R10 336 Find Cheap Flights to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 15/12. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Flight Deals

Cheap Flights to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights to Chicago 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Mon, Feb 2 - Mon, Feb 16
SWISS Logo
20:15 - 16:20JNB-ORD
28h 05m1 stop
SWISS Logo
18:35 - 10:30ORD-JNB
31h 55m2 stops
R15 841SWISS
Find Deal
Mon, Feb 2 - Mon, Feb 16
Air Canada Logo
20:15 - 19:30JNB-ORD
31h 15m2 stops
Air Canada Logo
15:55 - 10:30ORD-JNB
34h 35m2 stops
R15 997Air Canada
Find Deal
Wed, Mar 25 - Sun, Mar 29
Turkish Airlines Logo
19:05 - 19:25JNB-ORD
31h 20m1 stop
Turkish Airlines Logo
11:25 - 10:35ORD-JNB
40h 10m1 stop
R16 066Turkish Airlines
Find Deal
Thu, Nov 13 - Thu, Dec 4
Turkish Airlines Logo
19:10 - 10:05JNB-ORD
22h 55m1 stop
Turkish Airlines Logo
11:50 - 10:50ORD-JNB
39h 00m1 stop
R16 118Turkish Airlines
Find Deal
Sat, Dec 13 - Sat, Jan 10
KLM Logo
23:59 - 14:20JNB-ORD
22h 21m1 stop
KLM Logo
16:25 - 22:05ORD-JNB
21h 40m1 stop
R17 399KLM
Find Deal
Thu, Nov 13 - Thu, Dec 4
KLM Logo
23:59 - 18:13JNB-ORD
26h 14m2 stops
KLM Logo
11:15 - 22:05ORD-JNB
26h 50m2 stops
R17 434KLM
Find Deal
Wed, Mar 11 - Sun, Mar 15
British Airways Logo
20:35 - 17:33CPT-ORD
27h 58m2 stops
British Airways Logo
21:45 - 12:40ORD-CPT
31h 55m2 stops
R18 957British Airways
Find Deal
Wed, Mar 11 - Sun, Mar 15
British Airways Logo
20:35 - 14:50CPT-ORD
25h 15m1 stop
British Airways Logo
21:45 - 12:40ORD-CPT
31h 55m2 stops
R19 546British Airways
Find Deal
Sat, Dec 13 - Sat, Jan 3
United Airlines Logo
20:50 - 10:44CPT-ORD
21h 54m1 stop
United Airlines Logo
7:00 - 16:10ORD-CPT
25h 10m2 stops
R20 602United Airlines
Find Deal
Sat, Dec 13 - Sat, Jan 3
United Airlines Logo
20:50 - 16:53CPT-ORD
28h 03m2 stops
United Airlines Logo
7:00 - 16:10ORD-CPT
25h 10m2 stops
R21 554United Airlines
Find Deal

Everything you should know

When to travel
February
Cheapest • 10% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
R15 841
Overall average: R16 447
SWISS
Mon 2/2Mon 16/2
JNB - ORD • 1 stop
Cheapest one-way flight
R10 336
Typical prices: R10 682-R13 677
Turkish Airlines
Mon 15/12
CPT - ORD • 1 stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is February, where tickets cost R16 759 on average for one-way flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from South Africa is R21 468 and R20 654 respectively. For return trips, the best month to travel is February with an average price of R16 759.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 46 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of R2 572.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR10 336
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Cape Town to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago 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.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and the city centre of Chicago is 14 km, which makes it the closest of the 3 Chicago airports airports. Chicago O'Hare Airport is 26 km away from the centre and Chicago Greater Rockford is 126 km away.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as R19 414. On the other hand, the most expensive day to fly is Saturday, where prices are R21 475 on average.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the evening, when flights cost R17 855 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is R18 429.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop to Chicago.
Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

South Africa to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Reviews of the top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from South Africa to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7,7
KLMOverall score based on 1405 reviews
7,3Food
7,7Comfort
7,8Boarding
7,1Entertainment
8,4Crew
Airline reviews

Flight was ok but lack of communication cost me to literally beg to be put on another flight as connecting flight had departed

2,0 MediocreAbisola, Oct 2025CDG - AMS
Read more KLM reviews

Flight was ok but lack of communication cost me to literally beg to be put on another flight as connecting flight had departed

They forgot to serve food and the crew was very unfriendly. Never experienced such a bad KLM flight. Usually fly from Toronto. New York was different.

Couldn’t get boarding pass in SLC even with help from a redcoat, so had to find a desk in AMS to get boarding pass. Technical problems so not sure why. Very inconvenient. The KLM app is not as user friendly as most apps. Also had to wait almost an hour on the tarmac for a fuel truck, which caused us to miss a connecting bus in LUX.

The immigration hall in Amsterdam was understaffed, so passport checking was slower than it should be for a major airport. They need to get the automatic readers up and running for non EU passport holders. Waiting in line after a long flight feels a bit abusive.

Short flight so it was okay. Nice crew, all very pleasant and professional. We were near the back in row 27 so just as we got our drinks, we started our descent so had to drink very quickly!

KLM remains a quality flag carrier airline which maintains its standards whilst all their competitors are lowering theirs.

Our first flight was delayed so we missed our connecting flight. However it was easy to book a later flight on their app.

Klm start boarding while somw air issue in the plan

The service was great. However the lounge only gets passing grade

Cabin crew professional, polite and friendly, boarding was seemless, but come on KLM surely you can do better than a pack of cheesy biscuits as an inflight snack

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

They can my date of travel and let me standard in Istanbul for three days stop over and only pay for one day in a hotel with only one breakfast for three days.

the flight was cancelled and I was rebooked twice, once 26 hours later, then another 24 hours later. In total the flight was delayed for 40 hours. Never again will I use kayak or Turkish Airlines for my travel.

Worst experience with boarding once we left the wheel chair even traveling business we had to wait with all the crowd for the bus to take us to the plane then climb the stairs with our bags When you pay extra for comfort and convenience and you don’t get any is disappointing

Food is very turkish. No regard for other natinalities taste and preference. The entertainment can be improved- it was the same menu on 10/8/25 and 10/25/25. The boarding is the worst in the airline industry- I suggest you ask your staff to and watch how other airlines do it.

The best airline for international travel in terms of value you get in business class (service/cost)

I liked the overall flight experience. However, Turkish officials could do a better job at guiding non-Turkish speakers to their connecting flight gates in such a huge & vast airport.

Very small and cramped aisles and seats. Food was poor but the fresh hot roll and hummus was good. No cans of soda given but they had small bottles of water. Crew was nice and pleasant and kept bathroom clean.

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

Small seat space for 13 hours flight, they charged for baggage , very bad quality of food,

I was sitting almost in the back, the seats are very tight and there’s no legroom, it’s uncomfortable for a long distance

POSITIVES The hostesses were mostly pleasant, NEGATIVES The full flight wifi was horrible, hardly able to use it. My charger port was not working which made me use my neighbour's port which resulted in an accident which ruined her flight. During dinner, meat ran out when the cart got to us forcing us to eat vegetarian which was not great. We watched everyone around us eating meat. My wifi did not transfer to the second leg of my trip as they promised as they changed the plane. I was thrown off the window seat I booked for the 2nd leg of my journey as they changed planes, all done at my expense. This was not a cheap flight ($2600) which i hurriedly had to book to attend my mother's funeral who passed away suddenly. I was honestly disappointed with the whole saga as I heard Ethiopian Airlines was one of Africa's best.

The food was terrible and the seating was uncomfortable, but the airline did a great thing letting us board in Abbis Ababa on our connecting flight after our original flight was very delayed.

Food hardly ever changes Videos not often updated for often travel.

The flight is packed and it feels like the space per individual has gotten smaller. Excruciating for a 14hr flight.

Were not told that carryon laggage has to be only 12 kgs but my bag was heavier asked to pay an additional $550.00. I could have upgraded to a bussiness class for that price and no one at the gate to upgrade but able to take money for the extra weight. I felt like this was a setup scam.

Lost suite case and pillow that’s used by senior and they didn’t leave it at the airport

The flight itself was fine. The exception is that my luggage was destroyed, and I filed a claim that I haven't heard from anyone.

Im if Ethiopian can allow customers to use their mileage for in flight connexion it will be great.

United was best airlines I have seen since I got there choose united airlines

It was wonderful best Air lines covert and all very happy with their service they have been very helpful and friendly

Airlines have to stop assuming passengers bring entertainment. Provide it like you used to in business class and above!! N

Great flight. One unique individual assisting in business class who should have not been there. Need more generic meals, not British centric.

Not my definition of first class. No leg room and barely any recline. The food was good. The crew was great. The comfort for the price I paid for London to Cairo was highway robbery. The Wi-Fi didn't work for me either.

There might be more food options for people who can't eat so much starch/sugar/bread/rice. Meat, cheese, walnuts/pecans for snack, maybe jerky or other kinds of meat-based snacks would be better than bread and rice and sweets. I had an extra chardonnay, which was fine. The entertainment was great.

Unfortunately, my flight was cancelled because of some sort of emergency over the Atlantic and had to return to London. While I think British Airways made every effort to mitigate the situation, I must say it was still pretty unpleasant. I do appreciate the fact, however, that British Airways put my safety first…and I think the effort to correct a bad situation was very sincere. But I think the process might be handled better in future.

Crew service was poor and very little difference between premium economy and economy. Disappointed.

My bags never made it on the flight and I now have to wait for them to arrive hopefully tomorrow. You can’t even track your bags in the app to see where they are since they didn’t arrive. You have to file a claim and then wait for them to inform you when you will receive your bag. We were already delayed for an hour due to baggage so I don’t understand how my bag didn’t make the flight.

One of the worst experience given the middle seat even asked for the change no one honored,boarded at the end and overall one of the worst experience

It was good although our flight to the UK was cancelled and rescheduled for two days later. This was after we were already seated on the plane. We missed the first leg of our trip. BA did put us up at a hotel and paid for our meals but we lost our hotel costs in Glasgow.

The crew was very nice and pleasant. We were very reluctant to book our flight with British Airlines because we had bad experience with their flight attendants on the previous trips, they were rude and not helpful.

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