R1 988+ 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 8/12. 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
Dec 9 — Dec 161
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 9 November 2025.

Good one-way deal

R3 868 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 9 November 2025.

Wed 19/1110:47MDW - CPT
1 stop24h 28mVirgin Atlantic
Sun 23/1121:30CPT - MDW
1 stop27h 09mVirgin Atlantic
Deal found 8/11R21 278
Wed 19/119:34MDW - CPT
2 stops25h 41mDelta
Sun 23/1121:30CPT - MDW
2 stops23h 37mDelta
Deal found 8/11R21 365
Sun 23/1110:47MDW - CPT
1 stop24h 28mDelta
Mon 1/1221:30CPT - MDW
1 stop26h 48mDelta
Deal found 8/11R22 143
Sat 22/1119:02MDW - CPT
2 stops40h 13mDelta
Thu 4/1221:30CPT - MDW
2 stops28h 30mDelta
Deal found 8/11R22 229
Sun 23/1113:15MDW - CPT
2 stops22h 00mDelta
Sun 30/1121:30CPT - MDW
2 stops52h 30mDelta
Deal found 8/11R22 436
Sun 23/1112:47MDW - CPT
1 stop22h 28mDelta
Wed 3/1223:45CPT - MDW
2 stops32h 02mDelta
Deal found 8/11R22 869
Tue 25/1113:15MDW - CPT
2 stops24h 40mDelta
Tue 9/1221:30CPT - MDW
2 stops23h 04mDelta
Deal found 8/11R22 938
Wed 3/1217:29MDW - CPT
1 stop17h 46mDelta
Tue 16/1221:30CPT - MDW
1 stop27h 04mDelta
Deal found 6/11R23 007
Wed 3/1213:14MDW - CPT
2 stops22h 01mDelta
Sun 14/1221:30CPT - MDW
1 stop20h 24mDelta
Deal found 6/11R23 093
Wed 3/1217:29MDW - CPT
1 stop17h 46mDelta
Thu 11/1221:30CPT - MDW
1 stop34h 17mDelta
Deal found 6/11R23 128
Sat 6/1218:46MDW - CPT
2 stops40h 29mDelta
Mon 15/1221:30CPT - MDW
1 stop20h 24mDelta
Deal found 6/11R23 301
Fri 28/119:34MDW - CPT
2 stops28h 21mDelta
Thu 11/1221:30CPT - MDW
1 stop22h 25mDelta
Deal found 8/11R23 646

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 9 November 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

Wed 19/11

10:47-19:15

1 stop24h 28m

Cape Town Intl

Sun 23/11

21:30-16:39

1 stop27h 09m

R21 278

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 19/11

9:34-19:15

2 stops25h 41m

Cape Town Intl

Sun 23/11

21:30-13:07

2 stops23h 37m

R21 365

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 22/11

18:48-19:15

2 stops40h 27m

Cape Town Intl

Thu 4/12

21:30-9:54

1 stop20h 24m

R22 229

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 22/11

18:48-19:15

2 stops40h 27m

Cape Town Intl

Mon 1/12

21:30-12:34

2 stops23h 04m

R22 229

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 23/11

19:02-19:15

2 stops40h 13m

Cape Town Intl

Mon 1/12

21:30-12:34

2 stops23h 04m

R22 229

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Tue 25/11

10:47-21:55

2 stops27h 08m

Cape Town Intl

Tue 9/12

21:30-16:34

1 stop27h 04m

R22 869

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 7/12

9:34-19:15

2 stops25h 41m

Cape Town Intl

Mon 15/12

21:30-9:54

1 stop20h 24m

R23 093

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 3/12

17:29-19:15

1 stop17h 46m

Cape Town Intl

Fri 12/12

21:30-18:06

2 stops28h 36m

R23 093

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 4/12

17:13-19:15

1 stop18h 02m

Cape Town Intl

Tue 16/12

21:30-13:10

2 stops23h 40m

R23 093

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 4/12

17:13-19:15

1 stop18h 02m

Cape Town Intl

Thu 11/12

21:30-23:47

1 stop34h 17m

R23 128

Flights are sorted by cheapest return flights first.

Deals found on 7/11

Showing 1-10 of 39 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: Orlando (148 flights per day), Detroit (110 flights per day) and Atlanta (94 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 946
Miami
Miami
From R3 868

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 868. Explore other affordable destinations below.

Miami
Miami
From R3 868
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 946

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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 9 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 9 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 868 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 657 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 265 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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