R9 700 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 10/12. 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

Wed, Oct 15 - Wed, Oct 22
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
13:55 - 8:20ORD-JNB
35h 25m1 stop
R14 351Etihad Airways
Find Deal
Fri, Oct 17 - Mon, Oct 27
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
14:10 - 8:20ORD-JNB
35h 10m1 stop
R14 698Etihad Airways
Find Deal
Fri, Oct 31 - Mon, Nov 24
Turkish Airlines Logo
19:05 - 19:25JNB-ORD
31h 20m1 stop
Turkish Airlines Logo
11:50 - 10:50ORD-JNB
39h 00m1 stop
R14 941Turkish Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Turkish Airlines Logo
16:00 - 11:05DUR-ORD
26h 05m2 stops
Turkish Airlines Logo
11:50 - 13:30ORD-DUR
41h 40m2 stops
R16 103Turkish Airlines
Find Deal
Mon, Nov 17 - Wed, Nov 26
United Airlines Logo
20:50 - 11:50CPT-ORD
23h 00m2 stops
United Airlines Logo
11:15 - 18:00ORD-CPT
22h 45m2 stops
R16 242United Airlines
Find Deal
Wed, Dec 24 - Fri, Jan 16
United Airlines Logo
19:45 - 13:10JNB-ORD
25h 25m1 stop
United Airlines Logo
15:35 - 18:35ORD-JNB
19h 00m1 stop
R16 520United Airlines
Find Deal
Mon, Dec 22 - Mon, Jan 12
British Airways Logo
22:00 - 13:50JNB-ORD
23h 50m1 stop
British Airways Logo
20:45 - 10:25ORD-JNB
29h 40m1 stop
R17 752British Airways
Find Deal
Tue, Dec 23 - Tue, Jan 13
British Airways Logo
19:35 - 13:50JNB-ORD
26h 15m1 stop
British Airways Logo
17:30 - 10:25ORD-JNB
32h 55m2 stops
R17 856British Airways
Find Deal
Wed, Oct 15 - Wed, Oct 22
KLM Logo
23:15 - 18:25JNB-MDW
26h 10m2 stops
KLM Logo
13:08 - 21:20MDW-JNB
25h 12m2 stops
R17 995KLM
Find Deal
Thu, Nov 20 - Wed, Nov 26
KLM Logo
23:45 - 18:18CPT-MDW
26h 33m2 stops
KLM Logo
13:05 - 21:55MDW-CPT
24h 50m2 stops
R31 651KLM
Find Deal

Everything you should know

When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 13% compared to booking last minute.
Insights
Insights
Insights
Insights
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
Cheapest return fare
R14 351
Typical prices: R15 496-18793
Etihad Airways
Wed 15/10Wed 22/10
JNB - ORD • 1 stop
Cheapest one-way flight
R9 700
Typical prices: R11 054-14142
Multiple Airlines
Wed 10/12
CPT - ORD • 3 stops
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 R16 849 on average for return flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from South Africa is R20 910 and R20 788 respectively. For one-way flights, the best month to travel is February with an average price of R16 849.

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 2 weeks before departure, which saves you about 13% 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 444.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 700
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 1% 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 459. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R21 524 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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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 1386 reviews
7,8Boarding
7,7Comfort
8,4Crew
7,3Food
7,2Entertainment
Airline reviews

Ad experience - been flying many years with them but they are losing out to other carriers with their service and bagage / seating policy. My 2 12-yo kids were not placed with the parent. Absurdity.

2,0 MediocreIlja, Aug 2025AGP - AMS
Read more KLM reviews

Ad experience - been flying many years with them but they are losing out to other carriers with their service and bagage / seating policy. My 2 12-yo kids were not placed with the parent. Absurdity.

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

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.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

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.

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

POSITIVES The hostesses were mostly pleasant, NEGATIVES The full flight wifi was horrible, hardly able to use it. My charger port was not working which made me use my neighbour's port which resulted in an accident which ruined her flight. During dinner, meat ran out when the cart got to us forcing us to eat vegetarian which was not great. We watched everyone around us eating meat. My wifi did not transfer to the second leg of my trip as they promised as they changed the plane. I was thrown off the window seat I booked for the 2nd leg of my journey as they changed planes, all done at my expense. This was not a cheap flight ($2600) which i hurriedly had to book to attend my mother's funeral who passed away suddenly. I was honestly disappointed with the whole saga as I heard Ethiopian Airlines was one of Africa's best.

The food was terrible and the seating was uncomfortable, but the airline did a great thing letting us board in Abbis Ababa on our connecting flight after our original flight was very delayed.

Food hardly ever changes Videos not often updated for often travel.

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

what would have been better would have been that my booking not been canceled by the system and had I been informed that the booking had been cancelled by the system I could have immediately rebooked and not found out that there was an issue when I was told by the system that I needed to book in. It would have also been good if either the booking agent or BA or anyone been in anyway useful. In the end I had to rebook a flight at an additional cost of $350. So no I'm not impressed by BA any of the other parties involved.

Boarding was poor. Why are first class passengers not boarded first?! Bus to the plane and then held on a packed bus because we were waiting for people on the bus before to finish boarding. Seat belt on the fist clas seat is very uncomfortable, cutting into your neck. Other than that crew, seating and food were all excellent. Entertainment, as usual - rubbish.

I paid for full WIFI- it was terrible, kept being in and out could not listen to a podcast

Flight was delayed but my previous flight was as well so It worked to my advantage. This was my first time in first class. I don't think they ever stopped feeding us. The seating area was very spacious and comfortable. The attendants were wonderful, warm, friendly and very personable.

Some how my flight was canceled, neither BA or Justfly.com accepted responsibility. I only found out about this the day before when I tried to check in. I had to book another flight which due to the time ( day before) cost me $300 more. I was still receiving notifications about the flight even when I was on another flight from you. So no my flight to London was not good.

We had a pretty good experience. Enjoyed both the flights. Crew was very good and helpful.

They issued seat assignments and sat my 2 year-old in the row behind me, separate from me and my daughter. Communication/ customer service was terrible. They told me to change it in London, then in London, they told me to talk to the cabin crew, then a supervisor came and stuck us in the back of the plane when we were supposed to be in row 25. Overall, they need to really work on their customer service. Additionally the food was terrible and they ran out of meals and didn’t have any kid options. To top it off there was no in-flight entertainment for the first hour of the trip.

We missed the connection because we had to wait for a shuttle from the plane to the Terminal. Also, we needed assistance and none was available.

When we arrived at the airport - 1st step - printing out your boarding pass - no issue. Not long lines as these machines. 2nd step - processing your bag drop off. There was only one associate there to help 10 kiosks. We had a family in front of us for 20 minutes trying to work on the machine and figure out every step for 4 pieces of luggage. My husband alerted the associate who was able to assist the family. Highly suggest that there are more associates to assist in this process. Besides this issue, security check went very quickly. Our flight was direct to Philadelphia. We had to carry our bags down two flights of steps, then out to the tarmac to a bus, then carry our bags up two flights of stairs to the plane. No one on the flight was expecting that long trek. I could see some people were struggling a bit. All in all - great flight crew, plane was clean and food was great!

There were no gluten-free vegan options available, so food was very limited on this flight, and some of the crew weren’t especially helpful about it. To make matters worse, a passenger was sick on board, and although the area was cleaned, the smell lingered for the rest of the journey. On top of that, we ended up circling for an extra hour, which only made the unpleasant situation drag on even longer.

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