R10 838 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 14/6. 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.
1 adult
1 adult, Economy, 0 bags

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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Everything you should know

Cheapest return fare
R16 709
Typical prices: R20 130-R16 207
United Airlines
Tue 16/6Sat 4/7
CPT - ORD • 1 stop
Cheapest one-way flight
R10 838
Typical prices: R10 427-R11 216
Etihad Airways
Sun 14/6
JNB - ORD • 2 stops
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 11% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
Good to know
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+1
Good to know
Good to know
+1
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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

 
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

Tue, Jun 16 - Sat, Jul 4
United Airlines Logo
20:00 - 9:36
CPT
-
ORD
20h 36m
1 stop
United Airlines Logo
8:40 - 15:20
ORD
-
CPT
23h 40m
1 stop
R16 709United Airlines
Tue, Jun 16 - Fri, Jul 3
United Airlines Logo
20:00 - 17:02
CPT
-
ORD
28h 02m
1 stop
United Airlines Logo
21:40 - 15:20
ORD
-
CPT
34h 40m
1 stop
R16 775United Airlines
Tue, Jun 16 - Fri, Jul 3
United Airlines Logo
20:00 - 9:36
CPT
-
ORD
20h 36m
1 stop
United Airlines Logo
21:40 - 15:20
ORD
-
CPT
34h 40m
1 stop
R16 840United Airlines
Sat, Aug 8 - Sat, Aug 22
Etihad Airways Logo
9:50 - 8:35
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
21:10 - 8:20
ORD
-
JNB
28h 10m
1 stop
R16 939Etihad Airways
Mon, Jun 29 - Thu, Aug 6
Etihad Airways Logo
9:50 - 15:40
JNB
-
ORD
36h 50m
1 stop
Etihad Airways Logo
14:00 - 8:20
ORD
-
JNB
35h 20m
1 stop
R17 482Etihad Airways
Tue, Jun 9 - Mon, Aug 17
KLM Logo
23:15 - 18:18
JNB
-
MDW
26h 03m
2 stops
KLM Logo
13:27 - 21:20
MDW
-
JNB
24h 53m
2 stops
R20 870KLM
Tue, Sep 15 - Sat, Sep 19
Turkish Airlines Logo
11:15 - 9:40
DUR
-
ORD
29h 25m
2 stops
Turkish Airlines Logo
11:25 - 13:15
ORD
-
DUR
42h 50m
2 stops
R22 399Turkish Airlines
Tue, Sep 15 - Sat, Sep 19
Turkish Airlines Logo
11:15 - 9:40
DUR
-
ORD
29h 25m
2 stops
Turkish Airlines Logo
11:25 - 19:50
ORD
-
DUR
49h 25m
2 stops
R23 336Turkish Airlines
Tue, Jul 21 - Tue, Aug 11
KLM Logo
23:15 - 18:18
CPT
-
MDW
26h 03m
2 stops
KLM Logo
13:27 - 21:25
MDW
-
CPT
24h 58m
2 stops
R23 484KLM
Tue, Sep 15 - Sat, Sep 19
British Airways Logo
11:15 - 12:30
DUR
-
ORD
32h 15m
2 stops
British Airways Logo
21:15 - 10:40
ORD
-
DUR
54h 25m
2 stops
R23 501British 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 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 R14 801 on average for return flights. On the other hand, the most expensive months are January and July, where the average cost of tickets from South Africa is R23 172 and R18 962 respectively. For one-way flights, the best month to travel is February with an average price of R14 801.

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 2 weeks before departure, which saves you about 11% 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 434.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR10 838
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly (7% more expensive 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.

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 1517 reviews
7,8Boarding
7,7Comfort
7,3Food
8,4Crew
7,2Entertainment
Airline reviews

Outstanding even though the 330 was one of the oldest in the fleet. The difference was the attentiveness and responsiveness of a really experienced flight attendant. For airline food great variety of interesting choices and good tastes supported by a good wine selection.

10,0 ExcellentBob, May 2026
AMS - YYZ
Read more KLM reviews

Outstanding even though the 330 was one of the oldest in the fleet. The difference was the attentiveness and responsiveness of a really experienced flight attendant. For airline food great variety of interesting choices and good tastes supported by a good wine selection.

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

Empty seats next to me - wish it had been for a longer flight!!

I’m grateful for the KLM Air France shuttle bus service to Ottawa. However due to construction and other issues related to the chaotic Uber pickup system at YUL, it’s a challenge to find the Kelios bus service to Ottawa. The signs are not clear or even available. No staff to guide passengers. It’s a stressful experience.

Delay on my previous leg, had to run to catch my flight. But that happens. Overall ok.

Delay and had to run between flight to get my connection due to this delay but besides that the overall experience was ok. I arrived with just an hour of delay.

At the airport, terrible, I do not want to even remember it. It was too humiliating for a business class passenger.

Couldn’t get boarding pass in SLC even with help from a redcoat, so had to find a desk in AMS to get boarding pass. Technical problems so not sure why. Very inconvenient. The KLM app is not as user friendly as most apps. Also had to wait almost an hour on the tarmac for a fuel truck, which caused us to miss a connecting bus in LUX.

First of all we couldn’t check in online, then we learn at the airport we were on stand by for KLM’s mistake of overbooking. The seats were not comfy at all. Our luggage got lost.

Ad experience - been flying many years with them but they are losing out to other carriers with their service and bagage / seating policy. My 2 12-yo kids were not placed with the parent. Absurdity.

We were experiencing delayed for 4 hours and of course they took us to Turkish airlines lounge but we could not rested up since there is no bedroom. It was tiring and long day for us🙏 Especially we didn’t fly until 5:45am morning for Miami🙏😢

On Turkish it is all about the food and the service. I am overwhelmed with the quality and variety of the dining service offered on business class. I prefer the updated A350 to the older B777 cabin layout, but both are comfortable. Flights left and arrived on time with updates from the captain. I will definitely fly with them again.

Excellent service. Friendly and attentive flight attendants, can lay back in business class and be pretty comfortable, and delicious food. Flight on time departing and arriving.

I will say the same as my previous comment. Great job over all! From 1-10, ten be the best… I will give 9!

had to wait 1 hour once boarded. so we were 1 hour late arriving.

They are absolutely impossible to get hold of. A death in the family caused us to delay our departure. They are impossible to get through to and after waiting 41/2 hours I was told they would not consider helping us. They cancelled our return flight and have not reimbursed anything. I strongly urge readers to consider a different airline.

A lot of snacks and provided on request by traveller. Preferred meals which were on their menu were not always sufficient for those who wanted them. We were told 2 different items and offer which we asked for were not offered initially. We rejected the 3rd item given as a substitute for our initial choices which we didn't want and so we didn't accept it. Eventually our initial choice was offered. During service of coffee and tea, the crew member didn't offer us and moved back. Luckily neither of us wanted tea at that time. Crew members must avoid behavior that may be suggestive of discrimination

The crew was awesome. My husband fell while traveling to the WC and got a head abrasion. The crew helped him greatly and a physician that was also on the flight checked him out as well. They all get an A+!

Online check in and seat assignments are terrible. All 4 flights

Cabin was kept very hot and it was uncomfortable. Entertainment system did not work at my seat. Crew and service is fantastic

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

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.

1 hour delay meant missed my connecting flight and 1st day of holiday

Unfortunately the flight was cancelled so I never got to go

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

The flight was over 1 hour late taking off ,when I arrived in Abu Dhabi ,I missed my connecting flight to Bangkok so I had to wait almost 6 hours for my flight arriving in Bangkok at 6:30 am ,So I missed a whole day of my vacation and my hotel room sat empty so I paid for hotel days that I was not there. In Abu Dhabi there was a woman that worked the desk at transfers that was so professional, courteous , helpful,and may I say absolutely beautiful .she got me food vouchers for my layover and was a very calming presence. Besides that I will never use Etihad again I will pay the Xtra money . I'm sure they won't read or see this but it's my "2 cents" I'll use an airline that respects me and my hard earned dollars

The flights were on time. Cabin crew were nice. The food was terrible! Checking in was not easy using my phone.

Crew were fantastic and the aircraft was extremely comfortable, but outdated. Headphone jacks were worn out and sound normally only came out of one ear unless positioned just right.

Departure was delayed leading to late arrival, 25 min wait for a gate. Basically, missed all our connections & had to be rebooted, which was a very long process.

Good flight, no turbulence. I felt safe and comfortable which is really important when I am just a passenger.

Somone switched seats to sit near friend causing us to be disconnected (3) business class. Very disappointed. Staff did nothing.

A shout-out to the flight attendent, Lauren, who was the main person assisting me. She was amazing - perfect balance of bright, cheerful, engaging, yet formal

1st class seats NOT REALLY 1st class or business class but like premier economy. Should be listed as such or named something else. I have flown 1st class with other airlines and they are nothing like it at all.

The flight from Dallas to madrid was delayed for 2 to 3 hours, the flight back from Dallas to Sacramento was fine , but there were 5 gate changes within the span of 2 hours, last one was in a differny terminal. Flight and crew was okay

I was downgraded from business class to economy class with no compensation. American Airlines is absolutely the worst airline for international travel. They treat their business class customers like dogs.

OK, except for a cabin attendant's lack of attention.

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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.