R2 241+ 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 9/9. 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 25 — Sep 11
1 adult

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 20 August 2025.

Good one-way deal

R3 949 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 20 August 2025.

Mon 2/210:35MDW - CPT
1 stop24h 40mDelta
Mon 16/221:30CPT - MDW
1 stop20h 26mDelta
Deal found 17/8R27 373
Mon 8/910:35MDW - JNB
1 stop26h 05mDelta
Wed 25/221:55JNB - MDW
1 stop22h 06mDelta
Deal found 17/8R27 814
Sat 10/117:25MDW - CPT
1 stop17h 50mDelta
Thu 29/121:30CPT - MDW
1 stop19h 53mDelta
Deal found 18/8R27 814
Tue 30/1212:10MDW - JNB
1 stop22h 50mDelta
Fri 16/121:55JNB - MDW
2 stops28h 39mDelta
Deal found 19/8R27 885
Wed 31/1210:08MDW - CPT
1 stop25h 07mDelta
Fri 16/121:30CPT - MDW
2 stops29h 04mDelta
Deal found 19/8R27 885
Sat 18/1010:35MDW - JNB
1 stop26h 05mVirgin Atlantic
Sun 23/1121:55JNB - MDW
1 stop31h 49mVirgin Atlantic
Deal found 19/8R27 903
Sat 27/913:08MDW - JNB
2 stops25h 27mKLM
Fri 10/1023:30JNB - MDW
2 stops25h 55mKLM
Deal found 17/8R27 938
Wed 31/1218:25MDW - JNB
2 stops40h 35mDelta
Fri 16/121:55JNB - MDW
1 stop26h 30mDelta
Deal found 19/8R28 114
Fri 16/117:25MDW - CPT
2 stops28h 45mDelta
Sun 25/121:30CPT - MDW
1 stop19h 53mDelta
Deal found 18/8R28 114
Sat 13/911:00MDW - JNB
1 stop25h 40mDelta
Sun 28/921:55JNB - MDW
1 stop20h 53mDelta
Deal found 19/8R28 256
Thu 18/910:35MDW - CPT
1 stop24h 15mDelta
Tue 30/920:05CPT - MDW
1 stop22h 43mDelta
Deal found 18/8R28 256
Tue 13/113:00MDW - CPT
2 stops24h 55mKLM
Mon 26/123:45CPT - MDW
2 stops26h 49mKLM
Deal found 18/8R28 308

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 20 August 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

Mon 2/2

10:35-19:15

1 stop24h 40m

Cape Town Intl

Mon 16/2

21:30-9:56

1 stop20h 26m

R27 373

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 30/12

12:10-19:00

1 stop22h 50m

Johannesburg OR Tambo

Fri 16/1

21:55-16:25

1 stop26h 30m

R27 814

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 1/1

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Sun 18/1

21:55-12:01

1 stop22h 06m

R27 814

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 30/12

12:10-19:00

1 stop22h 50m

Johannesburg OR Tambo

Sun 18/1

21:55-16:25

1 stop26h 30m

R27 814

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 30/12

10:08-19:00

1 stop24h 52m

Johannesburg OR Tambo

Sat 17/1

21:55-16:25

1 stop26h 30m

R27 814

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 1/1

15:30-19:00

1 stop19h 30m

Johannesburg OR Tambo

Sat 17/1

21:55-16:25

1 stop26h 30m

R27 814

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 1/1

15:30-19:00

1 stop19h 30m

Johannesburg OR Tambo

Fri 16/1

21:55-16:25

1 stop26h 30m

R27 814

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 14/1

17:25-19:15

1 stop17h 50m

Cape Town Intl

Fri 23/1

21:30-9:23

1 stop19h 53m

R27 814

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 15/1

17:25-19:15

1 stop17h 50m

Cape Town Intl

Mon 26/1

21:30-9:23

1 stop19h 53m

R27 814

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 31/12

10:08-19:15

1 stop25h 07m

Cape Town Intl

Sun 18/1

21:30-9:23

1 stop19h 53m

R27 814

Flights are sorted by cheapest return flights first.

Deals found on 18/8

Showing 1-10 of 29 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 (240 flights per day), Atlanta (181 flights per day) and Orlando (94 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 949. 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 20 August 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 20 August 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 Atlanta, Las Vegas, 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 949 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 459 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 459 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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