R10 763 Find Cheap Flights to Chicago – Compare and Save

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 1/12. 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, 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
R15 617
Typical prices: R17 273-R14 383
Turkish Airlines
Tue 27/10Wed 25/11
JNB - ORD • 1 stop
Cheapest one-way flight
R10 763
Typical prices: R11 932-R12 110
Turkish Airlines
Tue 1/12
CPT - ORD • 1 stop
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 11% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 52% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
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

Tue, Oct 27 - Wed, Nov 25
Turkish Airlines Logo
18:50 - 19:20
JNB
-
ORD
31h 30m
1 stop
Turkish Airlines Logo
20:15 - 11:00
ORD
-
JNB
30h 45m
1 stop
R15 617Turkish Airlines
Tue, Dec 1 - Tue, Jan 19
Delta Logo
20:50 - 16:50
CPT
-
MDW
28h 00m
2 stops
Delta Logo
17:59 - 18:35
MDW
-
CPT
40h 36m
2 stops
R16 136Delta
Tue, Jul 28 - Sat, Aug 15
KLM Logo
23:15 - 14:30
CPT
-
ORD
22h 15m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 363KLM
Tue, Jul 21 - Tue, Aug 25
United Airlines Logo
22:00 - 22:06
JNB
-
ORD
31h 06m
1 stop
United Airlines Logo
14:31 - 18:30
ORD
-
JNB
20h 59m
1 stop
R16 445United Airlines
Mon, Jul 6 - Mon, Aug 10
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
14:00 - 8:20
ORD
-
JNB
35h 20m
1 stop
R16 510Etihad Airways
Tue, Jul 14 - Sat, Aug 1
United Airlines Logo
20:00 - 11:48
CPT
-
ORD
22h 48m
1 stop
United Airlines Logo
11:03 - 15:20
ORD
-
CPT
21h 17m
1 stop
R16 526United Airlines
Mon, Sep 7 - Wed, Mar 3
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R16 623Etihad Airways
Fri, Jul 10 - Sat, Jul 25
KLM Logo
23:15 - 20:31
CPT
-
ORD
28h 16m
2 stops
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 932KLM
Tue, Jul 21 - Tue, Aug 18
British Airways Logo
11:15 - 12:30
DUR
-
ORD
32h 15m
2 stops
British Airways Logo
22:30 - 10:40
ORD
-
DUR
29h 10m
2 stops
R18 685British Airways
Sun, Nov 22 - Thu, Nov 26
British Airways Logo
11:15 - 18:45
DUR
-
ORD
39h 30m
2 stops
British Airways Logo
21:45 - 10:40
ORD
-
DUR
52h 55m
2 stops
R20 909British Airways
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 round-trip 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 March, where tickets cost R5 601 on average for return flights. On the other hand, the most expensive months are December and January, where the average cost of tickets from South Africa is R14 302 and R14 172 respectively. For one-way flights, the best month to travel is February with an average price of R4 042.

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 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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 260.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR10 763
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 9% 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.

  • 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.
7,8
KLMOverall score based on 1530 reviews
7,2Entertainment
7,3Food
7,7Comfort
8,4Crew
7,8Boarding
Airline reviews

The flight was 45 mins late leaving, we sat without a/c for some of this, 2nd Meal was a slice of pizza. Movies were good.

8,0 ExcellentAnonymous, Jun 2026
LHR - AMS
Read more KLM reviews

The flight was 45 mins late leaving, we sat without a/c for some of this, 2nd Meal was a slice of pizza. Movies were good.

Brand new plane lots of room the snack was very flavourful and enjoyable

As per usual when you Hit the UK it's a slow process through customs Not as efficient at Thailand for sure

There were no charge points for phones on the economy seats. The seats were comfortable overall. Food was okay.. flight was on time

It was really nice journey i personally recommend klm flight

Crew is not the cheerful type. very slow meal service (this is their style as have flown this many times)

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.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

i have book the flight with baggage. and i have paid $800.00 for the baggage. when i contacted to JUSTFLY Costumer Service they told me that my baggage was included in the booking. then why i have to pay. i am going to file a complain against it. $800.00 is not at all small amount

I payed for extra leg room but in last moment my seating place was changed and i got standard one seat. Staff was not able to do anything , so was very disappointed because of this.

It was very relaxing and staff were very quick to attend to any requests.

Limit the number of usage of wine or please arrange our seats. The passenger was drunk on this flight and not on Thiruvananthapuram to Abudhabi.

The seats seemed smaller than other business class offerings. The entertainment menu was limited. Flight crew was good.

It was excellent service in the snow storm gives us hotel and transportation. It will be more better if u can add one more meal because it’s a long flight boring journey. If you give extra meal time passes faster and can enjoy the trip better

Food quality and varites were very minimum. Surprised to have no desserts. Business class tickets should have lounge access and seats selection. They should be allowed to board while people with wheel chair, secial assistance and family with childrem.

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 following is a review for a flight from Johannesburg to Washington, DC with a connection at Addis Ababa, Ethiopia and refueling landing at Rome, Italy. The flight was provided by Ethiopian Airlines. There were two of us: me and my wife on this flight. Everything was on time. Enough legroom between the seats, I was able to stretch my legs and sleep for at least some time during the 14 hour second flight (19 hours in total for both flights). Very decent meals that included two lunches and one breakfast on the flight from Addis Ababa to Washington and one lunch on the flight from Johannesburg to Addis Ababa. The lunch choices were beef, chicken and fish, I think the vegetarian option was available as well, accompanied with beans. The breakfast was a choice between egg and pancake, accompanied with a fruit salad. The egg breakfast was awesome, it came with a scrambled egg and a sausage. However, my wife mentioned unusual taste of the pancake breakfast meal, by all means those were not pancakes. What wasn't good: Externally initiated commercials on the infosystem screens, you couldn't turn the screen off. These commercials were accompanied by loud and annoying music, transmitted through the entire cabin. Obviously, there was no escape from this music as well. Additional moment: on the flight from Addis Ababa to Washington, DC, we landed at Rome for refueling. This was totally fine and it was in the flight itinerary. But, the flight attendant asked me to straighten the seat while we were at the steady position during the refueling. I can't rationalize this order except that some people just like to be a boss of some kind. Keeping the light lit in the economy cabin while keeping it dimmed in the first class also didn't improve my and my wife's feelings. Overall, the services were very good and the flight, despite its longevity, went on very smoothly.

To the Ethiopian Airlines Customer Relations Team, I am writing to formally express my disappointment regarding my recent travel experience with Ethiopian Airlines on flight [I629/352] . Unfortunately, the level of service provided fell significantly short of the standards I expected from your airline. I would like to highlight the following serious issues encountered during the journey: • Cabin Condition and Hygiene: The aircraft cabin was notably poorly maintained. The seating area was dirty, and there was a persistent, unpleasant odor throughout the flight, which made the environment very uncomfortable for passengers. • Inadequate Service: The overall level of service provided by the staff was unsatisfactory and did not reflect a professional passenger experience. • Baggage Loss: Upon arrival, I was informed that my luggage was lost. This is particularly distressing as it has caused significant personal inconvenience and disruption to my schedule. As a frequent traveler, I value reliability and a clean cabin environment. I request that you investigate these matters immediately, provide an update on the status of my missing baggage, and outline how you intend to compensate for these failures in service. I look forward to your prompt response and a resolution to my lost luggage claim. Sincerely, Puguh

The crew were amazing. They should improve the inflight entertainment

Delay not posted, only departure time listed- not boarding time. We left an hour late and arrived 45 min late. Restrooms had backed up sinks and toilets not flushed ) passenger error). Lots of screen for entertainment didn’t work. But we arrived with our luggage

Check in took over an hour because printer was not working. Attendant did not know how to give free layover Addis Ababa hotel vouchers or update frequent flyer number. After repeated attempts, got voucher emailed. However hotel wanted printed voucher hence more delay. Bus time from hotel back to airport was printed 4:50 hours, but hotel reception called at 3 pm saying bus will leave at 4 pm. Then hotel reception called again saying 4:15 pm. We rushed at 4:15 pm and bus was not ready until 4:40 pm. Many audio outlets were not working in planes.

I had a memorable experience. I dont have any comments at this time regarding waht could be better.

Need to do a lot of improvement on service and cleaness

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.

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

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

Thanks to a delay of an hour of my flight to Philadelphia on American Airlines I missed my connecting flight to Amsterdam. On arrival at Philadelphia he crew on the delayed flight did not ask the passengers to let connecting passengers get off first and I arrived a few minutes after boarding was closed at the original time for the flight to AMS, this despite the fact that I had received a message from American Airlines that departure was delayed by 25 minutes. Overall very poor service, no effort from the part of American Airlines to accommodate the passenger, just rebook the flight for the next day.

Seats not as comfortable as I had hoped. Food was very nice, service was fine. Entertainment options very nice. Had thought the premium economy was a more plus 2-3-2 layout but it was a 2-4-2 with seats not as wide as I had expected.

I liked my seats on the return trip. Didn't like having to pay for luggage on an international flight. Also didn't like that it was on American airlines and not British Airways. I specifically selected a BA flight to experience that airline.

I flew four flights on British Airways within two weeks. I was unable to download the boarding pass to my phone for any of the four flights. I could check-in for my flight but the system would not give me boarding pass. I tried multiple ways and multiple times. I discovered many other passengers also had the same issue with their boarding passes. No explanation or acknowledgement by BA.

Lovely big plane. Excellent take off and landing. Cabin crew were so nice. Flight in time no delays

Because our ABZ-LHR flight was cancelled by BA for reasons they refuse to tell us--not weather--we did not make this flight and were booked on the following day. BA offered no assistance to us on the phone or in the airport, and we had to find a hotel at Heathrow on our own.

Horrible - flight was delayed by 6 hours - we boarded, were made to de-board due some technical fault; aircraft changed; special meals request on new flight - all went awry. Landed in Dulles airport; breezed thru immigration; as Business Class passengers or baggage was delivered almost 90 minutes after landing; air tags indicated the bags were just near the carousel but the unhelpful BA staff - Maria and Ghina refused to give any update - palming it off on some imaginary invisible “manager” despite air tags evidence showing it right there. So about 50-60 passengers waiting and getting infuriatingly impatient for their bags coz one container was not delivered. Finally after much argument by some other passengers Maria condescended to go to the “ramp” and within 5 minutes the baggage was delivered miraculously. Question is why couldn’t she have done it one hour earlier ? Poor poor experience once again on Business Class BA.

Cheap Flight Fares would not provide booking info. I canceled the reservation and we arbitrated with American Express. They provided erroneous info to Amex and it was determined that C.F.F. deserved the price of the ticket. Worse experience I've ever had.

Seating space is appalling. Seats and all surrounding area in "Economy" is built for individuals shorter than 4' 10" and below 120 lbs. Ridiculous. While I'm not expecting fine dining, the food was the worst airplane food that I can recall.

My luggage was lost at the airport but American Airlines contacted me and got it to me the next day.

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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.