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R2 175+ 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 6/4. 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 — JNB
Feb 26 — Mar 51
1 adult

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 21 February 2025.

Cheapest airline

United Airlines

Good one-way deal

R1 631 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago Midway (avg. price of R24 424).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

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 21 February 2025.

Wed 12/39:54MDW - JNB
1 stop26h 06mDelta
Tue 25/319:40JNB - MDW
2 stops29h 22mDelta
Deal found 19/2R29 201
Fri 14/314:55MDW - CPT
2 stops23h 35mDelta
Sun 23/321:15CPT - MDW
2 stops27h 47mDelta
Deal found 20/2R29 311
Mon 17/314:55MDW - CPT
2 stops23h 35mKLM
Mon 24/323:20CPT - MDW
2 stops30h 03mKLM
Deal found 20/2R29 403
Mon 7/414:57MDW - CPT
2 stops23h 33mMultiple Airlines
Mon 14/423:00CPT - MDW
2 stops26h 20mMultiple Airlines
Deal found 21/2R29 791
Mon 7/414:57MDW - JNB
2 stops23h 23mKLM
Mon 14/423:15JNB - MDW
2 stops26h 05mKLM
Deal found 20/2R29 864
Thu 20/318:42MDW - JNB
2 stops31h 48mAir France
Sun 6/418:50JNB - MDW
2 stops30h 12mAir France
Deal found 20/2R30 325

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 21 February 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 12/3

9:54-19:00

1 stop26h 06m

Johannesburg OR Tambo

Tue 25/3

19:40-18:02

2 stops29h 22m

R29 201

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Fri 14/3

14:55-21:30

2 stops23h 35m

Cape Town Intl

Sun 23/3

21:15-18:02

2 stops27h 47m

R29 311

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 17/3

14:55-21:30

2 stops23h 35m

Cape Town Intl

Mon 24/3

23:20-22:23

2 stops30h 03m

R29 403

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 7/4

14:57-21:30

2 stops23h 33m

Cape Town Intl

Mon 14/4

23:00-18:20

2 stops26h 20m

R29 791

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 7/4

14:57-21:20

2 stops23h 23m

Johannesburg OR Tambo

Mon 14/4

23:15-18:20

2 stops26h 05m

R29 864

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 20/3

18:42-9:30

2 stops31h 48m

Johannesburg OR Tambo

Sun 6/4

18:50-18:02

2 stops30h 12m

R30 325

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 11/4

13:03-7:10

2 stops59h 07m

R11 909

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 10/4

18:27-14:35

2 stops37h 08m

R17 421

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Wed 19/3

12:51-19:00

1 stop23h 09m

R28 168

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 1/5

10:20-17:50

2 stops24h 30m

R30 012

Flights are sorted by cheapest return flights first.

Deals found on 20/2

Showing 1-10 of 11 results
1
2

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 (174 flights per day), Atlanta (172 flights per day) and Orlando (152 flights per day).

Washington, D.C.

Washington, D.C.

From R88

Miami

Miami

From R224

Detroit

Detroit

From R104

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

The cheapest city to fly to from Chicago Midway Airport is Washington, D.C., with prices starting at R1 631. Explore other affordable destinations below.

Washington, D.C.

Washington, D.C.

From R88

Detroit

Detroit

From R104

Miami

Miami

From R224

Airline reviews for flights from Midway

Get insights into the airlines that provide service from Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Midway. In the last 7 days, Cheapflights users made a total of 594 507 searches.
Delta
8,0
Very Good
8 213 reviews
Check prices

Entertainment

7,9

Overall

8,0

Food

7,3

Crew

8,5

Boarding

8,2

Comfort

8,0

Reviews

1 / 20

10,0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8,0
Very Good
8 213 reviews
Delta
8,0
Very Good
8 213 reviews
Check prices

Entertainment

7,9

Overall

8,0

Food

7,3

Crew

8,5

Boarding

8,2

Comfort

8,0

Reviews

1 / 20

10,0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7,8
Good
1 331 reviews
Delta
8,0
Very Good
8 213 reviews
Check prices

Entertainment

7,9

Overall

8,0

Food

7,3

Crew

8,5

Boarding

8,2

Comfort

8,0

Reviews

1 / 20

10,0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France
7,4
Good
1 449 reviews
Delta
8,0
Very Good
8 213 reviews
Check prices

Entertainment

7,9

Overall

8,0

Food

7,3

Crew

8,5

Boarding

8,2

Comfort

8,0

Reviews

1 / 20

10,0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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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 21 February 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 21 February 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 Las Vegas, Atlanta, Miami. While Las Vegas, Atlanta, 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 R1 631 to Washington, D.C. Reagan-National Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for R2 733 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 881 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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