Can I find cheaper flights to Chicago if I am willing to have stopovers?

Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

What is the best airline to fly to Chicago?

Based on reviews from Cheapflights users, Etihad Airways is rated the highest out of the airlines that fly to Chicago.

What is the cheapest airport to fly to in Chicago?

Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost R1 416, while return flights cost around R4 206.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R10 301, however they can be found for as little as R4 206.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Johannesburg offers the quickest one-way flight (22 hours 0 minutes).

Does Chicago O'Hare Intl have car hire?

Yes. Those touching down at Chicago O'Hare Intl can take advantage of the car hire services offered upon their arrival.

Are there hotels close to Chicago O'Hare Intl?

Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0,0 km away from Chicago O'Hare Intl).

R11 449+ Cheap Flights to Chicago, Illinois

Flights to Chicago in 2025

Enter your travel dates to find the best prices.

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 22 décembre 2025.

ven. 26/1222:00JNB - ORD

2 stops31h 31mUnited Airlines

mer. 14/114:27ORD - JNB

1 stop20h 08mUnited Airlines

Deal found 22/12R15 594

ven. 26/1221:55JNB - MDW

1 stop32h 27mMultiple Airlines

mer. 14/117:31MDW - JNB

2 stops31h 34mMultiple Airlines

Deal found 22/12R16 563

mer. 24/1221:55JNB - ORD

2 stops46h 59mDelta

lun. 29/1218:30ORD - JNB

2 stops40h 30mDelta

Deal found 21/12R16 898

ven. 26/1221:55JNB - ORD

1 stop31h 19mDelta

mer. 14/116:25ORD - JNB

1 stop21h 40mDelta

Deal found 22/12R17 065

jeu. 25/1222:00JNB - ORD

1 stop28h 45mBritish Airways

mar. 30/1220:20ORD - JNB

2 stops30h 05mBritish Airways

Deal found 21/12R18 235

dim. 28/1219:35JNB - ORD

1 stop26h 15mBritish Airways

mar. 30/1220:20ORD - JNB

2 stops30h 05mBritish Airways

Deal found 21/12R18 619

jeu. 25/1222:00JNB - ORD

1 stop28h 45mBritish Airways

lun. 29/1216:41ORD - JNB

2 stops30h 54mBritish Airways

Deal found 21/12R18 953

sam. 27/1219:35JNB - ORD

1 stop27h 50mBritish Airways

lun. 29/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R19 338

mer. 24/1219:35JNB - ORD

1 stop26h 15mBritish Airways

dim. 28/1221:45ORD - JNB

1 stop28h 40mBritish Airways

Deal found 21/12R22 530

mer. 24/1219:35JNB - ORD

1 stop31h 10mBritish Airways

sam. 27/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R22 931

jeu. 25/1222:00JNB - ORD

1 stop23h 50mBritish Airways

sam. 27/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R23 316

Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 22 décembre 2025.

jeu. 16/417:50JNB - ORD

1 stop22h 50mTurkish Airlines

lun. 11/511:25ORD - JNB

1 stop40h 05mTurkish Airlines

Deal found 20/12R14 474

jeu. 12/319:45JNB - ORD

1 stop23h 25mUnited Airlines

dim. 29/313:00ORD - JNB

2 stops22h 30mUnited Airlines

Deal found 22/12R15 878

mer. 11/222:00JNB - ORD

2 stops29h 15mBritish Airways

dim. 15/216:30ORD - JNB

2 stops33h 55mBritish Airways

Deal found 20/12R16 497

lun. 25/58:45JNB - ORD

1 stop40h 30mMultiple Airlines

mer. 3/69:55ORD - JNB

2 stops37h 45mMultiple Airlines

Deal found 20/12R16 630

jeu. 16/421:55JNB - MDW

1 stop30h 50mDelta

lun. 11/513:00MDW - JNB

2 stops25h 20mDelta

Deal found 20/12R20 391

lun. 25/523:15JNB - MDW

2 stops25h 50mKLM

mer. 3/613:00MDW - JNB

2 stops25h 35mKLM

Deal found 20/12R21 260

mer. 11/219:05JNB - ORD

1 stop23h 00mTurkish Airlines

dim. 15/220:20ORD - JNB

1 stop30h 30mTurkish Airlines

Deal found 19/12R15 577

mar. 3/219:45JNB - ORD

2 stops30h 52mUnited Airlines

mar. 10/219:35ORD - JNB

2 stops39h 00mUnited Airlines

Deal found 20/12R15 978

lun. 25/523:15JNB - MDW

2 stops25h 50mDelta

mer. 3/613:05MDW - JNB

1 stop23h 35mDelta

Deal found 20/12R21 611

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 22 décembre 2025 and is based on user searches.

mer. 24/1221:55JNB - ORD

2 stops46h 59mDelta

lun. 29/1218:30ORD - JNB

2 stops40h 30mDelta

Deal found 21/12R16 898

mer. 24/1219:35JNB - ORD

1 stop26h 15mBritish Airways

dim. 28/1221:45ORD - JNB

1 stop28h 40mBritish Airways

Deal found 21/12R22 530

mer. 24/1219:35JNB - ORD

1 stop31h 10mBritish Airways

sam. 27/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R22 931

jeu. 25/1222:00JNB - ORD

1 stop28h 45mBritish Airways

mar. 30/1220:20ORD - JNB

2 stops30h 05mBritish Airways

Deal found 21/12R18 235

jeu. 25/1222:00JNB - ORD

1 stop28h 45mBritish Airways

lun. 29/1216:41ORD - JNB

2 stops30h 54mBritish Airways

Deal found 21/12R18 953

jeu. 25/1222:00JNB - ORD

1 stop23h 50mBritish Airways

sam. 27/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R23 316

ven. 26/1222:00JNB - ORD

2 stops24h 21mUnited Airlines

mer. 14/17:35ORD - JNB

2 stops27h 00mUnited Airlines

Deal found 22/12R15 594

ven. 26/1221:55JNB - MDW

1 stop32h 27mMultiple Airlines

mer. 14/117:31MDW - JNB

2 stops31h 34mMultiple Airlines

Deal found 22/12R16 563

ven. 26/1221:55JNB - ORD

1 stop31h 19mDelta

mer. 14/116:25ORD - JNB

1 stop21h 40mDelta

Deal found 22/12R17 065

sam. 27/1219:35JNB - ORD

1 stop27h 50mBritish Airways

lun. 29/1218:30ORD - JNB

1 stop29h 05mBritish Airways

Deal found 21/12R19 338

dim. 28/1219:35JNB - ORD

1 stop26h 15mBritish Airways

mar. 30/1220:20ORD - JNB

2 stops30h 05mBritish Airways

Deal found 21/12R18 619

One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 22 décembre 2025.

ven. 30/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

Deal found 22/12R11 449

ven. 30/114:30JNB - ORD

2 stops25h 10mEthiopian Air

Deal found 20/12R14 123

mar. 6/113:45JNB - MDW

2 stops40h 32mMultiple Airlines

Deal found 20/12R20 842

mar. 6/113:45JNB - ORD

2 stops53h 50mMultiple Airlines

Deal found 20/12R20 959

lun. 5/119:05JNB - ORD

1 stop31h 20mTurkish Airlines

Deal found 20/12R21 578

lun. 5/121:45JNB - ORD

3 stops55h 14mMultiple Airlines

Deal found 20/12R22 213

jeu. 28/511:20JNB - ORD

1 stop34h 05mCathay Pacific

Deal found 21/12R23 700

dim. 4/11:35JNB - ORD

2 stops48h 10mKenya Airways

Deal found 22/12R24 436

lun. 5/113:45JNB - MDW

3 stops55h 03mMultiple Airlines

Deal found 20/12R26 675

lun. 5/123:59JNB - MDW

2 stops26h 33mDelta

Deal found 22/12R40 431

mer. 31/129:50JNB - MDW

3 stops39h 36mMultiple Airlines

Deal found 22/12R58 064

mar. 6/121:55JNB - MDW

1 stop20h 32mDelta

Deal found 20/12R59 952

Find flight deals to Chicago

Return from	R14 474
One-way from	R11 449
Popular in	January
Cheapest in	February
Average price	R19 956

Turkish Airlines
16/4-11/5
2 total stops
62h 55m total
Johannesburg to Chicago

Search Deals

Turkish Airlines
30/1
1 total stop
23h 00m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R832 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (R209 potential savings vs. average return price).

Search Deals

Average for return flights in December 2025

Search Deals

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

jeu. 16/4

17:50-9:40

1 stop22h 50m

Chicago O'Hare Intl

lun. 11/5

11:25-10:30

1 stop40h 05m

R14 474

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

mer. 11/2

19:05-10:05

1 stop23h 00m

Chicago O'Hare Intl

dim. 15/2

20:20-10:50

1 stop30h 30m

R15 577

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

jeu. 12/3

19:45-12:10

1 stop23h 25m

Chicago O'Hare Intl

dim. 29/3

13:00-18:30

2 stops22h 30m

R15 878

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

mar. 3/2

19:45-18:37

2 stops30h 52m

Chicago O'Hare Intl

mar. 10/2

19:35-18:35

2 stops39h 00m

R15 978

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

mer. 11/2

22:00-19:15

2 stops29h 15m

Chicago O'Hare Intl

dim. 15/2

16:30-10:25

2 stops33h 55m

R16 497

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

lun. 25/5

8:45-18:15

1 stop40h 30m

Chicago O'Hare Intl

mer. 3/6

9:55-6:40

2 stops37h 45m

R16 630

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

jeu. 16/4

21:55-21:45

1 stop30h 50m

Chicago Midway

lun. 11/5

13:00-21:20

2 stops25h 20m

R20 391

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

lun. 25/5

23:15-18:05

2 stops25h 50m

Chicago Midway

mer. 3/6

13:00-21:35

2 stops25h 35m

R21 260

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

lun. 25/5

23:15-18:05

2 stops25h 50m

Chicago Midway

mer. 3/6

13:05-19:40

1 stop23h 35m

R21 611

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

ven. 30/1

19:05-18:25

1 stop31h 20m

R11 449

Flights are sorted by cheapest return flights first.

Deals found on 20/12

Showing 1-10 of 21 results

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.

Estimated return price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

The best time to book flights to Chicago is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

How long is the flight to Chicago?

On average, a flight from Johannesburg to Chicago takes 23 hours 55 minutes. Flights to Chicago from other popular cities in South Africa will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Users looking for the lowest fares to Chicago should consider flying on Tuesday evenings, when prices are typically cheapest. Budget-minded travellers will want to avoid Monday afternoons, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Johannesburg to Chicago are British Airways, KLM and Turkish Airlines.

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Johannesburg to Chicago are Etihad Airways, Turkish Airlines and Ethiopian Air.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM, Etihad Airways, andUnited Airlines to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

KLM

7,7

Good

1 434 reviews

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

Etihad Airways

7,4

Good

1 336 reviews

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

United Airlines

7,4

Good

9 103 reviews

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

Turkish Airlines

7,3

Good

4 111 reviews

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

British Airways

6,7

Okay

7 605 reviews

KLM

7,7

Good

1 434 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

FAQs about flying to Chicago

Can I find cheaper flights to Chicago if I am willing to have stopovers?
Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.
What is the best airline to fly to Chicago?
Based on reviews from Cheapflights users, Etihad Airways is rated the highest out of the airlines that fly to Chicago.
What is the cheapest airport to fly to in Chicago?
Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost R1 416, while return flights cost around R4 206.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R10 301, however they can be found for as little as R4 206.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Johannesburg offers the quickest one-way flight (22 hours 0 minutes).
Does Chicago O'Hare Intl have car hire?
Yes. Those touching down at Chicago O'Hare Intl can take advantage of the car hire services offered upon their arrival.
Are there hotels close to Chicago O'Hare Intl?
Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0,0 km away from Chicago O'Hare Intl).

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Airports serving Chicago

Flights to Midway

Flights to O'Hare Intl

Flights from Midway

Flights from O'Hare Intl

Most traveled routes by our users

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South Africa to Chania flights

Fly with Cheapflights

How does Cheapflights help users find flights to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights to Chicago.

Can Cheapflights find flights to Chicago with no change fees?

Certainly. Search results for flights to Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Chicago flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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R11 449+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 30/1. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 22 décembre 2025.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 22 décembre 2025.

Find flight deals to Chicago

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 594 507 searches and data was last updated on 22 décembre 2025.

Return from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights to Chicago that are best for you.

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Johannesburg to Chicago. Price data was last updated on 19 December 2025.

How long is the flight to Chicago?

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return from Johannesburg to Chicago. Price data was last updated on 16 December 2024.

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM, Etihad Airways, andUnited Airlines to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

FAQs about flying to Chicago

Can I find cheaper flights to Chicago if I am willing to have stopovers?

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a return flight to Chicago?

Where does the fastest flight to Chicago depart from?

Does Chicago O'Hare Intl have car hire?

Are there hotels close to Chicago O'Hare Intl?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Airports serving Chicago

Book a flight to or from one of these Chicago airports.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights to Chicago?

Why should you use Cheapflights to find cheap flight tickets to Chicago?

Can Cheapflights find flights to Chicago with no change fees?

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

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Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 22 décembre 2025.