R9 004 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 9/2. 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 14% 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
R17 612
Overall average: R16 392
British Airways
Fri 6/2Mon 9/2
JNB - ORD • 2 stops
Cheapest one-way flight
R9 004
Turkish Airlines
Mon 9/2
DUR - ORD • 2 stops
When to travel
February
Cheapest • 10% 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

Fri, Feb 6 - Mon, Feb 9
British Airways Logo
22:00 - 19:49JNB-ORD
29h 49m2 stops
British Airways Logo
20:45 - 10:25ORD-JNB
29h 40m1 stop
R17 612British Airways
Find Deal
Tue, Mar 10 - Wed, Jul 29
Lufthansa Logo
19:45 - 13:10JNB-ORD
24h 25m2 stops
Lufthansa Logo
21:40 - 6:40ORD-JNB
26h 00m1 stop
R17 647Lufthansa
Find Deal
Mon, Dec 15 - Thu, Jan 8
Ethiopian Air Logo
8:20 - 7:40JNB-ORD
31h 20m2 stops
Ethiopian Air Logo
9:45 - 20:10ORD-JNB
26h 25m1 stop
R17 698Ethiopian Air
Find Deal
Sun, Mar 8 - Sun, Aug 2
British Airways Logo
22:00 - 14:50JNB-ORD
23h 50m1 stop
British Airways Logo
18:35 - 7:00ORD-JNB
29h 25m2 stops
R17 784British Airways
Find Deal
Sun, Dec 14 - Wed, Dec 31
KLM Logo
23:59 - 14:20JNB-ORD
22h 21m1 stop
KLM Logo
16:25 - 22:05ORD-JNB
21h 40m1 stop
R17 956KLM
Find Deal
Wed, Feb 4 - Sun, Feb 8
Turkish Airlines Logo
17:15 - 10:05CPT-ORD
24h 50m1 stop
Turkish Airlines Logo
20:20 - 11:50ORD-CPT
31h 30m1 stop
R17 956Turkish Airlines
Find Deal
Sat, Feb 14 - Wed, Feb 18
Turkish Airlines Logo
11:15 - 18:25DUR-ORD
39h 10m2 stops
Turkish Airlines Logo
20:20 - 13:30ORD-DUR
33h 10m2 stops
R17 990Turkish Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 31
KLM Logo
19:20 - 16:22JNB-ORD
29h 02m2 stops
KLM Logo
16:25 - 22:05ORD-JNB
21h 40m1 stop
R18 007KLM
Find Deal
Wed, Mar 11 - Thu, Jul 30
United Airlines Logo
10:25 - 9:21JNB-ORD
29h 56m2 stops
United Airlines Logo
11:15 - 20:30ORD-JNB
26h 15m2 stops
R18 179United Airlines
Find Deal
Wed, Feb 4 - Sun, Feb 8
Ethiopian Air Logo
14:35 - 7:40CPT-ORD
25h 05m2 stops
Ethiopian Air Logo
9:45 - 13:00ORD-CPT
43h 15m1 stop
R22 544Ethiopian Air
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 R16 461 on average for one-way flights. On the other hand, the most expensive months are January and July, where the average cost of tickets from South Africa is R20 602 and R20 533 respectively. For return trips, the best month to travel is February with an average price of R16 461.

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 553.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 004
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Durban to Chicago

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 tickets can be as cheap as R19 269. On the other hand, the most expensive day to fly is Saturday, where prices are R21 314 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 flights cost R17 721 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 R18 290.

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, +75 more

ANA, Aer Lingus, +76 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to South Africa

Monday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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 1412 reviews
8,4Crew
7,1Entertainment
7,8Boarding
7,3Food
7,7Comfort
Airline reviews

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

2,0 MediocreAbisola, Oct 2025CDG - AMS
Read more KLM reviews

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.

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

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

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.

The best airline for international travel in terms of value you get in business class (service/cost)

I liked the overall flight experience. However, Turkish officials could do a better job at guiding non-Turkish speakers to their connecting flight gates in such a huge & vast airport.

Very small and cramped aisles and seats. Food was poor but the fresh hot roll and hummus was good. No cans of soda given but they had small bottles of water. Crew was nice and pleasant and kept bathroom clean.

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

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

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.

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

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

It was good. Couldn’t Check in online and select seats

It was great. Enough space and room for legs . Great service to.

⭐ British Airways Review — A Journey of Highs, Lows, and Lessons ⭐ I recently flew Business Class round-trip from Boston to Mumbai with British Airways, and my experience was a tale of two extremes — from disappointment to exceptional service, and then back to inconsistency. Boston → London: A Surprisingly Poor Start My journey began on a disappointing note. On a 6-hour Business Class flight, I was surprised to discover that there wasn’t a single proper vegetarian meal option available. I was offered a few bakery items only after repeatedly requesting something to eat. The flight attendant shrugged, offered no solution, and eventually — quite literally — threw some bread at me after much delay. This was not only disheartening, it was extremely surprising given my wonderful Business Class experience with BA last year. I stepped off that flight genuinely hungry and had to make a mad dash to the lounge just to get a proper meal. London → Mumbai: A Complete Turnaround The next sector restored my faith in British Airways. The entire crew was warm, welcoming, attentive, and genuinely caring. A special shoutout to Phiroze and the entire team serving the Business Class cabin — their professionalism, hospitality, and thoughtful service were extraordinary. They truly embodied what makes British Airways a global leader, and I am deeply grateful for the experience they provided. This is the BA I know and love. Mumbai → London: A Strange Meal Schedule This sector was generally fine, but the meal timing was puzzling. Lunch at 10:30 AM — for a Business cabin — felt unusual, and most passengers, including myself, barely touched it. The rest of the service was smooth, but the scheduling definitely needs a rethink. London → Boston: Mixed Experience Again The flight itself was decent, but the Business Lounge at Heathrow for this leg was a letdown. Arrived during lunch hours: no hot vegetarian options available Lounge area: dirty dishes everywhere Even after politely alerting the staff, the dishes were ignored and left uncleared For a premium cabin passenger — and at one of the world’s busiest international hubs — this was disappointing. Overall Impression My journey with British Airways felt inconsistent — two great sectors sandwiched between two that fell short of the BA standard. When BA is good, it is world-class. When it misses, the gap is noticeable. I genuinely hope the airline takes this feedback as constructive insight. I continue to believe in British Airways, and I commend the outstanding crew on the London → Mumbai sector — they were the highlight of my entire trip. With a little more focus on vegetarian meal availability, lounge service, and consistency across crews, BA can ensure every Business Class passenger experiences the premium journey they promise.

We were in business class and I had seat # 1. This was a night flight and after dinner was served, lights were dimmed and I went to sleep. The crew were loud and noisy so I didn’t get much sleep. I expect the crew to enjoy themselves but would Appreciate some decency in staying quiet while the passengers sleep

Have travelled business class with other airlines who profess to be the best in the world. They can however not beat the service and comfort that BA provide.

Well unfortunately our connecting was cancelled and next flight delayed. Was in airport 9 hours. Flight itself was good. I’m sure it was a FAA problem.

Great on board entertainment Tasty food Cattle class obviously crammed but not as bad as shorter hall flights

I was attacked in the Miami airport and the staff did nothing. On my flight from London to Miami one of the flight attendants screamed at me and demanded I keep my seat in the upright position at all times during the fight so the man behind me was comfortable for the flight. I will never in my life use British airways again

Logan gate staff was unhelpful. Arrived early, come to find out the airbus scheduled was reassigned and I did not have a seat. The desk agent spoke to his supervisor who instructed him to give me a boarding pass to get up to gate area, he was polite. At the gate the fellow was sitting to the side with two other BA staff . I asked him if he could help me, his answer was” we are on a break, we are closed” then turned his back. I am almost 70, drove 4 1/2 hours to Boston and had been looking forward to this trip for 5 months. I have worked in service many times in my life and this is not how it is done. I eventually (1/2 hr) before boarding was able to get a seat. The rest of the flight experience was unremarkable.

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.