R9 872 Find Cheap Flights to Chicago – Compare and Save

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 5/10. 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
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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest return fare
R16 164
Delta
Sun 19/7Tue 28/7
CPT - MDW • 1 stop
Cheapest one-way flight
R9 872
Turkish Airlines
Mon 5/10
DUR - ORD • 2 stops
Top routes
Cheapest
Most popular
Insights
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When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 28% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 52% price drop
Most popular
Good to know
Good to know
+1
+1
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+1
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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

Sun, Jul 19 - Tue, Jul 28
Delta Logo
20:05 - 10:05
CPT
-
MDW
21h 00m
1 stop
Delta Logo
18:58 - 17:50
MDW
-
CPT
63h 52m
2 stops
R16 164Delta
Sun, Jul 19 - Thu, Jul 30
Delta Logo
20:05 - 18:03
CPT
-
ORD
28h 58m
2 stops
Delta Logo
6:35 - 17:50
ORD
-
CPT
28h 15m
1 stop
R16 164Delta
Tue, Sep 8 - Sat, Sep 26
KLM Logo
23:15 - 14:30
CPT
-
ORD
22h 15m
1 stop
KLM Logo
16:20 - 5:50
ORD
-
CPT
30h 30m
1 stop
R16 344KLM
Sat, Jul 18 - Thu, Sep 10
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 377KLM
Tue, Jul 21 - Wed, Jul 29
United Airlines Logo
20:00 - 11:53
CPT
-
ORD
22h 53m
1 stop
United Airlines Logo
21:40 - 15:20
ORD
-
CPT
34h 40m
1 stop
R16 443United Airlines
Tue, Jul 21 - Sun, Aug 9
United Airlines Logo
20:00 - 16:14
CPT
-
ORD
27h 14m
2 stops
United Airlines Logo
11:15 - 17:10
ORD
-
CPT
22h 55m
2 stops
R16 492United Airlines
Sat, Aug 1 - Sat, Aug 8
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
20:25 - 8:20
ORD
-
JNB
28h 55m
1 stop
R17 297Etihad Airways
Mon, Sep 7 - Wed, Mar 3
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R17 396Etihad Airways
Wed, Nov 11 - Sun, Nov 15
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
20:40 - 10:40
ORD
-
DUR
54h 00m
2 stops
R17 938British Airways
Wed, Nov 25 - Thu, Jan 14
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
18:50 - 10:40
ORD
-
DUR
55h 50m
2 stops
R18 365British Airways
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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Durban, at R16 164 return. The most popular connection is from Johannesburg to Chicago and KAYAK users have found return deals for as low as R17 117 in the last 3 days.

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 round-trip 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 March, where tickets cost R5 667 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 R14 472 and R14 340 respectively. For one-way flights, the best month to travel is February with an average price of R4 090.

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 2 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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 551.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightR9 872
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 9% 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

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Durban, at R16 164 return. The most popular connection is from Johannesburg to Chicago and KAYAK users have found return deals for as low as R17 117 in the last 3 days.

  • 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.

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 1531 reviews
7,2Entertainment
8,4Crew
7,7Comfort
7,3Food
7,8Boarding
Airline reviews

Crew is not the cheerful type. very slow meal service (this is their style as have flown this many times)

6,0 GoodGlenn, Feb 2026
AMS - JFK
Read more KLM reviews

Crew is not the cheerful type. very slow meal service (this is their style as have flown this many times)

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

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

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

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

It was operated by Delta. Boarding took a long time. How difficult can it be? Overall decent trip. Liked the Salt Lake City airport. Better option than Chicago for transfers.

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

The boarding was one of the worst I’ve ever experienced. The fault lays on Ohare Airport and not so much the airline. The waiting area by the gate was the size to accommodate a regional flight for 20-30 people and right next to a busy walkway. When you cramped nearly 300 passengers into that space is was unbearable.

Seats actually fit a human! Snack options were a bit lame but that’s ok

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

Limit the number of usage of wine or please arrange our seats. The passenger was drunk on this flight and not on Thiruvananthapuram to Abudhabi.

The seats seemed smaller than other business class offerings. The entertainment menu was limited. Flight crew was good.

It was excellent service in the snow storm gives us hotel and transportation. It will be more better if u can add one more meal because it’s a long flight boring journey. If you give extra meal time passes faster and can enjoy the trip better

Food quality and varites were very minimum. Surprised to have no desserts. Business class tickets should have lounge access and seats selection. They should be allowed to board while people with wheel chair, secial assistance and family with childrem.

Good flight. There were a few issues with the flat bed. It was some technical issues. Otherwise everything was good

The crew could have been more friendly and could have offered to make the beds. Also, Ethiad should have more vegetarian food options.

From the start of my vacation at Logan Airport, Boston it was chaotic. I'm praying my flight home is better .I'm grateful that we landed safe

On this flight...fine. The one from India to Abu Dahbi, awful.

Horrible. After paying for seats, I was cramped, my daughters legs kept hitting the seat in front, I had no overhead bin space and no help from stewards on board, the food was served cold, when asked for snacks was told to wait and never received any, the flight was cold with no temperature controls. Entertainment was outdated. I booked this through partnership with American Airlines but will avoid in the future.

Nothing was good. Everything needs to improve. Everything was abysmal. Needs lots of improvement. The check-in and baggage drop at the New Delhi airport was manned by disrespectful people, horrible experience. We will never travel by Etihad ever again.

The following is a review for a flight from Johannesburg to Washington, DC with a connection at Addis Ababa, Ethiopia and refueling landing at Rome, Italy. The flight was provided by Ethiopian Airlines. There were two of us: me and my wife on this flight. Everything was on time. Enough legroom between the seats, I was able to stretch my legs and sleep for at least some time during the 14 hour second flight (19 hours in total for both flights). Very decent meals that included two lunches and one breakfast on the flight from Addis Ababa to Washington and one lunch on the flight from Johannesburg to Addis Ababa. The lunch choices were beef, chicken and fish, I think the vegetarian option was available as well, accompanied with beans. The breakfast was a choice between egg and pancake, accompanied with a fruit salad. The egg breakfast was awesome, it came with a scrambled egg and a sausage. However, my wife mentioned unusual taste of the pancake breakfast meal, by all means those were not pancakes. What wasn't good: Externally initiated commercials on the infosystem screens, you couldn't turn the screen off. These commercials were accompanied by loud and annoying music, transmitted through the entire cabin. Obviously, there was no escape from this music as well. Additional moment: on the flight from Addis Ababa to Washington, DC, we landed at Rome for refueling. This was totally fine and it was in the flight itinerary. But, the flight attendant asked me to straighten the seat while we were at the steady position during the refueling. I can't rationalize this order except that some people just like to be a boss of some kind. Keeping the light lit in the economy cabin while keeping it dimmed in the first class also didn't improve my and my wife's feelings. Overall, the services were very good and the flight, despite its longevity, went on very smoothly.

The crew were amazing. They should improve the inflight entertainment

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

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.

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.

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

My suitcase 🧳 got missing we still looking for it This not good for them 👎🏾👎🏾👎🏾🤦🏽‍♀️

it was a nice tripe but they need to work on the serving of soda,they should be abled to serve cain soda not on cup.At least each passenger should be entitled to one cain of soda not serving on cup.thanks.

On my return flight the TV did not work the entire flight! They knew it wasn’t working but they let me sit there. The guy sitting nièce to me told me he was ok the previous flight and it wasn’t working. This is business class by the way!

I will never want to book with these people. They are arrogant and rude. Food was really really bad, crew was even worst

Check-in in SAN was long. ORD was good. Flight delayed On board crew was ok. No warmth or personality. LHrR barely made connection

Check-in experience, for business call please provide a premium experience

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

Unfortunately, my flight was cancelled because of some sort of emergency over the Atlantic and had to return to London. While I think British Airways made every effort to mitigate the situation, I must say it was still pretty unpleasant. I do appreciate the fact, however, that British Airways put my safety first…and I think the effort to correct a bad situation was very sincere. But I think the process might be handled better in future.

The seat pads are past there sell by date now and are uncomfotable. Also, with screens in the back of the seat, the seats shouldnt be able to recline as this puts rhe screen in your face.

As I have said it sucked, the ticket counter to have to find and pay for another airline to get home. Now I understand this happened over the weekend but they should have someone there to talk to us instead of throwing the regular crew under the bus.

Poor all around experience. Sat at gate in Grand Rapids to Chicago for 2.5 hours. No food or water offered and no allowances to use restroom. Missed connecting flight to London and not offered any compensation including food or lodging. Not happy with AA, claims delay was weather related but no weather issues seen on radar. Take ownership for real reason behind delay which was actually the IT outage. Very disappointing and will not be recommending AA for domestic or international flights if this is the way that customers are treated.

Flight cancelled, lost luggage, crappy meal voucher. Nothing was good. Still dont have my luggage.

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

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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.