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Cheap flights from Cape Town to Chicago from R10 725

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
CPT — CHI
Jul 16 — Jul 231
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Cape Town to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Cape Town to Chicago
Explore the most affordable flight options available from Cape Town to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 June 2026.

Tue 1/1220:50
CPT
-
MDW
2 stops28h 00m
Delta
Tue 19/117:59
MDW
-
CPT
2 stops40h 36m
Delta
Deal found 15/6R16 079
Fri 10/720:05
CPT
-
ORD
1 stop29h 41m
Delta
Sat 25/77:00
ORD
-
CPT
1 stop27h 50m
Delta
Deal found 12/6R16 079
Mon 13/719:50
CPT
-
ORD
1 stop23h 16m
United Airlines
Sat 1/87:00
ORD
-
CPT
1 stop25h 20m
United Airlines
Deal found 11/6R16 273
Thu 18/619:50
CPT
-
ORD
1 stop29h 44m
United Airlines
Thu 9/78:40
ORD
-
CPT
1 stop23h 40m
United Airlines
Deal found 15/6R16 467
Thu 9/719:50
CPT
-
ORD
1 stop33h 16m
United Airlines
Fri 7/819:45
ORD
-
CPT
2 stops36h 35m
United Airlines
Deal found 13/6R16 516
Sun 12/723:15
CPT
-
ORD
1 stop22h 15m
Multiple Airlines
Sun 26/717:10
ORD
-
CPT
2 stops45h 40m
Multiple Airlines
Deal found 15/6R16 807
Fri 10/723:15
CPT
-
ORD
2 stops28h 16m
KLM
Sat 25/716:20
ORD
-
CPT
1 stop22h 05m
KLM
Deal found 12/6R16 872
Fri 10/720:05
CPT
-
MDW
2 stops23h 33m
Delta
Sat 25/76:00
MDW
-
CPT
1 stop28h 50m
Delta
Deal found 12/6R17 308
Thu 16/723:15
CPT
-
MDW
2 stops40h 58m
Delta
Sat 8/816:39
MDW
-
CPT
1 stop18h 11m
Delta
Deal found 12/6R19 832
Thu 16/723:15
CPT
-
MDW
2 stops40h 58m
Delta
Tue 4/818:42
MDW
-
CPT
2 stops64h 08m
Delta
Deal found 14/6R19 977
Fri 10/723:15
CPT
-
MDW
2 stops25h 37m
KLM
Sat 25/713:18
MDW
-
CPT
2 stops25h 07m
KLM
Deal found 13/6R20 527
Thu 9/723:15
CPT
-
MDW
2 stops26h 03m
KLM
Fri 7/813:27
MDW
-
CPT
2 stops24h 58m
KLM
Deal found 13/6R20 624

Find flight deals from Cape Town to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cape Town (CPT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 16 June 2026.

Round-trip from

R16 079

One-way from

R10 725

Popular in

January

Cheapest in

July

Average price

R17 874
Delta
  • Delta
  • 1/12-19/1
  • 4 total stops
  • 68h 36m total
  • Cape Town to Chicago
Search Deals
Turkish Airlines
  • Turkish Airlines
  • 1/12
  • 1 total stop
  • 24h 40m total
  • Cape Town to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (R24 717 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (R6 681 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Cape Town to Chicago 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, Cheapflights users made 594 507 searches. Data last updated 16 June 2026.
Use the filters below to find and compare flights from Cape Town to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Tue 1/12

20:50-16:50

2 stops28h 00m

Chicago Midway

Tue 19/1

17:59-18:35

2 stops40h 36m

R16 079
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 28/7

23:15-14:30

1 stop22h 15m

Chicago O'Hare Intl

Sat 15/8

16:20-21:25

1 stop22h 05m

R16 305

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 10/7

20:05-11:45

2 stops22h 40m

Chicago O'Hare Intl

Sat 25/7

7:00-17:50

1 stop27h 50m

R16 305

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 9/7

19:50-20:10

1 stop31h 20m

Chicago O'Hare Intl

Sun 2/8

6:00-17:10

1 stop28h 10m

R16 548

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 12/7

23:15-14:30

1 stop22h 15m

Chicago O'Hare Intl

Sun 26/7

16:20-21:25

1 stop22h 05m

R18 117

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Fri 10/7

23:15-17:52

2 stops25h 37m

Chicago Midway

Sat 25/7

6:00-17:50

1 stop28h 50m

R18 344

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 14/7

20:00-10:50

1 stop21h 50m

Chicago O'Hare Intl

Sun 2/8

8:00-17:10

2 stops26h 10m

R18 538

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 11/9

7:40-14:15

1 stop37h 35m

Chicago O'Hare Intl

Sun 27/9

16:20-21:25

1 stop22h 05m

R19 508

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 16/7

23:15-9:13

2 stops40h 58m

Chicago Midway

Tue 4/8

18:42-17:50

2 stops64h 08m

R19 977

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 9/7

23:15-18:18

2 stops26h 03m

Chicago Midway

Fri 7/8

13:27-21:25

2 stops24h 58m

R20 624

Flights are sorted by cheapest return flights first.

Deals found on 11/6

Showing 1-10 of 27 resultsSorted by cheapest first
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3

Best time to book a flight from Cape Town to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cape Town 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.

Cheapflights Insights

Everything you need to know about your flight from Cape Town to Chicago

What is the cheapest month to book a flight from Cape Town to Chicago?

Currently, March is the cheapest month in which you can book a flight from Cape Town to Chicago (average of R5 581). Flying from Cape Town to Chicago in January is currently the most expensive (average of R15 125). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost for a return flight from Cape Town to Chicago?

What’s the top stopover airport for flights from Cape Town to Chicago?

Share of one-stop return flights from Cape Town to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

Washington, D.C. (IAD) – chosen by Cheapflights users on 25% of one-stop itineraries from Cape Town to Chicago on Cheapflights.

What’s the cheapest stopover airport for flights from Cape Town to Chicago?

Average return fare for one-stop flights from Cape Town to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Washington, D.C. (IAD) is the most affordable one-stop option, with an average return flight price of R16 659.

What’s the fastest stopover option from Cape Town to Chicago?

Shortest average travel time for one-stop one-way flights from Cape Town to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via Newark (EWR) have the shortest average one-way travel time for one-stop routes: 20h 25m.

Which airport typically offers the quickest stopover for flights from Cape Town to Chicago?

Average stopover duration for one-stop one-way flights from Cape Town to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Newark (EWR) offer the fastest connection on this route, with an average stopover time of 1h 53m.

How far ahead should I book a flight from Cape Town to Chicago?

Booking 64 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cape Town to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 16 June 2026.
Get a feel of what it's like to fly with KLM,United Airlines, andQatar Airways from Cape Town to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
KLM
7,8
Good
1 529 reviews
Check prices

Food

7,3

Boarding

7,8

Overall

7,8

Comfort

7,7

Crew

8,4

Entertainment

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

OKC - ATL

Flight was ok - difficult as I had seat next to bathroom.. Food awful
KLM
7,8
Good
1 529 reviews
KLM
7,8
Good
1 529 reviews
Check prices

Food

7,3

Boarding

7,8

Overall

7,8

Comfort

7,7

Crew

8,4

Entertainment

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

OKC - ATL

Flight was ok - difficult as I had seat next to bathroom.. Food awful
United Airlines
7,4
Good
9 840 reviews
KLM
7,8
Good
1 529 reviews
Check prices

Food

7,3

Boarding

7,8

Overall

7,8

Comfort

7,7

Crew

8,4

Entertainment

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

OKC - ATL

Flight was ok - difficult as I had seat next to bathroom.. Food awful
Qatar Airways
7,3
Good
3 727 reviews
KLM
7,8
Good
1 529 reviews
Check prices

Food

7,3

Boarding

7,8

Overall

7,8

Comfort

7,7

Crew

8,4

Entertainment

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

OKC - ATL

Flight was ok - difficult as I had seat next to bathroom.. Food awful
Ethiopian Air
7,2
Good
1 007 reviews
KLM
7,8
Good
1 529 reviews
Check prices

Food

7,3

Boarding

7,8

Overall

7,8

Comfort

7,7

Crew

8,4

Entertainment

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

OKC - ATL

Flight was ok - difficult as I had seat next to bathroom.. Food awful

Related info for your journey

Find useful and relevant information for your journey from Cape Town to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Cape Town to Chicago?

    For a flight from Cape Town to Chicago, you will be flying from Cape Town Intl. Cape Town Intl (CPT) is just 15,6 km from the centre of the city. Cape Town Intl is the only Cape Town airport and it handles 0 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Cape Town Intl on a regular basis.

  • How long is the flight from Cape Town to Chicago?

    Airlines like Delta, KLM, and United Airlines fly from Cape Town to Chicago in about 22h 15m. The time it takes to get you to your destination can typically vary by up to 9h 05m. Cape Town and Chicago are separated by a distance of 13700 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Cape Town to Chicago round-trip?

    Cheapflights users have booked flights from Cape Town to Chicago round-trip from R5 607. Other airlines that can offer you cheap pricing are United Airlines, from R15 023, and Turkish Airlines, from R15 118. Ethiopian Air is 68% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Cape Town to Chicago that include hotel bookings?

    Yes. In addition to deals on Cape Town to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Cape Town to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cape Town to Chicago.

  • Can I find deals for business class flights from Cape Town to Chicago?

    Yes. Cheapflights offers flight deals from Cape Town to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cape Town to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Cape Town to Chicago (average of R5 581). Flying from Cape Town to Chicago in January is currently the most expensive (average of R15 125). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Fly from Cape Town to Chicago on these airlines

Choose from the following airlines for your flight from Cape Town to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 16 June 2026.
United Airlines flights from Cape Town Intl to Chicago
KLM flights from Cape Town Intl to Chicago
Qatar Airways flights from Cape Town Intl to Chicago

Top 5 airlines flying from Cape Town to Chicago

Discover the top 5 airlines that operate flights from Cape Town to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 594 507 searches. Data last updated 16 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Ethiopian AirCheapestR5 607AverageR20 042FlexibilityNo cancel feeOn-time72%
Search Ethiopian Air flights
United AirlinesCheapestR15 023AverageR15 980FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Turkish AirlinesCheapestR15 118AverageR15 959FlexibilityNo cancel feeOn-time77%
Search Turkish Airlines flights
KLMCheapestR16 570AverageR18 553FlexibilityNo cancel feeOn-time75%
Search KLM flights
Qatar AirwaysCheapestR18 049AverageR21 043FlexibilityNo cancel feeOn-time68%
Search Qatar Airways flights

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 Cape Town to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Cape Town to Chicago. 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 Cape Town to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Cape Town 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 Cape Town to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Cape Town? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Cape Town to Chicago become cheaper?

Of course! You can now track prices for flights from Cape Town to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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