R8 525 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 9/3. 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
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Everything you should know

Cheapest return fare
R13 333
Typical prices: R16 249-R23 156
Ethiopian Air
Wed 25/3Wed 1/4
JNB - ORD • 2 stops
Cheapest one-way flight
R8 525
Turkish Airlines
Mon 9/3
DUR - ORD • 2 stops
When to travel
February
Cheapest • 13% 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 hundreds 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 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, Mar 25 - Wed, Apr 1
Ethiopian Air Logo
14:30 - 8:40
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 - 20:10
ORD
-
JNB
26h 55m
1 stop
R13 333Ethiopian Air
Thu, Mar 19 - Wed, Apr 1
Turkish Airlines Logo
19:10 - 19:25
JNB
-
ORD
31h 15m
1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m
1 stop
R13 813Turkish Airlines
Thu, Mar 19 - Wed, Apr 1
Turkish Airlines Logo
19:10 - 11:05
JNB
-
ORD
22h 55m
1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m
1 stop
R13 909Turkish Airlines
Thu, Mar 5 - Thu, Mar 12
United Airlines Logo
20:50 - 11:51
CPT
-
ORD
23h 01m
2 stops
United Airlines Logo
16:30 - 12:40
ORD
-
CPT
37h 10m
2 stops
R16 105United Airlines
Thu, Feb 19 - Mon, Feb 23
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
33h 30m
2 stops
R17 275British Airways
Thu, Feb 19 - Mon, Feb 23
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
33h 30m
2 stops
R17 467British Airways
Thu, Mar 19 - Wed, Apr 1
KLM Logo
23:59 - 18:40
JNB
-
MDW
25h 41m
2 stops
KLM Logo
13:10 - 21:20
MDW
-
JNB
25h 10m
2 stops
R22 931KLM
Thu, Feb 19 - Mon, Feb 23
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m
1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m
1 stop
R23 685Emirates
Thu, Feb 19 - Mon, Feb 23
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m
1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m
1 stop
R23 957Emirates
Sat, Feb 21 - Mon, Mar 9
KLM Logo
23:59 - 18:40
JNB
-
MDW
26h 41m
2 stops
KLM Logo
13:10 - 22:05
MDW
-
JNB
25h 55m
2 stops
R27 130KLM
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 R15 015 on average for one-way flights. On the other hand, the most expensive months are January and July, where the average cost of tickets from South Africa is R20 416 and R19 422 respectively. For return trips, the best month to travel is February with an average price of R15 015.

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 Midway Airport, with an average flight price of R2 459.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR8 525
Best time to beat the crowds (2% less expensive on average)
Most popular time to fly (7% more expensive 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.

  • 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.

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 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 1450 reviews
7,1Entertainment
7,6Comfort
7,8Boarding
8,4Crew
7,3Food
Airline reviews

Delay on my previous leg, had to run to catch my flight. But that happens. Overall ok.

8,0 ExcellentKevin, Nov 2025
AMS - BOD
Read more KLM reviews

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

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

Good flight. There were a few issues with the flat bed. It was some technical issues. Otherwise everything was good

The crew could have been more friendly and could have offered to make the beds. Also, Ethiad should have more vegetarian food options.

From the start of my vacation at Logan Airport, Boston it was chaotic. I'm praying my flight home is better .I'm grateful that we landed safe

The flight was over 1 hour late taking off ,when I arrived in Abu Dhabi ,I missed my connecting flight to Bangkok so I had to wait almost 6 hours for my flight arriving in Bangkok at 6:30 am ,So I missed a whole day of my vacation and my hotel room sat empty so I paid for hotel days that I was not there. In Abu Dhabi there was a woman that worked the desk at transfers that was so professional, courteous , helpful,and may I say absolutely beautiful .she got me food vouchers for my layover and was a very calming presence. Besides that I will never use Etihad again I will pay the Xtra money . I'm sure they won't read or see this but it's my "2 cents" I'll use an airline that respects me and my hard earned dollars

On this flight...fine. The one from India to Abu Dahbi, awful.

Kayak and Aran grant issuing business class tickets without lounge access and sometimes 1 or 2 connections in economy class. It’s very disappointing to find out that after buying the ticket. Never buy tickets on kayak and Aran grant again

Very disappointing #1 - You have to pay extra to use the business lounge, or else you sit in the cold airport for 7 hours and fall sick #2 - Did an awful job with boarding, they turned on the "last call" notice on the monitor made the passengers come running to the gate, once the passengers came close the crew would tell them - hey we are not boarding yet, this included passengers with children also, this was happening all the time, it was pitiful to see #3 - Did not have the courtesy for the passengers in the business class, there is a reasons why people choose business class, because they need to get to work, that means sleep is very important for them, in the business class, the crew members would themselves cause so much noise by closing the door in a loud way, once the crew member does it then the other passengers are also doing it, #4 - the food did not smell good, #5 - The Abu Dhabi airport is small, so not a whole lot to do, especially when the layover is 7+ hours. #6 - Did not provide the slippers with pajamas, #7 - also the pajamas also I had to ask, only after asking it was provided. #8- Asked for an extra pillow because the pillow they provided was not tall enough, the crew member said there was no additional pillow and gave me something like a blanket, I tried my best to use that as a pillow, but my head kept on sliding and that messed up my sleep and did not get deep thorough sleep Overall the airlines did not have an understanding of how to care for the passengers, especially the business class ones. Overall it was a bad experience, I would much rather spend the money with Qatar airways, the experience with Qatar is so much better.

Seat space was tight and uncomfortable. There was hardly any cushioning giving me a terrible tail bone ache. Getting and out was extremely cramped. We paid for seat choices and felt totally ripped off. Food was mediocre. By the time the servers served 2 or 3 rows they ran out of this or that option as we saw on the inbound trip also. This is infuriating. Entertainment choices were extremely limited for such a long haul. The screen froze on occasion and did not switch off when the on off button was pressed. When it did it came back on its own in 5 seconds. The airlines has gone downhill since last year.

The flight from Abu Dabhi to Bangalore was terrible. The plane was an order model with no onboard entertainment. The beverage selection were very limited.

excellent, the staff was kind and the boarding process was with no issues or hassle

Very hot cabin made long flight uncomfortable, even in business class! Food was great. Istanbul business lounge had great food but too few bathrooms and seating . They also need more electric outlets for charging devices. Appreciate the ability to go through fast track lines w business class

The crew on this flight provided exceptional business class service to me.

The staff at the boarding or the rudest uninformative and no English whatsoever they’re very rude as if they are envious of you travelling I don’t understand how could someone would be this rude and this out of touch and cold

You charged me for luggage although the airline does not- you charged me for seat when customers can pick their own seat at checkout in I travel to Europe slot and I will not use kayak again

They oversold the tickets by one which was my ticket so I didn’t have a ticket till last second

Not good. I was supposed to be in Mint but got in economy class

Requested food options were always finished. Supplied food items were good but of course not the desired choices.

The airport staff never announced that boarding has started. Both at iad or Islamabad or Istanbul.

Very bad experience with turkish airline tk 0001. Very uncomfortable seats and food ran out and crew was not helpful

The airline could improve its business class seats and privacy in line with its competitors.

Our Jackson, Mississippi to Dallas Fort Worth flight was delayed on 1/19/26.. This was changed to Jackson to Charlotte in the last minute because of this delay. This started some kind of disconnect between American Airlines and British Airways bookings. We could not go past the passport control in London Heathrow. I had to go to the counter and waited for more than 30 minutes to get a new boarding pass. Problems did not end there. Somehow our entire return flight was canceled by someone. I had to make several phone calls over several days to fix the problem – this was not easy from India. Looks like there was some kind of disconnect between two airlines or some agent did not do it right. I’m anxious to know what went wrong.

My touch screen at my seat wasn't working, the films BA advertised on the website for this flight were not available, and the plane was a little dated, food was good and the staff were good, just let down by the aircraft facilities.

Did not like the seating configuration at all with 2+3+2 in business class. Lacking total privacy and comfort

The flight crew was kind, flexible, and accommodating. The seats on the plane were extremely uncomfortable.

Check-in experience, for business call please provide a premium experience

Lost my luggage, ran out of food choices in business class, ground crew was completely unapologetic.

Excellent. The crew and flight were great. Checking in was easy and everyone was very helpful.

Entertainment devices on A380 need to be fixed, the seats might do with updates.

Everything. Employees offered to help me because I had to use a cane.

Check-in and boarding were great. On flight staff were rude and disrespectful. Paid for extra room and found it incredibly cramped. Bathrooms kept in poor condition. Overall negative experience.

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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.