How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a stopover will also be longer. The most popular routes to Chicago on KAYAK are from Cape Town , which takes 20h 38m , Johannesburg , which takes 21h 55m, and Durban , which takes 34h 10m.

How far is Chicago Midway Airport from central Chicago?

Chicago Midway Airport is 14 km from the centre of Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK find such low prices on flights to Chicago Midway Airport?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travellers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights to Chicago Midway Airport?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

R15 686 CHEAP FLIGHTS to Chicago Midway (MDW) in 2025

MDW

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Cheap Flight Deals to Midway

Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

All Flight Deals

Recent return flight deals to Midway

Recommended return deals departing in the coming months from the most popular airlines that fly to Midway.

Discover the best prices and deals for you by selecting your travel dates.

Choose your dates

21:55 - 10:12JNB-MDW

20h 17m1 stop

13:26 - 19:00MDW-JNB

21h 34m2 stops

R17 811Delta

Find Deal

Wed, Feb 12 - Wed, Feb 19

19:40 - 16:20JNB-MDW

28h 40m2 stops

9:33 - 19:00MDW-JNB

25h 27m2 stops

R17 924Delta

Find Deal

Wed, Feb 12 - Wed, Feb 19

8:05 - 18:11CPT-MDW

42h 06m2 stops

15:41 - 19:00MDW-CPT

19h 19m1 stop

R17 943Delta

Find Deal

Wed, Feb 12 - Sat, Feb 22

23:20 - 18:11CPT-MDW

26h 51m2 stops

11:25 - 19:00MDW-CPT

23h 35m2 stops

R17 980Delta

Find Deal

Wed, Feb 12 - Sat, Feb 22

23:20 - 18:14CPT-MDW

26h 54m2 stops

9:33 - 6:30MDW-CPT

36h 57m2 stops

R18 074Delta

Find Deal

Mon, Jan 27 - Sun, Feb 9

23:55 - 18:11JNB-MDW

26h 16m2 stops

14:08 - 22:00MDW-JNB

23h 52m2 stops

R18 112KLM

Find Deal

Thu, Feb 6 - Thu, Feb 20

23:15 - 18:02JNB-MDW

25h 47m2 stops

14:57 - 21:20MDW-JNB

23h 23m2 stops

R18 394Delta

Find Deal

Mon, Mar 31 - Wed, Apr 9

23:55 - 18:11JNB-MDW

26h 16m2 stops

14:55 - 21:20MDW-JNB

23h 25m2 stops

R20 237KLM

Find Deal

Tue, Feb 18 - Tue, Apr 1

23:15 - 18:04JNB-MDW

25h 49m2 stops

13:05 - 21:20MDW-JNB

25h 15m2 stops

R25 842KLM

Find Deal

Mon, Jun 2 - Sun, Jun 15

23:35 - 22:29CPT-MDW

29h 54m2 stops

15:02 - 21:25MDW-CPT

23h 23m2 stops

R47 791

Find Deal

Tue, Apr 15 - Wed, Apr 30

Flights to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights to Midway to help you find the cheapest flights, the best time to fly and much more.

Prices

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as R26 272. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are R26 272 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

The cheapest time of day to fly to Chicago Midway Airport is generally in the evening, when round-trip flights cost R25 206 on average. The most expensive time of day to fly to Chicago Midway Airport is generally at night, which is peak travel time and where the average cost of a ticket is R27 809.

Cheapest flight	R14 294

Flight from Cape Town to Chicago Midway Airport

When to book flights to Midway

Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated return price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

How far is Chicago Midway Airport from central Chicago?
Chicago Midway Airport is 14 km from the centre of Chicago.
How does KAYAK find such low prices on flights to Chicago Midway Airport?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travellers know whether to wait or book now.
What is the Hacker Fare option on flights to Chicago Midway Airport?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

High season is considered to be January, February and December. The cheapest month to fly from South Africa is January.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Direct departures

South Africa to Chicago Midway

Monday