R9 949 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
R15 120
Typical prices: R16 216-R20 850
Ethiopian Air
Tue 11/12Tue 2/1
JNB - ORD • 2 stops
Cheapest one-way flight
R9 949
Typical prices: R10 630-R18 970
Qatar Airways
Sun 28/10
JNB - 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 26 weeks in advance save around 24% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 12% price drop
Most popular
Good to know
+1
Good to know
+1
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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

Fri, Dec 11 - Sat, Jan 2
Ethiopian Air Logo
14:30 - 7:40JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
25h 10m2 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 120Ethiopian Air
Wed, Nov 11 - Wed, Nov 18
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 - 13:00ORD  Chicago O'Hare Intl-CPT Cape Town Intl
43h 15m1 stop Addis Ababa Bole
R15 399Ethiopian Air
Mon, Feb 1 - Fri, Feb 19
Virgin Atlantic Logo
21:00 - 22:20CPT  Cape Town Intl-ORD Chicago O'Hare Intl
33h 20m2 stops London Heathrow Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
19:00 - 18:35ORD  Chicago O'Hare Intl-CPT Cape Town Intl
39h 35m1 stop Atlanta Hartsfield-Jackson
R15 514Virgin Atlantic
Mon, Feb 1 - Fri, Feb 19
Virgin Atlantic Logo
21:00 - 22:20CPT  Cape Town Intl-ORD Chicago O'Hare Intl
33h 20m2 stops London Heathrow Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
19:00 - 18:35ORD  Chicago O'Hare Intl-CPT Cape Town Intl
39h 35m1 stop Atlanta Hartsfield-Jackson
R15 580Virgin Atlantic
Sat, Nov 7 - Wed, Dec 2
United Airlines Logo
20:50 - 9:45CPT  Cape Town Intl-ORD Chicago O'Hare Intl
20h 55m1 stop Newark
United Airlines Logo
7:00 - 18:00ORD  Chicago O'Hare Intl-CPT Cape Town Intl
27h 00m2 stops Washington, D.C. Reagan-National Newark
R16 368United Airlines
Sat, Nov 7 - Sat, Nov 28
United Airlines Logo
20:50 - 9:45CPT  Cape Town Intl-ORD Chicago O'Hare Intl
20h 55m1 stop Newark
United Airlines Logo
8:50 - 16:10ORD  Chicago O'Hare Intl-CPT Cape Town Intl
23h 20m1 stop Washington, D.C. Dulles Intl
R16 368United Airlines
Sun, Nov 22 - Mon, Nov 30
Turkish Airlines Logo
0:20 - 18:20JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
26h 00m1 stop Istanbul
Turkish Airlines Logo
20:15 - 22:25ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
42h 10m1 stop Istanbul
R16 384Turkish Airlines
Sun, Nov 8 - Mon, Nov 16
Turkish Airlines Logo
0:20 - 18:20JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
26h 00m1 stop Istanbul
Turkish Airlines Logo
20:15 - 22:25ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
42h 10m1 stop Istanbul
R16 400Turkish Airlines
Wed, Oct 14 - Sun, Nov 8
Etihad Airways Logo
9:45 - 8:35JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
29h 50m1 stop Abu Dhabi Zayed Intl
Etihad Airways Logo
13:10 - 8:25ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
35h 15m1 stop Abu Dhabi Zayed Intl
R17 123Etihad Airways
Wed, Oct 14 - Sat, Nov 7
Etihad Airways Logo
9:45 - 8:35JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
29h 50m1 stop Abu Dhabi Zayed Intl
Etihad Airways Logo
13:10 - 8:25ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
35h 15m1 stop Abu Dhabi Zayed Intl
R17 484Etihad Airways
Booking Insights

Price, demand, and travel trends for South Africa to Chicago flights

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

What is the cheapest flight to Chicago?

Johannesburg OR Tambo Airport to Chicago is the cheapest route at R15 120 return, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Chicago?

A return flight to Chicago costs R17 721 on average, based on data over the past 12 months on KAYAK. Return fares from Cape Town average R17 489, while Johannesburg OR Tambo Airport runs a bit higher at R17 641.

What is the cheapest day to fly to Chicago?

Monday is the cheapest day to fly to Chicago at R17 057 return on average over the past 12 months on KAYAK. Saturday is the most expensive at R19 963.

What is the cheapest month to fly to Chicago?

•February is the cheapest month to fly to Chicago with an average price of R15 530 return.
•April (R21 309) and January (R20 209) 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 500 return on average. Afternoon flights are the most expensive at R19 257.

What is a good deal for flights to Chicago?

Flights under R16 216 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 R15 814.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 26 weeks before departure. Booking in this window typically costs about 24% 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

R9 949
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (3% more expensive on average)
Flights from Johannesburg OR Tambo Airport 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 216 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).

  • Where can I fly from to get the cheapest fares to Chicago?

    Based on fares booked in the past 5 days, the cheapest flights to Chicago are from:
    • Johannesburg, from R15 120 return

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago – booked within 2 weeks of departure – run 17% above the average return fare of R17 721.

  • 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, aim to book around 26 weeks before you fly. That window historically saves about 24% versus last-minute pricing based on KAYAK booking data over the last 12 months.
  • For flights to Chicago, recent KAYAK data shows that stronger deals tend to be around R16 216 return. If you see a fare below that threshold, it's a good deal – book before the price climbs back up.
  • If you can choose when to go, aim to travel to Chicago in February. Return fares historically average R15 530 that month – typically the cheapest month to travel based on 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 757 per return. Morning flights to Chicago average R17 500 compared to R19 257 for midday flights. See the time-of-day chart above for the full breakdown.
  • 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 1578 reviews
7,2Entertainment
7,8Boarding
8,4Crew
7,7Comfort
7,3Food
Airline reviews

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

4,0 OkayJessica, Sept 2026
Read more KLM reviews

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.

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

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.

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

After having bad experience last time This time they were very good

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

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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