R10 377 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 16/6. 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.
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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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Cheap Flight Deals 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.

Recent return flight deals to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Turkish Airlines Logo
17:50 - 9:40JNB-ORD
22h 50m1 stop
Turkish Airlines Logo
19:50 - 10:35ORD-JNB
31h 45m1 stop
R17 649Turkish Airlines
Find Deal
Tue, Jul 15 - Sun, Aug 10
SWISS Logo
19:35 - 15:55JNB-ORD
27h 20m1 stop
SWISS Logo
19:05 - 9:20ORD-JNB
31h 15m1 stop
R18 226SWISS
Find Deal
Sat, Jun 7 - Sat, Jun 14
KLM Logo
23:15 - 14:10CPT-ORD
21h 55m1 stop
KLM Logo
11:22 - 21:25ORD-CPT
27h 03m2 stops
R18 821KLM
Find Deal
Sat, Jun 7 - Sat, Jun 14
KLM Logo
23:15 - 17:46JNB-ORD
25h 31m2 stops
KLM Logo
11:22 - 21:20ORD-JNB
26h 58m2 stops
R18 895KLM
Find Deal
Sat, Jun 7 - Sat, Jun 14
United Airlines Logo
20:00 - 16:44CPT-ORD
27h 44m1 stop
United Airlines Logo
16:00 - 12:40ORD-CPT
37h 40m2 stops
R20 680United Airlines
Find Deal
Tue, May 6 - Tue, Sep 30
United Airlines Logo
20:00 - 13:06CPT-ORD
24h 06m2 stops
United Airlines Logo
14:20 - 17:20ORD-CPT
44h 00m2 stops
R20 773United Airlines
Find Deal
Tue, May 6 - Tue, Sep 30
British Airways Logo
19:25 - 11:50JNB-ORD
23h 25m1 stop
British Airways Logo
19:10 - 7:00ORD-JNB
28h 50m1 stop
R22 261British Airways
Find Deal
Fri, Jul 25 - Sat, Aug 16
British Airways Logo
19:25 - 15:55JNB-ORD
27h 30m1 stop
British Airways Logo
16:55 - 9:25ORD-JNB
33h 30m1 stop
R23 749British Airways
Find Deal
Fri, Aug 1 - Fri, Aug 22
Ethiopian Air Logo
13:50 - 8:15CPT-ORD
25h 25m2 stops
Ethiopian Air Logo
10:15 - 13:00ORD-CPT
43h 45m1 stop
R24 344Ethiopian Air
Find Deal
Sun, Jun 1 - Thu, Jul 10
Ethiopian Air Logo
13:50 - 8:15CPT-ORD
25h 25m2 stops
Ethiopian Air Logo
10:15 - 13:00ORD-CPT
43h 45m1 stop
R25 330Ethiopian Air
Find Deal
Sun, Jun 1 - Thu, Jul 10

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 day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as R20 855. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R23 068 on average.

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 R18 244 on average for return flights. On the other hand, the most expensive months are August and December, where the average cost of tickets from South Africa is R23 024 and R22 280 respectively. For one-way flights, the best month to travel is February with an average price of R18 244.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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.

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 20 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 949.

Good to know – Book Cheap Chicago Plane Tickets

Low season

February

High season

June

Cheapest flight

R10 377
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly and prices are also 0% lower on average.
Flight from Johannesburg 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.

See more FAQs

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?

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, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

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 1333 reviews
7,8Boarding
7,1Entertainment
7,7Comfort
7,2Food
8,4Crew
Airline reviews

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

8,0 ExcellentAnonymous, Apr 2025AMS - MAN
Read more KLM reviews

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

They only had vegetarian food left on the flight which I wasn’t happy about. I didn’t get any food to eat at all.

Overall very poor. Flight was disorganised, staff were rude and this is my second experience with KLM that I've had baggage go missing. It feels like, if you are an economy customer, KLM staff do not show you any care. I shall never fly with KLM again. Worst airline in Europe

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

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

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

It was wonderful best Air lines covert and all very happy with their service they have been very helpful and friendly

It was very bad experience with Ethiopian airlines . The flight was delayed in both ways . On the way coming back one of the crews dropped hot coffee on my whole body and other crew dropped used dirty glasses on top of me . The same crew that dropped hot coffee on me hit me with the food trolley on my knee while I was sleeping . I couldn’t sit properly due to the pain on my knee caused by those irresponsible crews . Very unprofessional airlines

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.

My experience was great. The flight attendants were very helpful and nice, and the food was very good.

Terrible customer service I lost my bag luggage and I still haven’t received any information

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.

I felt all of the food tasted the same. And we had five meals over the 16 hrs in the air.

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

Plane was late with no information or announcement … had to walk up n downstairs.., had not communicated this … and ppl had suitcase to carry .

The boarding process was quite loud and chaotic. The flight attendants kept barking over the PA system about people needing to only stow large items in the overhead bins. During the one and only service, I was hit by the service cart. At the same time, a passenger was returning from the bathroom and the crew definitely saw him but stopped a few seats short of allowing him to sit down before starting service and made him wait a good 10 minutes before passing his seat and allowing him to sit down, after which he had to ask for his snack and beverage or he would have been passed over. Neither flight attendant thanked passengers as they left; in fact, I did not see them again once the plane door was opened.

Flight Attendant Karen Lynn was an absolute delight. She assisted in every portion of the services provided throughout the flight, aided with any and all concerns expressed by passengers, and even helped comfort an upset child who was one of five of a traveling family. This quality of service is what keeps me coming back to American. Thank you!

The worst, flight cancelled because the aircraft was not full. Heathrow ground crew totally not helpful and arrogant. Lady proposed us flight with 40min layover instead of direct and said it is our problem of course she was unable to do anything as everything was beyond her control she claimed. after calling on hotline another flight was booked. Flight was cancelled last second so we could not take direct from Zurich but we had to stay overnight in London.

The seats in row 31 are terrible and small and uncomfortable. Don't ever sit there. The window seat is so close to the curve of the plane is so annoying. I paid extra for this seat and I hated all 10 hours in it.

Food was terrible , crew were excellent , IFE was dire . Overall comfortable seat and cabin. Nothing special .

If my tv wasn’t broken and I wasn’t in a seat that didn’t allow for sleeping

Delayed flight due to lack of crew caused me to miss my connection

Please make sure the number of seats matches the number of overhead bins and passengers don't carry on more than one bag.

Seating is tight if you don’t upgrade. Food was decent. Boarding and unboarding was efficient. Smooth flight. Could make upgrades more affordable

Boarding was chaotic. Glad we were group 5 and still had cabin storage available when we boarded. I was expecting crew would get our carryons at the gate since theyclaimed it was a full flight.

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