$574 Find Cheap Flights from South Africa to Chicago - Compare and Save

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 9/27. 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

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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

Wed, Sep 23 - Wed, Sep 30
Ethiopian Air Logo
1:50 pm - 8:15 am
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 am - 2:10 pm
ORD
-
CPT
20h 55m
1 stop
$878Ethiopian Air
Wed, Sep 23 - Wed, Sep 30
Ethiopian Air Logo
1:50 pm - 8:15 am
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 am - 2:10 pm
ORD
-
CPT
20h 55m
1 stop
$886Ethiopian Air
Fri, Sep 11 - Sun, Sep 27
Ethiopian Air Logo
1:50 pm - 8:15 am
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 am - 2:10 pm
ORD
-
CPT
20h 55m
1 stop
$939Ethiopian Air
Tue, Aug 11 - Mon, Aug 17
Delta Logo
8:05 pm - 12:39 pm
CPT
-
MDW
23h 34m
2 stops
Delta Logo
12:46 pm - 5:50 pm
MDW
-
CPT
22h 04m
1 stop
$954Delta
Tue, Aug 11 - Sat, Aug 22
Delta Logo
8:05 pm - 12:39 pm
CPT
-
MDW
23h 34m
2 stops
Delta Logo
10:56 am - 5:50 pm
MDW
-
CPT
23h 54m
1 stop
$954Delta
Tue, Aug 11 - Sat, Aug 22
Delta Logo
8:05 pm - 12:39 pm
CPT
-
MDW
23h 34m
2 stops
Delta Logo
9:59 am - 5:50 pm
MDW
-
CPT
24h 51m
2 stops
$954Delta
Tue, Aug 11 - Thu, Aug 20
Delta Logo
8:05 pm - 12:39 pm
CPT
-
MDW
23h 34m
2 stops
Delta Logo
9:24 am - 5:50 pm
MDW
-
CPT
25h 26m
2 stops
$954Delta
Tue, Aug 11 - Thu, Aug 20
Delta Logo
8:05 pm - 12:39 pm
CPT
-
MDW
23h 34m
2 stops
Delta Logo
12:46 pm - 5:50 pm
MDW
-
CPT
22h 04m
1 stop
$954Delta
Sun, Aug 9 - Sat, Aug 22
United Airlines Logo
8:00 pm - 3:02 pm
CPT
-
ORD
26h 02m
2 stops
United Airlines Logo
2:30 pm - 3:20 pm
ORD
-
CPT
17h 50m
1 stop
$989United Airlines
Sun, Aug 9 - Thu, Aug 20
United Airlines Logo
8:00 pm - 2:29 pm
CPT
-
ORD
25h 29m
1 stop
United Airlines Logo
12:56 pm - 3:20 pm
ORD
-
CPT
19h 24m
1 stop
$989United Airlines
Booking Insights

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 round-trip 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 $965 on average for return flights. On the other hand, the most expensive months are January and April, where the average cost of tickets from South Africa is $1,380 and $1,322 respectively. For one-way flights, the best month to travel is February with an average price of $588.

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 2 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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 $176.

Good to know

Low season

January

Cheapest flight

$574
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 14% 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.

  • 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.

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

    Each week there are around 30,501 direct flights from within South Africa to Chicago. The most common day for departures is Sunday, 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 airlines flying 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.
7.8
KLMOverall score based on 1551 reviews
8.4Crew
7.8Boarding
7.7Comfort
7.3Food
7.2Entertainment
Airline reviews

I think I previously submitted my feedback about flight lead Katherine in a different field by mistake. Please see those comments. Comments for Hyd to AMS are it was good. The flight lead and service met expectations for satisfactory high quality service but the flight lead did not stand out as exceptional as did the leads on the other two flights so I don’t remember anything specific one way or the other besides the fact I was satisfied.

10.0 ExcellentEmily, Jul 2026
ORD - MSP
Read more KLM reviews

I think I previously submitted my feedback about flight lead Katherine in a different field by mistake. Please see those comments. Comments for Hyd to AMS are it was good. The flight lead and service met expectations for satisfactory high quality service but the flight lead did not stand out as exceptional as did the leads on the other two flights so I don’t remember anything specific one way or the other besides the fact I was satisfied.

Flight lead was a gentleman with silver hair and he went out of his way to shake hands and interact with each passenger seated in business class. A medical emergency took place during our flight and he handled it with perfect poise and professionalism. He was gracious and confidently competent. Just what you want from a leader,

Crew is not the cheerful type. very slow meal service (this is their style as have flown this many times)

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

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

I flew premium economy and this was a good option. Although the seats didn’t recline much, I was able to get some sleep with my head propped against the window. The food was good and the entertainment was wonderful The staff were very attentive and professional

Overall very poor. Flight was disorganised, staff were rude and this is my second experience with KLM that I've had baggage go missing. It feels like, if you are an economy customer, KLM staff do not show you any care. I shall never fly with KLM again. Worst airline in Europe

Seats were nice and comfy. Crew was polite and attentive. Business class is awesome and worth the money.

It was operated by Delta. Boarding took a long time. How difficult can it be? Overall decent trip. Liked the Salt Lake City airport. Better option than Chicago for transfers.

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

Food was not great. Small seating area for business class

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

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.