R1 660+ 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 28/1. 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
Jan 16 — Jan 231
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 17 December 2025.

Good one-way deal

R3 753 or less
Price to beat on a one-way flight from Chicago Midway.
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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 December 2025.

Mon 2/212:48MDW - CPT
1 stop22h 27mDelta
Sun 15/221:30CPT - MDW
1 stop22h 29mDelta
Deal found 16/12R23 008
Mon 23/212:46MDW - CPT
1 stop22h 29mDelta
Mon 16/321:30CPT - MDW
1 stop21h 32mDelta
Deal found 16/12R24 517
Mon 2/36:00MDW - JNB
1 stop29h 00mDelta
Wed 11/321:55JNB - MDW
1 stop25h 58mDelta
Deal found 15/12R26 027
Mon 5/111:21MDW - CPT
1 stop23h 54mDelta
Mon 19/121:30CPT - MDW
1 stop22h 29mDelta
Deal found 15/12R26 446
Wed 18/213:49MDW - JNB
2 stops24h 16mMultiple Airlines
Mon 16/319:20JNB - MDW
2 stops28h 33mMultiple Airlines
Deal found 15/12R26 513
Thu 29/113:26MDW - JNB
2 stops24h 39mKLM
Thu 5/223:59JNB - MDW
2 stops26h 37mKLM
Deal found 15/12R26 563
Thu 29/16:00MDW - JNB
1 stop29h 00mDelta
Thu 5/219:20JNB - MDW
2 stops30h 35mDelta
Deal found 15/12R26 731
Sun 26/417:25MDW - JNB
1 stop19h 15mDelta
Thu 7/521:55JNB - MDW
1 stop25h 30mDelta
Deal found 16/12R26 865
Fri 16/111:21MDW - CPT
2 stops38h 04mMultiple Airlines
Fri 6/221:30CPT - MDW
1 stop32h 52mMultiple Airlines
Deal found 15/12R27 368
Wed 1/412:47MDW - JNB
1 stop23h 53mDelta
Wed 8/418:00JNB - MDW
2 stops29h 53mDelta
Deal found 15/12R27 570
Wed 14/113:28MDW - JNB
2 stops24h 37mKLM
Wed 21/123:59JNB - MDW
2 stops26h 37mKLM
Deal found 15/12R28 089
Fri 9/16:45MDW - JNB
1 stop28h 15mVirgin Atlantic
Fri 16/122:00JNB - MDW
2 stops32h 07mVirgin Atlantic
Deal found 15/12R28 609

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 December 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

Mon 19/1

12:48-19:15

1 stop22h 27m

Cape Town Intl

Tue 3/2

21:30-9:53

1 stop20h 23m

R23 008

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 5/2

10:48-19:15

1 stop24h 27m

Cape Town Intl

Sun 15/2

21:30-17:45

1 stop28h 15m

R23 008

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/2

12:48-19:15

1 stop22h 27m

Cape Town Intl

Sun 15/2

21:30-9:56

1 stop20h 26m

R23 008

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 5/2

12:48-19:15

1 stop22h 27m

Cape Town Intl

Sun 15/2

21:30-18:37

2 stops29h 07m

R23 092

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 23/2

12:46-19:15

1 stop22h 29m

Cape Town Intl

Mon 16/3

21:30-12:02

1 stop21h 32m

R24 517

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 2/3

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Wed 11/3

21:55-16:53

1 stop25h 58m

R26 027

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 5/1

11:21-19:15

1 stop23h 54m

Cape Town Intl

Mon 19/1

21:30-11:59

1 stop22h 29m

R26 446

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 11/3

14:03-22:05

2 stops25h 02m

Johannesburg OR Tambo

Wed 18/3

23:59-18:40

2 stops25h 41m

R26 513

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 29/1

13:26-22:05

2 stops24h 39m

Johannesburg OR Tambo

Thu 5/2

23:59-18:36

2 stops26h 37m

R26 563

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sun 26/4

17:25-19:40

1 stop19h 15m

Johannesburg OR Tambo

Thu 7/5

21:55-16:25

1 stop25h 30m

R26 865

Flights are sorted by cheapest return flights first.

Deals found on 15/12

Showing 1-10 of 28 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 (164 flights per day), Atlanta (145 flights per day) and Orlando (120 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 799
Miami
Miami
From R3 753

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 753. Explore other affordable destinations below.

Miami
Miami
From R3 753
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 799

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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 December 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 December 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, Miami. 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 753 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 518 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 988 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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