R10 636 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 5/9. 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

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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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, Jan 21 - Sat, Feb 7
SWISS Logo
20:15 - 16:20JNB-ORD
28h 05m1 stop
SWISS Logo
18:50 - 10:30ORD-JNB
31h 40m1 stop
R14 342SWISS
Find Deal
Sun, Sep 21 - Sun, Sep 28
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
13:55 - 8:20ORD-JNB
35h 25m1 stop
R14 485Etihad Airways
Find Deal
Mon, Oct 6 - Mon, Oct 13
Etihad Airways Logo
9:50 - 8:45JNB-ORD
29h 55m1 stop
Etihad Airways Logo
13:55 - 8:20ORD-JNB
35h 25m1 stop
R14 538Etihad Airways
Find Deal
Sun, Sep 21 - Sun, Sep 28
United Airlines Logo
21:20 - 21:16JNB-ORD
30h 56m2 stops
United Airlines Logo
8:00 - 17:45ORD-JNB
26h 45m2 stops
R14 663United Airlines
Find Deal
Sun, Jan 18 - Wed, Feb 4
United Airlines Logo
19:45 - 15:20JNB-ORD
27h 35m1 stop
United Airlines Logo
13:45 - 18:35ORD-JNB
20h 50m1 stop
R14 930United Airlines
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Mon, Oct 6 - Tue, Mar 24
Turkish Airlines Logo
17:55 - 9:40JNB-ORD
22h 45m1 stop
Turkish Airlines Logo
21:20 - 10:50ORD-JNB
30h 30m1 stop
R15 518Turkish Airlines
Find Deal
Tue, Jan 20 - Wed, Feb 4
Turkish Airlines Logo
19:10 - 10:05JNB-ORD
22h 55m1 stop
Turkish Airlines Logo
20:20 - 10:50ORD-JNB
30h 30m1 stop
R16 266Turkish Airlines
Find Deal
Thu, Dec 11 - Sun, Jan 4
British Airways Logo
22:00 - 13:50JNB-ORD
23h 50m1 stop
British Airways Logo
21:45 - 10:25ORD-JNB
28h 40m1 stop
R17 923British Airways
Find Deal
Sun, Sep 21 - Sun, Sep 28
KLM Logo
18:50 - 21:36JNB-MDW
33h 46m2 stops
KLM Logo
18:15 - 8:30MDW-JNB
31h 15m2 stops
R20 275KLM
Find Deal
Thu, Oct 9 - Fri, Oct 31
KLM Logo
23:15 - 18:25JNB-MDW
26h 10m2 stops
KLM Logo
15:00 - 22:05MDW-JNB
24h 05m2 stops
R78 553KLM
Find Deal
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 R17 300 on average for return flights. On the other hand, the most expensive months are December and January, where the average cost of tickets from South Africa is R21 718 and R21 326 respectively. For one-way flights, the best month to travel is February with an average price of R17 300.

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 5 weeks before departure, which saves you about 15% compared to booking last minute. 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 163.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonFebruary
Cheapest flightR10 636
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly and prices are also 2% 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

  • 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as R19 979. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R22 100 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost R1 031 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is R1 064.

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.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop 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, +78 more

ANA, Aer Lingus, +79 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, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

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 1381 reviews
7,3Food
7,8Boarding
7,7Comfort
7,1Entertainment
8,4Crew
Airline reviews

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

6,0 GoodKathleen P, Jun 2025EDI - AMS
Read more KLM reviews

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

Klm start boarding while somw air issue in the plan

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

Cabin crew professional, polite and friendly, boarding was seemless, but come on KLM surely you can do better than a pack of cheesy biscuits as an inflight snack

Cabin crew were excellent, very proffesional, polite and friendly, in flight snack was underwhelming, a packet of cheese biscuits, im sure KLM could run to a sandwich!

Legroom not all it could be, especially when the seat in front is reclined. Otherwise it was good, food and beverage were nice.

This portion of the flight was through Indigo. A local carrier. So all economy seating. No real service some refreshments for purchase standard economy stuff.

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

They only had vegetarian food left on the flight which I wasn’t happy about. I didn’t get any food to eat at all.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Small seat space for 13 hours flight, they charged for baggage , very bad quality of food,

I was sitting almost in the back, the seats are very tight and there’s no legroom, it’s uncomfortable for a long distance

Absolute worst airline. Charged us $720 to check 4 bags (2 of which were carry-on). Entertainment systems didnt work. And on a 12 hour flight they served 2 meals and never once came around outside of those 2 meals with a beverage or cup of water. Will never fly them again.

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.

Amazing trip! No delays, no broken or lost luggage, and amazing food.

The food we received during the flight was excellent. The service was very friendly. Definitely the best value for the money when flying across the Atlantic.

I use a wheelchair for mobility. Both in my flight from Houston and back to Houston from Istanbul, the Turkish airline staff asked that I claim my wheelchair at the luggage area. On arrival to Istanbul, parts of the wheelchair were in disarray at that time I raised no objection however upon claiming my wheelchair in Houston parts where outright missing. In both occasions, upon arriving in Houston and arriving in Istanbul, I asked multiple times why am made to pick up my wheelchair in the baggage claim rather than at the jet bridge. Getting the wheelchair at the jet bridge minimizes the probability of loosing parts because they can be hopefully reclaimed on the spot. I was told in Houston that a manager turned down my request to claim the wheelchair at the jet bridge in Houston. This is extremely frustrating because a wheelchair is not a set of clean underwear or a toothbrush- this is the way I move. A Turkish Arline staff took my complaint at the luggage claim area in Houston but as of the writing of this review the only contact I have received from the airline is because I initiated a claim rather than her as she told me she would.

The security at the airport was excellent. The one criticism is the boarding process just before entering the plane. There were only 2 boarding lines and there were no barriers thus leading to a mass rush to enter the plane. I suggest that they board by rows, eight or ten rows at a time to prevent the mass rush to enter the plane. Otherwise, I would highly recommend Turkish Airlines

Everything was very good, except that the plane was an hour and a half late

The flight is packed and it feels like the space per individual has gotten smaller. Excruciating for a 14hr flight.

Were not told that carryon laggage has to be only 12 kgs but my bag was heavier asked to pay an additional $550.00. I could have upgraded to a bussiness class for that price and no one at the gate to upgrade but able to take money for the extra weight. I felt like this was a setup scam.

Lost suite case and pillow that’s used by senior and they didn’t leave it at the airport

The flight itself was fine. The exception is that my luggage was destroyed, and I filed a claim that I haven't heard from anyone.

Im if Ethiopian can allow customers to use their mileage for in flight connexion it will be great.

United was best airlines I have seen since I got there choose united airlines

It was wonderful best Air lines covert and all very happy with their service they have been very helpful and friendly

No Asian Vegetarian food was available on this sector but only fish and chicken and pasta were offered.

Needs improvement because some of the tvs and charging ports weren’t working

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.

The booking agent, cheapflightsfares, messed up, and the information for the seats we paid extra for was not sent to American Airlines. We were separated on the return flight and sent to the lowest economy section. The flight attendant helped arrange seating at the back of the plane to allow my wife and me to sit together.

I liked the comfort of the seats, very attentive crew, and the meals were excellent.

We were kicked off this flight by British Airways due to delays on our connecting flight also operated by British airways and were rebooked on a different carrier which delayed our arrival home by > 26 hours.

Everything about the flight check-in was smooth no line the plane is clean and bathroom

Excellent everywhere but Philly, the most rotten airport in the world.

Check in was not the greatest as had to talk to an agent to clarify things and then he transferred us to another agent who had difficulty processing my credit card as there was a system glitch and not a card error.

I was put into business class. Wow! My flight attendant was great! The food amazing’

The gate at London Gatwick had confusing signs for the different zones and the staff seemed harried because people didn't know when it was their turn to come to the desk. Plus, with there were too many carry-on bag travelers, myself included. The charge scheme for checking bags is frustrating. If you travel light, you want the freedom to leave as soon as you deplane. When you are forced to gate-check your bag simply because the flight is fully booked, you lose whatever time you'd hoped to save because you're still stuck waiting for your bag to come off the conveyor belt.

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

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

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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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