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 R942, while return flights cost around R8 290.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R19 258, however they can be found for as little as R8 290.

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 856+ 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 August 2026.

Tue 29/920:15 -

2 stops33h 29m

Tue 6/1017:09 -

1 stop19h 31m

Deal found 30/8R15 986

Tue 29/920:15 -

2 stops31h 41m

Tue 6/108:05 -

1 stop28h 35m

Deal found 30/8R15 986

Thu 1/1020:15 -

2 stops34h 44m

Sat 10/1010:35 -

1 stop26h 05m

Deal found 29/8R16 131

Thu 1/1022:00 -

1 stop25h 34m

Sat 10/1015:00 -

1 stop20h 30m

Deal found 29/8R16 308

Thu 8/1022:00 -

2 stops27h 41m

Sun 18/107:00 -

2 stops28h 30m

Deal found 28/8R16 373

Thu 8/1022:00 -

1 stop27h 39m

Sat 17/1013:55 -

1 stop21h 35m

Deal found 27/8R16 437

Thu 17/99:45 -

1 stop36h 55m

Thu 8/1020:25 -

1 stop28h 50m

Deal found 30/8R16 550

Wed 14/109:45 -

1 stop36h 55m

Sat 17/1014:00 -

1 stop35h 20m

Deal found 27/8R16 841

Sun 11/1021:55 -

1 stop33h 02m

Sun 18/1013:23 -

1 stop23h 17m

Deal found 26/8R16 954

Tue 29/922:00 -

1 stop30h 32m

Tue 6/1016:00 -

1 stop19h 30m

Deal found 30/8R17 163

Sun 11/1018:50 -

2 stops28h 20m

Sun 18/1016:15 -

1 stop22h 05m

Deal found 26/8R17 228

Mon 7/918:50 -

1 stop27h 20m

Wed 3/316:25 -

1 stop21h 35m

Deal found 31/8R17 357

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 August 2026.

Thu 1/1020:15 -

2 stops34h 44m

Sat 10/1010:35 -

1 stop26h 05m

Deal found 29/8R16 131

Thu 8/1022:00 -

1 stop31h 28m

Sun 18/1014:00 -

2 stops21h 30m

Deal found 28/8R16 373

Thu 28/118:50 -

1 stop31h 30m

Sun 31/120:15 -

1 stop30h 45m

Deal found 28/8R17 131

Wed 23/923:15 -

1 stop22h 00m

Wed 30/98:05 -

1 stop28h 35m

Deal found 26/8R17 938

Thu 28/119:35 -

2 stops31h 40m

Sun 31/120:40 -

1 stop29h 45m

Deal found 30/8R19 502

Fri 16/1014:05 -

2 stops29h 11m

Fri 30/1019:50 -

1 stop36h 45m

Deal found 26/8R19 841

Tue 15/921:55 -

1 stop31h 49m

Mon 21/913:00 -

2 stops26h 25m

Deal found 31/8R22 180

Thu 8/1022:00 -

1 stop27h 39m

Sat 17/1013:55 -

1 stop21h 35m

Deal found 27/8R16 437

Sun 11/1021:55 -

1 stop33h 02m

Sun 18/1013:23 -

1 stop23h 17m

Deal found 26/8R16 954

Fri 5/221:20 -

1 stop27h 05m

Fri 5/39:30 -

2 stops28h 30m

Deal found 29/8R18 018

Tue 29/922:00 -

1 stop30h 32m

Tue 6/1016:00 -

1 stop19h 30m

Deal found 30/8R17 163

Mon 12/1021:55 -

1 stop31h 38m

Mon 19/106:04 -

1 stop30h 36m

Deal found 28/8R18 180

Wed 14/1020:15 -

2 stops33h 18m

Wed 21/1010:59 -

1 stop25h 41m

Deal found 30/8R18 518

Thu 15/1019:00 -

1 stop24h 55m

Thu 22/1010:32 -

2 stops24h 58m

Deal found 26/8R18 341

Thu 15/1020:15 -

2 stops33h 18m

Thu 22/1012:49 -

2 stops26h 36m

Deal found 26/8R23 164

Fri 11/1223:59 -

2 stops26h 02m

Sat 2/19:30 -

2 stops25h 40m

Deal found 26/8R21 793

Thu 15/1020:15 -

2 stops33h 18m

Thu 22/1017:09 -

1 stop19h 11m

Deal found 26/8R21 906

Thu 1/1021:55 -

1 stop25h 20m

Sat 10/1011:33 -

1 stop25h 07m

Deal found 29/8R22 648

Thu 8/1021:55 -

2 stops27h 05m

Sat 17/1011:33 -

1 stop25h 07m

Deal found 27/8R22 712

Find flight deals to Chicago

Return from	R15 986
One-way from	R9 856
Popular in	January
Cheapest in	February
Average price	R17 276

Virgin Atlantic
29/9-6/10
3 total stops
60h 16m total
Johannesburg to Chicago

Search Deals

Qatar Airways
16/9
1 total stop
25h 10m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R879 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (R455 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

Thu 1/10

20:15-23:59

2 stops34h 44m

Chicago O'Hare Intl

Sat 10/10

10:35-19:40

1 stop26h 05m

R16 131

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 8/10

22:00-22:28

1 stop31h 28m

Chicago O'Hare Intl

Sun 18/10

14:00-18:30

2 stops21h 30m

R16 373

Fastest return journey

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 8/10

22:00-18:39

1 stop27h 39m

Chicago O'Hare Intl

Sat 17/10

13:55-18:30

1 stop21h 35m

R16 437

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 11/10

21:55-23:57

1 stop33h 02m

Chicago O'Hare Intl

Sun 18/10

13:23-19:40

1 stop23h 17m

R16 954

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

R17 131

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Tue 29/9

22:00-21:32

1 stop30h 32m

Chicago O'Hare Intl

Tue 6/10

16:00-18:30

1 stop19h 30m

R17 163

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 23/9

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Wed 30/9

8:05-19:40

1 stop28h 35m

R17 938

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Fri 5/2

21:20-16:25

1 stop27h 05m

Chicago Midway

Fri 5/3

9:30-22:00

2 stops28h 30m

R18 018

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Mon 12/10

21:55-22:33

1 stop31h 38m

Chicago Midway

Mon 19/10

6:04-19:40

1 stop30h 36m

R18 180

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 15/10

19:00-12:55

1 stop24h 55m

Chicago O'Hare Intl

Thu 22/10

10:32-18:30

2 stops24h 58m

R18 341

Flights are sorted by cheapest return flights first.

Deals found on 27/8

Showing 1-10 of 35 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 47 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 21 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

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very friendly and helpful

KLM

7,8

Good

1 570 reviews

KLM

7,8

Good

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very friendly and helpful

Qatar Airways

7,4

Good

3 722 reviews

KLM

7,8

Good

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very friendly and helpful

Turkish Airlines

7,4

Good

4 476 reviews

KLM

7,8

Good

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very friendly and helpful

United Airlines

7,4

Good

10 147 reviews

KLM

7,8

Good

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very friendly and helpful

Etihad Airways

7,3

Good

1 529 reviews

KLM

7,8

Good

1 570 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Meghana,Aug 2026

QRO - ATL

It was a good one. They were very 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 R942, while return flights cost around R8 290.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R19 258, however they can be found for as little as R8 290.
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

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Complete your trip

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Airports serving Chicago

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 856+ 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 16/9. 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 31 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 31 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 31 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 31 August 2026.

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

Discover last-minute flight deals to Chicago. Data last updated 31 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 31 August 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 31 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 25 hours 47 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 21 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

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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 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 31 August 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 31 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 31 August 2026.