$631 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
$861
Overall average: $1,106
Turkish Airlines
Thu 4/16Mon 5/11
JNB - ORD • 1 stop
Cheapest one-way
$597
Typical prices: $771-$2,166
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
Start a new search
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, Apr 16 - Mon, May 11
Turkish Airlines Logo
5:50 pm - 6:15 pm
JNB
-
ORD
31h 25m1 stop
Turkish Airlines Logo
11:25 am - 10:30 am
ORD
-
JNB
40h 05m1 stop
$861Turkish Airlines
Thu, Mar 12 - Sun, Mar 29
Turkish Airlines Logo
7:10 pm - 7:25 pm
JNB
-
ORD
31h 15m1 stop
Turkish Airlines Logo
7:50 pm - 10:30 am
ORD
-
JNB
31h 40m1 stop
$876Turkish Airlines
Thu, Apr 16 - Mon, May 11
Ethiopian Air Logo
8:20 am - 8:15 am
JNB
-
ORD
30h 55m2 stops
Ethiopian Air Logo
10:15 am - 1:05 pm
ORD
-
JNB
19h 50m1 stop
$912Ethiopian Air
Wed, Feb 11 - Sun, Feb 15
Ethiopian Air Logo
8:20 am - 7:40 am
JNB
-
ORD
31h 20m2 stops
Ethiopian Air Logo
9:45 am - 8:10 pm
ORD
-
JNB
26h 25m1 stop
$913Ethiopian Air
Thu, Feb 5 - Thu, Feb 12
United Airlines Logo
10:00 pm - 10:53 am
JNB
-
ORD
20h 53m1 stop
United Airlines Logo
9:00 am - 6:35 pm
ORD
-
JNB
25h 35m2 stops
$933United Airlines
Sat, Feb 7 - Sat, Feb 14
United Airlines Logo
8:50 pm - 7:50 pm
CPT
-
ORD
31h 00m2 stops
United Airlines Logo
7:10 am - 4:10 pm
ORD
-
CPT
25h 00m2 stops
$991United Airlines
Thu, May 28 - Thu, Jun 4
Delta Logo
11:15 pm - 2:15 pm
CPT
-
ORD
22h 00m1 stop
Delta Logo
4:20 pm - 9:25 pm
ORD
-
CPT
22h 05m1 stop
$1,123Delta
Thu, May 28 - Thu, Jun 4
Delta Logo
11:15 pm - 7:43 pm
CPT
-
ORD
27h 28m2 stops
Delta Logo
2:10 pm - 9:25 pm
ORD
-
CPT
24h 15m2 stops
$1,127Delta
Thu, Apr 16 - Mon, May 11
KLM Logo
11:15 pm - 6:45 pm
JNB
-
MDW
26h 30m2 stops
KLM Logo
1:00 pm - 9:20 pm
MDW
-
JNB
25h 20m2 stops
$1,422KLM
Sat, Feb 7 - Sat, Feb 14
KLM Logo
11:45 pm - 10:22 pm
CPT
-
MDW
30h 37m2 stops
KLM Logo
11:45 am - 9:55 pm
MDW
-
CPT
26h 10m2 stops
$2,214KLM
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 $1,194 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$597
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

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 12,710 direct flights from within South Africa to Chicago. The most common day for departures is Monday, 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 8013 reviews
8.1Boarding
7.3Food
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

Advertised fruit trays with cheese, but only snacks handed out!

8.0 ExcellentAnonymous, Dec 2025
MSP - BOS
Read more Delta reviews

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Every single flight that we got on was delayed by several hours or more. I honestly didn’t think we would get out of Atlanta because our flight was supposed to leave at 7:59 and it kept getting kicked back further and further. Delta stands for Don’t Ever Leave The Airport!

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

Great seat in premium economy, great food and drinks throughout lots of in flight entertainment. 1 hour 40 min delayed flying out , 2 1/2 hour wait at passport control in tampa

Plane was extremely delayed, but not all of it was BA fault (some was). Worst part was lack of room - this had as much space as an Allegiant flight. I thought transatlantic usually gave you an extra inch or two, but not this one. Entertainment system sporadically worked and didn’t have great options. Overhead bins are old and tiny, not as good as aunties new planes.

My seat cushion was poor. The cushion was compressed and was uncomfortable for such a long flight.

Besides having a LONG layover in Philadelphia to begin with, our flight was delayed and left late. We spent 7 hours in the Philadelphia airport after being in the air 7 hours from Portugal to Philly. It turned into a 24 hour day of travel which was exhausting. I know you can't help weather but our layover was difficult as my husband is handicapped. The staff was EXTREMELY helpful with his wheelchair tho!!

I was in a bulkhead seat and my tray table wasn't level. Eating was difficult.

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.

Traveling to a place near Chicago?

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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.