R9 557 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 16/11. 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

Sat, Nov 8 - Tue, Nov 25
Turkish Airlines Logo
19:10 - 10:05JNB-ORD
22h 55m1 stop
Turkish Airlines Logo
11:50 - 10:50ORD-JNB
39h 00m1 stop
R15 263Turkish Airlines
Find Deal
Fri, Nov 7 - Wed, Nov 26
Ethiopian Air Logo
8:20 - 7:40JNB-ORD
31h 20m2 stops
Ethiopian Air Logo
9:45 - 20:10ORD-JNB
26h 25m1 stop
R15 315Ethiopian Air
Find Deal
Thu, Nov 13 - Thu, Dec 4
Turkish Airlines Logo
19:10 - 10:05JNB-ORD
22h 55m1 stop
Turkish Airlines Logo
11:50 - 10:50ORD-JNB
39h 00m1 stop
R15 419Turkish Airlines
Find Deal
Wed, Nov 5 - Thu, Feb 5
United Airlines Logo
20:50 - 19:40CPT-ORD
30h 50m2 stops
United Airlines Logo
11:00 - 16:10ORD-CPT
21h 10m2 stops
R16 078United Airlines
Find Deal
Sun, Jan 18 - Sun, Jan 25
United Airlines Logo
20:50 - 9:43CPT-ORD
20h 53m1 stop
United Airlines Logo
14:27 - 18:00ORD-CPT
19h 33m1 stop
R16 113United Airlines
Find Deal
Sun, Apr 5 - Mon, Apr 13
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
14:00 - 8:20ORD-JNB
35h 20m1 stop
R16 599Etihad Airways
Find Deal
Mon, Nov 3 - Fri, Nov 7
British Airways Logo
19:35 - 19:23JNB-ORD
31h 48m2 stops
British Airways Logo
18:30 - 7:35ORD-JNB
29h 05m1 stop
R17 639British Airways
Find Deal
Sat, Nov 8 - Tue, Nov 25
KLM Logo
23:59 - 18:13JNB-ORD
26h 14m2 stops
KLM Logo
11:19 - 22:05ORD-JNB
26h 46m2 stops
R17 934KLM
Find Deal
Mon, Nov 3 - Fri, Nov 7
British Airways Logo
22:00 - 17:45JNB-ORD
27h 45m2 stops
British Airways Logo
17:25 - 7:35ORD-JNB
30h 10m2 stops
R17 986British Airways
Find Deal
Mon, Dec 1 - Mon, Dec 8
KLM Logo
23:59 - 20:35JNB-ORD
28h 36m2 stops
KLM Logo
13:23 - 22:05ORD-JNB
24h 42m2 stops
R18 350KLM
Find Deal

Everything you should know

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
R15 263
Typical prices: R15 870-R22 097
Turkish Airlines
Sat 8/11Tue 25/11
JNB - ORD • 1 stop
Cheapest one-way flight
R9 557
Turkish Airlines
Sun 16/11
DUR - ORD • 2 stops
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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 789 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 R21 507 and R20 675 respectively. For return trips, the best month to travel is February with an average price of R16 789.

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 83 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 Midway Airport, with an average flight price of R2 879.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 557
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Durban to Chicago

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 tickets can be as cheap as R19 450. On the other hand, the most expensive day to fly is Saturday, where prices are R21 514 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 flights cost R17 888 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 R18 463.

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, +74 more

ANA, Aer Lingus, +75 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Friday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 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, +74 more

ANA, Aer Lingus, +75 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Friday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 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.
7,7
KLMOverall score based on 1402 reviews
7,1Entertainment
7,3Food
7,8Boarding
7,6Comfort
8,4Crew
Airline reviews

Flight was ok but lack of communication cost me to literally beg to be put on another flight as connecting flight had departed

2,0 MediocreAbisola, Oct 2025CDG - AMS
Read more KLM reviews

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

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

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.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

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.

The best airline for international travel in terms of value you get in business class (service/cost)

I liked the overall flight experience. However, Turkish officials could do a better job at guiding non-Turkish speakers to their connecting flight gates in such a huge & vast airport.

Very small and cramped aisles and seats. Food was poor but the fresh hot roll and hummus was good. No cans of soda given but they had small bottles of water. Crew was nice and pleasant and kept bathroom clean.

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.

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

One of the worst experience given the middle seat even asked for the change no one honored,boarded at the end and overall one of the worst experience

It was good although our flight to the UK was cancelled and rescheduled for two days later. This was after we were already seated on the plane. We missed the first leg of our trip. BA did put us up at a hotel and paid for our meals but we lost our hotel costs in Glasgow.

The crew was very nice and pleasant. We were very reluctant to book our flight with British Airlines because we had bad experience with their flight attendants on the previous trips, they were rude and not helpful.

I am a 25+ years American Airlines member. British Airways is simply above and beyond in every customer satisfaction category.

The seat pads are past there sell by date now and are uncomfotable. Also, with screens in the back of the seat, the seats shouldnt be able to recline as this puts rhe screen in your face.

1. The website didn’t allow me to checkin from London as I have Bangladesh passport with US permanent resident card. This pushed me to sit with my wife in the middle of two aisle seats, terrible experience! 2. BA should allow within 24 hours to checkin with other passport holders to choose better seats. A 2nd verification of travel documents can be done at the desk about immigration status. 3. Food options were poor for vegetarian passengers, try to introduce healthy options avoiding carb-dense food ingredients.

Cabin crew lovely and accommodating and I'll always fly BA in the future

It was perfect. The service was exceptional. I would never want to cross the Atlantic in anyone else's sardine tins.

As I have said it sucked, the ticket counter to have to find and pay for another airline to get home. Now I understand this happened over the weekend but they should have someone there to talk to us instead of throwing the regular crew under the bus.

Everything excellent except for bag drop off. We started at the D area and that was so slow that it was eventually closed just as we were about to go to a station. We then went to F. We got one suitcase checked and then the screen showed that the station was no longer operable. There were long lines everywhere so we had to ask if we could butt in to the next station to finish. Again, this was the only incident, otherwise it was an excellent flying experience

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