R9 318 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 29/5. 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
R14 833
Typical prices: R20 332-R16 438
Etihad Airways
Wed 24/6Fri 24/7
JNB - ORD • 1 stop
Cheapest one-way flight
R9 318
Typical prices: R9 582-R14 389
Qatar Airways
Fri 29/5
JNB - ORD • 1 stop
When to book
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 12% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
+1
+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.
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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

Wed, Jun 24 - Fri, Jul 24
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
R14 833Etihad Airways
Fri, Oct 16 - Fri, Oct 30
Etihad Airways Logo
9:50 - 8:35
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
14:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R15 163Etihad Airways
Wed, Jun 24 - Fri, Jul 24
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
R15 311Etihad Airways
Mon, May 25 - Mon, Aug 10
Qatar Airways Logo
12:40 - 16:50
JNB
-
ORD
35h 10m
1 stop
Qatar Airways Logo
19:20 - 9:00
ORD
-
JNB
30h 40m
1 stop
R16 776Qatar Airways
Fri, Aug 7 - Fri, Aug 21
United Airlines Logo
22:00 - 20:27
JNB
-
ORD
29h 27m
2 stops
United Airlines Logo
16:05 - 8:35
ORD
-
JNB
33h 30m
1 stop
R17 830United Airlines
Thu, Jul 16 - Mon, Aug 17
Turkish Airlines Logo
16:35 - 9:40
CPT
-
ORD
24h 05m
1 stop
Turkish Airlines Logo
11:25 - 11:50
ORD
-
CPT
41h 25m
1 stop
R18 686Turkish Airlines
Wed, Oct 7 - Wed, Oct 21
Emirates Logo
18:40 - 15:45
DUR
-
ORD
28h 05m
1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m
1 stop
R20 529Emirates
Wed, Jun 3 - Wed, Jun 10
KLM Logo
23:15 - 18:33
JNB
-
MDW
26h 18m
2 stops
KLM Logo
13:16 - 21:20
MDW
-
JNB
25h 04m
2 stops
R22 439KLM
Wed, Jun 3 - Wed, Jun 10
KLM Logo
23:15 - 18:33
CPT
-
MDW
26h 18m
2 stops
KLM Logo
13:16 - 21:25
MDW
-
CPT
25h 09m
2 stops
R25 650KLM
Tue, Jun 2 - Tue, Jun 9
Emirates Logo
18:40 - 15:45
DUR
-
ORD
28h 05m
1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m
1 stop
R56 781Emirates
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 751 on average for return flights. On the other hand, the most expensive months are July and December, where the average cost of tickets from South Africa is R19 229 and R18 998 respectively. For one-way flights, the best month to travel is February with an average price of R14 751.

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 4 weeks before departure, which saves you about 12% 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 438.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 318
Best time to beat the crowds (4% less expensive on average)
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 1507 reviews
8,4Crew
7,3Food
7,8Boarding
7,7Comfort
7,1Entertainment
Airline reviews

The crew were unprofessional with a racist element. I was physically abused as well from one of the crew members

2,0 MediocreNewton, Mar 2026
IAD - AMS
Read more KLM reviews

The crew were unprofessional with a racist element. I was physically abused as well from one of the crew members

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

Flight was ok but lack of communication cost me to literally beg to be put on another flight as connecting flight had departed

They forgot to serve food and the crew was very unfriendly. Never experienced such a bad KLM flight. Usually fly from Toronto. New York was different.

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.

The immigration hall in Amsterdam was understaffed, so passport checking was slower than it should be for a major airport. They need to get the automatic readers up and running for non EU passport holders. Waiting in line after a long flight feels a bit abusive.

Short flight so it was okay. Nice crew, all very pleasant and professional. We were near the back in row 27 so just as we got our drinks, we started our descent so had to drink very quickly!

KLM remains a quality flag carrier airline which maintains its standards whilst all their competitors are lowering theirs.

Our first flight was delayed so we missed our connecting flight. However it was easy to book a later flight on their app.

The service was great. However the lounge only gets passing grade

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

Extremely bad BAD BAD BAD. NEVER TURKISH AIRLINES EVER AGAIN..PIRATES COMPANY.

Typically great service from Turkish with comfortable seat and amenitie, good food and great attention from staff.

Delicious food, comfortable and clean plane. It's a little cramped in the hall in front of the gate.

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.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

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

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

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

Kayak and Aran grant issuing business class tickets without lounge access and sometimes 1 or 2 connections in economy class. It’s very disappointing to find out that after buying the ticket. Never buy tickets on kayak and Aran grant again

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.

efficient. on time. cabin crew were very professional and very nice to deal with. would definately fly BA again.

It was great overall. A few slight improvements could be made on the onboarding process at the Gates with announcements and clarity of communications (both at the gate and in flight). The movies in the entertainment options could be improved for bollywood, hollywood.

I alrady responded to this request, and expllaned at length that this was the worst flying experience in my 77 years. I will NEVER fly BA again.

Airbus A350 is poorly designed for wheelchair users and reduced mobility passengers. The angle of the pods makes it awkward to transfer. I was able to but I have ab stability. It could be a real challenge for people with more severe mobility impairments. You'd think Airbus would have come up with a solution for this or thought more about us disabled folks more when designing this aircraft.

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

The crew has always been great on BA. They are very friendly and accommodating. I like that they have vegetarian options already in the menu. And the free wine is a nice perk.) I noticed (both directions of my trip) minor upgrades/ replacements needed on the plane itself (touch screen didn't work with touch; bathroom light didn't go on). However, this is one of my favorite airlines.

Charging for the internet in business is penny wise pound foolish. WIn €20 lose customer goodwill

Everything was spectacular except the boarding. It was just a mob of people while all groups were called over the public address system.

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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.