R2 395+ 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 20/1. 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 30 — Feb 61
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 31 December 2025.

Good one-way deal

R3 721 or less
Price to beat on a one-way flight from Chicago Midway.
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Find flights from 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 31 December 2025.

Thu 5/212:46MDW - CPT
1 stop22h 29mDelta
Thu 12/221:30CPT - MDW
1 stop28h 15mDelta
Deal found 29/12R22 831
Thu 5/29:53MDW - CPT
2 stops25h 22mDelta
Tue 10/221:30CPT - MDW
1 stop20h 23mDelta
Deal found 29/12R22 898
Thu 22/113:26MDW - CPT
2 stops24h 29mKLM
Wed 11/223:45CPT - MDW
2 stops25h 52mKLM
Deal found 28/12R23 314
Thu 22/110:48MDW - CPT
1 stop24h 27mDelta
Wed 11/223:45CPT - MDW
2 stops25h 52mDelta
Deal found 28/12R23 530
Thu 22/112:48MDW - CPT
1 stop22h 27mMultiple Airlines
Sat 7/214:00CPT - MDW
2 stops40h 22mMultiple Airlines
Deal found 28/12R23 729
Thu 22/19:32MDW - CPT
2 stops25h 43mDelta
Sat 7/27:55CPT - MDW
2 stops40h 21mDelta
Deal found 28/12R23 812
Thu 26/212:45MDW - CPT
1 stop22h 30mDelta
Fri 6/321:30CPT - MDW
1 stop25h 51mDelta
Deal found 29/12R24 328
Tue 10/212:46MDW - CPT
2 stops36h 59mMultiple Airlines
Wed 18/220:50CPT - MDW
2 stops28h 55mMultiple Airlines
Deal found 30/12R24 644
Thu 12/26:00MDW - JNB
1 stop29h 00mDelta
Tue 10/321:55JNB - MDW
1 stop21h 07mDelta
Deal found 29/12R25 824
Wed 11/218:14MDW - JNB
1 stop40h 46mVirgin Atlantic
Wed 11/321:55JNB - MDW
1 stop31h 36mVirgin Atlantic
Deal found 29/12R25 991
Tue 20/113:31MDW - JNB
2 stops24h 34mKLM
Wed 28/123:59JNB - MDW
2 stops26h 37mKLM
Deal found 31/12R26 307
Tue 20/16:00MDW - JNB
1 stop29h 00mDelta
Wed 28/119:20JNB - MDW
2 stops30h 09mDelta
Deal found 31/12R26 506

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 31 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

Sun 18/1

11:21-19:15

1 stop23h 54m

Cape Town Intl

Sun 25/1

21:30-11:59

1 stop22h 29m

R22 831

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

R22 831

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 5/2

13:26-19:15

2 stops21h 49m

Cape Town Intl

Sun 8/2

21:30-12:46

2 stops23h 16m

R22 898

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 31/1

13:26-21:55

2 stops24h 29m

Cape Town Intl

Wed 11/2

23:45-17:37

2 stops25h 52m

R23 314

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 22/1

13:26-21:55

2 stops24h 29m

Cape Town Intl

Wed 11/2

23:45-17:37

2 stops25h 52m

R23 314

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 31/1

10:46-19:15

1 stop24h 29m

Cape Town Intl

Wed 11/2

23:45-22:31

2 stops30h 46m

R23 530

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 22/1

10:48-19:15

1 stop24h 27m

Cape Town Intl

Wed 11/2

23:45-17:37

2 stops25h 52m

R23 530

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 22/1

12:48-19:15

1 stop22h 27m

Cape Town Intl

Sat 7/2

14:00-22:22

2 stops40h 22m

R23 729

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 12/2

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Tue 10/3

21:55-12:02

1 stop21h 07m

R25 824

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 18/2

13:28-22:05

2 stops24h 37m

Johannesburg OR Tambo

Mon 16/3

19:20-16:55

2 stops28h 35m

R26 307

Flights are sorted by cheapest return flights first.

Deals found on 28/12

Showing 1-10 of 26 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 (150 flights per day), Detroit (124 flights per day) and Orlando (106 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 758
Miami
Miami
From R3 721

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 721. Explore other affordable destinations below.

Miami
Miami
From R3 721
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 758

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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 31 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 31 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 721 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 480 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 913 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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