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 R941, while return flights cost around R2 419.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R2 419, however they can be found for as little as R2 419.

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).

R9 912+ 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 21 August 2026.

Sat 3/108:20 -

2 stops30h 55m

Sat 10/1010:15 -

1 stop26h 55m

Deal found 19/8R15 489

Sun 11/1018:00 -

1 stop22h 40m

Sat 24/1011:25 -

1 stop28h 00m

Deal found 18/8R15 521

Mon 12/1022:50 -

2 stops40h 25m

Mon 2/119:45 -

1 stop26h 25m

Deal found 16/8R15 570

Tue 22/922:50 -

2 stops40h 25m

Wed 30/910:15 -

1 stop34h 40m

Deal found 20/8R15 683

Thu 15/1017:55 -

1 stop22h 45m

Sat 31/1021:15 -

1 stop30h 45m

Deal found 16/8R15 908

Wed 30/920:15 -

2 stops33h 17m

Tue 6/1015:40 -

1 stop21h 00m

Deal found 17/8R16 069

Fri 11/120:20 -

1 stop26h 00m

Sat 9/111:45 -

1 stop26h 40m

Deal found 21/8R16 134

Wed 7/1022:00 -

2 stops32h 32m

Sun 18/1012:40 -

2 stops22h 50m

Deal found 19/8R16 263

Mon 12/1018:00 -

1 stop31h 15m

Sat 31/1012:45 -

1 stop26h 40m

Deal found 16/8R16 327

Mon 5/109:45 -

1 stop29h 50m

Mon 12/1020:25 -

1 stop28h 55m

Deal found 21/8R16 505

Wed 30/99:45 -

1 stop29h 50m

Tue 6/1020:25 -

1 stop28h 55m

Deal found 17/8R16 537

Mon 12/1021:55 -

1 stop21h 18m

Fri 30/1013:55 -

2 stops22h 15m

Deal found 16/8R16 811

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 21 August 2026.

Tue 22/922:50 -

2 stops40h 25m

Wed 30/910:15 -

1 stop34h 40m

Deal found 20/8R15 683

Wed 7/1022:00 -

2 stops32h 32m

Sun 18/1012:40 -

2 stops22h 50m

Deal found 19/8R16 263

Thu 28/118:50 -

1 stop31h 30m

Sun 31/120:15 -

1 stop30h 45m

Deal found 20/8R16 408

Mon 12/1021:55 -

1 stop20h 59m

Mon 2/1113:27 -

2 stops21h 43m

Deal found 16/8R16 811

Wed 9/99:45 -

1 stop36h 55m

Wed 3/313:10 -

1 stop35h 10m

Deal found 21/8R17 230

Mon 7/923:15 -

2 stops28h 15m

Wed 3/316:25 -

1 stop21h 35m

Deal found 17/8R17 391

Sun 13/920:15 -

2 stops33h 29m

Sun 20/917:10 -

1 stop19h 30m

Deal found 16/8R20 034

Sun 11/1021:55 -

1 stop31h 38m

Sat 24/109:29 -

2 stops26h 41m

Deal found 18/8R16 859

Sun 4/1022:00 -

1 stop31h 28m

Sun 11/1012:09 -

1 stop23h 21m

Deal found 20/8R17 359

Wed 7/1023:15 -

1 stop22h 00m

Sun 18/1016:15 -

1 stop22h 05m

Deal found 19/8R17 472

Sun 11/1021:55 -

2 stops27h 34m

Sat 24/1013:55 -

2 stops22h 15m

Deal found 18/8R16 908

Mon 7/922:00 -

2 stops25h 52m

Wed 3/313:12 -

2 stops21h 23m

Deal found 17/8R17 456

Wed 7/1018:50 -

2 stops28h 29m

Sun 18/1013:27 -

2 stops24h 53m

Deal found 19/8R18 552

Thu 15/1023:15 -

2 stops29h 16m

Fri 30/106:00 -

2 stops30h 10m

Deal found 16/8R17 842

Mon 5/1023:15 -

2 stops30h 18m

Mon 12/1017:09 -

1 stop19h 31m

Deal found 21/8R18 052

Mon 7/923:15 -

2 stops30h 29m

Wed 3/39:30 -

2 stops28h 30m

Deal found 20/8R20 260

Tue 15/1221:20 -

1 stop26h 54m

Thu 31/129:30 -

2 stops25h 40m

Deal found 20/8R20 679

Wed 9/923:15 -

2 stops26h 04m

Wed 3/313:00 -

2 stops25h 00m

Deal found 17/8R21 453

Find flight deals to Chicago

Return from	R15 489
One-way from	R9 912
Popular in	January
Cheapest in	February
Average price	R17 391

Ethiopian Air
3/10-10/10
3 total stops
57h 50m total
Johannesburg to Chicago

Search Deals

Qatar Airways
14/9
1 total stop
32h 00m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R822 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (R452 potential savings vs. average return price).

Search Deals

Average for return flights in August 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

Tue 22/9

22:50-8:15

2 stops40h 25m

Chicago O'Hare Intl

Wed 30/9

10:15-3:55

1 stop34h 40m

R15 683

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 7/10

22:00-23:32

2 stops32h 32m

Chicago O'Hare Intl

Sun 18/10

12:40-18:30

2 stops22h 50m

R16 263

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 28/1

18:50-18:20

1 stop31h 30m

Chicago O'Hare Intl

Sun 31/1

20:15-11:00

1 stop30h 45m

R16 408

Fastest return journey

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Mon 12/10

21:55-11:54

1 stop20h 59m

Chicago Midway

Mon 2/11

13:27-19:10

2 stops21h 43m

R16 811

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sun 11/10

21:55-22:33

1 stop31h 38m

Chicago Midway

Sat 24/10

9:29-19:10

2 stops26h 41m

R16 859

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 11/10

21:55-18:29

2 stops27h 34m

Chicago O'Hare Intl

Sat 24/10

13:55-19:10

2 stops22h 15m

R16 908

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 9/9

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Wed 3/3

13:10-8:20

1 stop35h 10m

R17 230

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 4/10

22:00-22:28

1 stop31h 28m

Chicago O'Hare Intl

Sun 11/10

12:09-18:30

1 stop23h 21m

R17 359

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 7/9

23:15-20:30

2 stops28h 15m

Chicago O'Hare Intl

Wed 3/3

16:25-22:00

1 stop21h 35m

R17 391

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 7/9

22:00-16:52

2 stops25h 52m

Chicago O'Hare Intl

Wed 3/3

13:12-18:35

2 stops21h 23m

R17 456

Flights are sorted by cheapest return flights first.

Deals found on 18/8

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 23 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, Etihad Airways and Qatar Airways.

What are the cheapest airlines that fly to Chicago?

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

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

KLM

7,8

Good

1 563 reviews

KLM

7,8

Good

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

Qatar Airways

7,4

Good

3 737 reviews

KLM

7,8

Good

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

Turkish Airlines

7,4

Good

4 481 reviews

KLM

7,8

Good

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

United Airlines

7,4

Good

10 106 reviews

KLM

7,8

Good

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

Etihad Airways

7,3

Good

1 506 reviews

KLM

7,8

Good

1 563 reviews

Check prices

Reviews

1 / 20

4,0

Okay

Abhisek,Aug 2026

JFK - AMS

They didn’t offer any options for breakfast and had only one option which was cold meat and cheese. I would expect at least one more option in premium economy

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 R941, while return flights cost around R2 419.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R2 419, however they can be found for as little as R2 419.
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

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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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R9 912+ 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 14/9. 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 21 August 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 21 August 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 21 August 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 21 August 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 21 August 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 21 August 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 21 August 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 21 August 2026.

Find flight deals to Chicago

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Popular 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 23 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, Etihad Airways and Qatar Airways.

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Johannesburg to Chicago are Etihad Airways, Turkish Airlines 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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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 21 August 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 21 August 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 21 August 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 21 August 2026.