R9 777 Find Cheap Flights to Chicago – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 13% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest return fare
R14 600
Typical prices: R16 127-R19 367
Ethiopian Air
Wed 30/9Wed 7/10
CPT - ORD • 2 stops
Cheapest one-way flight
R9 777
Turkish Airlines
Mon 5/10
DUR - ORD • 2 stops
Top routes
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 16% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

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

Recent return flight deals to Chicago

Wed, Sep 30 - Wed, Oct 7
Ethiopian Air Logo
13:50 - 8:15CPT  Cape Town Intl-ORD Chicago O'Hare Intl
25h 25m2 stops Addis Ababa Bole Rome Fiumicino
Ethiopian Air Logo
10:15 - 14:10ORD  Chicago O'Hare Intl-CPT Cape Town Intl
20h 55m1 stop Addis Ababa Bole
R14 600Ethiopian Air
Fri, Sep 11 - Thu, Sep 24
Ethiopian Air Logo
13:50 - 8:15CPT  Cape Town Intl-ORD Chicago O'Hare Intl
25h 25m2 stops Addis Ababa Bole Rome Fiumicino
Ethiopian Air Logo
10:15 - 14:10ORD  Chicago O'Hare Intl-CPT Cape Town Intl
20h 55m1 stop Addis Ababa Bole
R14 682Ethiopian Air
Fri, Sep 11 - Thu, Sep 24
Virgin Atlantic Logo
20:05 - 16:37CPT  Cape Town Intl-ORD Chicago O'Hare Intl
27h 32m1 stop Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
11:29 - 17:50ORD  Chicago O'Hare Intl-CPT Cape Town Intl
23h 21m1 stop Atlanta Hartsfield-Jackson
R15 201Virgin Atlantic
Sun, Oct 11 - Sat, Oct 24
Turkish Airlines Logo
18:00 - 9:40JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
22h 40m1 stop Istanbul
Turkish Airlines Logo
11:25 - 22:25ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
28h 00m1 stop Istanbul
R15 640Turkish Airlines
Fri, Sep 11 - Fri, Sep 18
Virgin Atlantic Logo
20:05 - 23:59CPT  Cape Town Intl-ORD Chicago O'Hare Intl
34h 54m1 stop Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
18:25 - 17:50ORD  Chicago O'Hare Intl-CPT Cape Town Intl
40h 25m1 stop Atlanta Hartsfield-Jackson
R15 867Virgin Atlantic
Sun, Jan 17 - Sun, Jan 31
Turkish Airlines Logo
0:20 - 18:20JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
26h 00m1 stop Istanbul
Turkish Airlines Logo
20:15 - 11:00ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
30h 45m1 stop Istanbul
R15 965Turkish Airlines
Fri, Sep 11 - Sun, Sep 27
KLM Logo
7:40 - 14:15CPT  Cape Town Intl-ORD Chicago O'Hare Intl
37h 35m1 stop Amsterdam Schiphol
KLM Logo
16:15 - 21:10ORD  Chicago O'Hare Intl-CPT Cape Town Intl
21h 55m1 stop Amsterdam Schiphol
R16 257KLM
Fri, Sep 11 - Sun, Sep 27
KLM Logo
7:40 - 14:15CPT  Cape Town Intl-ORD Chicago O'Hare Intl
37h 35m1 stop Amsterdam Schiphol
KLM Logo
16:15 - 21:10ORD  Chicago O'Hare Intl-CPT Cape Town Intl
21h 55m1 stop Amsterdam Schiphol
R16 273KLM
Wed, Oct 7 - Sun, Oct 18
United Airlines Logo
22:00 - 23:32JNB  Johannesburg OR Tambo-ORD Chicago O'Hare Intl
32h 32m2 stops Newark Washington, D.C. Reagan-National
United Airlines Logo
12:40 - 18:30ORD  Chicago O'Hare Intl-JNB Johannesburg OR Tambo
22h 50m2 stops Washington, D.C. Reagan-National Newark
R16 387United Airlines
Sun, Sep 13 - Mon, Nov 30
United Airlines Logo
20:00 - 9:38CPT  Cape Town Intl-ORD Chicago O'Hare Intl
20h 38m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
21:48 - 18:00ORD  Chicago O'Hare Intl-CPT Cape Town Intl
36h 12m1 stop Newark
R16 452United Airlines
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 flight to Chicago?

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Durban, at R14 600 return. The most popular connection is from Johannesburg to Chicago, while KAYAK users have found return deals for as low as R15 607 in the last 5 days.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is February, where tickets cost R15 802 on average for return flights. On the other hand, the most expensive months are January and April, where the average cost of tickets from South Africa is R22 412 and R21 649 respectively. For one-way flights, the best month to travel is February with an average price of R9 549.

How far in advance should I book a flight to Chicago?

To get a below average price, you should book around 2 weeks before departure, which saves you about 16% 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 173.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

Cheapest flight

R9 777
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Durban to Chicago

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

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Durban, at R14 600 return. The most popular connection is from Johannesburg to Chicago, while KAYAK users have found return deals for as low as R15 607 in the last 5 days.

  • 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

 
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 1560 reviews
8,4Crew
7,2Entertainment
7,3Food
7,7Comfort
7,8Boarding
Airline reviews

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.

10,0 ExcellentEmily, Jul 2026
Read more KLM reviews

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

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

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.

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.

When we checked in at the Siem Reap Airport in Cambodia, we were only given three boarding passes and told that we would have to check in with American when we arrived in Boston. This was a source of stress for us. After we landed in Boston, we had a long passage from Terminal E to Terminal B (American Airline ticketing counter). Because the electronic ticketing kiosks for check-in would not recognize our Confirmation Code, we had to wait for an hour in a long line where only two AA reps were taking care of Special Services passengers. In many years of both business and recreational travel, I have never had this experience. I would expect more from AA being in partnership with other airlines to do a better job with this.

Qatar Airways is an excellent service provider. The crew members were attentive and helpful. The aircraft was very clean. This was the longest leg of our journey, so it would have been nice to have more leg room for comfort. We appreciated the crew's service of four hot meals to all of us during this long flight. Also, it was helpful that the crew asked us to keep the window shades down for the entire journey, allowing the environment to get lots of rest during the trip. For families traveling with little children, this was helpful to them to keep them settled.

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

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.

Not worth pay business class and get service economy class

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
New Buffalo
Hammond

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago