R9 577 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 22/1. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest return fare
R14 299
Typical prices: R15 645-R20 871
Turkish Airlines
Wed 29/4Fri 8/5
JNB - ORD • 1 stop
Cheapest one-way flight
R9 577
Typical prices: R26 865-R62 035
Multiple Airlines
Thu 22/1
CPT - ORD • 3 stops
When to travel
February
Cheapest • 11% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Apr 29 - Fri, May 8
Turkish Airlines Logo
18:00 - 9:40
JNB
-
ORD
22h 40m1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m1 stop
R14 299Turkish Airlines
Sun, Feb 1 - Sun, Feb 8
Turkish Airlines Logo
19:05 - 10:05
JNB
-
ORD
23h 00m1 stop
Turkish Airlines Logo
20:20 - 10:50
ORD
-
JNB
30h 30m1 stop
R14 795Turkish Airlines
Mon, Feb 16 - Mon, Feb 23
Turkish Airlines Logo
16:00 - 18:25
DUR
-
ORD
34h 25m2 stops
Turkish Airlines Logo
11:50 - 13:30
ORD
-
DUR
41h 40m2 stops
R15 092Turkish Airlines
Fri, Jan 16 - Thu, Jan 29
United Airlines Logo
20:50 - 13:15
CPT
-
ORD
24h 25m2 stops
United Airlines Logo
11:00 - 16:10
ORD
-
CPT
21h 10m2 stops
R15 422United Airlines
Fri, Jan 16 - Thu, Jan 29
United Airlines Logo
20:50 - 13:15
CPT
-
ORD
24h 25m2 stops
United Airlines Logo
10:52 - 16:10
ORD
-
CPT
21h 18m2 stops
R15 439United Airlines
Wed, Apr 29 - Fri, May 8
Ethiopian Air Logo
8:20 - 8:15
JNB
-
ORD
30h 55m2 stops
Ethiopian Air Logo
10:15 - 13:05
ORD
-
JNB
19h 50m1 stop
R16 627Ethiopian Air
Thu, May 28 - Thu, Jun 4
British Airways Logo
18:50 - 19:15
CPT
-
ORD
31h 25m2 stops
British Airways Logo
16:53 - 11:00
ORD
-
CPT
35h 07m2 stops
R17 635British Airways
Thu, May 28 - Thu, Jun 4
British Airways Logo
18:50 - 19:15
CPT
-
ORD
31h 25m2 stops
British Airways Logo
16:53 - 11:00
ORD
-
CPT
35h 07m2 stops
R17 651British Airways
Wed, Apr 29 - Fri, May 8
KLM Logo
23:15 - 22:29
JNB
-
MDW
30h 14m2 stops
KLM Logo
9:20 - 21:20
MDW
-
JNB
29h 00m2 stops
R21 796KLM
Sat, Jun 27 - Wed, Jul 15
KLM Logo
23:15 - 21:45
CPT
-
MDW
29h 30m2 stops
KLM Logo
13:05 - 21:25
MDW
-
CPT
25h 20m2 stops
R44 747KLM
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 R15 818 on average for one-way flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from South Africa is R20 475 and R19 682 respectively. For return trips, the best month to travel is February with an average price of R15 818.

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 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 46 days 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, with an average flight price of R2 612.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 577
Most popular time to fly and prices are also 3% lower 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.

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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 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.
7,7
KLMOverall score based on 1435 reviews
7,2Food
8,4Crew
7,1Entertainment
7,6Comfort
7,7Boarding
Airline reviews

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

8,0 ExcellentKevin, Nov 2025
AMS - BOD
Read more KLM reviews

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

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

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

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Very bad experience with turkish airline tk 0001. Very uncomfortable seats and food ran out and crew was not helpful

The airline could improve its business class seats and privacy in line with its competitors.

To be prepared for being treated with disrespect by the ground crew.

Seats too much and for the price we paid eve thought economy we still had to pay $169 to check a ba that’s ridiculous and also my daughter needed water so she can take her medicine we push the boton for the attendant to get us water they never came we push it 3 times no one came and ask what we needed . Am not happy with the service at all I will not fly with TK anymore

Boarding experience was a mess- both to and from Istanbul airport. No one knew anything. They asked everyone to line up according to their sit numbers- it was unbelievable. Business class had a separate line, but it was hard to find- I had to go through all that mess before finding it. Would not recommend

Excellent food and service on my international flight. Most notable is the food provided by Turkish even for coach passengers is very good.

They can my date of travel and let me standard in Istanbul for three days stop over and only pay for one day in a hotel with only one breakfast for three days.

the flight was cancelled and I was rebooked twice, once 26 hours later, then another 24 hours later. In total the flight was delayed for 40 hours. Never again will I use kayak or Turkish Airlines for my travel.

Worst experience with boarding once we left the wheel chair even traveling business we had to wait with all the crowd for the bus to take us to the plane then climb the stairs with our bags When you pay extra for comfort and convenience and you don’t get any is disappointing

Food is very turkish. No regard for other natinalities taste and preference. The entertainment can be improved- it was the same menu on 10/8/25 and 10/25/25. The boarding is the worst in the airline industry- I suggest you ask your staff to and watch how other airlines do it.

Delay not posted, only departure time listed- not boarding time. We left an hour late and arrived 45 min late. Restrooms had backed up sinks and toilets not flushed ) passenger error). Lots of screen for entertainment didn’t work. But we arrived with our luggage

Check in took over an hour because printer was not working. Attendant did not know how to give free layover Addis Ababa hotel vouchers or update frequent flyer number. After repeated attempts, got voucher emailed. However hotel wanted printed voucher hence more delay. Bus time from hotel back to airport was printed 4:50 hours, but hotel reception called at 3 pm saying bus will leave at 4 pm. Then hotel reception called again saying 4:15 pm. We rushed at 4:15 pm and bus was not ready until 4:40 pm. Many audio outlets were not working in planes.

I had a memorable experience. I dont have any comments at this time regarding waht could be better.

It is nice and great but the houstees crew are all the way back arguing with customers and behavior issues same of the crew i saw that also all the trips were very much butter!

The food was terrible and the seating was uncomfortable, but the airline did a great thing letting us board in Abbis Ababa on our connecting flight after our original flight was very delayed.

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.

Entertainment devices on A380 need to be fixed, the seats might do with updates.

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

Check-in and boarding were great. On flight staff were rude and disrespectful. Paid for extra room and found it incredibly cramped. Bathrooms kept in poor condition. Overall negative experience.

Great seat in premium economy, great food and drinks throughout lots of in flight entertainment. 1 hour 40 min delayed flying out , 2 1/2 hour wait at passport control in tampa

Plane was extremely delayed, but not all of it was BA fault (some was). Worst part was lack of room - this had as much space as an Allegiant flight. I thought transatlantic usually gave you an extra inch or two, but not this one. Entertainment system sporadically worked and didn’t have great options. Overhead bins are old and tiny, not as good as aunties new planes.

My seat cushion was poor. The cushion was compressed and was uncomfortable for such a long flight.

Besides having a LONG layover in Philadelphia to begin with, our flight was delayed and left late. We spent 7 hours in the Philadelphia airport after being in the air 7 hours from Portugal to Philly. It turned into a 24 hour day of travel which was exhausting. I know you can't help weather but our layover was difficult as my husband is handicapped. The staff was EXTREMELY helpful with his wheelchair tho!!

I was in a bulkhead seat and my tray table wasn't level. Eating was difficult.

Audi visual not working for a whole group of seats in first class. How does a plane leave the main hub in such poor condition? How much that we can’t see so immediately is also compromised?

main meals are horrible but then you dont fly for the food

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
New Buffalo

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.