Cheap flights from Cape Town to Chicago from R10 151
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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
CPT — CHI
Dec 14 — Dec 211
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Cape Town Intl to Chicago are usually found in September or October, booked 9 days in advance, depart on a Sunday or Tuesday and return on a Saturday
Find 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 14 November 2025.
Thu 20/1120:50CPT - ORD
2 stops23h 00mUnited Airlines
Wed 3/1215:38ORD - CPT
1 stop18h 22mUnited Airlines
Deal found 11/11R15 755
Tue 2/1220:50CPT - ORD
1 stop20h 46mUnited Airlines
Sun 11/119:50ORD - CPT
2 stops36h 20mUnited Airlines
Deal found 13/11R15 823
Thu 20/1121:30CPT - MDW
1 stop27h 08mVirgin Atlantic
Wed 3/1210:49MDW - CPT
1 stop24h 26mVirgin Atlantic
Deal found 11/11R16 062
Mon 1/1220:50CPT - ORD
2 stops31h 45mDelta
Sun 11/17:05ORD - CPT
1 stop28h 10mDelta
Deal found 13/11R17 067
Sat 6/1223:45CPT - ORD
1 stop22h 35mDelta
Sun 11/17:05ORD - CPT
1 stop28h 10mDelta
Deal found 13/11R17 169
Tue 18/1123:45CPT - ORD
1 stop22h 35mKLM
Tue 25/1114:35ORD - CPT
2 stops23h 20mKLM
Deal found 11/11R17 237
Thu 20/1121:30CPT - MDW
1 stop22h 22mDelta
Wed 3/1213:14MDW - CPT
2 stops24h 41mDelta
Deal found 11/11R17 254
Mon 1/1221:30CPT - MDW
1 stop34h 17mVirgin Atlantic
Sun 11/16:45MDW - CPT
1 stop28h 30mVirgin Atlantic
Deal found 13/11R17 782
Fri 5/1221:30CPT - MDW
2 stops28h 36mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R17 918
Sat 6/1220:50CPT - ORD
2 stops24h 22mUnited Airlines
Sun 11/112:38ORD - CPT
2 stops21h 22mUnited Airlines
Deal found 13/11R18 123
Tue 18/1120:50CPT - ORD
1 stop28h 10mBritish Airways
Tue 25/1120:40ORD - CPT
1 stop29h 40mBritish Airways
Deal found 11/11R18 566
Sat 6/1220:50CPT - MDW
2 stops29h 28mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R19 332
Best flights from Cape Town to Chicago
Discover carefully curated flight deals from Cape Town to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 14 November 2025.
Fri 5/1220:50CPT - ORD
1 stop20h 46mUnited Airlines
Sun 11/120:00ORD - CPT
2 stops36h 10mUnited Airlines
Deal found 13/11R15 823
Mon 1/1220:50CPT - ORD
2 stops31h 45mDelta
Sun 11/17:05ORD - CPT
1 stop28h 10mDelta
Deal found 13/11R17 067
Tue 2/1221:30CPT - MDW
1 stop34h 17mVirgin Atlantic
Sun 11/117:31MDW - CPT
1 stop17h 44mVirgin Atlantic
Deal found 13/11R17 782
Wed 11/317:15CPT - ORD
1 stop24h 50mTurkish Airlines
Sun 15/321:20ORD - CPT
1 stop31h 30mTurkish Airlines
Deal found 11/11R17 935
Wed 11/314:35CPT - ORD
2 stops25h 05mEthiopian Air
Sun 15/310:15ORD - CPT
1 stop43h 45mEthiopian Air
Deal found 11/11R18 089
Fri 5/1223:45CPT - MDW
2 stops26h 21mKLM
Sun 11/113:28MDW - CPT
2 stops24h 27mKLM
Deal found 13/11R22 091
Tue 2/1220:50CPT - ORD
1 stop20h 46mUnited Airlines
Sun 11/119:50ORD - CPT
2 stops36h 20mUnited Airlines
Deal found 13/11R15 823
Tue 2/1221:30CPT - ORD
1 stop22h 33mDelta
Sun 11/15:33ORD - CPT
1 stop29h 42mDelta
Deal found 13/11R17 101
Mon 1/1221:30CPT - MDW
1 stop34h 17mVirgin Atlantic
Sun 11/16:45MDW - CPT
1 stop28h 30mVirgin Atlantic
Deal found 13/11R17 782
Fri 5/1221:30CPT - ORD
1 stop22h 36mDelta
Sun 11/15:33ORD - CPT
1 stop29h 42mDelta
Deal found 13/11R17 101
Sat 6/1220:50CPT - ORD
2 stops24h 22mUnited Airlines
Sun 11/112:38ORD - CPT
2 stops21h 22mUnited Airlines
Deal found 13/11R18 123
Sat 6/1223:45CPT - ORD
1 stop22h 35mDelta
Sun 11/17:05ORD - CPT
1 stop28h 10mDelta
Deal found 13/11R17 169
Tue 2/1223:45CPT - MDW
2 stops26h 33mKLM
Sun 11/113:28MDW - CPT
2 stops24h 27mKLM
Deal found 13/11R22 091
Mon 1/1221:30CPT - MDW
2 stops23h 40mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R17 918
Sun 28/1221:30CPT - MDW
1 stop26h 50mVirgin Atlantic
Sun 4/117:05MDW - CPT
1 stop18h 10mVirgin Atlantic
Deal found 13/11R22 415
Fri 5/1221:30CPT - MDW
2 stops28h 36mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R17 918
Tue 2/1221:30CPT - MDW
2 stops23h 04mDelta
Sun 11/16:45MDW - CPT
1 stop28h 30mDelta
Deal found 13/11R17 918
Sat 6/1220:50CPT - MDW
2 stops29h 28mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R19 332
Last-minute flights from Cape Town to Chicago
Discover last-minute flight deals from Cape Town to Chicago. Data last updated 14 November 2025 and is based on user searches.
Tue 18/1123:45CPT - ORD
1 stop22h 35mKLM
Tue 25/1114:35ORD - CPT
2 stops23h 20mKLM
Deal found 11/11R17 237
Tue 18/1120:50CPT - ORD
1 stop28h 10mBritish Airways
Tue 25/1120:40ORD - CPT
1 stop29h 40mBritish Airways
Deal found 11/11R18 566
Tue 18/1113:40CPT - ORD
3 stops35h 40mMultiple Airlines
Tue 25/1118:30ORD - CPT
2 stops31h 30mMultiple Airlines
Deal found 11/11R24 271
Thu 20/1120:50CPT - ORD
2 stops23h 00mUnited Airlines
Wed 3/1215:38ORD - CPT
1 stop18h 22mUnited Airlines
Deal found 11/11R15 755
Thu 20/1121:30CPT - MDW
1 stop27h 08mVirgin Atlantic
Wed 3/1210:49MDW - CPT
1 stop24h 26mVirgin Atlantic
Deal found 11/11R16 062
Thu 20/1121:30CPT - MDW
2 stops23h 04mDelta
Wed 3/1213:14MDW - CPT
2 stops24h 41mDelta
Deal found 11/11R17 254
Mon 1/1221:30CPT - MDW
1 stop34h 17mVirgin Atlantic
Sun 11/16:45MDW - CPT
1 stop28h 30mVirgin Atlantic
Deal found 13/11R17 782
Mon 1/1221:30CPT - MDW
2 stops23h 40mDelta
Sun 11/19:50MDW - CPT
2 stops25h 25mDelta
Deal found 13/11R20 950
Tue 2/1223:45CPT - MDW
2 stops26h 33mKLM
Sun 11/113:28MDW - CPT
2 stops24h 27mKLM
Deal found 13/11R22 091
Fri 5/1221:30CPT - MDW
2 stops28h 36mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R17 918
Sat 6/1220:50CPT - MDW
2 stops29h 28mDelta
Sun 11/117:31MDW - CPT
1 stop17h 44mDelta
Deal found 13/11R19 332
Sun 28/1221:30CPT - MDW
1 stop26h 50mVirgin Atlantic
Sun 4/117:05MDW - CPT
1 stop18h 10mVirgin Atlantic
Deal found 13/11R22 415
One-way flights from Cape Town to Chicago
Search for one-way flight options from Cape Town to Chicago. Find affordable one-way fares based on user searches. Data last updated 14 November 2025.
Mon 15/1217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 11/11R10 151
Fri 1/516:40CPT - ORD
1 stop24h 00mTurkish Airlines
Deal found 13/11R10 867
Wed 14/118:55CPT - MDW
3 stops56h 28mMultiple Airlines
Deal found 11/11R11 395
Wed 14/112:35CPT - ORD
3 stops54h 23mMultiple Airlines
Deal found 11/11R11 395
Wed 25/323:25CPT - ORD
2 stops54h 18mMultiple Airlines
Deal found 13/11R11 599
Mon 15/1220:50CPT - ORD
2 stops32h 57mDelta
Deal found 12/11R11 940
Mon 12/117:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 11/11R12 042
Wed 25/312:35CPT - ORD
1 stop34h 10mQatar Airways
Deal found 13/11R12 110
Tue 13/117:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 11/11R12 178
Mon 12/115:20CPT - ORD
2 stops26h 45mMultiple Airlines
Deal found 11/11R12 315
Sat 28/312:35CPT - ORD
1 stop33h 30mQatar Airways
Deal found 13/11R12 366
Tue 13/115:30CPT - MDW
3 stops50h 35mMultiple Airlines
Deal found 11/11R14 580
Cheap 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 14 November 2025.
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 14 November 2025.
Use the filters below to find and compare flights from Cape Town to Chicago that are best for you.
Fly from
Cape Town
Fly to
Chicago
Route
Depart
Return
Price
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Fri 5/12
20:50-9:36
1 stop20h 46m
Chicago O'Hare Intl
Sun 11/1
20:00-16:10
2 stops36h 10m
R15 823
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Tue 2/12
20:50-9:36
1 stop20h 46m
Chicago O'Hare Intl
Sun 11/1
19:50-16:10
2 stops36h 20m
R15 823
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Mon 1/12
20:50-20:35
2 stops31h 45m
Chicago O'Hare Intl
Sun 11/1
7:05-19:15
1 stop28h 10m
R17 067
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Tue 2/12
21:30-12:03
1 stop22h 33m
Chicago O'Hare Intl
Sun 11/1
5:33-19:15
1 stop29h 42m
R17 101
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Fri 5/12
21:30-12:06
1 stop22h 36m
Chicago O'Hare Intl
Sun 11/1
5:33-19:15
1 stop29h 42m
R17 101
Cape TownChicago
CPT - ORD
CPTORD
Cape Town Intl
Sat 6/12
23:45-14:20
1 stop22h 35m
Chicago O'Hare Intl
Sun 11/1
7:05-19:15
1 stop28h 10m
R17 169
Cape TownChicago
CPT - MDW
CPTMDW
Cape Town Intl
Tue 2/12
21:30-23:47
1 stop34h 17m
Chicago Midway
Sun 11/1
17:31-19:15
1 stop17h 44m
R17 782
Cape TownChicago
CPT - MDW
CPTMDW
Cape Town Intl
Mon 1/12
21:30-23:47
1 stop34h 17m
Chicago Midway
Sun 11/1
6:45-19:15
1 stop28h 30m
R17 782
Cape TownChicago
CPT - MDW
CPTMDW
Cape Town Intl
Mon 1/12
21:30-13:10
2 stops23h 40m
Chicago Midway
Sun 11/1
17:31-19:15
1 stop17h 44m
R17 918
Cape TownChicago
CPT - MDW
CPTMDW
Cape Town Intl
Fri 5/12
21:30-18:06
2 stops28h 36m
Chicago Midway
Sun 11/1
17:31-19:15
1 stop17h 44m
R17 918
Flights are sorted by cheapest return flights first.
Deals found on 11/11
Showing 1-10 of 35 results
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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
How far ahead should I book a flight from Cape Town to Chicago?
Use this chart to determine the optimal time to book a return flight from Cape Town to Chicago. Price data was last updated on 7 November 2025.
Booking 9 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.
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 R13 967). Flying from Cape Town to Chicago in August is currently the most expensive (average of R17 254). 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.
What is the cheapest time of day to fly from CPT to CHI?
Find hourly flight availability from Cape Town to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 14 November 2025.
It’s typically best to fly out from Cape Town to Chicago in the morning. Doing so could potentially save you 16% on the flight price compared to flying in the evening, which is usually more expensive.
What is the cheapest day to fly from Cape Town to Chicago?
Use this chart to determine the cheapest time to fly return from Cape Town to Chicago. Price data was last updated on 16 December 2024.
Travellers seeking maximum savings on their Cape Town to Chicago flight should consider departing on Monday mornings when fares are most often at their lowest. Sunday at midday flights should be avoided if possible as fares are typically the most expensive at this time.
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.
Istanbul (IST) – chosen by Cheapflights users on 32% 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.
Doha (DOH) is the most affordable one-stop option, with an average return flight price of R18 547.
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 28m.
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 Addis Ababa (ADD) offer the fastest connection on this route, with an average stopover time of 0h 56m.
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 14 November 2025.
Get a feel of what it's like to fly with KLM, United Airlines, andTurkish Airlines 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.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
The food option was finished and what wa left was vegan pasta so I had to go without food for an 8 hour flight without any sort of empathy from crew that was mean.
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 United Airlines, Delta, and Virgin Atlantic fly from Cape Town to Chicago in about 20h 46m. The time it takes to get you to your destination can typically vary by up to 13h 31m. 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 R14 566. Other airlines that can offer you cheap pricing are United Airlines, from R15 818, and Turkish Airlines, from R16 569. Ethiopian Air is 26% cheaper than the average price of flights available within the next 90 days to this destination.
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 R13 967). Flying from Cape Town to Chicago in August is currently the most expensive (average of R17 254). 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.
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 14 November 2025.
Browse through other flights departing from Cape Town. Flights are based on user searches made on Cheapflights and were last updated on 14 November 2025.
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 14 November 2025.
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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