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, KLM 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 R1 075, while return flights cost around R6 375.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R6 375, however they can be found for as little as R6 375.

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 47 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).

R10 397+ Cheap Flights to Chicago, Illinois

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

Cheapest

Best

Last-minute

One-way

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 31 October 2026.

Wed 25/118:20 -

2 stops31h 20m

Sun 24/19:45 -

1 stop19h 45m

Deal found 28/10R15 495

Sun 15/118:20 -

2 stops31h 20m

Sat 28/119:45 -

1 stop19h 45m

Deal found 27/10R15 545

Fri 13/110:20 -

1 stop41h 40m

Fri 27/1120:15 -

1 stop30h 40m

Deal found 28/10R15 579

Sun 15/1114:30 -

2 stops25h 10m

Sat 21/119:45 -

1 stop26h 25m

Deal found 27/10R15 612

Sun 1/110:20 -

1 stop27h 00m

Mon 16/1120:15 -

1 stop30h 40m

Deal found 26/10R15 629

Thu 19/1118:50 -

1 stop23h 10m

Mon 18/120:15 -

1 stop30h 40m

Deal found 28/10R15 729

Sun 15/1118:50 -

1 stop23h 10m

Sat 28/1111:45 -

1 stop26h 40m

Deal found 27/10R15 812

Mon 23/1118:50 -

1 stop23h 10m

Mon 7/1220:15 -

1 stop42h 10m

Deal found 26/10R16 545

Fri 20/119:50 -

1 stop29h 45m

Tue 19/113:15 -

1 stop35h 10m

Deal found 28/10R16 562

Mon 2/1123:00 -

2 stops40h 40m

Mon 16/119:45 -

1 stop19h 45m

Deal found 26/10R16 645

Tue 24/1118:50 -

1 stop31h 30m

Tue 1/1211:45 -

1 stop26h 40m

Deal found 27/10R16 662

Mon 2/1121:40 -

2 stops34h 17m

Mon 16/1115:59 -

1 stop19h 11m

Deal found 26/10R16 745

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 31 October 2026.

Tue 24/1122:00 -

2 stops29h 30m

Tue 1/1220:07 -

2 stops38h 28m

Deal found 27/10R17 095

Tue 16/221:20 -

1 stop20h 32m

Wed 11/810:35 -

1 stop26h 05m

Deal found 30/10R17 545

Thu 28/123:00 -

2 stops40h 40m

Sun 31/19:45 -

1 stop19h 45m

Deal found 30/10R17 562

Tue 10/1121:40 -

2 stops29h 25m

Tue 17/1118:15 -

2 stops30h 25m

Deal found 26/10R17 745

Mon 23/1123:59 -

2 stops28h 18m

Mon 7/1216:25 -

1 stop21h 35m

Deal found 26/10R18 011

Fri 20/1116:20 -

2 stops31h 58m

Tue 19/117:45 -

2 stops30h 55m

Deal found 28/10R18 361

Thu 28/118:50 -

1 stop31h 30m

Sun 31/120:15 -

1 stop30h 45m

Deal found 30/10R18 545

Thu 28/117:00 -

2 stops32h 19m

Sun 31/16:30 -

2 stops33h 55m

Deal found 30/10R19 311

Sun 15/1119:35 -

1 stop31h 10m

Sat 21/1118:30 -

1 stop31h 55m

Deal found 27/10R20 994

Tue 26/121:20 -

1 stop34h 35m

Sun 25/76:00 -

1 stop30h 40m

Deal found 28/10R17 595

Mon 23/1123:59 -

2 stops26h 05m

Mon 7/1212:39 -

2 stops25h 21m

Deal found 26/10R19 261

Fri 12/221:20 -

1 stop27h 05m

Thu 25/210:35 -

1 stop24h 35m

Deal found 29/10R17 695

Tue 26/123:55 -

2 stops28h 37m

Sun 25/75:30 -

1 stop31h 10m

Deal found 28/10R18 645

Tue 10/1121:40 -

2 stops33h 14m

Tue 17/1113:05 -

1 stop22h 05m

Deal found 26/10R24 626

Tue 16/221:20 -

2 stops29h 17m

Tue 10/810:35 -

1 stop26h 05m

Deal found 28/10R18 845

Tue 24/1123:59 -

2 stops30h 55m

Tue 1/1213:41 -

2 stops24h 19m

Deal found 27/10R19 811

Find flight deals to Chicago

Return from	R15 462
One-way from	R10 364
Popular in	January
Cheapest in	February
Average price	R17 278

Ethiopian Air
19/3-24/4
3 total stops
45h 25m total
Johannesburg to Chicago

Search Deals

Qatar Airways
12/3-31/12
1 total stop
32h 45m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 0% potential increase in price (R158 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (R365 potential savings vs. average return price).

Search Deals

Average for return flights in October 2026

Search Deals

Fly from

Route

Depart

Return

Price

Cheapest return flight

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 9/11

20:20-14:30

1 stop26h 10m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R10 397

Fastest return journey

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 25/11

0:20-18:20

1 stop26h 00m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R10 564

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 9/11

8:55-10:00

2 stops33h 05m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R11 613

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 2/12

13:30-18:20

2 stops36h 50m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 863

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 26/11

9:50-16:40

2 stops38h 50m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R15 412

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sat 26/12

21:20-22:22

1 stop33h 02m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 112

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sat 13/2

21:20-16:25

1 stop27h 05m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 145

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Fri 12/2

21:20-16:25

1 stop27h 05m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 145

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Mon 8/2

23:55-18:00

2 stops26h 05m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 379

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Tue 30/3

20:15-16:25

2 stops27h 10m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 395

Flights are sorted by cheapest return flights first.

Deals found on 27/10

Showing 1-10 of 34 resultsSorted by cheapest first

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.

ZA1-CHI

JNB-ORD

JNB-MDW

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

ZA1-CHI

JNB-ORD

JNB-MDW

How long is the flight to Chicago?

On average, a flight from Johannesburg to Chicago takes 24 hours 48 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 United Airlines, Qatar Airways and Etihad Airways.

What are the cheapest airlines that fly to Chicago?

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

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

The best time to book flights to Chicago is 62 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.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM,Turkish Airlines, andQatar 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

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

KLM

7,8

Good

1 595 reviews

KLM

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

Turkish Airlines

7,4

Good

4 460 reviews

KLM

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

Qatar Airways

7,3

Good

3 709 reviews

KLM

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

Etihad Airways

7,3

Good

1 552 reviews

KLM

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

United Airlines

7,3

Good

10 462 reviews

KLM

7,8

Good

1 595 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Kushal,Sept 2026

QRO - ATL

It was a nice one. Crew were friendly and helpful.

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, KLM 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 R1 075, while return flights cost around R6 375.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R6 375, however they can be found for as little as R6 375.
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 47 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 nearby

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Flights to Midway

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Flights from Midway

Flights from O'Hare Intl

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 397+ Cheap flights to Chicago

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2026

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 31 October 2026.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 31 October 2026.

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 31 October 2026.

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 31 October 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 31 October 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 31 October 2026 and is based on user searches.

One-way flights to ChicagoSearch for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 31 October 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 31 October 2026.

Find flight deals to Chicago

Return from

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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

How long is the flight to Chicago?

On average, a flight from Johannesburg to Chicago takes 24 hours 48 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 United Airlines, Qatar Airways and Etihad Airways.

What are the cheapest airlines that fly to Chicago?

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

Rainfall in Chicago by month

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

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

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

The best time to book flights to Chicago is 62 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.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM,Turkish Airlines, andQatar 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

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Search flights to Chicago by cabin class

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Find the best flight deals from Chicago

Some of the lowest fares we’ve come across for flights from Chicago.

Other flight destinations closest to Chicago

Book a flight to other destinations in United States.

Complete your trip

Reserve a car hire and hotel room to complete your trip to Chicago.

Most traveled routes by our users

Browse our most popular destinations

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Popular United States flight routes

Browse through the most popular flight routes to the United States at this time.

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Fly with Cheapflights

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 31 October 2026.

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 31 October 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 31 October 2026 and is based on user searches.

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 31 October 2026.