$600 Find Cheap Flights from South Africa 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 9/29. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flights from South Africa to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from South Africa 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 round-trip flight deals from South Africa to Chicago

Thu, Nov 6 - Mon, Nov 10
Etihad Airways Logo
9:50 am - 8:15 amJNB-ORD
30h 25m1 stop
Etihad Airways Logo
1:10 pm - 8:20 amORD-JNB
35h 10m1 stop
$839Etihad Airways
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Thu, Nov 6 - Mon, Nov 10
Ethiopian Air Logo
2:30 pm - 7:40 amJNB-ORD
25h 10m2 stops
Ethiopian Air Logo
9:45 am - 8:10 pmORD-JNB
26h 25m1 stop
$860Ethiopian Air
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Thu, Nov 6 - Mon, Nov 10
British Airways Logo
7:35 pm - 2:00 pmJNB-ORD
26h 25m2 stops
British Airways Logo
4:34 pm - 7:35 amORD-JNB
31h 01m2 stops
$988British Airways
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Thu, Nov 6 - Mon, Nov 10
British Airways Logo
7:35 pm - 2:00 pmJNB-ORD
26h 25m2 stops
British Airways Logo
4:34 pm - 7:35 amORD-JNB
31h 01m2 stops
$994British Airways
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Sun, Aug 24 - Sun, Aug 31
United Airlines Logo
8:00 pm - 8:41 pmCPT-ORD
31h 41m2 stops
United Airlines Logo
3:45 pm - 5:10 pmORD-CPT
18h 25m1 stop
$1,001United Airlines
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Mon, Aug 25 - Mon, Sep 1
United Airlines Logo
7:50 pm - 4:43 pmCPT-ORD
27h 53m2 stops
United Airlines Logo
2:32 pm - 3:20 pmORD-CPT
17h 48m1 stop
$1,004United Airlines
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Fri, Sep 5 - Sat, Sep 13
Delta Logo
8:05 pm - 12:28 pmCPT-MDW
23h 23m2 stops
Delta Logo
9:20 am - 5:50 pmMDW-CPT
25h 30m2 stops
$1,008Delta
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Fri, Sep 5 - Sat, Sep 13
Delta Logo
8:05 pm - 2:19 pmCPT-ORD
25h 14m1 stop
Delta Logo
3:45 pm - 5:50 pmORD-CPT
19h 05m1 stop
$1,008Delta
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Mon, Sep 15 - Fri, Sep 26
KLM Logo
11:15 pm - 5:59 pmJNB-ORD
25h 44m2 stops
KLM Logo
2:05 pm - 9:20 pmORD-JNB
24h 15m2 stops
$1,037KLM
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Mon, Sep 15 - Fri, Sep 26
KLM Logo
11:15 pm - 5:59 pmJNB-ORD
25h 44m2 stops
KLM Logo
2:05 pm - 9:20 pmORD-JNB
24h 15m2 stops
$1,049KLM
Find Deal
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KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for 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 $974 on average for return flights. On the other hand, the most expensive months are December and August, where the average cost of tickets from South Africa is $1,219 and $1,215 respectively. For one-way flights, the best month to travel is February with an average price of $971.

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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 17 weeks 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 Greater Rockford Airport (RFD), with an average flight price of $103.


Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$600
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Cape Town to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $967. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $1,318 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 travelers 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 morning, when round-trip flights cost $1,005 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,099.

  • How many direct flights to Chicago are there each week?

    Each week there are around 13,387 direct flights from within South Africa to Chicago. The most common day for departures is Friday, with 15% of flights taking off on this day.

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.

Reviews of the top 4 airlines serving from South Africa 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.
8.0
DeltaOverall score based on 7950 reviews
7.3Food
8.5Crew
8.2Boarding
7.9Comfort
7.9Entertainment
Airline reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

4.0 OkayJames, Jul 2025MSN - ATL
Read more Delta reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Leaving on time and having my luggage on my connecting flight

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

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

Cabin crew were excellent, very proffesional, polite and friendly, in flight snack was underwhelming, a packet of cheese biscuits, im sure KLM could run to a sandwich!

Legroom not all it could be, especially when the seat in front is reclined. Otherwise it was good, food and beverage were nice.

This portion of the flight was through Indigo. A local carrier. So all economy seating. No real service some refreshments for purchase standard economy stuff.

You should not have to pay for WiFi in business class

Transfer at Amsterdam airport is very convenient and the airport is easy to navigate. Boarding was also quick and easy. Cabin crew were excellent and the meals were good, although lacking in options.

This fight left ahead of time which meant it arrived early which was great. Staff were very professional, but as with all these Short hop Flights the food was a disappointing snack There was no entertainment on this flight, but I did not expect any

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

3/4 bags delayed and 1/4 damaged at the other end. Flight was freezing

The crew were good. The flight was on time. The entertainment choice was ok. But the food was bad, tasted and texture were awful.

After boarding we were waiting in the plane for more than one hour to take off without AC with very high temperature inside

The flight was an hour late leaving Heathrow. The food was mediocre. When we got to Austin, my husband’s luggage was missing. He filled out information at baggage claim. We are waiting to hear something. His name is Henry Jacob Braunig.

The food was very good and it came multiple times

Flight from LGW to JFK delayed by 4 hrs No explanation given until the pilot said the delay due to planned maintenance on the aircraft

We arrived late to London, and consequently were 5 min. late to be allowed through security for our next flight. Even though dozens of people missed the same flight, BA did not radio ahead to hold open security for an extra 5-10 min. to allow people to get on the flight. This caused an additional 6 hour delay in London after waiting over an hour in Customer Service to get rebooked. They did not have enough staff on hand to help people in a timely manner. Not at all happy with the BA's customer care or customer service.

All service prior to the flight was terrible: online check-in not working, no customer service tel,, multiple airport scanners not working, A huge mess.

CONSTANT ERROR MESSAGE THAT THE WIFI COULD NOT BE PURCHASED DUE TO INABILITY TO CONNECT PAYMENT SYSTEM VIA SATELLITE. THIS HAPPENED IN BOTH DIRECTIONS. THE MAIN REASON I TRAVEL IN PRIORITY IS TO BE ABLE TO WORK FOR WHICH I NEED ACCESS TO INTERNET. .

They lost my luggage. Lady who was helping with it in Austin was rude. Not very helpful!

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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