R2 379+ 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 7/10. 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
Oct 17 — Oct 241
1 adult
1 adult, Economy

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 17 September 2025.

Good one-way deal

R3 886 or less
Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

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 17 September 2025.

Thu 6/1117:09MDW - CPT
1 stop18h 06mVirgin Atlantic
Thu 20/1121:30CPT - MDW
1 stop27h 08mVirgin Atlantic
Deal found 16/9R23 981
Thu 6/1113:48MDW - CPT
2 stops21h 27mDelta
Thu 20/1121:30CPT - MDW
2 stops23h 04mDelta
Deal found 16/9R24 068
Fri 7/1118:23MDW - CPT
2 stops27h 27mDelta
Thu 20/1121:30CPT - MDW
1 stop22h 22mDelta
Deal found 16/9R24 710
Mon 10/1117:34MDW - CPT
1 stop17h 41mDelta
Thu 27/1121:30CPT - MDW
1 stop20h 22mDelta
Deal found 16/9R25 891
Mon 29/910:35MDW - JNB
1 stop26h 05mDelta
Wed 8/1021:55JNB - MDW
1 stop25h 14mDelta
Deal found 15/9R27 367
Mon 5/117:25MDW - CPT
1 stop17h 50mVirgin Atlantic
Mon 19/121:30CPT - MDW
1 stop26h 55mVirgin Atlantic
Deal found 16/9R27 367
Tue 30/912:43MDW - JNB
1 stop23h 57mDelta
Wed 8/1021:55JNB - MDW
2 stops26h 48mDelta
Deal found 15/9R27 437
Sun 4/19:29MDW - CPT
2 stops25h 46mDelta
Sun 18/121:30CPT - MDW
2 stops29h 04mDelta
Deal found 16/9R27 454
Tue 3/310:35MDW - JNB
1 stop24h 25mDelta
Tue 10/319:40JNB - MDW
2 stops29h 28mDelta
Deal found 15/9R27 645
Mon 23/213:05MDW - JNB
1 stop21h 55mDelta
Sat 7/322:00JNB - MDW
2 stops27h 08mDelta
Deal found 16/9R27 853
Mon 29/913:08MDW - JNB
2 stops25h 12mKLM
Wed 8/1023:15JNB - MDW
2 stops26h 10mKLM
Deal found 15/9R27 871
Tue 7/1017:04MDW - CPT
2 stops33h 41mMultiple Airlines
Fri 17/1020:05CPT - MDW
1 stop33h 09mMultiple Airlines
Deal found 17/9R27 871

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 17 September 2025. 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 6/11

13:08-19:15

2 stops22h 07m

Cape Town Intl

Thu 20/11

21:30-12:34

2 stops23h 04m

R24 068

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Fri 7/11

18:23-5:50

2 stops27h 27m

Cape Town Intl

Thu 20/11

21:30-18:08

2 stops28h 38m

R24 797

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 5/1

17:25-19:15

1 stop17h 50m

Cape Town Intl

Mon 19/1

21:30-16:25

1 stop26h 55m

R27 367

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 4/1

17:00-19:15

1 stop18h 15m

Cape Town Intl

Sun 18/1

21:30-16:25

1 stop26h 55m

R27 367

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 29/9

10:35-19:40

1 stop26h 05m

Johannesburg OR Tambo

Wed 8/10

21:55-16:09

1 stop25h 14m

R27 367

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 5/1

17:25-19:15

1 stop17h 50m

Cape Town Intl

Mon 19/1

21:30-16:25

1 stop26h 55m

R27 367

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 18/2

14:00-22:05

2 stops24h 05m

Johannesburg OR Tambo

Mon 16/3

23:59-18:34

2 stops25h 35m

R27 437

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 4/1

12:43-19:15

1 stop22h 32m

Cape Town Intl

Sun 18/1

21:30-12:35

2 stops23h 05m

R27 454

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 8/10

17:04-9:45

2 stops33h 41m

Cape Town Intl

Fri 17/10

20:05-22:14

1 stop33h 09m

R27 871

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 5/11

13:08-22:05

2 stops24h 57m

Johannesburg OR Tambo

Thu 13/11

23:59-18:18

2 stops26h 19m

R27 871

Flights are sorted by cheapest return flights first.

Deals found on 17/9

Showing 1-10 of 35 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 (204 flights per day), Atlanta (175 flights per day) and Minneapolis (109 flights per day).

Miami
Miami
From R224

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 886. Explore other affordable destinations below.

Miami
Miami
From R224

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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 17 September 2025.
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 17 September 2025.

  • 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 Las Vegas, Atlanta, Orlando Airport. While Atlanta, Las Vegas, Cancún 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 886 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 388 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 R9 307 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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