R10 288 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 7/5. 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.
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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
8:20 - 8:40JNB-ORD
31h 20m1 stop
10:15 - 20:00ORD-JNB
26h 45m1 stop
R15 772Ethiopian Air
Find Deal
Wed, Mar 19 - Thu, Mar 27
17:50 - 17:55JNB-ORD
31h 05m1 stop
19:50 - 10:35ORD-JNB
31h 45m1 stop
R16 011Turkish Airlines
Find Deal
Tue, Jun 10 - Wed, Jun 18
19:25 - 14:00JNB-ORD
25h 35m2 stops
17:16 - 9:25ORD-JNB
33h 09m2 stops
R18 348British Airways
Find Deal
Sun, Jun 22 - Wed, Jul 2
21:15 - 11:50JNB-ORD
21h 35m1 stop
20:40 - 7:00ORD-JNB
51h 20m2 stops
R18 514British Airways
Find Deal
Tue, Jun 10 - Thu, Jun 19
19:50 - 14:16CPT-ORD
25h 26m2 stops
16:45 - 17:20ORD-CPT
41h 35m2 stops
R19 655United Airlines
Find Deal
Mon, May 26 - Mon, Oct 13
18:25 - 14:10CPT-ORD
26h 45m2 stops
13:25 - 21:10ORD-CPT
24h 45m2 stops
R19 931KLM
Find Deal
Sun, Apr 13 - Sun, Apr 27
18:25 - 15:45CPT-ORD
28h 20m1 stop
20:35 - 11:35ORD-CPT
32h 00m1 stop
R21 274Emirates
Find Deal
Sun, Jun 1 - Mon, Oct 13
20:00 - 18:05CPT-ORD
29h 05m2 stops
10:45 - 15:20ORD-CPT
21h 35m1 stop
R21 495United Airlines
Find Deal
Sun, Jun 1 - Thu, Jul 10
23:15 - 18:28JNB-MDW
26h 13m2 stops
13:00 - 21:20MDW-JNB
25h 20m2 stops
R23 280KLM
Find Deal
Tue, Jun 10 - Thu, Jun 19
18:50 - 15:45JNB-ORD
27h 55m1 stop
20:35 - 16:15ORD-JNB
36h 40m1 stop
R28 617Emirates
Find Deal
Sat, Mar 29 - Wed, Apr 16

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 R20 638. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are R22 828 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 October, where tickets cost R18 017 on average for return flights. On the other hand, the most expensive months are August and January, where the average cost of tickets from South Africa is R22 176 and R21 863 respectively. For one-way flights, the best month to travel is October with an average price of R18 017.

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 evening, when round-trip flights cost R18 980 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 R19 590.

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. For the absolute cheapest price, our data suggests you should book 20 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 662.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

June

Cheapest flight

R10 288
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly (4% more expensive 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.

  • 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 October.
  • 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, +75 more

ANA, Aer Lingus, +76 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, +78 more

ANA, Aer Lingus, +79 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, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 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, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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 1331 reviews
7,2Entertainment
7,8Boarding
8,3Crew
7,3Food
7,7Comfort
Airline reviews

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.

2,0 Mediocredale, Feb 2025ACC - AMS
Read more KLM reviews

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.

Overall very poor. Flight was disorganised, staff were rude and this is my second experience with KLM that I've had baggage go missing. It feels like, if you are an economy customer, KLM staff do not show you any care. I shall never fly with KLM again. Worst airline in Europe

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

Great boarding, great short flight but no entertainment whatsoever. It was supposed to have wifi but that did not work.

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 food. Excellent crew service. Clean aircraft. Narrow seats and isle.

There was fog in Amsterdam so many flights were delayed because of the weather. Air France knew that the flight would be delayed by two hours but still boarded the plane on time. Instead of letting the passengers wait at the gate we were crammed into the plane. It was uncomfortable. No refreshments were given. I couldn’t charge my devices onboard.

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.

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

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

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

In sharp contrast to the modern glitzy airport, boarding facilities were primitive. Passengers had to board buses and walk up steep stairs in bitter cold with carry-on baggages. I found no reason why aerobridge was not provided.

Service and food were decent, seats are a bit too narrow. Leg room is normal. Bathroom should be cleaned more frequently. WiFi is cumbersome and should be simplified.

they have cancell the flight with no reasons, My parents were in the cold weather in the airport for 24 hours they did not give any hotel and food. I hate Turkish Airline, this is our last time that we ha ve chosen Turkish Airline.

Same as before boarding process and lack of crew experience in the process

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.

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

It was very bad experience with Ethiopian airlines . The flight was delayed in both ways . On the way coming back one of the crews dropped hot coffee on my whole body and other crew dropped used dirty glasses on top of me . The same crew that dropped hot coffee on me hit me with the food trolley on my knee while I was sleeping . I couldn’t sit properly due to the pain on my knee caused by those irresponsible crews . Very unprofessional airlines

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.

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

Terrible customer service I lost my bag luggage and I still haven’t received any information

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: It arrived, Dislike: Boarding was a separate corridor with no counter announcements at the passenger waiting area. Very dirty airplane and toilets, food options were terrible - everything even the vegetarian option was a curry spice. Many other passengers using the toilets would not lock the door and kept door partially open during use - flight attendants would not enforce or direct them to lock it and light turns on, no entertainment options at all, other passengers would be singing and not peaceful. Atrocious flight experience.

Seating is tight if you don’t upgrade. Food was decent. Boarding and unboarding was efficient. Smooth flight. Could make upgrades more affordable

Boarding was chaotic. Glad we were group 5 and still had cabin storage available when we boarded. I was expecting crew would get our carryons at the gate since theyclaimed it was a full flight.

Boarding crew is unfriendly as i was asked to handover carryon luggage too upto final destination Bangalore I was not prepared for that and i had to travel without my diabetic and hypertension medicines

American Airlines seemed to run a 'dry' flight. No alcohol was offered at any point with meals. Breakfast was a bit tasteless. The 'hot pocket' whatever that is, was horrid breadish pastry with very little filling. Decaf coffee was horrid. Seats didn't seem as wide or spacious as usual, especually for a ten hour flight.

They did not provide free WiFi, It could be purchased for, I think, around $25, This seemed excessive.

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

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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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