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, Ethiopian Air 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 034, while return flights cost around R6 128.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R6 128, however they can be found for as little as R6 128.

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 2 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 883+ 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 10 September 2026.

Thu 22/1017:55 -

1 stop22h 45m

Thu 29/1012:45 -

1 stop26h 40m

Deal found 7/9R16 066

Mon 12/1018:00 -

1 stop22h 40m

Sun 25/1021:15 -

1 stop30h 45m

Deal found 9/9R16 098

Wed 21/1018:00 -

1 stop22h 40m

Wed 28/1021:15 -

1 stop42h 10m

Deal found 6/9R16 146

Tue 20/1022:00 -

1 stop31h 28m

Tue 27/1015:56 -

2 stops43h 39m

Deal found 5/9R16 306

Mon 7/922:00 -

1 stop30h 00m

Wed 3/37:10 -

1 stop27h 25m

Deal found 7/9R16 370

Thu 1/109:45 -

1 stop36h 55m

Sat 10/1020:25 -

1 stop28h 55m

Deal found 5/9R16 755

Sun 13/921:55 -

1 stop33h 04m

Sun 20/911:29 -

1 stop25h 11m

Deal found 8/9R16 803

Tue 15/1218:50 -

1 stop23h 10m

Mon 11/120:15 -

1 stop42h 10m

Deal found 8/9R16 915

Wed 23/1218:50 -

1 stop23h 10m

Mon 28/1220:15 -

1 stop42h 10m

Deal found 8/9R16 995

Thu 15/1019:00 -

1 stop24h 55m

Thu 5/118:50 -

2 stops25h 45m

Deal found 9/9R17 139

Tue 20/1015:15 -

2 stops31h 59m

Tue 27/1012:49 -

2 stops36h 31m

Deal found 5/9R17 331

Thu 1/1023:15 -

2 stops30h 29m

Sat 10/1011:33 -

1 stop25h 07m

Deal found 5/9R17 940

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 10 September 2026.

Wed 21/1018:00 -

1 stop22h 40m

Wed 28/1021:15 -

1 stop42h 10m

Deal found 6/9R16 146

Thu 4/222:00 -

1 stop21h 00m

Thu 4/315:45 -

1 stop18h 50m

Deal found 8/9R16 242

Thu 28/19:50 -

1 stop30h 05m

Sun 31/113:10 -

1 stop35h 10m

Deal found 8/9R16 995

Mon 5/1023:15 -

2 stops29h 28m

Mon 12/109:51 -

1 stop26h 49m

Deal found 5/9R17 844

Fri 16/1014:05 -

2 stops33h 45m

Fri 30/1019:50 -

1 stop36h 45m

Deal found 6/9R19 366

Mon 12/1020:15 -

2 stops33h 18m

Sun 25/1012:49 -

2 stops36h 31m

Deal found 9/9R19 494

Thu 28/119:35 -

2 stops31h 40m

Sun 31/120:40 -

1 stop29h 45m

Deal found 8/9R19 526

Mon 1/222:00 -

1 stop21h 00m

Thu 4/37:10 -

1 stop27h 25m

Deal found 8/9R16 242

Thu 28/118:50 -

1 stop31h 30m

Sun 31/120:15 -

1 stop30h 45m

Deal found 5/9R17 187

Wed 3/221:20 -

1 stop20h 47m

Wed 3/311:30 -

2 stops26h 30m

Deal found 8/9R17 860

Wed 21/1019:00 -

2 stops29h 05m

Wed 28/1010:55 -

2 stops24h 40m

Deal found 6/9R17 347

Thu 1/1023:15 -

2 stops30h 29m

Sat 10/1011:33 -

1 stop25h 07m

Deal found 5/9R17 940

Thu 22/1020:15 -

2 stops33h 18m

Thu 29/1012:49 -

2 stops36h 31m

Deal found 7/9R21 096

Wed 21/1023:15 -

2 stops30h 18m

Wed 28/106:04 -

2 stops32h 56m

Deal found 6/9R19 077

Fri 23/1019:00 -

1 stop24h 55m

Fri 30/106:59 -

2 stops28h 36m

Deal found 8/9R19 398

Wed 21/1021:55 -

1 stop25h 19m

Wed 28/1010:59 -

2 stops38h 21m

Deal found 6/9R21 816

Sun 13/923:15 -

2 stops26h 04m

Sun 20/913:19 -

2 stops23h 21m

Deal found 8/9R20 375

Sat 31/1021:20 -

1 stop33h 13m

Wed 25/119:30 -

2 stops28h 30m

Deal found 8/9R20 375

Mon 12/1021:55 -

1 stop25h 19m

Sun 25/106:04 -

2 stops32h 56m

Deal found 9/9R21 800

Thu 22/1021:55 -

1 stop31h 38m

Thu 29/109:29 -

2 stops26h 41m

Deal found 7/9R22 489

Fri 23/1023:15 -

2 stops30h 18m

Fri 30/1017:09 -

1 stop19h 01m

Deal found 8/9R23 915

Find flight deals to Chicago

Return from	R16 034
One-way from	R9 771
Popular in	January
Cheapest in	November
Average price	R17 027

Turkish Airlines
1/2-1/3
2 total stops
73h 40m total
Johannesburg to Chicago

Search Deals

Qatar Airways
17/11-31/12
1 total stop
32h 45m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 5% potential increase in price (R998 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (R423 potential savings vs. average return price).

Search Deals

Average for return flights in September 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

Sat 30/1

13:45-14:30

1 stop32h 45m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R10 924

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sat 30/1

9:50-17:43

2 stops39h 53m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R11 853

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 1/11

20:20-5:40

2 stops41h 20m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R12 542

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 2/11

18:35-14:30

3 stops51h 55m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 263

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sun 20/9

20:55-17:46

2 stops51h 51m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R14 704

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 20/9

10:05-20:12

3 stops41h 07m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R15 201

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 21/10

18:00-9:40

1 stop22h 40m

Chicago O'Hare Intl

Wed 28/10

21:15-22:25

1 stop42h 10m

R16 146

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 4/2

22:00-11:00

1 stop21h 00m

Chicago O'Hare Intl

Thu 4/3

15:45-18:35

1 stop18h 50m

R16 242

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 1/2

22:00-11:00

1 stop21h 00m

Chicago O'Hare Intl

Thu 4/3

7:10-18:35

1 stop27h 25m

R16 242

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 28/1

9:50-7:55

1 stop30h 05m

Chicago O'Hare Intl

Sun 31/1

13:10-8:20

1 stop35h 10m

R16 995

Flights are sorted by cheapest return flights first.

Deals found on 8/9

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 25 hours 53 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 65 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,Qatar Airways, 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

1 573 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

1 573 reviews

KLM

7,8

Good

1 573 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

7,4

Good

3 731 reviews

KLM

7,8

Good

1 573 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

4 474 reviews

KLM

7,8

Good

1 573 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

7,4

Good

10 192 reviews

KLM

7,8

Good

1 573 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

1 534 reviews

KLM

7,8

Good

1 573 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, Ethiopian Air 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 034, while return flights cost around R6 128.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R6 128, however they can be found for as little as R6 128.
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 2 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

Flights by cabin class

Flights from Chicago

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Complete your trip

Popular routes

Popular destinations

Popular flights

Popular United States flight routes

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Airports serving Chicago

Flights to Midway

Flights to O'Hare Intl

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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R9 883+ 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 20/9. 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 10 September 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 10 September 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 10 September 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 10 September 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 10 September 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 10 September 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 10 September 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 10 September 2026.

Find flight deals to Chicago

Return from

One-way from

Popular in

Cheapest in

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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 25 hours 53 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 65 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,Qatar Airways, 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?

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 10 September 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 10 September 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 10 September 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 10 September 2026.