R2 330+ 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 24/1. 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 — CPT
Jan 21 — Jan 281
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 22 December 2025.

Good one-way deal

R3 751 or less
Price to beat on a one-way flight from Chicago Midway.
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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 22 December 2025.

Mon 2/210:46MDW - CPT
1 stop24h 29mDelta
Sun 15/221:30CPT - MDW
1 stop20h 24mDelta
Deal found 20/12R23 015
Mon 19/112:48MDW - CPT
1 stop22h 27mVirgin Atlantic
Tue 3/221:30CPT - MDW
1 stop27h 59mVirgin Atlantic
Deal found 21/12R23 434
Tue 3/29:33MDW - CPT
2 stops28h 22mDelta
Tue 10/221:30CPT - MDW
1 stop20h 23mDelta
Deal found 20/12R23 719
Tue 3/213:26MDW - CPT
2 stops24h 29mKLM
Tue 10/223:45CPT - MDW
2 stops26h 51mKLM
Deal found 20/12R23 770
Wed 4/212:46MDW - CPT
1 stop22h 29mDelta
Wed 18/223:45CPT - MDW
2 stops41h 21mDelta
Deal found 21/12R23 803
Fri 23/112:48MDW - CPT
2 stops36h 57mMultiple Airlines
Sun 1/221:30CPT - MDW
1 stop27h 59mMultiple Airlines
Deal found 21/12R23 837
Fri 6/212:46MDW - CPT
2 stops36h 59mMultiple Airlines
Fri 20/221:30CPT - MDW
1 stop33h 01mMultiple Airlines
Deal found 21/12R23 920
Mon 16/213:26MDW - CPT
2 stops21h 49mDelta
Wed 25/27:55CPT - MDW
2 stops41h 42mDelta
Deal found 21/12R24 004
Mon 19/113:26MDW - CPT
2 stops24h 29mKLM
Tue 3/28:00CPT - MDW
2 stops41h 55mKLM
Deal found 21/12R24 272
Fri 23/112:48MDW - JNB
1 stop22h 12mDelta
Sun 15/221:55JNB - MDW
1 stop22h 04mDelta
Deal found 20/12R26 032
Sat 24/116:30MDW - JNB
1 stop18h 30mDelta
Sun 8/221:55JNB - MDW
2 stops28h 41mDelta
Deal found 20/12R26 100
Wed 28/118:14MDW - JNB
1 stop40h 46mDelta
Fri 13/221:55JNB - MDW
1 stop25h 26mDelta
Deal found 20/12R26 150

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 22 December 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

Mon 2/2

10:46-19:15

1 stop24h 29m

Cape Town Intl

Sun 15/2

21:30-9:54

1 stop20h 24m

R23 015

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 19/2

9:34-19:15

2 stops25h 41m

Cape Town Intl

Thu 26/2

21:30-17:45

1 stop28h 15m

R23 082

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 19/1

12:48-19:15

1 stop22h 27m

Cape Town Intl

Tue 3/2

21:30-17:29

1 stop27h 59m

R23 434

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/2

12:46-19:15

1 stop22h 29m

Cape Town Intl

Wed 18/2

23:45-9:06

2 stops41h 21m

R23 803

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 16/2

12:45-19:15

1 stop22h 30m

Cape Town Intl

Wed 25/2

14:00-17:45

2 stops35h 45m

R23 837

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 16/2

13:26-19:15

2 stops21h 49m

Cape Town Intl

Wed 25/2

7:55-17:37

2 stops41h 42m

R24 004

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 19/1

13:26-21:55

2 stops24h 29m

Cape Town Intl

Tue 3/2

8:00-17:55

2 stops41h 55m

R24 272

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Fri 23/1

12:48-9:45

2 stops36h 57m

Cape Town Intl

Sun 1/2

20:50-22:22

2 stops33h 32m

R24 842

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Fri 6/2

13:26-21:55

2 stops24h 29m

Cape Town Intl

Fri 20/2

21:30-16:14

2 stops26h 44m

R25 295

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 27/1

12:48-19:00

1 stop22h 12m

Johannesburg OR Tambo

Sat 7/2

21:55-15:38

1 stop25h 43m

R26 032

Flights are sorted by cheapest return flights first.

Deals found on 21/12

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: Atlanta (155 flights per day), Orlando (150 flights per day) and Detroit (136 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 797
Miami
Miami
From R3 751

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 751. Explore other affordable destinations below.

Miami
Miami
From R3 751
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 797

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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 22 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 22 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 751 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 516 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 984 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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