R10 774 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 25/3. 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.
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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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Cheap Flight Deals 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.

Recent return flight deals to Chicago

Recommended return deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
17:50 - 9:50JNB-ORD
23h 00m1 stop
19:50 - 10:35ORD-JNB
31h 45m1 stop
R15 912Turkish Airlines
Find Deal
ث, أبريل 22 - ن, مايو 5
19:05 - 18:35JNB-ORD
31h 30m1 stop
20:30 - 10:45ORD-JNB
30h 15m1 stop
R15 951Turkish Airlines
Find Deal
ر, فبراير 12 - ر, فبراير 19
8:20 - 8:05JNB-ORD
30h 45m2 stops
10:15 - 13:05ORD-JNB
19h 50m1 stop
R17 173Ethiopian Air
Find Deal
ن, أبريل 21 - ث, مايو 6
14:35 - 7:40JNB-ORD
25h 05m2 stops
10:15 - 13:10ORD-JNB
19h 55m1 stop
R17 651Ethiopian Air
Find Deal
س, مارس 1 - س, مارس 15
22:00 - 14:34JNB-ORD
24h 34m2 stops
10:35 - 18:35ORD-JNB
24h 00m2 stops
R17 956United Airlines
Find Deal
خ, فبراير 6 - خ, فبراير 20
18:30 - 9:01CPT-ORD
46h 31m2 stops
21:05 - 18:00ORD-CPT
36h 55m2 stops
R18 090United Airlines
Find Deal
ر, فبراير 12 - س, فبراير 22
23:20 - 18:11CPT-MDW
26h 51m2 stops
11:25 - 22:10MDW-CPT
26h 45m2 stops
R18 186KLM
Find Deal
ر, فبراير 12 - س, فبراير 22
21:15 - 17:38JNB-ORD
28h 23m2 stops
21:45 - 10:20ORD-JNB
28h 35m1 stop
R18 472British Airways
Find Deal
ن, يناير 27 - خ, يناير 30
19:25 - 18:45JNB-ORD
31h 20m1 stop
21:45 - 10:20ORD-JNB
28h 35m1 stop
R18 568British Airways
Find Deal
ن, يناير 27 - خ, يناير 30
23:55 - 14:30JNB-ORD
22h 35m1 stop
17:25 - 22:00ORD-JNB
21h 35m1 stop
R20 745KLM
Find Deal
س, مارس 1 - س, مارس 15

Flights to Chicago - Travel Insights & Trends

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 day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as R21 422. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R23 695 on average.

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 November, where tickets cost R18 415 on average for return flights. On the other hand, the most expensive months are August and June, where the average cost of tickets from South Africa is R29 055 and R24 451 respectively. For one-way flights, the best month to travel is February with an average price of R17 593.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost R21 052 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is R22 479.

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 8 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 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 228.

Good to know

Low season

January

High season

June

Cheapest flight

R10 774
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Cape Town 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly from South Africa is February.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

South Africa to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Sunday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Sunday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

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 1336 reviews
7,2Entertainment
7,7Comfort
8,4Crew
7,3Food
7,8Boarding
Airline reviews

Great boarding, great short flight but no entertainment whatsoever and no wifi. Prepare to disembark by a staircase.

10,0 ExcellentAnonymous, Dec 2024BRU - AMS
Read more KLM reviews

Great boarding, great short flight but no entertainment whatsoever and no wifi. Prepare to disembark by a staircase.

Transfer at CDG to connecting KLM flight to Amsterdam was a NIGHTMARE. LONG WALKWAYS, NO MOVING WALKWAYS, POOR signage, Have to take a train & No staff visible to help navigate the maze. AVOID TRANSFER AT CDG AT ALL COST.

Good flight with KLM, friendly staff. Food was good, had much worse on other airlines. Selection of drinks also good enough for us. Entertainment was also good. The economy seats are ok and that’s it. For a 12 hour flight I think a little more comfort in the economy seats in pitch and softness would be highly appreciated by the customers and can makte the difference.

I tried to upgrade to premium economy anis seat online during the checkin process. The payment didn’t work due to a technical glitch on KLM’s website. I wasn’t able to change my seat unless I called Amsterdam. Since I was in Canada and there’s a time difference this wasn’t practical. So when I arrived early to Ottawa airport my seat wasn’t available and I could only get a middle seat in premium economy which isn’t great. These middle seats are priced at the same rate as an aisle seat which makes no sense.

The food & entertainment really stood out in terms of quality. The nasi goreng & chicken satay were absolutely delicious. It’s great that KLM feature international cuisine.

Transavia flight, was booked as KLM but i couldnt select seat or access boarding pass with KLM at all. Crammed seating and very no frills experience all around. First and last time.

Transavia flight. Couldn't select seat or anything prior to flight. No connection with klm systems. Seats are very crammed. Extremely no frills.

Seats were nice and comfy. Crew was polite and attentive. Business class is awesome and worth the money.

Overall a very pleasant flight. No significant issues on either flight. Amsterdam airport is very convenient for connecting

The IFE was quite old, but it worked fine and the content was good. The cabin crew were excellent and the food was as also very good

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Turkish Airlines is amazing. I have a problem with the ticket I purchased through the kayak website. I have filed a complaint related to the fact that I was contacted by phone on the day I purchased the ticket and told that the amount that the ticket had been advertised for was not accurate and that I had to pay more. This is totally fraudulent. I will look into addressing this further tomorrow and will never ever use kayak again.

Bad service and food was not good. Give very less food.

Crew members, pilots and flight attendants are excellent. Beside, that, customer service is very lacking in all aspects of Turkish airlines

The ac did not work and the plane was deployed for the AC BUT IT NEVER WORKED. I have high blood pressure and I was SWEATING AND NEARLY PASSED OUT. Do better.

For me it was a good experience… thank you Turkish Airlines

Old aircraft, very very low business class standards, no privacy between the seats, horrible old TVs, tiny bathrooms.

Good service, the airline also provided a traveling kit bag (tooth brush, socks, slippers, visor for sleeping).

The seats have to be one of the worst when it comes to comfort and you have to scramble around to out your handbag in the overhead. The food is still awful. Definitely will not travel on Turkish again and wouldn’t recommend it to anyone for sure.

It was very good and it was not my first time I always take Turkish air line for my travels

Food excellent Bathrooms improve cleanliness needed Staff fairly well attentive Entertainment fair Seats lie flat worked well

The plane was overbooked and the crew was very rude. My luggage was never put on the plane. I got to NY and waited 2 hours just to find out that my luggage was left.

My experience was great. The flight attendants were very helpful and nice, and the food was very good.

Food was really not appealing. There was a blocked sink in the toilet. Toilet is cramped and the wall between the 2 toilets are not secured properly.

I felt all of the food tasted the same. And we had five meals over the 16 hrs in the air.

Plane was late with no information or announcement … had to walk up n downstairs.., had not communicated this … and ppl had suitcase to carry .

Like: Plane made it to the destination. Dislike: Food is terrible, no entertainment, very dirty airplane.

The food needs to improve especially the fish as there where only 3 fish cubes in my plate.

I had a full row so can't imagine how this could be better

Boarding was delayed and people were just sitting there like lost.

The boarding area was too small with only one agent checking passengers into their standing bus

Less than average, low level of shared required information needed during the transfer from airport to another, also the used team during boarding In Indianapolis station is Not Professional

Reliable, great value, but not outstanding in any aspect. This is similar to the experience you get in most international carriers like Etihad or Delta.

Flight got diverted because of an emergency and the crew were fantastic and probably saved that passenger’s life. While in emergency landing some measures could have been taken to prevent additional delays. In general not great experience with BA. I used to fly BA years ago all the time, very disappointed by the whole experience, seats were tight, bathrooms tight.

Business class area too small and chair and equipment not comfortable .

Lost my luggage in London Was double charged for luggage

Boarding could have been better organized. The one member of staff disappeared for a while so boarding by group relied on honesty.

I never made this flight but the staff helped to get me rebooked (see previous review)

No land services during boarding, specially while moving from terminal to another

Even the carry-ons were not allowed and upon getting down, we had the wait for the longest time for the baggage to put on the jet aisle. We had a short connection which British Airways kept changing and made out entire experience poor. I would never fly BA again.

The seat was very uncomfortable. It helped to use the foot rest. Could not sleep because of the seat.

Book Cheap Chicago Plane Tickets

Recent return flight deals

 
These are the cheapest return flights to Chicago found on KAYAK in the last 72 hours.
22/4ث
1 stopTurkish Airlines
23h 00mJNB-ORD
5/5ن
1 stopTurkish Airlines
31h 45mORD-JNB
R15 912
12/2ر
1 stopTurkish Airlines
31h 30mJNB-ORD
19/2ر
1 stopTurkish Airlines
30h 15mORD-JNB
R15 951
21/4ن
2 stopsEthiopian Air
30h 45mJNB-ORD
6/5ث
1 stopEthiopian Air
19h 50mORD-JNB
R17 173
1/3س
2 stopsEthiopian Air
25h 05mJNB-ORD
15/3س
1 stopEthiopian Air
19h 55mORD-JNB
R17 651
6/2خ
2 stopsUnited Airlines
24h 34mJNB-ORD
20/2خ
2 stopsUnited Airlines
24h 00mORD-JNB
R17 956
12/2ر
2 stopsUnited Airlines
46h 31mCPT-ORD
22/2س
2 stopsUnited Airlines
36h 55mORD-CPT
R18 090
12/2ر
2 stopsKLM
26h 51mCPT-MDW
22/2س
2 stopsKLM
26h 45mMDW-CPT
R18 186
27/1ن
2 stopsBritish Airways
28h 23mJNB-ORD
30/1خ
1 stopBritish Airways
28h 35mORD-JNB
R18 472
27/1ن
1 stopBritish Airways
31h 20mJNB-ORD
30/1خ
1 stopBritish Airways
28h 35mORD-JNB
R18 568
1/3س
1 stopKLM
22h 35mJNB-ORD
15/3س
1 stopKLM
21h 35mORD-JNB
R20 745

Search by stops

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
25/3ث
1 stopTurkish Airlines
24h 55mCPT-ORD
R10 774
16/4ر
1 stopTurkish Airlines
24h 15mCPT-ORD
R11 137
26/2ر
1 stopEtihad Airways
30h 25mJNB-ORD
R11 576
31/1ج
1 stopQatar Airways
37h 40mJNB-ORD
R11 595
25/3ث
2 stopsEthiopian Air
25h 50mCPT-ORD
R13 639
25/2ث
3 stopsEthiopian Air
35h 40mJNB-ORD
R17 307
16/4ر
2 stopsKLM
26h 04mCPT-MDW
R20 058
19/3ر
2 stopsKLM
39h 00mCPT-ORD
R43 859
17/3ن
1 stopBritish Airways
25h 05mCPT-ORD
R78 530
3/6ث
3 stopsUnited Airlines
27h 48mJNB-ORD
R241 322

Search by stops

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Search by price

Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
15/1ر
multi-stopBritish Airways
25h 30mJNB-ORD
19/1ح
multi-stopBritish Airways
31h 45mORD-JNB
R22 025
15/1ر
multi-stopAmerican Airlines
28h 09mJNB-ORD
19/1ح
multi-stopAmerican Airlines
28h 20mORD-JNB
R22 885
15/1ر
multi-stopAmerican Airlines
28h 09mJNB-ORD
19/1ح
multi-stopAmerican Airlines
30h 00mORD-JNB
R22 961
15/1ر
multi-stop
26h 30mJNB-ORD
19/1ح
multi-stop
28h 20mORD-JNB
R26 935
15/1ر
multi-stopAmerican Airlines
26h 30mJNB-ORD
19/1ح
multi-stopAmerican Airlines
30h 00mORD-JNB
R27 317
15/1ر
multi-stopAmerican Airlines
28h 23mJNB-ORD
19/1ح
multi-stopAmerican Airlines
30h 00mORD-JNB
R30 411
15/1ر
multi-stopDelta
26h 26mJNB-MDW
19/1ح
multi-stopDelta
23h 41mMDW-JNB
R33 086
15/1ر
multi-stopDelta
30h 07mJNB-MDW
19/1ح
multi-stopDelta
25h 26mMDW-JNB
R33 200
15/1ر
multi-stopDelta
30h 07mJNB-MDW
19/1ح
multi-stopDelta
29h 00mMDW-JNB
R33 257
15/1ر
multi-stopDelta
32h 25mJNB-MDW
19/1ح
multi-stopDelta
29h 00mMDW-JNB
R54 595

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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.

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