$584 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 6/11. 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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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

Sun, May 3 - Mon, May 18
Etihad Airways Logo
9:45 am - 8:35 am
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
2:00 pm - 8:15 am
ORD
-
JNB
35h 15m
1 stop
$837Etihad Airways
Wed, Jun 3 - Wed, Jun 17
Etihad Airways Logo
9:50 am - 8:35 am
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
9:10 pm - 8:20 am
ORD
-
JNB
28h 10m
1 stop
$854Etihad Airways
Wed, Sep 9 - Wed, Jan 20
Turkish Airlines Logo
6:00 pm - 6:15 pm
JNB
-
ORD
31h 15m
1 stop
Turkish Airlines Logo
8:20 pm - 10:50 am
ORD
-
JNB
30h 30m
1 stop
$897Turkish Airlines
Wed, Sep 9 - Wed, Jan 20
Turkish Airlines Logo
6:00 pm - 6:15 pm
JNB
-
ORD
31h 15m
1 stop
Turkish Airlines Logo
11:50 am - 10:50 am
ORD
-
JNB
39h 00m
1 stop
$909Turkish Airlines
Fri, Apr 24 - Wed, May 6
Qatar Airways Logo
1:00 pm - 3:05 pm
CPT
-
ORD
33h 05m
1 stop
Qatar Airways Logo
7:20 pm - 11:30 am
ORD
-
CPT
33h 10m
1 stop
$1,177Qatar Airways
Thu, May 28 - Thu, Jun 4
Qatar Airways Logo
7:30 pm - 4:50 pm
CPT
-
ORD
28h 20m
1 stop
Qatar Airways Logo
7:20 pm - 12:55 pm
ORD
-
CPT
34h 35m
1 stop
$1,181Qatar Airways
Sat, May 16 - Wed, May 27
KLM Logo
11:15 pm - 5:56 pm
JNB
-
MDW
25h 41m
2 stops
KLM Logo
1:22 pm - 9:20 pm
MDW
-
JNB
24h 58m
2 stops
$1,420KLM
Sun, Apr 26 - Sun, May 3
KLM Logo
11:15 pm - 6:36 pm
JNB
-
MDW
26h 21m
2 stops
KLM Logo
1:24 pm - 9:20 pm
MDW
-
JNB
24h 56m
2 stops
$1,478KLM
Sun, Apr 26 - Sun, May 3
Delta Logo
8:25 pm - 5:58 pm
JNB
-
MDW
28h 33m
2 stops
Delta Logo
6:00 am - 7:40 pm
MDW
-
JNB
30h 40m
1 stop
$1,585Delta
Mon, Apr 27 - Mon, May 4
Delta Logo
5:55 pm - 5:58 pm
JNB
-
MDW
31h 03m
2 stops
Delta Logo
1:24 pm - 9:20 pm
MDW
-
JNB
24h 56m
2 stops
$1,589Delta
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 $900 on average for return flights. On the other hand, the most expensive months are July and December, where the average cost of tickets from South Africa is $1,222 and $1,154 respectively. For one-way flights, the best month to travel is February with an average price of $900.

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 17% 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 $160.

Good to know

Low seasonJanuary
Cheapest flight$584
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 8% increase in price.
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 12,809 direct flights from within South Africa to Chicago. The most common day for departures is Thursday, 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.
7.9
DeltaOverall score based on 8371 reviews
7.8Entertainment
8.5Crew
7.2Food
7.9Comfort
8.1Boarding
Airline reviews

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

8.0 ExcellentEarl, Apr 2026
ORD - DTW
Read more Delta reviews

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Our recent international travel was from Newark, NJ to Grenada via Atlanta. During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta as it did not wait for arriving passengers. Consequently, we were delayed by 24 hours before the next available flight was provided. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for me as a resident of New Jersey.

This was my first flight with Delta, the overall experience was good. I would definitely consider them more with my future flights.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

The crew were unprofessional with a racist element. I was physically abused as well from one of the crew members

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

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.

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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.