Cheap flights from Cape Town to Chicago from R11 486

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cape Town to Chicago departing on 20/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap return flights

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Virgin Atlantic Logo
21:30 - 16:14CPT-MDW
26h 44m1 stop
Virgin Atlantic Logo
12:47 - 19:15MDW-CPT
22h 28m1 stop
R16 024Virgin Atlantic
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Thu, Nov 6 - Sun, Nov 16
Virgin Atlantic Logo
23:10 - 22:14CPT-MDW
31h 04m2 stops
Virgin Atlantic Logo
10:47 - 19:15MDW-CPT
24h 28m1 stop
R16 908Virgin Atlantic
Find Deal
Thu, Nov 6 - Sun, Nov 16
Delta Logo
21:30 - 12:28CPT-MDW
22h 58m2 stops
Delta Logo
13:47 - 19:15MDW-CPT
21h 28m2 stops
R17 410Delta
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Thu, Nov 6 - Sun, Nov 16
Delta Logo
23:45 - 23:40CPT-MDW
31h 55m2 stops
Delta Logo
13:14 - 19:15MDW-CPT
22h 01m2 stops
R18 398Delta
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Wed, Nov 26 - Wed, Dec 3
Delta Logo
23:45 - 12:35CPT-MDW
43h 50m2 stops
Delta Logo
9:30 - 19:15MDW-CPT
26h 45m2 stops
R30 611Delta
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Wed, Mar 11 - Sun, Mar 15
Delta Logo
23:45 - 18:34CPT-MDW
25h 49m2 stops
Delta Logo
17:59 - 19:15MDW-CPT
42h 16m2 stops
R30 646Delta
Find Deal
Wed, Mar 11 - Sun, Mar 15
Delta Logo
23:45 - 18:34CPT-MDW
25h 49m2 stops
Delta Logo
10:35 - 19:15MDW-CPT
25h 40m1 stop
R31 529Delta
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Wed, Mar 11 - Sun, Mar 15
Multiple Airlines Logo
13:40 - 15:20CPT-MDW
33h 40m3 stops
Multiple Airlines Logo
9:59 - 5:50MDW-CPT
35h 51m3 stops
R42 945Multiple Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
13:40 - 15:20CPT-MDW
33h 40m3 stops
Multiple Airlines Logo
13:14 - 5:50MDW-CPT
32h 36m2 stops
R44 331Multiple Airlines
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Thu, Nov 27 - Thu, Dec 4

Virgin Atlantic flights from Cape Town to Chicago Midway Airport

Our best Virgin Atlantic deals on Cape Town to Chicago Midway Airport flight tickets
Virgin Atlantic
Nov 6
CPT21:30Cape Town Intl
26h 44m
1 stop
MDW16:14Chicago Midway
Nov 16
MDW12:47Chicago Midway
22h 28m
1 stop
CPT19:15Cape Town Intl
R16 024
Find similar
Virgin Atlantic
Nov 6
CPT23:10Cape Town Intl
31h 04m
2 stops
MDW22:14Chicago Midway
Nov 16
MDW10:47Chicago Midway
24h 28m
1 stop
CPT19:15Cape Town Intl
R16 908
Find similar

Delta flights from Cape Town to Chicago Midway Airport

Our best Delta deals on Cape Town to Chicago Midway Airport flight tickets
Delta
Nov 6
CPT21:30Cape Town Intl
22h 58m
2 stops
MDW12:28Chicago Midway
Nov 16
MDW13:47Chicago Midway
21h 28m
2 stops
CPT19:15Cape Town Intl
R17 410
Find similar
Delta
Nov 26
CPT23:45Cape Town Intl
31h 55m
2 stops
MDW23:40Chicago Midway
Dec 3
MDW13:14Chicago Midway
22h 01m
2 stops
CPT19:15Cape Town Intl
R18 398
Find similar
Delta
Mar 11
CPT23:45Cape Town Intl
43h 50m
2 stops
MDW12:35Chicago Midway
Mar 15
MDW9:30Chicago Midway
26h 45m
2 stops
CPT19:15Cape Town Intl
R30 611
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momondo Fare Finder

 
Customise your flight search to find flights from Cape Town to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 13 550 searches. Data last updated 14 October 2025.
Use the filters below to find and compare flights from Cape Town to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 6/11

21:30-16:14

1 stop26h 44m

Chicago Midway

Sun 16/11

12:47-19:15

1 stop22h 28m

R16 024

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 6/11

23:10-22:14

2 stops31h 04m

Chicago Midway

Sun 16/11

10:47-19:15

1 stop24h 28m

R16 908

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 6/11

21:30-12:28

2 stops22h 58m

Chicago Midway

Sun 16/11

13:47-19:15

2 stops21h 28m

R17 410

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 26/11

23:45-23:40

2 stops31h 55m

Chicago Midway

Wed 3/12

13:14-19:15

2 stops22h 01m

R18 398

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 11/3

23:45-12:35

2 stops43h 50m

Chicago Midway

Sun 15/3

9:30-19:15

2 stops26h 45m

R30 611

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 11/3

23:45-18:34

2 stops25h 49m

Chicago Midway

Sun 15/3

17:59-19:15

2 stops42h 16m

R30 646

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 11/3

23:45-18:34

2 stops25h 49m

Chicago Midway

Sun 15/3

10:35-19:15

1 stop25h 40m

R31 529

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 27/11

13:40-15:20

3 stops33h 40m

Chicago Midway

Thu 4/12

9:59-5:50

3 stops35h 51m

R42 945

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 27/11

13:40-15:20

3 stops33h 40m

Chicago Midway

Thu 4/12

13:14-5:50

2 stops32h 36m

R44 331

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 20/11

12:30-23:29

2 stops42h 59m

R11 486

Flights are sorted by cheapest return flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Cape Town to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our data shows that the cheapest Cape Town to Chicago Midway Airport flights are usually those with departure times in the afternoon. Our users have found flights to Chicago Midway Airport in the afternoon for as low as R23 217. Try not to purchase tickets in the evening because they tend to be around R25 615. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Cape Town to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Cape Town to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Cape Town to Chicago Midway Airport (CPT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cape Town to Chicago Midway Airport

Direct flights

None
There are no direct flights from Cape Town to Chicago Midway Airport. There are no popular flight routes from Cape Town to Chicago Midway Airport.
  • How far is Cape Town Intl to Chicago Midway by plane?

    Chicago Midway is 13665,7 km away from Cape Town Intl. By plane, this route typically takes 22h 58m.

  • When did momondo last update prices for flights from Cape Town Intl Airport to Chicago Midway Airport?

    Prices for flights from Cape Town Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Cape Town Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cape Town Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond

Why use momondo?

Why should I use momondo to find a flight deal from Cape Town to Chicago?

Finding the right flight to Chicago from Cape Town is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Cape Town to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Cape Town which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Cape Town to Chicago?

momondo helps you find the best flight between Cape Town and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Cape Town to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Cape Town to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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1 adult
Thu 13/11
Thu 20/11

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