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 413, while return flights cost around R4 196.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R10 277, however they can be found for as little as R4 196.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Cape Town Intl offers the quickest one-way flight (20 hours 23 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).

R9 772+ Cheap Flights to Chicago, Illinois

Flights to Chicago in 2025

Enter your travel dates to find the best prices.

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 30 grudnia 2025.

śr. 11/28:20JNB - ORD

2 stops31h 20mEthiopian Air

śr. 18/29:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 28/12R13 741

pon. 16/219:05JNB - ORD

1 stop31h 20mTurkish Airlines

śr. 18/220:20ORD - JNB

1 stop30h 30mTurkish Airlines

Deal found 29/12R15 558

ndz. 25/122:00JNB - ORD

2 stops24h 16mUnited Airlines

pon. 9/214:00ORD - JNB

2 stops20h 35mUnited Airlines

Deal found 28/12R15 608

śr. 11/221:55JNB - MDW

1 stop27h 50mVirgin Atlantic

śr. 18/218:40MDW - JNB

1 stop40h 20mVirgin Atlantic

Deal found 28/12R15 758

śr. 11/221:55JNB - MDW

1 stop27h 50mMultiple Airlines

śr. 18/210:49MDW - JNB

2 stops37h 21mMultiple Airlines

Deal found 28/12R16 576

śr. 11/222:00JNB - MDW

2 stops28h 40mDelta

śr. 18/213:28MDW - JNB

2 stops35h 07mDelta

Deal found 28/12R16 826

pon. 25/523:15JNB - MDW

2 stops25h 50mKLM

ndz. 7/613:00MDW - JNB

2 stops25h 20mKLM

Deal found 28/12R22 128

ndz. 25/114:30JNB - ORD

2 stops25h 10mEthiopian Air

pon. 9/29:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 28/12R14 574

pt. 9/122:00JNB - ORD

1 stop22h 05mUnited Airlines

pon. 19/18:00ORD - JNB

2 stops26h 35mUnited Airlines

Deal found 29/12R15 625

ndz. 25/122:00JNB - MDW

2 stops28h 36mDelta

pon. 9/212:46MDW - JNB

1 stop22h 14mDelta

Deal found 28/12R16 859

ndz. 1/222:00JNB - ORD

2 stops23h 15mUnited Airlines

ndz. 15/210:35ORD - JNB

2 stops24h 00mUnited Airlines

Deal found 29/12R15 625

ndz. 25/121:55JNB - MDW

1 stop27h 34mVirgin Atlantic

pon. 9/218:14MDW - JNB

1 stop40h 46mVirgin Atlantic

Deal found 28/12R18 160

czw. 12/221:30JNB - MDW

2 stops29h 10mDelta

czw. 19/29:50MDW - JNB

2 stops25h 10mDelta

Deal found 29/12R16 859

czw. 12/222:00JNB - ORD

2 stops26h 51mUnited Airlines

czw. 19/28:40ORD - JNB

2 stops25h 55mUnited Airlines

Deal found 29/12R15 625

pt. 13/221:55JNB - MDW

1 stop25h 26mDelta

pt. 20/210:49MDW - JNB

1 stop24h 11mDelta

Deal found 29/12R16 892

czw. 29/122:00JNB - ORD

2 stops26h 49mUnited Airlines

śr. 6/58:00ORD - JNB

2 stops27h 30mUnited Airlines

Deal found 29/12R15 625

ndz. 1/222:00JNB - MDW

2 stops28h 36mDelta

ndz. 15/211:45MDW - JNB

2 stops26h 20mDelta

Deal found 29/12R17 026

pt. 13/219:45JNB - ORD

1 stop23h 25mUnited Airlines

pt. 20/28:53ORD - JNB

2 stops25h 42mUnited Airlines

Deal found 30/12R15 892

śr. 28/119:45JNB - ORD

1 stop25h 40mUnited Airlines

czw. 7/514:00ORD - JNB

2 stops21h 30mUnited Airlines

Deal found 29/12R15 908

pon. 25/523:15JNB - MDW

2 stops25h 50mDelta

ndz. 7/66:00MDW - JNB

1 stop30h 40mDelta

Deal found 28/12R18 693

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 30 grudnia 2025 and is based on user searches.

ndz. 25/114:30JNB - ORD

2 stops25h 10mEthiopian Air

pon. 9/29:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 28/12R14 574

ndz. 25/122:00JNB - ORD

2 stops24h 16mUnited Airlines

pon. 9/214:00ORD - JNB

2 stops20h 35mUnited Airlines

Deal found 28/12R15 608

ndz. 25/122:00JNB - MDW

2 stops28h 36mDelta

pon. 9/29:33MDW - JNB

2 stops25h 27mDelta

Deal found 28/12R16 859

pon. 26/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

czw. 7/520:10ORD - JNB

1 stop31h 20mTurkish Airlines

Deal found 29/12R15 141

pon. 26/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

śr. 6/511:25ORD - JNB

1 stop40h 05mTurkish Airlines

Deal found 29/12R15 542

pon. 26/120:15JNB - ORD

2 stops46h 51mAir Canada

śr. 6/510:40ORD - JNB

2 stops39h 40mAir Canada

Deal found 29/12R15 558

pon. 26/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

śr. 28/111:50ORD - JNB

1 stop39h 00mTurkish Airlines

Deal found 27/12R15 575

wt. 27/119:10JNB - ORD

1 stop31h 15mTurkish Airlines

czw. 7/511:25ORD - JNB

1 stop40h 05mTurkish Airlines

Deal found 29/12R14 791

śr. 28/119:05JNB - ORD

1 stop31h 20mTurkish Airlines

śr. 6/519:50ORD - JNB

1 stop31h 40mTurkish Airlines

Deal found 29/12R14 374

czw. 29/122:00JNB - ORD

2 stops26h 49mUnited Airlines

śr. 6/515:45ORD - JNB

1 stop19h 45mUnited Airlines

Deal found 29/12R15 625

pt. 30/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

czw. 7/511:25ORD - JNB

1 stop40h 05mTurkish Airlines

Deal found 29/12R14 891

pt. 30/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

śr. 6/511:25ORD - JNB

1 stop40h 05mTurkish Airlines

Deal found 29/12R15 292

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 30 grudnia 2025.

wt. 21/417:00JNB - ORD

2 stops28h 41mMultiple Airlines

Deal found 29/12R9 772

pon. 20/411:55JNB - ORD

1 stop34h 05mQatar Airways

Deal found 29/12R10 272

pt. 30/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

Deal found 30/12R11 423

pon. 20/418:00JNB - ORD

1 stop22h 40mTurkish Airlines

Deal found 29/12R11 656

śr. 21/119:05JNB - ORD

1 stop23h 00mTurkish Airlines

Deal found 28/12R12 423

pon. 20/416:20JNB - ORD

2 stops48h 20mMultiple Airlines

Deal found 29/12R12 523

wt. 21/417:00JNB - MDW

3 stops29h 20mMultiple Airlines

Deal found 29/12R13 190

pon. 20/418:00JNB - MDW

2 stops47h 05mMultiple Airlines

Deal found 28/12R14 391

pon. 20/423:15JNB - MDW

2 stops26h 30mKLM

Deal found 29/12R14 725

pon. 20/421:55JNB - MDW

1 stop25h 41mDelta

Deal found 29/12R16 025

śr. 17/623:15JNB - MDW

2 stops25h 50mDelta

Deal found 27/12R16 175

wt. 6/19:25JNB - MDW

2 stops44h 52mMultiple Airlines

Deal found 28/12R17 076

Find flight deals to Chicago

Return from	R13 407
One-way from	R9 772
Popular in	January
Cheapest in	February
Average price	R19 877

Etihad Airways
11/2-18/2
2 total stops
64h 55m total
Johannesburg to Chicago

Search Deals

21/4
2 total stops
28h 41m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 5% potential increase in price (R965 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (R256 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

śr. 11/2

8:20-7:40

2 stops31h 20m

Chicago O'Hare Intl

śr. 18/2

9:45-20:10

1 stop26h 25m

R13 741

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

ndz. 25/1

14:30-7:40

2 stops25h 10m

Chicago O'Hare Intl

pon. 9/2

9:45-20:10

1 stop26h 25m

R14 574

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

pon. 16/2

19:05-18:25

1 stop31h 20m

Chicago O'Hare Intl

śr. 18/2

20:20-10:50

1 stop30h 30m

R15 558

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

ndz. 25/1

22:00-14:16

2 stops24h 16m

Chicago O'Hare Intl

pon. 9/2

14:00-18:35

2 stops20h 35m

R15 608

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

pt. 9/1

22:00-12:05

1 stop22h 05m

Chicago O'Hare Intl

pon. 19/1

8:00-18:35

2 stops26h 35m

R15 625

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

ndz. 1/2

22:00-13:15

2 stops23h 15m

Chicago O'Hare Intl

ndz. 15/2

10:35-18:35

2 stops24h 00m

R15 625

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

czw. 12/2

22:00-16:51

2 stops26h 51m

Chicago O'Hare Intl

czw. 19/2

8:40-18:35

2 stops25h 55m

R15 625

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

czw. 29/1

22:00-16:49

2 stops26h 49m

Chicago O'Hare Intl

śr. 6/5

8:00-18:30

2 stops27h 30m

R15 625

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

śr. 11/2

21:55-17:45

1 stop27h 50m

Chicago Midway

śr. 18/2

18:40-19:00

1 stop40h 20m

R15 758

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

pt. 13/2

19:45-11:10

1 stop23h 25m

Chicago O'Hare Intl

pt. 20/2

8:53-18:35

2 stops25h 42m

R15 892

Flights are sorted by cheapest return flights first.

Deals found on 29/12

Showing 1-10 of 38 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 57 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.

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, United Airlines, andEtihad Airways 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

1 435 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

1 435 reviews

KLM

7,7

Good

1 435 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

9 123 reviews

KLM

7,7

Good

1 435 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

7,3

Good

1 348 reviews

KLM

7,7

Good

1 435 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

4 132 reviews

KLM

7,7

Good

1 435 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

7 626 reviews

KLM

7,7

Good

1 435 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 413, while return flights cost around R4 196.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R10 277, however they can be found for as little as R4 196.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Cape Town Intl offers the quickest one-way flight (20 hours 23 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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Frankfurt am Main Airport to Johannesburg OR Tambo Airport flights

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South Africa to South Korea flights

Johannesburg OR Tambo Airport to Cape Town flights

Nairobi to Dar Es Salaam flights

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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Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

R9 772+ 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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

Best flights to ChicagoDiscover 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 30 grudnia 2025.

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 30 grudnia 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 30 grudnia 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 26 December 2025.

How long is the flight to Chicago?

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, andEtihad Airways 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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Travel Smart

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 30 grudnia 2025.