R2 707+ 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 6/5. 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
Apr 25 — May 21
1 adult
1 adult, Economy, 0 bags

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 26 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

Sun 6/9

16:30-19:40

1 stop20h 10m

Johannesburg OR Tambo

Sun 20/9

21:55-18:31

2 stops27h 36m

R33 582

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 1/5

9:27-21:20

2 stops28h 53m

Johannesburg OR Tambo

Mon 11/5

21:55-11:56

1 stop21h 01m

R34 191

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 23/4

10:41-17:50

1 stop24h 09m

Cape Town Intl

Wed 6/5

23:15-18:33

2 stops26h 18m

R35 087

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 4/5

14:12-19:40

2 stops22h 28m

Johannesburg OR Tambo

Tue 7/7

21:55-22:15

1 stop31h 20m

R35 544

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 19/5

9:22-21:20

2 stops28h 58m

Johannesburg OR Tambo

Mon 29/6

18:00-16:46

2 stops29h 46m

R35 882

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 24/5

9:22-21:25

2 stops29h 03m

Cape Town Intl

Sun 7/6

20:05-16:16

1 stop27h 11m

R36 288

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 24/5

13:22-21:25

2 stops25h 03m

Cape Town Intl

Sun 7/6

23:15-18:18

2 stops26h 03m

R36 593

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 1/6

6:23-19:40

1 stop30h 17m

Johannesburg OR Tambo

Mon 8/6

23:15-18:18

2 stops26h 03m

R37 084

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 23/5

13:22-21:25

2 stops25h 03m

Cape Town Intl

Sun 31/5

23:15-17:56

2 stops25h 41m

R37 456

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 24/5

13:22-21:25

2 stops25h 03m

Cape Town Intl

Sun 31/5

23:15-17:56

2 stops25h 41m

R37 456

Flights are sorted by cheapest return flights first.

Deals found on 24/3

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 (204 flights per day), Atlanta (176 flights per day) and Orlando (134 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 841

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 841. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 841

Browse thousands of different options on Cheapflights for your next trip

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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 26 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 26 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, Phoenix Sky Harbor Intl Airport, Las Vegas. 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 841 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for R4 841 to fly from Chicago Midway Airport.

  • 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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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