$622 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 12/3. 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
$923
Overall average: $986
United Airlines
Sun 12/14Tue 12/30
CPT - ORD • 1 stop
Cheapest one-way
$599
Multiple Airlines
Wed 12/3
DUR - ORD • 3 stops
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
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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

Sun, Dec 14 - Tue, Dec 30
United Airlines Logo
8:50 pm - 11:50 amCPT-ORD
23h 00m1 stop
United Airlines Logo
9:10 pm - 6:00 pmORD-CPT
36h 50m1 stop
$923United Airlines
Find Deal
Fri, May 15 - Mon, Jun 1
United Airlines Logo
8:00 pm - 2:50 pmCPT-ORD
25h 50m2 stops
United Airlines Logo
2:24 pm - 3:20 pmORD-CPT
17h 56m1 stop
$927United Airlines
Find Deal
Wed, May 13 - Wed, Jun 3
Ethiopian Air Logo
2:35 pm - 8:15 amCPT-ORD
24h 40m2 stops
Ethiopian Air Logo
10:15 am - 2:35 pmORD-CPT
21h 20m1 stop
$979Ethiopian Air
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Wed, May 13 - Thu, Jun 4
Delta Logo
7:40 am - 2:15 pmCPT-ORD
37h 35m1 stop
Delta Logo
4:20 pm - 9:25 pmORD-CPT
22h 05m1 stop
$1,013Delta
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Sun, May 17 - Tue, Jun 2
Delta Logo
8:05 pm - 12:39 pmCPT-ORD
23h 34m2 stops
Delta Logo
6:10 pm - 9:25 pmORD-CPT
44h 15m2 stops
$1,014Delta
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Wed, Apr 15 - Tue, Apr 28
KLM Logo
11:15 pm - 2:15 pmJNB-ORD
22h 00m1 stop
KLM Logo
1:35 pm - 9:20 pmORD-JNB
24h 45m2 stops
$1,026KLM
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Tue, Feb 3 - Wed, Feb 18
KLM Logo
11:59 pm - 6:36 pmJNB-MDW
26h 37m2 stops
KLM Logo
1:49 pm - 10:05 pmMDW-JNB
24h 16m2 stops
$1,030KLM
Find Deal
Thu, Apr 16 - Sun, Apr 26
Ethiopian Air Logo
2:30 pm - 8:15 amJNB-ORD
24h 45m2 stops
Ethiopian Air Logo
10:15 am - 1:05 pmORD-JNB
19h 50m1 stop
$1,040Ethiopian Air
Find Deal
Sat, Feb 14 - Wed, Feb 18
British Airways Logo
11:15 am - 6:45 pmDUR-ORD
39h 30m2 stops
British Airways Logo
9:45 pm - 10:40 amORD-DUR
52h 55m2 stops
$1,072British Airways
Find Deal
Sat, Feb 14 - Wed, Feb 18
British Airways Logo
11:15 am - 1:50 pmDUR-ORD
34h 35m2 stops
British Airways Logo
8:45 pm - 10:40 amORD-DUR
53h 55m2 stops
$1,085British Airways
Find Deal
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 December and July, where the average cost of tickets from South Africa is $1,201 and $1,195 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 $148.

Good to know

Low seasonJanuary
Cheapest flight$599
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Durban 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 13,937 direct flights from within South Africa to Chicago. The most common day for departures is Friday, 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 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 7998 reviews
8.5Crew
7.3Food
8.1Boarding
7.9Comfort
7.9Entertainment
Airline reviews

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

2.0 MediocreAnonymous, Nov 2025ATL - TPA
Read more Delta reviews

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

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.

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.

Klm start boarding while somw air issue in the plan

The service was great. However the lounge only gets passing grade

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

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.

We were in business class and I had seat # 1. This was a night flight and after dinner was served, lights were dimmed and I went to sleep. The crew were loud and noisy so I didn’t get much sleep. I expect the crew to enjoy themselves but would Appreciate some decency in staying quiet while the passengers sleep

Have travelled business class with other airlines who profess to be the best in the world. They can however not beat the service and comfort that BA provide.

Well unfortunately our connecting was cancelled and next flight delayed. Was in airport 9 hours. Flight itself was good. I’m sure it was a FAA problem.

Great on board entertainment Tasty food Cattle class obviously crammed but not as bad as shorter hall flights

I was attacked in the Miami airport and the staff did nothing. On my flight from London to Miami one of the flight attendants screamed at me and demanded I keep my seat in the upright position at all times during the fight so the man behind me was comfortable for the flight. I will never in my life use British airways again

Logan gate staff was unhelpful. Arrived early, come to find out the airbus scheduled was reassigned and I did not have a seat. The desk agent spoke to his supervisor who instructed him to give me a boarding pass to get up to gate area, he was polite. At the gate the fellow was sitting to the side with two other BA staff . I asked him if he could help me, his answer was” we are on a break, we are closed” then turned his back. I am almost 70, drove 4 1/2 hours to Boston and had been looking forward to this trip for 5 months. I have worked in service many times in my life and this is not how it is done. I eventually (1/2 hr) before boarding was able to get a seat. The rest of the flight experience was unremarkable.

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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.