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 R953, while return flights cost around R6 216.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R6 216, however they can be found for as little as R6 216.

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 15 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 894+ 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 September 2026.

Mon 2/1123:00 -

2 stops40h 40m

Mon 9/119:45 -

1 stop19h 45m

Deal found 18/9R15 126

Fri 11/1214:30 -

2 stops25h 10m

Sat 2/19:45 -

1 stop19h 45m

Deal found 18/9R15 142

Wed 4/1114:30 -

2 stops25h 10m

Wed 11/119:45 -

1 stop26h 25m

Deal found 20/9R15 158

Sat 31/1023:00 -

2 stops40h 40m

Wed 25/119:45 -

1 stop26h 25m

Deal found 17/9R15 386

Sat 19/98:20 -

2 stops30h 55m

Sat 26/910:15 -

1 stop26h 55m

Deal found 18/9R15 418

Wed 4/1119:40 -

2 stops29h 40m

Wed 11/1119:00 -

2 stops32h 25m

Deal found 20/9R16 068

Fri 30/100:20 -

1 stop26h 00m

Wed 25/1120:15 -

1 stop42h 10m

Deal found 17/9R16 263

Mon 2/1118:50 -

1 stop24h 10m

Mon 9/1111:45 -

1 stop39h 10m

Deal found 18/9R16 360

Wed 4/1118:50 -

1 stop24h 10m

Wed 11/1120:15 -

1 stop42h 10m

Deal found 20/9R16 377

Sun 1/1122:00 -

2 stops31h 30m

Sun 8/119:00 -

2 stops25h 35m

Deal found 17/9R16 393

Mon 2/1121:40 -

2 stops32h 53m

Mon 9/1117:13 -

2 stops31h 27m

Deal found 18/9R17 027

Mon 2/1123:59 -

2 stops26h 01m

Mon 9/1111:27 -

2 stops26h 33m

Deal found 18/9R17 384

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 September 2026.

Sun 1/1122:00 -

2 stops31h 30m

Sun 8/119:00 -

2 stops25h 35m

Deal found 17/9R16 393

Mon 1/318:50 -

1 stop31h 30m

Wed 31/320:10 -

1 stop31h 20m

Deal found 17/9R16 815

Mon 2/1123:59 -

2 stops26h 01m

Mon 9/1111:27 -

2 stops26h 33m

Deal found 18/9R17 384

Wed 23/1221:20 -

1 stop30h 39m

Tue 25/56:00 -

2 stops32h 20m

Deal found 20/9R17 953

Wed 4/1121:20 -

1 stop33h 13m

Wed 11/1113:05 -

2 stops25h 20m

Deal found 20/9R18 213

Fri 16/1021:45 -

1 stop38h 30m

Fri 30/1010:30 -

1 stop37h 40m

Deal found 16/9R19 220

Sun 20/1219:35 -

2 stops32h 45m

Tue 25/518:00 -

1 stop32h 25m

Deal found 18/9R19 870

Thu 3/1221:40 -

2 stops33h 15m

Sun 3/19:58 -

2 stops38h 42m

Deal found 17/9R24 809

Wed 27/118:50 -

1 stop23h 10m

Sun 31/111:45 -

1 stop39h 15m

Deal found 20/9R17 368

Sat 31/1015:05 -

2 stops26h 40m

Wed 25/117:00 -

2 stops27h 35m

Deal found 17/9R17 546

Sun 11/1023:15 -

1 stop22h 15m

Tue 27/1013:55 -

2 stops25h 05m

Deal found 17/9R18 732

Mon 1/323:59 -

2 stops26h 38m

Wed 31/317:25 -

1 stop19h 15m

Deal found 17/9R19 236

Thu 3/1215:05 -

2 stops26h 40m

Sun 3/16:00 -

1 stop28h 35m

Deal found 17/9R19 821

Sat 31/1021:40 -

2 stops32h 53m

Sat 7/116:04 -

2 stops42h 36m

Deal found 16/9R24 857

Sat 31/1021:20 -

1 stop33h 13m

Wed 25/119:30 -

2 stops28h 30m

Deal found 17/9R23 785

Tue 1/1221:40 -

2 stops33h 14m

Sun 3/117:05 -

2 stops31h 35m

Deal found 18/9R27 181

Fri 16/1023:15 -

2 stops30h 18m

Fri 30/109:29 -

2 stops26h 41m

Deal found 16/9R26 255

Sat 31/1021:20 -

1 stop33h 13m

Sat 7/1111:33 -

1 stop23h 37m

Deal found 16/9R27 035

Find flight deals to Chicago

Return from	R15 126
One-way from	R9 894
Popular in	January
Cheapest in	November
Average price	R18 066

Ethiopian Air
2/11-9/11
3 total stops
60h 25m total
Johannesburg to Chicago

Search Deals

Qatar Airways
3/11-31/12
1 total stop
26h 10m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R900 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (R409 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

Fastest return journey

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sat 31/10

20:20-15:30

1 stop26h 10m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R10 138

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Tue 3/11

20:20-18:16

2 stops29h 56m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R10 495

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sat 31/10

6:25-18:47

3 stops43h 22m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R12 981

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sat 21/11

16:40-18:20

2 stops33h 40m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 485

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sat 31/10

8:00-19:45

3 stops42h 45m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 615

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 22/11

20:20-13:44

2 stops49h 24m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 972

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sun 22/11

20:20-7:02

2 stops42h 42m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R14 151

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Fri 20/11

0:20-13:33

3 stops45h 13m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R15 239

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Sun 1/11

22:00-21:30

2 stops31h 30m

Chicago O'Hare Intl

Sun 8/11

9:00-18:35

2 stops25h 35m

R16 393

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Mon 1/3

18:50-18:20

1 stop31h 30m

Chicago O'Hare Intl

Wed 31/3

20:10-10:30

1 stop31h 20m

R16 815

Flights are sorted by cheapest return flights first.

Deals found on 16/9

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 26 hours 22 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 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,Turkish Airlines, andUnited 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

1 575 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

1 575 reviews

KLM

7,8

Good

1 575 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

4 465 reviews

KLM

7,8

Good

1 575 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

10 219 reviews

KLM

7,8

Good

1 575 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

3 731 reviews

KLM

7,8

Good

1 575 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

1 531 reviews

KLM

7,8

Good

1 575 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 R953, while return flights cost around R6 216.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R6 216, however they can be found for as little as R6 216.
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 15 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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R9 894+ 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 3/11. 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 21 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 21 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 21 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 21 September 2026.

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

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

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

Find flight deals to Chicago

Return from

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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 26 hours 22 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 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,Turkish Airlines, andUnited 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 21 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 21 September 2026.

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