R9 344 Find Cheap Flights to Chicago – Compare and Save

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 13/7. 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, 0 bags

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Everything you should know

Cheapest return fare
R16 223
Typical prices: R15 744-R21 082
KLM
Fri 9/10Sat 14/11
CPT - ORD • 1 stop
Cheapest one-way flight
R9 344
Typical prices: R12 751-R17 748
Qatar Airways
Mon 13/7
JNB - ORD • 1 stop
Top routes
Cheapest
Most popular
Insights
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When to book
in advance
Our data shows that travellers who book at least 9 weeks in advance save around 35% compared to booking last minute.
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When to travel
Cheapest • 50% price drop
Most popular
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Booking Insights
Flight 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

Fri, Oct 9 - Sat, Nov 14
KLM Logo
7:40 - 14:15
CPT
-
ORD
37h 35m
1 stop
KLM Logo
16:25 - 22:40
ORD
-
CPT
22h 15m
1 stop
R16 223KLM
Fri, Oct 9 - Sat, Nov 14
KLM Logo
23:15 - 21:32
CPT
-
ORD
29h 17m
2 stops
KLM Logo
16:25 - 22:40
ORD
-
CPT
22h 15m
1 stop
R16 385KLM
Fri, Oct 9 - Sat, Nov 14
United Airlines Logo
20:00 - 14:26
CPT
-
ORD
25h 26m
1 stop
United Airlines Logo
6:25 - 16:10
ORD
-
CPT
25h 45m
1 stop
R16 418United Airlines
Fri, Jul 17 - Fri, Aug 21
Ethiopian Air Logo
8:20 - 8:15
JNB
-
ORD
30h 55m
2 stops
Ethiopian Air Logo
10:15 - 13:25
ORD
-
JNB
20h 10m
1 stop
R16 418Ethiopian Air
Fri, Oct 9 - Sat, Nov 14
United Airlines Logo
20:00 - 12:54
CPT
-
ORD
23h 54m
2 stops
United Airlines Logo
10:00 - 16:10
ORD
-
CPT
22h 10m
2 stops
R16 482United Airlines
Mon, Sep 7 - Wed, Mar 3
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R17 180Etihad Airways
Mon, Jul 27 - Mon, Aug 10
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
9:42 - 8:20
ORD
-
JNB
39h 38m
2 stops
R17 634Etihad Airways
Sat, Oct 24 - Tue, Nov 10
Qatar Airways Logo
18:55 - 15:30
DUR
-
ORD
27h 35m
2 stops
Qatar Airways Logo
18:50 - 10:55
ORD
-
DUR
32h 05m
2 stops
R18 024Qatar Airways
Sat, Oct 24 - Tue, Nov 10
Qatar Airways Logo
18:55 - 15:30
DUR
-
ORD
27h 35m
2 stops
Qatar Airways Logo
9:31 - 10:55
ORD
-
DUR
41h 24m
3 stops
R19 403Qatar Airways
Wed, Aug 19 - Wed, Aug 26
British Airways Logo
11:15 - 15:55
DUR
-
ORD
35h 40m
2 stops
British Airways Logo
20:45 - 10:40
ORD
-
DUR
54h 55m
2 stops
R20 798British Airways
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?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Johannesburg, at R16 223 return. The most popular connection is from Cape Town to Chicago and KAYAK users have found return deals for as low as R16 223 in the last 3 days.

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 round-trip 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 March, where tickets cost R5 597 on average for return flights. On the other hand, the most expensive months are January and November, where the average cost of tickets from South Africa is R14 163 and R12 978 respectively. For one-way flights, the best month to travel is July with an average price of R3 601.

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 9 weeks before departure, which saves you about 35% 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 507.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 344
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 9% 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

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Johannesburg, at R16 223 return. The most popular connection is from Cape Town to Chicago and KAYAK users have found return deals for as low as R16 223 in the last 3 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

 
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 1534 reviews
7,3Food
8,4Crew
7,7Comfort
7,2Entertainment
7,8Boarding
Airline reviews

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

6,0 GoodGlenn, Feb 2026
AMS - JFK
Read more KLM reviews

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.

The boarding was one of the worst I’ve ever experienced. The fault lays on Ohare Airport and not so much the airline. The waiting area by the gate was the size to accommodate a regional flight for 20-30 people and right next to a busy walkway. When you cramped nearly 300 passengers into that space is was unbearable.

Seats actually fit a human! Snack options were a bit lame but that’s ok

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The flight was delayed an hour and a half while you tried to fix the plane so I missed my connecting flight in Chicago. In Chicago, it took an hour to get the luggage. Then the conveyor belt was broken where I have to transfer my flight from an international flight to the continuing flight so I had to carry a large suitcase through the airport. The elevators were broken in the airport. I paid people to carry the luggage for me up the escalators in two different areas. The person who helped me get the new flight was outstanding. The temperature in the airport in Chicago was horrible. We were all sweating. It was the day from hell. That was after two hours in a security line in Athens. I have TSA pre-checked and global entry and I still waited. Two hours in a security line. Something has got to be done to stream line this service. After I’ve been through all of that in Athens, why do I have to go through it again in Chicago. It was the worst travel experience I have had in a long time. Your bathrooms have gotten so small that you can hardly get your butt on the toilet. You’ve taken the airspace out of the inside of the top of the toilet. It really makes for a miserable experience. Also on a 4 1/2 hour flight from Chicago to Los Angeles. The only thing we’re given is a bag of pretzels. REALLY!!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

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.

The seat cushions are absolutely lacking, not sure if they know the passengers are traveling for 14 hours straight, but the padding made our back and butt ache like crazy. The entertainment console had its own problems, either the headphone jack wasn't working or the power outlet via usb or ac outlet was not working. Not to mention the seat handles were not adjustable in some planes in the middle or on the aisle. Qatar/Indigo may be operating a very old fleet of planes to make as much profit as possible, but passengers may not be following them for long, should this treatment of its customers continue. Qatar/Indigo, wake up and do it right by your customers, or they may not be your customers anymore.

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

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

The crew could have been more friendly and could have offered to make the beds. Also, Ethiad should have more vegetarian food options.

From the start of my vacation at Logan Airport, Boston it was chaotic. I'm praying my flight home is better .I'm grateful that we landed safe

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.

I will never want to book with these people. They are arrogant and rude. Food was really really bad, crew was even worst

Check-in in SAN was long. ORD was good. Flight delayed On board crew was ok. No warmth or personality. LHrR barely made connection

Check-in experience, for business call please provide a premium experience

Everything. Employees offered to help me because I had to use a cane.

Unfortunately, my flight was cancelled because of some sort of emergency over the Atlantic and had to return to London. While I think British Airways made every effort to mitigate the situation, I must say it was still pretty unpleasant. I do appreciate the fact, however, that British Airways put my safety first…and I think the effort to correct a bad situation was very sincere. But I think the process might be handled better in future.

The seat pads are past there sell by date now and are uncomfotable. Also, with screens in the back of the seat, the seats shouldnt be able to recline as this puts rhe screen in your face.

As I have said it sucked, the ticket counter to have to find and pay for another airline to get home. Now I understand this happened over the weekend but they should have someone there to talk to us instead of throwing the regular crew under the bus.

Poor all around experience. Sat at gate in Grand Rapids to Chicago for 2.5 hours. No food or water offered and no allowances to use restroom. Missed connecting flight to London and not offered any compensation including food or lodging. Not happy with AA, claims delay was weather related but no weather issues seen on radar. Take ownership for real reason behind delay which was actually the IT outage. Very disappointing and will not be recommending AA for domestic or international flights if this is the way that customers are treated.

Flight cancelled, lost luggage, crappy meal voucher. Nothing was good. Still dont have my luggage.

Not so good with their baggage handling as they damaged one of my check in luggage

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Everything you need to know for your flight to Chicago

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.