R10 688 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 14/10. 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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Flights 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

Mon, Jul 21 - Mon, Aug 4
Ethiopian Air Logo
14:35 - 8:15CPT-ORD
24h 40m2 stops
Ethiopian Air Logo
10:15 - 14:35ORD-CPT
21h 20m1 stop
R14 482Ethiopian Air
Find Deal
Thu, Nov 13 - Thu, Dec 4
Turkish Airlines Logo
19:10 - 18:25JNB-ORD
31h 15m1 stop
Turkish Airlines Logo
20:20 - 10:50ORD-JNB
30h 30m1 stop
R15 782Turkish Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
Etihad Airways Logo
9:50 - 8:15JNB-ORD
30h 25m1 stop
Etihad Airways Logo
13:10 - 8:20ORD-JNB
35h 10m1 stop
R15 818Etihad Airways
Find Deal
Mon, Sep 15 - Fri, Sep 26
British Airways Logo
21:15 - 13:50JNB-ORD
23h 35m1 stop
British Airways Logo
20:25 - 7:00ORD-JNB
51h 35m2 stops
R17 510British Airways
Find Deal
Mon, Sep 15 - Fri, Sep 26
British Airways Logo
19:25 - 13:50JNB-ORD
25h 25m1 stop
British Airways Logo
20:25 - 7:00ORD-JNB
51h 35m2 stops
R17 528British Airways
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Mon, Aug 11 - Mon, Aug 18
United Airlines Logo
19:50 - 8:39CPT-ORD
19h 49m1 stop
United Airlines Logo
10:50 - 15:20ORD-CPT
21h 30m1 stop
R19 273United Airlines
Find Deal
Mon, Aug 11 - Mon, Aug 18
United Airlines Logo
19:50 - 9:39CPT-ORD
20h 49m1 stop
United Airlines Logo
14:24 - 15:20ORD-CPT
17h 56m1 stop
R19 398United Airlines
Find Deal
Mon, Sep 15 - Fri, Sep 26
KLM Logo
23:15 - 18:35JNB-MDW
26h 20m2 stops
KLM Logo
13:08 - 21:20MDW-JNB
25h 12m2 stops
R22 141KLM
Find Deal
Mon, Sep 15 - Fri, Sep 26
KLM Logo
23:15 - 18:35JNB-MDW
26h 20m2 stops
KLM Logo
13:08 - 21:20MDW-JNB
25h 12m2 stops
R22 159KLM
Find Deal
Thu, Jul 17 - Sat, Jul 26
Qatar Airways Logo
12:05 - 5:40DUR-ORD
48h 35m3 stops
Qatar Airways Logo
14:37 - 10:35ORD-DUR
36h 58m3 stops
R33 185Qatar Airways
Find Deal
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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 350 on average for return flights. On the other hand, the most expensive months are December and August, where the average cost of tickets from South Africa is R21 714 and R21 696 respectively. For one-way flights, the best month to travel is February with an average price of R17 350.

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. For the absolute cheapest price, our data suggests you should book 17 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 R2 278.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonFebruary
High seasonJune
Cheapest flightR10 688
Best time to beat the crowds (6% 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 975. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R22 095 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, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, +78 more

ANA, Aer Lingus, +79 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, +77 more

ANA, Aer Lingus, +78 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 1365 reviews
7,8Boarding
8,4Crew
7,2Food
7,1Entertainment
7,7Comfort
Airline reviews

Klm start boarding while somw air issue in the plan

8,0 ExcellentA, Jun 2025AMS - YYZ
Read more KLM reviews

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.

You should not have to pay for WiFi in business class

Transfer at Amsterdam airport is very convenient and the airport is easy to navigate. Boarding was also quick and easy. Cabin crew were excellent and the meals were good, although lacking in options.

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

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

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

The check in process at Istanbul airport caused my family a great deal of stress and disappointment due to the following factors: 1) WE HAD TO PAY US$330 for check on bags, despite holding Economy tickets that Turkish airlines website clearly states that flights from Istanbul to Miami had a 2 checked bags allowance. 2) Airport staff not only lacked empathy for senior travelers (75 yrs old and 71 yrs old), but were also rude as well. The supervisor at check it offered "if you don't pay for the bags, you can just remain and sleep at the airport for however long you wish. What a terrible way to treat customers !!! 3) We were bumped from agent to agent to agent FIVE times, showing everyone the communication we received telling us we had the 2 bags entitlement. Two elderly people lugging 4 suitcase around and around the Turkish terminal. Again, what a sad way to treat customers !!! 4) We need a case opened to get a refund for the amount we paid. Something is amiss, screams unethical, and sounds unscrupulous......At First , we were told we must pay for 4 bags. All of a sudden, it became 2 bags, and finally all 4 bags were checked on with payments demanded for 2. Why did it vary from agent to agent???? 5) OVERALL, A TERRIBLE AND SUSPICIOUSLLY UNSCRUPULOUS EXPERIENCE FLYING WITH TURKISH AIRLINES. WE ARE TERRIBLY DISAPPOINTED AND SAD THAT OUR VISIT TO A BEAUTIFUL CITY ENDED IN SUCH A HORRIBLE EXPERIENCE

I recently flew with Turkish Airlines, and I can confidently say it was one of the best travel experiences I’ve ever had. From the moment I boarded, the crew was incredibly attentive, warm, and professional. They went above and beyond to ensure everyone was comfortable and well taken care of throughout the flight. The highlight, however, was the food! I’ve flown with many airlines, but Turkish Airlines sets the bar incredibly high when it comes to in-flight dining. Every meal was fresh, flavorful, and beautifully presented. The variety of dishes, even on a long-haul flight, was impressive. It felt like dining at a high-end restaurant at 35,000 feet! The seats were comfortable, the entertainment options were great, and the overall atmosphere made the journey enjoyable. Turkish Airlines truly excels in combining luxury and hospitality. I wouldn’t hesitate to fly with them again—highly recommend!

One of the best flights I have been on in a while.

Here's a sample answer: "Honestly, I was really impressed with Turkish Airlines, but if I had to suggest one area for improvement, it would be: - *More efficient boarding process*: I noticed that boarding took a bit longer than expected, which might be frustrating for passengers with tight connections.

Not worth pay business class and get service economy class

In this long haul flight, flight attendants never stopped moving and giving excellent service. Very impressive. Very comfortable seats and excellent food

In sharp contrast to the modern glitzy airport, boarding facilities were primitive. Passengers had to board buses and walk up steep stairs in bitter cold with carry-on baggages. I found no reason why aerobridge was not provided.

Service and food were decent, seats are a bit too narrow. Leg room is normal. Bathroom should be cleaned more frequently. WiFi is cumbersome and should be simplified.

they have cancell the flight with no reasons, My parents were in the cold weather in the airport for 24 hours they did not give any hotel and food. I hate Turkish Airline, this is our last time that we ha ve chosen Turkish Airline.

Same as before boarding process and lack of crew experience in the process

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.

Very bad experience flight was over 5 hours delayed 😑 not a chance to be put on another flight we had to stay at the hotel we lost 2 days on our vacation. Never again I will fligh with Ethiopian airlines.

The ailine departed and arrived late foe every leg of the trip, causing myself and my travel companions to miss every connecting flight. It was very unorganized given theat there was a lot of miscommunication. The flights offered are unrealistic and when you call they assure you that the plane waits for you. I missed an. entire day of my vacation and any entire day of rest back home because of the airline. I do not plan to support the airline again. Thank you

Food was really not appealing. There was a blocked sink in the toilet. Toilet is cramped and the wall between the 2 toilets are not secured properly.

The use of a domestic carrier without entertainment was disappointing and a let down

Flight from LGW to JFK delayed by 4 hrs No explanation given until the pilot said the delay due to planned maintenance on the aircraft

We arrived late to London, and consequently were 5 min. late to be allowed through security for our next flight. Even though dozens of people missed the same flight, BA did not radio ahead to hold open security for an extra 5-10 min. to allow people to get on the flight. This caused an additional 6 hour delay in London after waiting over an hour in Customer Service to get rebooked. They did not have enough staff on hand to help people in a timely manner. Not at all happy with the BA's customer care or customer service.

All service prior to the flight was terrible: online check-in not working, no customer service tel,, multiple airport scanners not working, A huge mess.

CONSTANT ERROR MESSAGE THAT THE WIFI COULD NOT BE PURCHASED DUE TO INABILITY TO CONNECT PAYMENT SYSTEM VIA SATELLITE. THIS HAPPENED IN BOTH DIRECTIONS. THE MAIN REASON I TRAVEL IN PRIORITY IS TO BE ABLE TO WORK FOR WHICH I NEED ACCESS TO INTERNET. .

They lost my luggage. Lady who was helping with it in Austin was rude. Not very helpful!

Waited 3.25 hours in plane only to have the flight cancelled.

bad, made it to connecting flight and they didnt let me board

More space, of course. a footrest! more room to walk. Movie selection was awful. Some good documentaries would help if the movies can't be better. The flight itself was great, crew was great.

Our flight was cancelled on Sunday morning. We were supposed to take a short flight to Dallas from Austin, then a nonstop to Barcelona. We were rerouted from Austin to Miami on American Airlines due to storms we sat at the gate for 2 1/2 hours, pilot announced we needed fuel. In air pilot said we were rerouted to Fort Myers 30 minutes from Zmiami. Sat on tarmac waiting for a gate. Deplaned at 10:09. Pilot gave conflicting info about what to do. Missed Miami flight to Barcelona. Pilot announced crew was timed out and we would have to wait for a new crew. Waited a couple of hours. Got to Miami at 2:30 am. Gate agents at Fort Myers told us to go to D30 for hotel vouchers. No one was there. So we slept a little on the floor. Husband is 80 and I am 74. Rerouted to JFK at 9:54 am on Monday, then flight to Barcelona at 5 pm. We arrived in Barcelona a day late and missed the first night of our Oceania Marina cruise. We feel that we are due a lot of compensation for this trip from hell.

Better synchronizing the boarding processes. The audio announcements, the personnel and the digital signage were not saying the same thing. All confusion.

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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.

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