55-16:26

1 stop25h 31m

R28 236

Flights are sorted by cheapest return flights first.

Deals found on 18/2

Showing 1-10 of 36 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 (202 flights per day), Atlanta (182 flights per day) and Orlando (134 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 586

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 586. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 586

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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 22 February 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 22 February 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, Phoenix Sky Harbor Intl Airport, Orlando 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 586 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 586 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 589 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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