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 17/1. 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 — JNB
Dec 30 — Jan 61
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 November 2025.

Good one-way deal

R3 829 or less
Price to beat on a one-way flight from Chicago Midway.
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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 November 2025.

Mon 2/212:48MDW - CPT
1 stop22h 27mDelta
Sun 15/221:30CPT - MDW
1 stop33h 12mDelta
Deal found 28/11R23 559
Thu 26/210:53MDW - CPT
1 stop24h 22mDelta
Tue 17/321:30CPT - MDW
1 stop21h 32mDelta
Deal found 29/11R25 013
Thu 26/213:49MDW - CPT
2 stops21h 26mDelta
Thu 12/321:30CPT - MDW
1 stop21h 32mDelta
Deal found 29/11R25 082
Fri 30/112:48MDW - CPT
2 stops26h 47mMultiple Airlines
Fri 6/220:50CPT - MDW
2 stops33h 32mMultiple Airlines
Deal found 29/11R25 373
Tue 17/218:40MDW - CPT
1 stop40h 35mMultiple Airlines
Wed 4/315:20CPT - MDW
2 stops34h 25mMultiple Airlines
Deal found 28/11R25 937
Sat 17/18:22MDW - JNB
2 stops39h 58mMultiple Airlines
Sat 31/120:30JNB - MDW
2 stops33h 49mMultiple Airlines
Deal found 28/11R26 108
Sat 28/216:13MDW - JNB
1 stop18h 47mDelta
Wed 18/321:55JNB - MDW
1 stop21h 07mDelta
Deal found 28/11R26 553
Sat 28/216:13MDW - CPT
1 stop19h 02mDelta
Sun 15/321:30CPT - MDW
1 stop26h 23mDelta
Deal found 29/11R26 553
Sat 17/113:28MDW - JNB
2 stops21h 32mDelta
Sat 31/121:55JNB - MDW
2 stops28h 00mDelta
Deal found 28/11R26 622
Mon 2/39:34MDW - CPT
2 stops25h 41mDelta
Mon 16/321:30CPT - MDW
1 stop21h 32mDelta
Deal found 29/11R26 622
Sun 1/318:40MDW - JNB
1 stop40h 20mDelta
Wed 18/321:55JNB - MDW
1 stop21h 07mDelta
Deal found 28/11R26 673
Sun 18/117:59MDW - JNB
1 stop41h 01mDelta
Sat 31/121:55JNB - MDW
1 stop32h 27mDelta
Deal found 28/11R26 793

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 November 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 26/2

13:49-19:15

2 stops21h 26m

Cape Town Intl

Mon 16/3

21:30-12:29

2 stops21h 59m

R25 082

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 2/3

12:46-19:00

1 stop22h 14m

Johannesburg OR Tambo

Tue 17/3

21:55-12:02

1 stop21h 07m

R26 553

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

12:46-19:15

1 stop22h 29m

Cape Town Intl

Tue 17/3

21:30-16:53

1 stop26h 23m

R26 553

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 28/2

16:13-19:15

1 stop19h 02m

Cape Town Intl

Fri 13/3

21:30-15:25

1 stop24h 55m

R26 553

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/3

12:46-19:15

1 stop22h 29m

Cape Town Intl

Sun 15/3

21:30-16:53

1 stop26h 23m

R26 553

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 17/1

11:21-19:00

1 stop23h 39m

Johannesburg OR Tambo

Sat 31/1

21:55-22:22

1 stop32h 27m

R26 673

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 17/2

10:53-22:50

2 stops27h 57m

Cape Town Intl

Wed 4/3

14:00-17:45

2 stops35h 45m

R26 690

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 18/1

17:59-19:00

1 stop41h 01m

Johannesburg OR Tambo

Sat 31/1

21:55-22:22

1 stop32h 27m

R26 793

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 2/3

13:49-22:05

2 stops24h 16m

Johannesburg OR Tambo

Mon 16/3

19:20-16:53

2 stops28h 33m

R26 895

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 24/3

17:38-19:00

1 stop18h 22m

Johannesburg OR Tambo

Mon 6/4

21:55-16:53

1 stop25h 58m

R26 981

Flights are sorted by cheapest return flights first.

Deals found on 28/11

Showing 1-10 of 33 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: Atlanta (107 flights per day), Detroit (64 flights per day) and Minneapolis (41 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 896
Miami
Miami
From R3 829

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 829. Explore other affordable destinations below.

Miami
Miami
From R3 829
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 896

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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 November 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 30 November 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, Orlando Airport, Dallas/Fort Worth 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 829 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 610 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 170 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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