R2 470+ 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 3/3. 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 — CPT
Mar 1 — Mar 81
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 30 January 2026.

Good one-way deal

R3 521 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 30 January 2026.

Thu 5/310:49
MDW
-
CPT
1 stop24h 26m
Virgin Atlantic
Mon 9/321:30
CPT
-
MDW
1 stop26h 52m
Virgin Atlantic
Deal found 29/1R21 634
Thu 5/313:29
MDW
-
CPT
2 stops21h 46m
Delta
Mon 9/321:30
CPT
-
MDW
2 stops28h 10m
Delta
Deal found 29/1R21 713
Sun 15/313:10
MDW
-
CPT
2 stops23h 05m
Delta
Tue 24/321:30
CPT
-
MDW
2 stops42h 23m
Delta
Deal found 29/1R21 902
Wed 4/312:45
MDW
-
CPT
1 stop22h 30m
Virgin Atlantic
Wed 18/320:50
CPT
-
MDW
2 stops28h 50m
Virgin Atlantic
Deal found 28/1R22 358
Wed 4/313:49
MDW
-
CPT
2 stops21h 26m
Delta
Wed 18/323:45
CPT
-
MDW
2 stops40h 08m
Delta
Deal found 28/1R22 453
Thu 19/39:35
MDW
-
CPT
2 stops37h 15m
Delta
Tue 24/321:30
CPT
-
MDW
2 stops42h 23m
Delta
Deal found 29/1R22 578
Sun 15/318:07
MDW
-
CPT
1 stop18h 08m
Delta
Mon 23/37:55
CPT
-
MDW
2 stops55h 58m
Delta
Deal found 29/1R22 594
Sun 22/310:45
MDW
-
CPT
1 stop25h 30m
Kenya Airways
Fri 3/420:05
CPT
-
MDW
1 stop20h 51m
Kenya Airways
Deal found 30/1R22 830
Thu 19/314:05
MDW
-
CPT
2 stops32h 45m
Delta
Mon 23/37:55
CPT
-
MDW
2 stops59h 34m
Delta
Deal found 29/1R23 271
Sun 22/318:07
MDW
-
CPT
1 stop18h 08m
Delta
Thu 2/420:25
CPT
-
MDW
2 stops28h 29m
Delta
Deal found 30/1R23 507
Tue 24/310:45
MDW
-
JNB
1 stop25h 15m
Kenya Airways
Sat 4/421:55
JNB
-
MDW
1 stop21h 07m
Kenya Airways
Deal found 30/1R26 481
Mon 23/312:47
MDW
-
JNB
1 stop23h 13m
Kenya Airways
Thu 2/421:55
JNB
-
MDW
1 stop21h 07m
Kenya Airways
Deal found 30/1R27 582

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 30 January 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

Thu 5/3

13:29-19:15

2 stops21h 46m

Cape Town Intl

Mon 9/3

21:30-17:54

2 stops27h 24m

R21 713

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 18/3

18:07-19:15

1 stop18h 08m

Cape Town Intl

Tue 24/3

21:30-8:53

2 stops42h 23m

R21 902

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 16/3

13:10-19:15

2 stops23h 05m

Cape Town Intl

Tue 24/3

21:30-8:53

2 stops42h 23m

R21 902

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 15/3

13:10-19:15

2 stops23h 05m

Cape Town Intl

Tue 24/3

21:30-8:53

2 stops42h 23m

R21 902

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Wed 18/3

20:50-18:40

2 stops28h 50m

R22 358

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

13:49-19:15

2 stops21h 26m

Cape Town Intl

Wed 18/3

23:45-8:53

2 stops40h 08m

R22 453

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 16/3

10:45-19:15

1 stop25h 30m

Cape Town Intl

Mon 23/3

7:55-8:53

2 stops55h 58m

R22 594

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 17/3

19:20-19:15

2 stops40h 55m

Cape Town Intl

Mon 23/3

7:55-17:54

2 stops64h 59m

R22 673

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 18/3

14:05-19:15

2 stops22h 10m

Cape Town Intl

Mon 23/3

7:55-12:29

2 stops59h 34m

R22 673

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 22/3

10:45-19:15

1 stop25h 30m

Cape Town Intl

Fri 3/4

20:05-9:56

1 stop20h 51m

R22 830

Flights are sorted by cheapest return flights first.

Deals found on 28/1

Showing 1-10 of 39 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 (178 flights per day), Atlanta (163 flights per day) and Orlando (92 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 502
Miami
Miami
From R3 521

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 521. Explore other affordable destinations below.

Miami
Miami
From R3 521
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 502

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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 30 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 30 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 521 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 239 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 433 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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