$602 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 3/23. 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
$826
Typical prices: $1,014-$1,445
Etihad Airways
Thu 3/19Thu 4/2
JNB - ORD • 1 stop
Cheapest one-way
$618
Multiple Airlines
Mon 3/23
CPT - MDW • 2 stops
When to travel
February
Cheapest • 13% 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

Thu, Mar 19 - Thu, Apr 2
Etihad Airways Logo
9:50 am - 8:35 am
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
2:00 pm - 8:20 am
ORD
-
JNB
35h 20m
1 stop
$826Etihad Airways
Wed, Mar 11 - Mon, Mar 23
Ethiopian Air Logo
2:30 pm - 8:40 am
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 am - 1:05 pm
ORD
-
JNB
19h 50m
1 stop
$834Ethiopian Air
Tue, Mar 10 - Mon, Mar 23
Ethiopian Air Logo
2:30 pm - 8:40 am
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 am - 1:05 pm
ORD
-
JNB
19h 50m
1 stop
$843Ethiopian Air
Tue, Mar 10 - Thu, Mar 26
Ethiopian Air Logo
2:30 pm - 8:40 am
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 am - 1:05 pm
ORD
-
JNB
19h 50m
1 stop
$863Ethiopian Air
Thu, Mar 5 - Fri, Apr 3
Turkish Airlines Logo
7:10 pm - 10:05 am
JNB
-
ORD
22h 55m
1 stop
Turkish Airlines Logo
8:10 pm - 10:30 am
ORD
-
JNB
31h 20m
1 stop
$924Turkish Airlines
Wed, Mar 11 - Mon, Mar 23
Delta Logo
10:00 pm - 6:40 pm
JNB
-
MDW
27h 40m
2 stops
Delta Logo
1:10 pm - 7:00 pm
MDW
-
JNB
22h 50m
2 stops
$1,017Delta
Thu, Mar 5 - Fri, Apr 3
Delta Logo
9:30 pm - 6:40 pm
JNB
-
MDW
29h 10m
2 stops
Delta Logo
9:35 am - 7:40 pm
MDW
-
JNB
27h 05m
2 stops
$1,018Delta
Tue, Mar 10 - Mon, Mar 23
SAUDIA Logo
10:00 pm - 6:40 pm
JNB
-
MDW
27h 40m
2 stops
SAUDIA Logo
6:07 pm - 7:00 pm
MDW
-
JNB
17h 53m
1 stop
$1,024SAUDIA
Thu, May 28 - Thu, Jun 4
KLM Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m
1 stop
KLM Logo
4:20 pm - 9:25 pm
ORD
-
CPT
22h 05m
1 stop
$1,121KLM
Fri, Mar 27 - Sun, Apr 5
KLM Logo
11:45 pm - 6:40 pm
CPT
-
MDW
25h 55m
2 stops
KLM Logo
1:10 pm - 9:25 pm
MDW
-
CPT
25h 15m
2 stops
$1,980KLM
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 $948 on average for one-way flights. On the other hand, the most expensive months are January and July, where the average cost of tickets from South Africa is $1,274 and $1,212 respectively. For return trips, the best month to travel is February with an average price of $937.

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 $132.

Good to know

Low seasonJanuary
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 7% increase in price.

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 14,277 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 4 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 8200 reviews
8.1Boarding
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
Airline reviews

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

2.0 MediocreMansoor, Feb 2026
DTW - RIC
Read more Delta reviews

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Awful - both legs. The check in was awful, getting on the plane required walking down a spiral staircase (dangerous), then taking a bus about 5 miles out from the terminal. The seat was broken (I was in business), there was no internet during the flight (both legs). The aircraft was very old. I saw rust in some place, tape holding things up in the bathroom. This was an unacceptable experience for such a long haul flight.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

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

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The seats were comfortable. So many empty seats allowed for stretching out and sleeping. The onboard entertainment was pretty good. The cabin crew were so kind and kept the passengers well- hydrated, and well fed.

We had American Airlines on our return and it was confusing if we were going with Aa or BA I had 2 different flight numbers and didn’t get our gate until it was boarding. So we were a bit nervous as the which it was

Our Jackson, Mississippi to Dallas Fort Worth flight was delayed on 1/19/26.. This was changed to Jackson to Charlotte in the last minute because of this delay. This started some kind of disconnect between American Airlines and British Airways bookings. We could not go past the passport control in London Heathrow. I had to go to the counter and waited for more than 30 minutes to get a new boarding pass. Problems did not end there. Somehow our entire return flight was canceled by someone. I had to make several phone calls over several days to fix the problem – this was not easy from India. Looks like there was some kind of disconnect between two airlines or some agent did not do it right. I’m anxious to know what went wrong.

My touch screen at my seat wasn't working, the films BA advertised on the website for this flight were not available, and the plane was a little dated, food was good and the staff were good, just let down by the aircraft facilities.

Did not like the seating configuration at all with 2+3+2 in business class. Lacking total privacy and comfort

The flight crew was kind, flexible, and accommodating. The seats on the plane were extremely uncomfortable.

Check-in experience, for business call please provide a premium experience

Lost my luggage, ran out of food choices in business class, ground crew was completely unapologetic.

Excellent. The crew and flight were great. Checking in was easy and everyone was very helpful.

Entertainment devices on A380 need to be fixed, the seats might do with updates.

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.