$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 7/15. 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 31 - Sat, Jun 13
Delta Logo
8:05 pm - 9:09 pm
CPT
-
MDW
32h 04m
1 stop
Delta Logo
9:17 am - 5:50 pm
MDW
-
CPT
25h 33m
2 stops
$999Delta
Sun, May 31 - Sat, Jun 13
Delta Logo
8:05 pm - 8:26 pm
CPT
-
ORD
31h 21m
1 stop
Delta Logo
5:30 am - 5:50 pm
ORD
-
CPT
29h 20m
1 stop
$999Delta
Tue, Jun 16 - Thu, Jun 25
Delta Logo
8:05 pm - 4:16 pm
CPT
-
MDW
27h 11m
1 stop
Delta Logo
12:50 pm - 5:50 pm
MDW
-
CPT
22h 00m
1 stop
$1,004Delta
Sun, Jun 21 - Sat, Jul 4
United Airlines Logo
8:00 pm - 11:26 pm
CPT
-
ORD
34h 26m
1 stop
United Airlines Logo
1:30 pm - 3:20 pm
ORD
-
CPT
18h 50m
1 stop
$1,011United Airlines
Sun, Jun 21 - Sat, Jul 4
United Airlines Logo
8:00 pm - 10:50 am
CPT
-
ORD
21h 50m
1 stop
United Airlines Logo
8:43 am - 3:20 pm
ORD
-
CPT
23h 37m
1 stop
$1,016United Airlines
Mon, Jun 15 - Tue, Jun 23
KLM Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m
1 stop
KLM Logo
2:07 pm - 9:25 pm
ORD
-
CPT
24h 18m
2 stops
$1,017KLM
Mon, Jun 15 - Tue, Jun 23
KLM Logo
11:15 pm - 9:25 pm
CPT
-
ORD
29h 10m
2 stops
KLM Logo
11:23 am - 9:25 pm
ORD
-
CPT
27h 02m
2 stops
$1,026KLM
Tue, Jun 9 - Mon, Aug 17
Qatar Airways Logo
7:50 pm - 4:50 pm
JNB
-
ORD
28h 00m
1 stop
Qatar Airways Logo
7:20 pm - 4:00 am
ORD
-
JNB
25h 40m
1 stop
$1,040Qatar Airways
Mon, Sep 7 - Wed, Mar 3
Etihad Airways Logo
9:50 am - 8:35 am
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
1:10 pm - 8:20 am
ORD
-
JNB
35h 10m
1 stop
$1,055Etihad Airways
Sun, Aug 2 - Mon, Aug 17
Qatar Airways Logo
8:55 pm - 3:05 pm
JNB
-
ORD
25h 10m
1 stop
Qatar Airways Logo
7:20 pm - 9:00 am
ORD
-
JNB
30h 40m
1 stop
$1,099Qatar 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 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 January and July, where the average cost of tickets from South Africa is $1,409 and $1,145 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 11% 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 $130.

Good to know

Low seasonJanuary
Cheapest flight$598
Best time to beat the crowds but there is an average 8% increase 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 47,970 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 1518 reviews
7.2Entertainment
7.3Food
8.4Crew
7.7Comfort
7.8Boarding
Airline reviews

Outstanding even though the 330 was one of the oldest in the fleet. The difference was the attentiveness and responsiveness of a really experienced flight attendant. For airline food great variety of interesting choices and good tastes supported by a good wine selection.

10.0 ExcellentBob, May 2026
AMS - YYZ
Read more KLM reviews

Outstanding even though the 330 was one of the oldest in the fleet. The difference was the attentiveness and responsiveness of a really experienced flight attendant. For airline food great variety of interesting choices and good tastes supported by a good wine selection.

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

Empty seats next to me - wish it had been for a longer flight!!

I’m grateful for the KLM Air France shuttle bus service to Ottawa. However due to construction and other issues related to the chaotic Uber pickup system at YUL, it’s a challenge to find the Kelios bus service to Ottawa. The signs are not clear or even available. No staff to guide passengers. It’s a stressful experience.

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

Delay and had to run between flight to get my connection due to this delay but besides that the overall experience was ok. I arrived with just an hour of delay.

At the airport, terrible, I do not want to even remember it. It was too humiliating for a business class passenger.

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.

First of all we couldn’t check in online, then we learn at the airport we were on stand by for KLM’s mistake of overbooking. The seats were not comfy at all. Our luggage got lost.

Ad experience - been flying many years with them but they are losing out to other carriers with their service and bagage / seating policy. My 2 12-yo kids were not placed with the parent. Absurdity.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

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
Schererville
Chesterton
Munster
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.