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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost R663, while return flights cost around R3 388.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R231, however they can be found for as little as R192.

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 2 minutes).

Which airport is closest to Chicago Riverwalk?

f being close to Chicago Riverwalk is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

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).

R10 423+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	R14 402
One-way from	R10 423
Popular in	December
Cheapest in	February
Average price	R17 694

Etihad Airways
20/10-26/10
2 total stops
65h 05m total
Johannesburg to Chicago

Search Deals

2/10
2 total stops
30h 51m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 7% potential increase in price (R25 666 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (R3 895 potential savings vs. average return price).

Search Deals

Average for return flights in September 2025

Search Deals

Find flight deals to Chicago

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 2 September 2025.

Mon 20/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Sun 26/1014:10ORD - JNB

1 stop35h 10mEtihad Airways

Deal found 31/8R14 772

Thu 13/119:50JNB - ORD

1 stop30h 05mEtihad Airways

Thu 4/1213:10ORD - JNB

1 stop35h 10mEtihad Airways

Deal found 31/8R15 758

Thu 16/1014:30JNB - ORD

2 stops24h 45mEthiopian Air

Thu 23/1010:15ORD - JNB

1 stop19h 50mEthiopian Air

Deal found 1/9R15 828

Sun 21/99:50JNB - ORD

2 stops41h 59mEtihad Airways

Sun 5/1013:55ORD - JNB

1 stop35h 35mEtihad Airways

Deal found 31/8R16 074

Thu 16/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Thu 23/1013:55ORD - JNB

1 stop35h 25mEtihad Airways

Deal found 1/9R16 620

Thu 16/1019:00JNB - ORD

2 stops26h 10mUnited Airlines

Thu 23/1010:00ORD - JNB

2 stops24h 45mUnited Airlines

Deal found 1/9R17 483

Sun 21/923:30JNB - MDW

2 stops26h 05mDelta

Sun 5/1013:08MDW - JNB

2 stops23h 32mDelta

Deal found 31/8R17 518

Mon 20/1021:15JNB - ORD

2 stops25h 51mAmerican Airlines

Sun 26/1019:25ORD - JNB

1 stop29h 10mAmerican Airlines

Deal found 31/8R17 553

Thu 13/118:20JNB - ORD

2 stops31h 20mEthiopian Air

Thu 4/129:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 1/9R17 870

Thu 11/1222:00JNB - ORD

1 stop23h 50mBritish Airways

Sun 4/116:11ORD - JNB

2 stops34h 14mBritish Airways

Deal found 31/8R17 941

Thu 13/1122:00JNB - ORD

2 stops27h 34mBritish Airways

Thu 4/1211:47ORD - JNB

2 stops38h 38mBritish Airways

Deal found 31/8R18 486

Thu 16/1020:40JNB - MDW

2 stops28h 45mDelta

Thu 23/1012:48MDW - JNB

1 stop23h 52mDelta

Deal found 1/9R18 557

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 2 September 2025.

Mon 20/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Sun 26/1014:10ORD - JNB

1 stop35h 10mEtihad Airways

Deal found 31/8R14 772

Thu 16/1014:30JNB - ORD

2 stops24h 45mEthiopian Air

Thu 23/1010:15ORD - JNB

1 stop19h 50mEthiopian Air

Deal found 1/9R15 828

Thu 16/1019:00JNB - ORD

2 stops26h 10mUnited Airlines

Thu 23/1010:00ORD - JNB

2 stops24h 45mUnited Airlines

Deal found 1/9R17 483

Sun 21/923:30JNB - MDW

2 stops26h 05mDelta

Sun 5/1013:08MDW - JNB

2 stops23h 32mDelta

Deal found 31/8R17 518

Mon 20/1021:15JNB - ORD

2 stops25h 51mAmerican Airlines

Sun 26/1019:25ORD - JNB

1 stop29h 10mAmerican Airlines

Deal found 31/8R17 553

Thu 16/1021:55JNB - MDW

1 stop31h 19mVirgin Atlantic

Thu 23/1012:48MDW - JNB

1 stop23h 52mVirgin Atlantic

Deal found 1/9R19 402

Thu 16/1023:15JNB - MDW

2 stops26h 10mKLM

Thu 23/1013:08MDW - JNB

2 stops25h 27mKLM

Deal found 1/9R20 810

Thu 13/119:50JNB - ORD

1 stop30h 05mEtihad Airways

Thu 4/1213:10ORD - JNB

1 stop35h 10mEtihad Airways

Deal found 31/8R15 758

Sun 21/99:50JNB - ORD

2 stops41h 59mEtihad Airways

Sun 5/1013:55ORD - JNB

1 stop35h 35mEtihad Airways

Deal found 31/8R16 074

Thu 16/1020:40JNB - MDW

2 stops28h 45mDelta

Thu 23/1012:48MDW - JNB

1 stop23h 52mDelta

Deal found 1/9R18 557

Thu 16/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Thu 23/1013:55ORD - JNB

1 stop35h 25mEtihad Airways

Deal found 1/9R16 620

Fri 19/1221:55JNB - MDW

1 stop32h 21mDelta

Thu 15/19:30MDW - JNB

2 stops28h 35mDelta

Deal found 1/9R18 874

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 2 September 2025 and is based on user searches.

Wed 10/91:25JNB - ORD

2 stops47h 20mMultiple Airlines

Wed 10/127:00ORD - JNB

2 stops24h 50mMultiple Airlines

Deal found 1/9R20 053

Wed 10/93:10JNB - ORD

2 stops42h 55mQatar Airways

Wed 10/1218:50ORD - JNB

1 stop25h 05mQatar Airways

Deal found 1/9R36 304

Thu 11/919:35JNB - ORD

1 stop27h 20mSWISS

Wed 10/1218:50ORD - JNB

1 stop31h 40mSWISS

Deal found 1/9R18 786

Thu 11/921:20JNB - ORD

2 stops32h 21mUnited Airlines

Wed 10/1222:35ORD - JNB

1 stop26h 55mUnited Airlines

Deal found 1/9R19 173

Sat 20/91:25JNB - ORD

2 stops41h 51mKenya Airways

Sun 5/107:00ORD - JNB

2 stops25h 50mKenya Airways

Deal found 31/8R25 846

Sun 21/99:50JNB - ORD

2 stops41h 59mEtihad Airways

Sun 5/1013:55ORD - JNB

1 stop35h 35mEtihad Airways

Deal found 31/8R16 074

Sun 21/923:30JNB - MDW

2 stops26h 05mDelta

Sun 5/1013:08MDW - JNB

2 stops23h 32mDelta

Deal found 31/8R17 518

Sun 21/921:15JNB - ORD

2 stops25h 42mAmerican Airlines

Sun 5/1022:15ORD - JNB

2 stops25h 45mAmerican Airlines

Deal found 31/8R20 863

Sun 21/99:50JNB - ORD

3 stops35h 10mMultiple Airlines

Sun 5/1015:45ORD - JNB

3 stops33h 45mMultiple Airlines

Deal found 31/8R21 268

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 2 September 2025.

Thu 2/1017:00JNB - ORD

2 stops30h 51mMultiple Airlines

Deal found 1/9R10 423

Sat 4/1017:00JNB - ORD

3 stops54h 17mMultiple Airlines

Deal found 1/9R10 863

Sun 5/1012:10JNB - ORD

2 stops36h 01mMultiple Airlines

Deal found 1/9R11 162

Tue 30/917:00JNB - ORD

2 stops30h 51mMultiple Airlines

Deal found 1/9R11 215

Sun 7/99:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 31/8R11 743

Thu 2/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 1/9R11 990

Wed 1/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 1/9R12 201

Fri 3/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 1/9R12 307

Wed 10/99:50JNB - MDW

3 stops44h 30mMultiple Airlines

Deal found 31/8R13 909

Tue 9/917:00JNB - MDW

3 stops53h 58mMultiple Airlines

Deal found 31/8R14 243

Sun 7/921:45JNB - MDW

3 stops49h 13mMultiple Airlines

Deal found 31/8R14 631

Mon 8/917:55JNB - MDW

3 stops53h 03mMultiple Airlines

Deal found 31/8R14 912

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 20/10

9:50-8:45

1 stop29h 55m

Chicago O'Hare Intl

Sun 26/10

14:10-8:20

1 stop35h 10m

R14 772

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 13/11

9:50-7:55

1 stop30h 05m

Chicago O'Hare Intl

Thu 4/12

13:10-8:20

1 stop35h 10m

R15 758

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 16/10

14:30-8:15

2 stops24h 45m

Chicago O'Hare Intl

Thu 23/10

10:15-13:05

1 stop19h 50m

R15 828

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 21/9

9:50-20:49

2 stops41h 59m

Chicago O'Hare Intl

Sun 5/10

13:55-8:30

1 stop35h 35m

R16 074

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 16/10

9:50-8:45

1 stop29h 55m

Chicago O'Hare Intl

Thu 23/10

13:55-8:20

1 stop35h 25m

R16 620

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 16/10

19:00-14:10

2 stops26h 10m

Chicago O'Hare Intl

Thu 23/10

10:00-17:45

2 stops24h 45m

R17 483

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sun 21/9

23:30-18:35

2 stops26h 05m

Chicago Midway

Sun 5/10

13:08-19:40

2 stops23h 32m

R17 518

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 20/10

21:15-16:06

2 stops25h 51m

Chicago O'Hare Intl

Sun 26/10

19:25-7:35

1 stop29h 10m

R17 553

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 16/10

20:40-18:25

2 stops28h 45m

Chicago Midway

Thu 23/10

12:48-19:40

1 stop23h 52m

R18 557

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Fri 19/12

21:55-22:16

1 stop32h 21m

Chicago Midway

Thu 15/1

9:30-22:05

2 stops28h 35m

R18 874

Flights are sorted by cheapest return flights first.

Deals found on 1/9

Showing 1-10 of 29 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 22 hours 56 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 Monday 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 United Airlines.

What are the cheapest airlines that fly to Chicago?

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

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, United Airlines, andTurkish 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

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

KLM

7,8

Good

1 382 reviews

KLM

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

United Airlines

7,4

Good

8 937 reviews

KLM

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

Turkish Airlines

7,3

Good

3 952 reviews

KLM

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

Ethiopian Air

7,2

Good

851 reviews

KLM

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

British Airways

6,7

Okay

7 336 reviews

KLM

7,8

Good

1 382 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost R663, while return flights cost around R3 388.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R231, however they can be found for as little as R192.
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 2 minutes).
Which airport is closest to Chicago Riverwalk?
f being close to Chicago Riverwalk is important to you, you’ll want to land at Chicago O'Hare Intl Airport.
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

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Flights to O'Hare Intl

Flights from Midway

Flights from O'Hare Intl

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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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R10 423+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

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 2 September 2025.

Return from

One-way from

Popular in

Cheapest in

Average price

Find flight deals to Chicago

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 2 September 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 2 September 2025.

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 29 August 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, United Airlines, andTurkish 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?

Which airport is closest to Chicago Riverwalk?

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 2 September 2025.