$601 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 10/5. 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.
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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, Jul 29 - Wed, Aug 5
KLM Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m
1 stop
KLM Logo
4:50 pm - 9:25 pm
ORD
-
CPT
21h 35m
1 stop
$997KLM
Wed, Jul 29 - Wed, Aug 5
KLM Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m
1 stop
KLM Logo
4:50 pm - 9:25 pm
ORD
-
CPT
21h 35m
1 stop
$998KLM
Wed, Jul 29 - Wed, Aug 5
KLM Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m
1 stop
KLM Logo
1:59 pm - 9:25 pm
ORD
-
CPT
24h 26m
2 stops
$1,001KLM
Sun, Jul 12 - Fri, Jul 24
United Airlines Logo
8:00 pm - 11:53 am
CPT
-
ORD
22h 53m
1 stop
United Airlines Logo
9:40 pm - 3:20 pm
ORD
-
CPT
34h 40m
1 stop
$1,006United Airlines
Tue, Jul 21 - Sun, Aug 9
United Airlines Logo
8:00 pm - 4:14 pm
CPT
-
ORD
27h 14m
2 stops
United Airlines Logo
12:11 pm - 5:10 pm
ORD
-
CPT
21h 59m
1 stop
$1,007United Airlines
Wed, Oct 7 - Sat, Oct 17
Etihad Airways Logo
9:45 am - 8:35 am
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
2:00 pm - 8:20 am
ORD
-
JNB
35h 20m
1 stop
$1,034Etihad Airways
Fri, Jul 17 - Fri, Aug 21
Ethiopian Air Logo
2:30 pm - 8:15 am
JNB
-
ORD
24h 45m
2 stops
Ethiopian Air Logo
10:15 am - 8:10 pm
ORD
-
JNB
26h 55m
1 stop
$1,043Ethiopian Air
Mon, Sep 7 - Wed, Mar 3
Multiple Airlines Logo
6:50 pm - 3:10 pm
JNB
-
ORD
27h 20m
1 stop
Multiple Airlines Logo
4:25 pm - 10:00 pm
ORD
-
JNB
21h 35m
1 stop
$1,046Multiple Airlines
Mon, Sep 7 - Tue, May 25
Multiple Airlines Logo
6:50 pm - 3:10 pm
JNB
-
ORD
27h 20m
1 stop
Multiple Airlines Logo
4:20 pm - 9:20 pm
ORD
-
JNB
22h 00m
1 stop
$1,048Multiple Airlines
Sat, Aug 1 - Sat, Aug 8
Etihad Airways Logo
9:45 am - 8:35 am
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
2:00 pm - 8:20 am
ORD
-
JNB
35h 20m
1 stop
$1,054Etihad Airways
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 March, where tickets cost $345 on average for return flights. On the other hand, the most expensive months are December and January, where the average cost of tickets from South Africa is $881 and $873 respectively. For one-way flights, the best month to travel is February with an average price of $249.

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 20% 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 $142.

Good to know

Low seasonJanuary
Cheapest flight$601
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Durban 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 43,166 direct flights from within South Africa to Chicago. The most common day for departures is Sunday, with 16% 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 1532 reviews
8.4Crew
7.7Comfort
7.3Food
7.2Entertainment
7.8Boarding
Airline reviews

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

6.0 GoodGlenn, Feb 2026
AMS - JFK
Read more KLM reviews

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.

The boarding was one of the worst I’ve ever experienced. The fault lays on Ohare Airport and not so much the airline. The waiting area by the gate was the size to accommodate a regional flight for 20-30 people and right next to a busy walkway. When you cramped nearly 300 passengers into that space is was unbearable.

Seats actually fit a human! Snack options were a bit lame but that’s ok

The flight was delayed an hour and a half while you tried to fix the plane so I missed my connecting flight in Chicago. In Chicago, it took an hour to get the luggage. Then the conveyor belt was broken where I have to transfer my flight from an international flight to the continuing flight so I had to carry a large suitcase through the airport. The elevators were broken in the airport. I paid people to carry the luggage for me up the escalators in two different areas. The person who helped me get the new flight was outstanding. The temperature in the airport in Chicago was horrible. We were all sweating. It was the day from hell. That was after two hours in a security line in Athens. I have TSA pre-checked and global entry and I still waited. Two hours in a security line. Something has got to be done to stream line this service. After I’ve been through all of that in Athens, why do I have to go through it again in Chicago. It was the worst travel experience I have had in a long time. Your bathrooms have gotten so small that you can hardly get your butt on the toilet. You’ve taken the airspace out of the inside of the top of the toilet. It really makes for a miserable experience. Also on a 4 1/2 hour flight from Chicago to Los Angeles. The only thing we’re given is a bag of pretzels. REALLY!!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

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.