$598 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 1/19. 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, 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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Everything you should know

Cheapest round-trip
$853
Turkish Airlines
Mon 3/23Mon 4/13
DUR - ORD • 2 stops
Cheapest one-way
$598
Typical prices: $621-$2,404
Turkish Airlines
Mon 1/19
CPT - ORD • 1 stop
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
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

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

Mon, Mar 23 - Mon, Apr 13
Turkish Airlines Logo
4:00 pm - 11:05 am
DUR
-
ORD
26h 05m2 stops
Turkish Airlines Logo
8:10 pm - 1:15 pm
ORD
-
DUR
34h 05m2 stops
$853Turkish Airlines
Tue, Mar 24 - Wed, Apr 15
Turkish Airlines Logo
7:10 pm - 7:25 pm
JNB
-
ORD
31h 15m1 stop
Turkish Airlines Logo
7:50 pm - 10:35 am
ORD
-
JNB
31h 45m1 stop
$862Turkish Airlines
Thu, Mar 5 - Mon, Mar 9
Turkish Airlines Logo
7:10 pm - 10:05 am
JNB
-
ORD
22h 55m1 stop
Turkish Airlines Logo
12:50 pm - 10:50 am
ORD
-
JNB
39h 00m1 stop
$921Turkish Airlines
Thu, May 28 - Thu, Jun 4
United Airlines Logo
7:50 pm - 10:47 am
CPT
-
ORD
21h 57m1 stop
United Airlines Logo
11:15 am - 3:20 pm
ORD
-
CPT
21h 05m1 stop
$935United Airlines
Tue, Mar 24 - Wed, Apr 15
British Airways Logo
7:35 pm - 6:55 pm
JNB
-
ORD
30h 20m2 stops
British Airways Logo
5:10 pm - 7:00 am
ORD
-
JNB
30h 50m2 stops
$991British Airways
Thu, Mar 5 - Mon, Mar 9
British Airways Logo
7:35 pm - 2:00 pm
JNB
-
ORD
26h 25m2 stops
British Airways Logo
4:19 pm - 7:35 am
ORD
-
JNB
32h 16m2 stops
$992British Airways
Tue, Mar 24 - Wed, Apr 15
Delta Logo
10:00 pm - 6:40 pm
JNB
-
MDW
27h 40m2 stops
Delta Logo
1:05 pm - 7:40 pm
MDW
-
JNB
23h 35m1 stop
$1,005Delta
Thu, Jan 22 - Thu, Jan 29
Delta Logo
9:30 pm - 12:46 pm
CPT
-
MDW
23h 16m2 stops
Delta Logo
1:26 pm - 7:15 pm
MDW
-
CPT
21h 49m2 stops
$1,008Delta
Mon, Mar 9 - Sat, Mar 21
KLM Logo
11:59 pm - 8:37 pm
JNB
-
ORD
27h 38m2 stops
KLM Logo
2:20 pm - 10:05 pm
ORD
-
JNB
24h 45m2 stops
$1,012KLM
Wed, May 20 - Fri, May 29
KLM Logo
11:15 pm - 6:05 pm
JNB
-
MDW
25h 50m2 stops
KLM Logo
1:00 pm - 9:20 pm
MDW
-
JNB
25h 20m2 stops
$1,232KLM
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 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 $958 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 $1,207 and $1,192 respectively. For return trips, the best month to travel is February with an average price of $958.

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 Greater Rockford Airport, with an average flight price of $172.

Good to know

Low seasonJanuary
Cheapest flight$598
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Cape Town to Chicago O'Hare Airport

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 tickets can be as cheap as $967. On the other hand, the most expensive day to fly is Thursday, where 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 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 16,122 direct flights from within South Africa to Chicago. The most common day for departures is Tuesday, with 17% 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 3 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.
7.9
DeltaOverall score based on 8011 reviews
7.3Food
7.9Entertainment
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

The food is terrible. The staff is wonderful. Comfort is good.

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

Delay on my previous leg, had to run to catch my flight. But that happens. Overall ok.

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.

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

Audi visual not working for a whole group of seats in first class. How does a plane leave the main hub in such poor condition? How much that we can’t see so immediately is also compromised?

main meals are horrible but then you dont fly for the food

It was good. Couldn’t Check in online and select seats

It was great. Enough space and room for legs . Great service to.

⭐ British Airways Review — A Journey of Highs, Lows, and Lessons ⭐ I recently flew Business Class round-trip from Boston to Mumbai with British Airways, and my experience was a tale of two extremes — from disappointment to exceptional service, and then back to inconsistency. Boston → London: A Surprisingly Poor Start My journey began on a disappointing note. On a 6-hour Business Class flight, I was surprised to discover that there wasn’t a single proper vegetarian meal option available. I was offered a few bakery items only after repeatedly requesting something to eat. The flight attendant shrugged, offered no solution, and eventually — quite literally — threw some bread at me after much delay. This was not only disheartening, it was extremely surprising given my wonderful Business Class experience with BA last year. I stepped off that flight genuinely hungry and had to make a mad dash to the lounge just to get a proper meal. London → Mumbai: A Complete Turnaround The next sector restored my faith in British Airways. The entire crew was warm, welcoming, attentive, and genuinely caring. A special shoutout to Phiroze and the entire team serving the Business Class cabin — their professionalism, hospitality, and thoughtful service were extraordinary. They truly embodied what makes British Airways a global leader, and I am deeply grateful for the experience they provided. This is the BA I know and love. Mumbai → London: A Strange Meal Schedule This sector was generally fine, but the meal timing was puzzling. Lunch at 10:30 AM — for a Business cabin — felt unusual, and most passengers, including myself, barely touched it. The rest of the service was smooth, but the scheduling definitely needs a rethink. London → Boston: Mixed Experience Again The flight itself was decent, but the Business Lounge at Heathrow for this leg was a letdown. Arrived during lunch hours: no hot vegetarian options available Lounge area: dirty dishes everywhere Even after politely alerting the staff, the dishes were ignored and left uncleared For a premium cabin passenger — and at one of the world’s busiest international hubs — this was disappointing. Overall Impression My journey with British Airways felt inconsistent — two great sectors sandwiched between two that fell short of the BA standard. When BA is good, it is world-class. When it misses, the gap is noticeable. I genuinely hope the airline takes this feedback as constructive insight. I continue to believe in British Airways, and I commend the outstanding crew on the London → Mumbai sector — they were the highlight of my entire trip. With a little more focus on vegetarian meal availability, lounge service, and consistency across crews, BA can ensure every Business Class passenger experiences the premium journey they promise.

We were in business class and I had seat # 1. This was a night flight and after dinner was served, lights were dimmed and I went to sleep. The crew were loud and noisy so I didn’t get much sleep. I expect the crew to enjoy themselves but would Appreciate some decency in staying quiet while the passengers sleep

Have travelled business class with other airlines who profess to be the best in the world. They can however not beat the service and comfort that BA provide.

Well unfortunately our connecting was cancelled and next flight delayed. Was in airport 9 hours. Flight itself was good. I’m sure it was a FAA problem.

Great on board entertainment Tasty food Cattle class obviously crammed but not as bad as shorter hall flights

I was attacked in the Miami airport and the staff did nothing. On my flight from London to Miami one of the flight attendants screamed at me and demanded I keep my seat in the upright position at all times during the fight so the man behind me was comfortable for the flight. I will never in my life use British airways again

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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.