R11 016 Find Cheap Flights 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 8/10. 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

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
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Flight Deals

Cheap Flights to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights 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 return flight deals to Chicago

Tue, Oct 14 - Wed, Nov 12
SWISS Logo
19:35 - 15:55JNB-ORD
27h 20m1 stop
SWISS Logo
18:50 - 10:30ORD-JNB
31h 40m1 stop
R14 155SWISS
Find Deal
Tue, Oct 14 - Wed, Nov 12
 Logo
19:35 - 12:55JNB-ORD
24h 20m1 stop
 Logo
10:38 - 10:30ORD-JNB
39h 52m2 stops
R14 333
Find Deal
Wed, Sep 24 - Wed, Oct 1
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
13:55 - 8:20ORD-JNB
35h 25m1 stop
R14 368Etihad Airways
Find Deal
Thu, Nov 6 - Mon, Nov 10
Turkish Airlines Logo
19:10 - 18:25JNB-ORD
31h 15m1 stop
Turkish Airlines Logo
11:50 - 10:50ORD-JNB
39h 00m1 stop
R16 266Turkish Airlines
Find Deal
Sun, Sep 7 - Sun, Sep 21
United Airlines Logo
21:20 - 13:08JNB-ORD
22h 48m1 stop
United Airlines Logo
15:45 - 17:45ORD-JNB
19h 00m1 stop
R17 703United Airlines
Find Deal
Thu, Nov 13 - Thu, Dec 4
British Airways Logo
22:00 - 17:55JNB-ORD
27h 55m2 stops
British Airways Logo
16:28 - 10:25ORD-JNB
33h 57m2 stops
R17 738British Airways
Find Deal
Sat, Dec 6 - Sat, Jan 3
British Airways Logo
22:00 - 17:55JNB-ORD
27h 55m2 stops
British Airways Logo
17:10 - 10:25ORD-JNB
33h 15m1 stop
R18 537British Airways
Find Deal
Sun, Nov 23 - Fri, Jan 2
United Airlines Logo
22:00 - 16:53JNB-ORD
26h 53m2 stops
United Airlines Logo
11:15 - 18:35ORD-JNB
23h 20m2 stops
R19 690United Airlines
Find Deal
Wed, Sep 10 - Tue, Sep 30
KLM Logo
18:25 - 14:10CPT-ORD
26h 45m2 stops
KLM Logo
16:15 - 21:25ORD-CPT
22h 10m1 stop
R21 463KLM
Find Deal
Wed, Sep 10 - Tue, Sep 30
KLM Logo
23:15 - 14:10CPT-ORD
21h 55m1 stop
KLM Logo
16:15 - 21:25ORD-CPT
22h 10m1 stop
R21 765KLM
Find Deal
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends into 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 R17 259 on average for return flights. On the other hand, the most expensive months are December and July, where the average cost of tickets from South Africa is R21 641 and R21 197 respectively. For one-way flights, the best month to travel is February with an average price of R17 259.

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 5 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 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 Midway Airport (MDW), with an average flight price of R3 612.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonFebruary
Cheapest flightR11 016
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly and prices are also 2% lower on average.
Flight from Cape Town to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and the city centre of Chicago is 14 km, which makes it the closest of the 3 Chicago airports airports. Chicago O'Hare Airport is 26 km away from the centre and Chicago Greater Rockford is 126 km away.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as R19 892. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R22 003 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 travellers 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 evening, when round-trip flights cost R1 031 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is R1 064.

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.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop to Chicago.
Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

South Africa to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Reviews of the top 5 airlines flying 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 1381 reviews
7,8Boarding
7,7Comfort
7,3Food
8,4Crew
7,1Entertainment
Airline reviews

Our first flight was delayed so we missed our connecting flight. However it was easy to book a later flight on their app.

6,0 GoodKathleen P, Jun 2025EDI - AMS
Read more KLM reviews

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

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

Cabin crew were excellent, very proffesional, polite and friendly, in flight snack was underwhelming, a packet of cheese biscuits, im sure KLM could run to a sandwich!

Legroom not all it could be, especially when the seat in front is reclined. Otherwise it was good, food and beverage were nice.

This portion of the flight was through Indigo. A local carrier. So all economy seating. No real service some refreshments for purchase standard economy stuff.

This fight left ahead of time which meant it arrived early which was great. Staff were very professional, but as with all these Short hop Flights the food was a disappointing snack There was no entertainment on this flight, but I did not expect any

I flew premium economy and this was a good option. Although the seats didn’t recline much, I was able to get some sleep with my head propped against the window. The food was good and the entertainment was wonderful The staff were very attentive and professional

They only had vegetarian food left on the flight which I wasn’t happy about. I didn’t get any food to eat at all.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

Small seat space for 13 hours flight, they charged for baggage , very bad quality of food,

I was sitting almost in the back, the seats are very tight and there’s no legroom, it’s uncomfortable for a long distance

Absolute worst airline. Charged us $720 to check 4 bags (2 of which were carry-on). Entertainment systems didnt work. And on a 12 hour flight they served 2 meals and never once came around outside of those 2 meals with a beverage or cup of water. Will never fly them again.

Took forever to board. They made announcements without the loudspeaker and since the waiting room was full of screaming kids, no one could hear what they were saying. The business class sleeper seats were designed for tall skinny people. When partially reclined there was nowhere to rest my feet because they did not reach the footrest. and when fully reclined there wasn't room at my sides for my arms. Definitely one of the worst sleeper seats I have ever had.

About an hour delay but we made it to Chicago. I feel that the smaller connecting flights are the ones that cause the delays on the bigger planes that fly international.

Amazing trip! No delays, no broken or lost luggage, and amazing food.

The food we received during the flight was excellent. The service was very friendly. Definitely the best value for the money when flying across the Atlantic.

I use a wheelchair for mobility. Both in my flight from Houston and back to Houston from Istanbul, the Turkish airline staff asked that I claim my wheelchair at the luggage area. On arrival to Istanbul, parts of the wheelchair were in disarray at that time I raised no objection however upon claiming my wheelchair in Houston parts where outright missing. In both occasions, upon arriving in Houston and arriving in Istanbul, I asked multiple times why am made to pick up my wheelchair in the baggage claim rather than at the jet bridge. Getting the wheelchair at the jet bridge minimizes the probability of loosing parts because they can be hopefully reclaimed on the spot. I was told in Houston that a manager turned down my request to claim the wheelchair at the jet bridge in Houston. This is extremely frustrating because a wheelchair is not a set of clean underwear or a toothbrush- this is the way I move. A Turkish Arline staff took my complaint at the luggage claim area in Houston but as of the writing of this review the only contact I have received from the airline is because I initiated a claim rather than her as she told me she would.

The security at the airport was excellent. The one criticism is the boarding process just before entering the plane. There were only 2 boarding lines and there were no barriers thus leading to a mass rush to enter the plane. I suggest that they board by rows, eight or ten rows at a time to prevent the mass rush to enter the plane. Otherwise, I would highly recommend Turkish Airlines

The flight is packed and it feels like the space per individual has gotten smaller. Excruciating for a 14hr flight.

Were not told that carryon laggage has to be only 12 kgs but my bag was heavier asked to pay an additional $550.00. I could have upgraded to a bussiness class for that price and no one at the gate to upgrade but able to take money for the extra weight. I felt like this was a setup scam.

Lost suite case and pillow that’s used by senior and they didn’t leave it at the airport

The flight itself was fine. The exception is that my luggage was destroyed, and I filed a claim that I haven't heard from anyone.

Im if Ethiopian can allow customers to use their mileage for in flight connexion it will be great.

United was best airlines I have seen since I got there choose united airlines

It was wonderful best Air lines covert and all very happy with their service they have been very helpful and friendly

No Asian Vegetarian food was available on this sector but only fish and chicken and pasta were offered.

Needs improvement because some of the tvs and charging ports weren’t working

The plane was overbooked and the crew was very rude. My luggage was never put on the plane. I got to NY and waited 2 hours just to find out that my luggage was left.

The company that I bought my tickets through, Cheapflightsfares, failed to provide my confirmation information in a timely manner, so I was unable to check on at the country and therefore unable to make my flight. As a matter of fact, I STILL have not received the confirmation. After having read more and more reviews about the company, Cheapflightsfares appears to have scammed hundreds of hopeful travelers out of thousands of dollars. Please look into this company and, for the sake of anyone planning their next trip, stop allowing them to do business through you.

I checked in to bags, one arrived one was delayed. I did not receive the bag for 4 days - arrived on Tuesday, received bag on Saturday!

It was ok. Our flight was delayed 2 hours, and then again on arrival. The explanation given felt feeble.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

The booking agent, cheapflightsfares, messed up, and the information for the seats we paid extra for was not sent to American Airlines. We were separated on the return flight and sent to the lowest economy section. The flight attendant helped arrange seating at the back of the plane to allow my wife and me to sit together.

I liked the comfort of the seats, very attentive crew, and the meals were excellent.

We were kicked off this flight by British Airways due to delays on our connecting flight also operated by British airways and were rebooked on a different carrier which delayed our arrival home by > 26 hours.

Everything about the flight check-in was smooth no line the plane is clean and bathroom

Excellent everywhere but Philly, the most rotten airport in the world.

Check in was not the greatest as had to talk to an agent to clarify things and then he transferred us to another agent who had difficulty processing my credit card as there was a system glitch and not a card error.

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