R2 263+ 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 15/4. 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
Apr 5 — Apr 121
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 6 March 2026.

Good one-way deal

R4 727 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 6 March 2026.

Sun 22/312:47
MDW
-
CPT
1 stop23h 28m
Delta
Sun 5/420:05
CPT
-
MDW
1 stop22h 57m
Delta
Deal found 3/3R27 535
Thu 26/312:47
MDW
-
CPT
1 stop23h 28m
Multiple Airlines
Fri 3/420:05
CPT
-
MDW
1 stop26h 20m
Multiple Airlines
Deal found 2/3R27 865
Mon 23/310:45
MDW
-
CPT
1 stop25h 30m
Multiple Airlines
Wed 15/49:55
CPT
-
MDW
2 stops37h 34m
Multiple Airlines
Deal found 3/3R28 460
Mon 13/417:21
MDW
-
JNB
1 stop19h 19m
Virgin Atlantic
Tue 28/421:55
JNB
-
MDW
1 stop25h 31m
Virgin Atlantic
Deal found 1/3R29 121
Mon 13/414:12
MDW
-
JNB
2 stops22h 28m
Delta
Tue 28/421:55
JNB
-
MDW
2 stops27h 03m
Delta
Deal found 1/3R29 187
Thu 7/512:51
MDW
-
JNB
1 stop23h 49m
Virgin Atlantic
Fri 15/521:55
JNB
-
MDW
1 stop30h 14m
Virgin Atlantic
Deal found 2/3R29 451
Thu 7/59:22
MDW
-
JNB
2 stops27h 18m
Delta
Fri 15/521:55
JNB
-
MDW
1 stop30h 14m
Delta
Deal found 2/3R29 517
Thu 26/312:47
MDW
-
JNB
1 stop23h 13m
Virgin Atlantic
Sun 5/421:55
JNB
-
MDW
1 stop31h 36m
Virgin Atlantic
Deal found 3/3R29 600
Wed 18/310:45
MDW
-
CPT
1 stop25h 30m
Delta
Mon 30/320:25
CPT
-
MDW
2 stops28h 29m
Delta
Deal found 5/3R29 748
Tue 14/410:41
MDW
-
JNB
1 stop25h 59m
Delta
Tue 21/418:00
JNB
-
MDW
2 stops30h 58m
Delta
Deal found 1/3R29 798
Thu 7/513:22
MDW
-
JNB
2 stops24h 58m
KLM
Fri 15/523:15
JNB
-
MDW
2 stops26h 18m
KLM
Deal found 2/3R29 897
Thu 26/318:07
MDW
-
JNB
1 stop17h 53m
Delta
Thu 2/418:00
JNB
-
MDW
2 stops30h 54m
Delta
Deal found 2/3R30 194

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 6 March 2026. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 13/4

14:12-19:40

2 stops22h 28m

Johannesburg OR Tambo

Tue 28/4

21:55-17:58

2 stops27h 03m

R29 187

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 18/3

10:45-19:15

1 stop25h 30m

Cape Town Intl

Mon 30/3

20:25-17:54

2 stops28h 29m

R29 748

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 30/3

13:10-21:20

2 stops25h 10m

Johannesburg OR Tambo

Mon 6/4

18:00-17:54

2 stops30h 54m

R30 574

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 6/4

10:45-17:50

1 stop24h 05m

Cape Town Intl

Sun 19/4

20:05-12:07

1 stop23h 02m

R31 152

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 27/4

10:41-17:50

1 stop24h 09m

Cape Town Intl

Sun 10/5

20:05-11:56

1 stop22h 51m

R31 169

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 16/4

13:24-17:50

2 stops21h 26m

Cape Town Intl

Fri 24/4

20:05-13:32

2 stops24h 27m

R31 235

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 23/4

12:52-17:50

1 stop21h 58m

Cape Town Intl

Wed 6/5

23:15-18:33

2 stops26h 18m

R31 829

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 20/4

13:24-17:50

2 stops21h 26m

Cape Town Intl

Wed 29/4

23:15-22:28

2 stops30h 13m

R31 912

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 22/4

17:21-9:45

2 stops33h 24m

Cape Town Intl

Sat 2/5

7:00-16:26

2 stops40h 26m

R32 193

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Sat 23/5

13:22-21:20

2 stops24h 58m

Johannesburg OR Tambo

Sun 31/5

23:15-17:56

2 stops25h 41m

R32 490

Flights are sorted by cheapest return flights first.

Deals found on 2/3

Showing 1-10 of 37 resultsSorted by cheapest first
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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 (96 flights per day), Atlanta (75 flights per day) and Minneapolis (42 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 727

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 727. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 727

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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 6 March 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 6 March 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 Orlando Airport, Las Vegas, Phoenix Sky Harbor Intl 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 727 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 727 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 853 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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