R2 496+ 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 22/4. 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 15 — Mar 221
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 13 February 2026.

Good one-way deal

R4 549 or less
Price to beat on a one-way flight from Chicago Midway.
Search Deals

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 13 February 2026.

Sun 1/312:45
MDW
-
CPT
1 stop22h 30m
Delta
Wed 11/37:55
CPT
-
MDW
2 stops40h 59m
Delta
Deal found 10/2R22 732
Mon 9/318:07
MDW
-
CPT
1 stop18h 08m
Virgin Atlantic
Sun 12/420:05
CPT
-
MDW
1 stop33h 23m
Virgin Atlantic
Deal found 10/2R27 628
Mon 9/312:47
MDW
-
CPT
1 stop23h 28m
Delta
Sun 12/420:05
CPT
-
MDW
1 stop33h 23m
Delta
Deal found 13/2R27 644
Sat 9/516:30
MDW
-
JNB
1 stop20h 10m
Virgin Atlantic
Mon 18/521:55
JNB
-
MDW
1 stop25h 22m
Virgin Atlantic
Deal found 10/2R28 009
Sat 2/517:21
MDW
-
JNB
1 stop19h 19m
Virgin Atlantic
Sun 17/521:55
JNB
-
MDW
1 stop30h 14m
Virgin Atlantic
Deal found 11/2R28 025
Mon 30/312:47
MDW
-
JNB
1 stop23h 53m
Virgin Atlantic
Mon 13/421:55
JNB
-
MDW
1 stop25h 34m
Virgin Atlantic
Deal found 10/2R28 073
Sat 7/311:06
MDW
-
JNB
1 stop23h 54m
Delta
Tue 7/421:55
JNB
-
MDW
1 stop21h 07m
Delta
Deal found 12/2R28 089
Sat 7/39:34
MDW
-
JNB
2 stops25h 26m
Delta
Sun 5/421:55
JNB
-
MDW
1 stop21h 07m
Delta
Deal found 12/2R28 153
Fri 6/318:40
MDW
-
JNB
1 stop40h 20m
Delta
Sun 5/421:55
JNB
-
MDW
1 stop21h 07m
Delta
Deal found 12/2R28 200
Fri 8/59:23
MDW
-
JNB
2 stops28h 57m
Multiple Airlines
Fri 22/518:00
JNB
-
MDW
2 stops34h 09m
Multiple Airlines
Deal found 11/2R28 470
Thu 5/313:29
MDW
-
JNB
2 stops24h 36m
KLM
Tue 17/323:59
JNB
-
MDW
2 stops25h 41m
KLM
Deal found 12/2R28 598
Fri 8/510:46
MDW
-
JNB
1 stop25h 54m
Delta
Fri 22/518:00
JNB
-
MDW
2 stops30h 56m
Delta
Deal found 11/2R28 677

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 13 February 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

Sun 1/3

9:34-19:15

2 stops25h 41m

Cape Town Intl

Wed 11/3

7:55-17:54

2 stops40h 59m

R22 795

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 9/3

9:35-19:15

2 stops26h 40m

Cape Town Intl

Sun 12/4

20:05-22:28

1 stop33h 23m

R27 707

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 9/5

16:30-19:40

1 stop20h 10m

Johannesburg OR Tambo

Mon 18/5

21:55-16:17

1 stop25h 22m

R28 025

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 8/5

12:51-19:40

1 stop23h 49m

Johannesburg OR Tambo

Fri 22/5

21:55-15:26

1 stop24h 31m

R28 025

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 30/3

12:47-19:40

1 stop23h 53m

Johannesburg OR Tambo

Mon 13/4

21:55-16:29

1 stop25h 34m

R28 073

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 9/5

16:30-19:40

1 stop20h 10m

Johannesburg OR Tambo

Mon 18/5

21:55-18:14

2 stops27h 19m

R28 089

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 10/3

10:45-19:00

1 stop25h 15m

Johannesburg OR Tambo

Sun 5/4

21:55-12:02

1 stop21h 07m

R28 089

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 10/3

10:45-19:00

1 stop25h 15m

Johannesburg OR Tambo

Tue 7/4

21:55-12:02

1 stop21h 07m

R28 089

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 9/3

12:47-19:00

1 stop23h 13m

Johannesburg OR Tambo

Sun 5/4

21:55-12:02

1 stop21h 07m

R28 089

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 9/3

12:47-19:00

1 stop23h 13m

Johannesburg OR Tambo

Tue 7/4

21:55-12:02

1 stop21h 07m

R28 089

Flights are sorted by cheapest return flights first.

Deals found on 13/2

Showing 1-10 of 34 results
1
2
3
4

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 (84 flights per day), Atlanta (77 flights per day) and Orlando (68 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 549

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Atlanta Hartsfield-Jackson, with prices starting at R4 549. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 549

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 13 February 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 13 February 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 Atlanta, Phoenix Sky Harbor Intl Airport, Orlando Airport. 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 R4 549 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 549 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 520 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.

See more FAQs

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.