R2 989+ 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 30/10. 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
Aug 7 — Aug 141
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 8 July 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 29/12

17:35-18:35

2 stops41h 00m

Cape Town Intl

Thu 14/1

20:50-18:37

2 stops29h 47m

R29 732
Fastest return journey

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 9/11

12:30-18:35

2 stops22h 05m

Cape Town Intl

Thu 26/11

20:50-9:52

1 stop21h 02m

R29 732

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 18/8

13:25-21:25

2 stops25h 00m

Cape Town Intl

Tue 25/8

23:15-22:36

2 stops30h 21m

R29 992

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 17/8

12:46-21:25

2 stops25h 39m

Cape Town Intl

Mon 24/8

23:00-18:01

2 stops26h 01m

R30 073

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 9/8

9:24-21:25

2 stops29h 01m

Cape Town Intl

Tue 25/8

20:05-11:51

1 stop22h 46m

R30 317

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 4/8

10:54-21:25

2 stops27h 31m

Cape Town Intl

Fri 14/8

20:05-10:10

1 stop21h 05m

R30 317

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 17/8

6:05-17:50

1 stop28h 45m

Cape Town Intl

Mon 24/8

23:15-22:36

2 stops30h 21m

R30 317

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 20/8

12:46-21:25

2 stops25h 39m

Cape Town Intl

Thu 27/8

23:15-18:01

2 stops25h 46m

R32 137

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 9/9

11:35-21:25

2 stops26h 50m

Cape Town Intl

Wed 16/9

23:15-18:19

2 stops26h 04m

R32 218

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 16/9

13:00-19:40

1 stop23h 40m

Johannesburg OR Tambo

Tue 10/11

21:55-11:56

1 stop22h 01m

R33 729

Flights are sorted by cheapest return flights first.

Deals found on 6/7

Showing 1-10 of 38 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 (202 flights per day), Atlanta (169 flights per day) and Orlando (116 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 649

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 649. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 649

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 8 July 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 8 July 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, Dallas/Fort Worth Airport, Houston Hobby Airport. While Atlanta, Orlando Airport, Las Vegas 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 649 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 649 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

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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