R8 581 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
R14 964
Typical prices: R16 630-R21 579
Virgin Atlantic
Mon 12/11Sun 25/11
CPT - ORD • 2 stops
Cheapest one-way flight
R8 581
Typical prices: R10 739-R19 180
Turkish Airlines
Fri 23/11
CPT - ORD • 1 stop
Top airlines
Best reviews • 7,8 score
Airline reviews
Airline reviews
Top routes
Cheapest • 8% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 21 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 8% price drop
Most popular
Good to know
+1
Good to know
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Flight Deals

Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Thu, Nov 12 - Wed, Nov 25
Virgin Atlantic Logo
21:00 - 21:42CPT  Cape Town Intl-ORD Chicago O'Hare Intl
32h 42m2 stops London Heathrow New York John F Kennedy Intl
Virgin Atlantic Logo
15:59 - 18:35ORD  Chicago O'Hare Intl-CPT Cape Town Intl
18h 36m1 stop Atlanta Hartsfield-Jackson
R14 964Virgin Atlantic
Thu, Nov 12 - Wed, Nov 25
Virgin Atlantic Logo
21:00 - 18:04CPT  Cape Town Intl-MDW Chicago Midway
29h 04m2 stops London Heathrow Detroit Metropolitan Wayne County
Virgin Atlantic Logo
11:27 - 18:35MDW  Chicago Midway-CPT Cape Town Intl
23h 08m1 stop Atlanta Hartsfield-Jackson
R15 146Virgin Atlantic
Sun, Nov 1 - Mon, Nov 16
Turkish Airlines Logo
0:20 - 19:20JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
27h 00m1 stop Istanbul
Turkish Airlines Logo
20:15 - 10:55ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
30h 40m1 stop Istanbul
R15 443Turkish Airlines
Mon, Nov 2 - Mon, Nov 16
Ethiopian Air Logo
23:00 - 7:40JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
40h 40m2 stops Addis Ababa Bole Rome Fiumicino
Ethiopian Air Logo
9:45 - 13:30ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
19h 45m1 stop Addis Ababa Bole
R15 675Ethiopian Air
Wed, Nov 25 - Wed, Dec 2
Ethiopian Air Logo
13:50 - 7:40CPT  Cape Town Intl-ORD Chicago O'Hare Intl
25h 50m2 stops Addis Ababa Bole Rome Fiumicino
Ethiopian Air Logo
9:45 - 13:30ORD  Chicago O'Hare Intl-CPT Cape Town Intl
43h 45m1 stop Addis Ababa Bole
R15 906Ethiopian Air
Wed, Nov 11 - Wed, Nov 25
KLM Logo
0:30 - 18:30CPT  Cape Town Intl-ORD Chicago O'Hare Intl
26h 00m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
KLM Logo
11:19 - 22:40ORD  Chicago O'Hare Intl-CPT Cape Town Intl
27h 21m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol
R16 435KLM
Fri, Nov 20 - Thu, Dec 3
United Airlines Logo
22:00 - 10:48JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
20h 48m1 stop Newark
United Airlines Logo
14:30 - 18:35ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
20h 05m1 stop Newark
R16 535United Airlines
Tue, Nov 24 - Wed, Dec 2
United Airlines Logo
22:00 - 11:47JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
21h 47m1 stop Newark
United Airlines Logo
15:36 - 18:35ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
18h 59m1 stop Newark
R16 535United Airlines
Wed, Dec 9 - Thu, Jan 14
Turkish Airlines Logo
0:20 - 10:00JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
41h 40m1 stop Istanbul
Turkish Airlines Logo
20:15 - 11:00ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
30h 45m1 stop Istanbul
R16 816Turkish Airlines
Mon, Nov 2 - Mon, Nov 16
KLM Logo
23:59 - 18:00JNB  Johannesburg OR Tambo-MDW Chicago Midway
26h 01m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
KLM Logo
11:27 - 22:00MDW  Chicago Midway-JNB Johannesburg OR Tambo
26h 33m2 stops Atlanta Hartsfield-Jackson Amsterdam Schiphol
R17 427KLM
Booking Insights

Price, demand, and travel trends for flights to Chicago

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Chicago?

Cape Town to Chicago is the cheapest route at R14 964 return, found in the past 5 days on KAYAK. Johannesburg OR Tambo Airport to Chicago is the most popular connection with return deals from R15 443.

How much is a flight to Chicago?

On average, a return flight from South Africa to Chicago costs R18 211, based on KAYAK data over the past 12 months. Return fares from Cape Town average R17 834, while Johannesburg OR Tambo Airport runs a bit higher at R18 129.

What is the cheapest day to fly to Chicago?

Monday is the cheapest day to fly to Chicago at R17 824 return on average over the past 12 months on KAYAK. Saturday is the most expensive at R20 271.

What is the cheapest month to fly to Chicago?

•November is the cheapest month to fly to Chicago with an average price of R16 683 return.
•April (R21 429) and March (R19 560) are the most expensive.
•Based on KAYAK data over the past 12 months.

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

Morning flights to Chicago are the cheapest at R17 841 return on average. Afternoon flights are the most expensive at R19 312.

What is a good deal for flights to Chicago?

Flights under R16 630 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Cape Town R16 351.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 21 weeks before departure. Booking in this window typically costs about 22% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Chicago

Low season

February

Cheapest flight

R8 581
Beat the crowds with an average 52% drop in traveller numbers.
The most popular month to fly with an average 55% increase in traveller numbers.
One-way flight from Cape Town to Chicago O'Hare Intl 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

Your questions about flights to Chicago, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago is a good deal?

    A good deal on a flight to Chicago is around R16 630 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • Which airports serve Chicago?

    Flights to Chicago arrive at: Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which city has the cheapest flights to Chicago?

    Based on fares booked in the past 5 days, the cheapest flights to Chicago are from Johannesburg, starting at R15 443 return.

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago (booked within two weeks of departure) are typically 16% higher than the average return fare of R18 211.

  • What is the difference between the most popular and the most frequent airline at Chicago?

    Qatar Airways operates the most flights from South Africa to Chicago at 0 per week, while United Airlines is the airline most often selected by KAYAK users searching for flights from South Africa to Chicago. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80,5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

Your guide to booking Chicago flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Chicago, book around 21 weeks before departure. Based on KAYAK data from the last 12 months, fares are historically about 22% lower during this window than last-minute fares.
  • For flights to Chicago, a good return fare is around R16 630. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Chicago in November. Return fares historically average R16 683, making November the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to morning to save up to R1 472 on a return flight. Morning flights to Chicago average R17 841 compared to R19 312 for midday flights.
  • Once you arrive in Chicago, a few great places to start are McCormick Place, United Center, and Chicago Riverwalk. These are popular with first-time visitors and can give you a good feel for the area.

Reviews of the top 5 airlines flying to Chicago

 
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 1589 reviews
7,3Food
7,2Entertainment
8,4Crew
7,8Boarding
7,7Comfort
Airline reviews

I wanted to give them a five‑star rating across the board, but they lost my luggage, and that really affected the experience.

8,0 ExcellentNikola, Oct 2026
Read more KLM reviews

I wanted to give them a five‑star rating across the board, but they lost my luggage, and that really affected the experience.

The flight itself was fine, food was expired and gross, staff were mostly amazing! KLM messed up rebooking for our first two flights that got cancelled and we almost didn’t make it to Amsterdam for an additional two days

I think I previously submitted my feedback about flight lead Katherine in a different field by mistake. Please see those comments. Comments for Hyd to AMS are it was good. The flight lead and service met expectations for satisfactory high quality service but the flight lead did not stand out as exceptional as did the leads on the other two flights so I don’t remember anything specific one way or the other besides the fact I was satisfied.

Flight lead was a gentleman with silver hair and he went out of his way to shake hands and interact with each passenger seated in business class. A medical emergency took place during our flight and he handled it with perfect poise and professionalism. He was gracious and confidently competent. Just what you want from a leader,

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

Legroom not all it could be, especially when the seat in front is reclined. Otherwise it was good, food and beverage were nice.

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

Seats were nice and comfy. Crew was polite and attentive. Business class is awesome and worth the money.

It was operated by Delta. Boarding took a long time. How difficult can it be? Overall decent trip. Liked the Salt Lake City airport. Better option than Chicago for transfers.

Bussing in a major flight is idiotic. Cabin was too warm. Food was bland and felt old

Horrible service at the baggage claim. Stuck on plane for an hour due to taxing and no gate.

I really would like it if they provided at least some limited free wi-fi.

Excellent food and service on my international flight. Most notable is the food provided by Turkish even for coach passengers is very good.

Food is very turkish. No regard for other natinalities taste and preference. The entertainment can be improved- it was the same menu on 10/8/25 and 10/25/25. The boarding is the worst in the airline industry- I suggest you ask your staff to and watch how other airlines do it.

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

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.

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.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

The employees seemed impatient with their guests. It seemed like they were giving us orders, instead of easily assisting. Our flight was delayed waiting on a flight attendant. It was alright.

My easiest trip ever. Flights left on time, and came in a few minutes early. The flights weren’t full so it was very comfortable. Thank you United

Quinoa chocolate cookies are my favorite! Would be nice to have internet service like American

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

Old plane, no amenities. Very abrupt landing. Unnecessarily long taxi time.

Legroom in Economy was fair to good. Seat was omay; I was hit in the shoulder twice by the cart as it was being whisked through the aisle. Overhead space was good for my carryon. Lighting environment was nice

We were delay because so many bags needed to be gate checked and it was disappointing not to have outlets in the seats for such a long flight.

Raleigh to Chicago was OK. The problem was Chicago to Lincoln. Flight was delayed 4 hours. Give them credit for the updates and reason why it was delayed

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

One hour before landing was the most scary part of my life. The plane just dropped from the air . No explanation or apologies from the captain. Women and children screaming everywhere. Would like to know what happened

My flight going to doha had economy seats that had a little more leg room. Coming back the leg room was not there. I'm 6'3" and my knees were against the chair in front of me. I couldn't slide my feet under the chair. The 15 hour flight felt like torture from the lack of sleep I was getting being so uncomfortable. Food and crew were great though.

It was excellent except for at the very end. I woke up about 1.5 hrs before touchdown and wanted to order food in the Business class. I was told they had shut down food service. It would have been good to get a heads up before they closed the service. Anna the air hostess was wonderful. She did get me 2 bowls of fruit and I was very appreciative of her. Wonderful human and a hostess.

Amazing airline accommodations. The cabins were so great. The food was very good and the flight attendants were so nice. Made a 15 hour flight seem easy.

I paid extra for seating when first booking flight to be in a comfortable economy seat They still changed it to a middle seat regardless. When I asked for it to be changed back to aisle, they could only give me one at the back of the plane in the least comfortable seats.

Same as already mentioned. This was more comforting as I got my aisle seat for my knee.

Seats very small and unable to pre purchase internet or seat upgrades

It was good no problems made it on time for the next flight overseas!

Boarding was orderly, staff at the counter were friendly and so as most of the staff in the flight. Room for some improvement in entertainment, but overall very good flight.

Sitting arrangement is very poor and for entertainment options for Bollywood fans , need to add more movies and Hindi TV shows . Bcz mostly Indian people are spend more money to fly with Qatar so for their better entertainments please add more good TV shows . Thank you

Good could be better. Crew is good but not great. Not much snack options for kids. Bathrooms were not cleaned on time

The crew were really bad mannered! And spoiled all my mood throughout the flight!

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

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

Horrible. After paying for seats, I was cramped, my daughters legs kept hitting the seat in front, I had no overhead bin space and no help from stewards on board, the food was served cold, when asked for snacks was told to wait and never received any, the flight was cold with no temperature controls. Entertainment was outdated. I booked this through partnership with American Airlines but will avoid in the future.

Nothing was good. Everything needs to improve. Everything was abysmal. Needs lots of improvement. The check-in and baggage drop at the New Delhi airport was manned by disrespectful people, horrible experience. We will never travel by Etihad ever again.

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