$583 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 6/25. 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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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, Jun 14 - Mon, Sep 7
Turkish Airlines Logo
2:45 pm - 9:40 am
DUR
-
ORD
25h 55m
2 stops
Turkish Airlines Logo
8:10 pm - 1:15 pm
ORD
-
DUR
34h 05m
2 stops
$944Turkish Airlines
Sun, Jun 14 - Mon, Sep 7
Turkish Airlines Logo
2:45 pm - 9:40 am
DUR
-
ORD
25h 55m
2 stops
Turkish Airlines Logo
11:25 am - 1:15 pm
ORD
-
DUR
42h 50m
2 stops
$1,027Turkish Airlines
Sun, Sep 13 - Fri, Sep 18
Qatar Airways Logo
8:55 pm - 3:05 pm
JNB
-
ORD
25h 10m
1 stop
Qatar Airways Logo
7:20 pm - 4:00 am
ORD
-
JNB
25h 40m
1 stop
$1,032Qatar Airways
Wed, Jul 22 - Fri, Jul 31
Qatar Airways Logo
12:40 pm - 3:05 pm
JNB
-
ORD
33h 25m
1 stop
Qatar Airways Logo
7:20 pm - 4:00 am
ORD
-
JNB
25h 40m
1 stop
$1,042Qatar Airways
Tue, Oct 27 - Wed, Nov 25
Multiple Airlines Logo
5:00 pm - 12:36 pm
JNB
-
ORD
26h 36m
2 stops
Multiple Airlines Logo
6:00 am - 3:50 pm
ORD
-
JNB
25h 50m
2 stops
$1,078Multiple Airlines
Sun, Jul 12 - Thu, Jul 30
Delta Logo
8:05 pm - 10:05 am
CPT
-
MDW
21h 00m
1 stop
Delta Logo
11:05 am - 5:50 pm
MDW
-
CPT
23h 45m
1 stop
$1,339Delta
Mon, Sep 7 - Tue, Mar 2
Delta Logo
8:25 pm - 6:31 pm
JNB
-
MDW
29h 06m
2 stops
Delta Logo
12:30 pm - 7:00 pm
MDW
-
JNB
22h 30m
2 stops
$1,345Delta
Mon, Jun 1 - Tue, Jun 30
KLM Logo
11:15 pm - 5:56 pm
CPT
-
MDW
25h 41m
2 stops
KLM Logo
1:26 pm - 9:25 pm
MDW
-
CPT
24h 59m
2 stops
$1,560KLM
Mon, Jul 13 - Mon, Aug 24
Multiple Airlines Logo
8:25 pm - 10:15 pm
JNB
-
MDW
32h 50m
2 stops
Multiple Airlines Logo
12:46 pm - 9:35 pm
MDW
-
JNB
25h 49m
2 stops
$1,589Multiple Airlines
Sun, May 31 - Sun, Jun 7
KLM Logo
11:15 pm - 5:56 pm
JNB
-
MDW
25h 41m
2 stops
KLM Logo
1:21 pm - 9:20 pm
MDW
-
JNB
24h 59m
2 stops
$1,667KLM
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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Johannesburg, at $944 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $151 in the last 3 days.

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 $896 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 $1,168 and $1,154 respectively. For one-way flights, the best month to travel is February with an average price of $896.

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 4 weeks before departure, which saves you about 13% 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 $132.

Good to know

Low seasonJanuary
Cheapest flight$583
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Johannesburg to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Johannesburg, at $944 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $151 in the last 3 days.

  • 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 36,155 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 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 8459 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

10.0 ExcellentIrmara, May 2026
MCO - BOS
Read more Delta reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Seats were comfortable, 8 hours. One flight attendant was not appropriate in his verbal response: "Please, DON'T touch me.", after being tapped near his elbow after being made unaware he skipped serving me & had passed further down the aisle.

Boarding in Amsterdam is always chaotic. More complicated than needs to be ( boarding pass checked twice, once for general security, then by the airline). The bathrooms on this flight are dirty, and smelly. The food was mediocre at best The crew was decent

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

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.

Brand new plane lots of room the snack was very flavourful and enjoyable

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)

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.

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.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

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
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.