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 047, while return flights cost around R6 209.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R6 209, however they can be found for as little as R6 209.

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 (22 hours 4 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 899+ 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 15 September 2026.

Wed 14/108:20 -

2 stops30h 55m

Sat 7/119:45 -

1 stop26h 25m

Deal found 14/9R15 222

Wed 14/108:20 -

2 stops30h 55m

Thu 14/19:45 -

1 stop34h 10m

Deal found 14/9R15 271

Thu 29/1018:50 -

1 stop31h 30m

Thu 5/1112:45 -

1 stop25h 40m

Deal found 14/9R16 277

Fri 30/100:20 -

1 stop26h 00m

Wed 25/1120:15 -

1 stop42h 10m

Deal found 13/9R16 358

Wed 14/1018:00 -

1 stop22h 40m

Wed 4/1121:15 -

1 stop41h 10m

Deal found 14/9R16 553

Wed 14/1018:00 -

1 stop22h 40m

Sat 7/1112:45 -

1 stop25h 40m

Deal found 14/9R16 667

Wed 14/1018:00 -

1 stop22h 40m

Thu 14/111:45 -

1 stop26h 40m

Deal found 14/9R16 813

Thu 29/1021:40 -

2 stops31h 53m

Thu 5/116:04 -

2 stops42h 36m

Deal found 14/9R17 186

Wed 14/1020:15 -

2 stops34h 42m

Thu 5/1112:00 -

2 stops36h 40m

Deal found 14/9R17 186

Sat 10/109:45 -

1 stop29h 50m

Sat 17/1014:00 -

1 stop35h 20m

Deal found 12/9R17 300

Thu 29/1015:05 -

2 stops26h 43m

Thu 5/118:40 -

2 stops25h 55m

Deal found 14/9R17 624

Sat 31/1015:05 -

2 stops26h 40m

Wed 25/117:00 -

2 stops27h 35m

Deal found 13/9R17 640

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 15 September 2026.

Thu 28/19:50 -

1 stop30h 05m

Sun 31/113:10 -

1 stop35h 10m

Deal found 10/9R17 137

Thu 29/1021:40 -

2 stops33h 17m

Thu 5/1112:00 -

2 stops36h 40m

Deal found 14/9R17 186

Thu 29/1015:05 -

2 stops26h 43m

Thu 5/118:40 -

2 stops25h 55m

Deal found 14/9R17 624

Thu 28/119:35 -

2 stops31h 40m

Sun 31/120:40 -

1 stop29h 45m

Deal found 10/9R19 685

Fri 16/1020:55 -

2 stops32h 15m

Fri 30/1019:50 -

1 stop36h 45m

Deal found 13/9R20 204

Thu 29/1023:59 -

2 stops29h 34m

Thu 5/1111:38 -

1 stop23h 32m

Deal found 14/9R20 870

Thu 29/1010:25 -

1 stop36h 20m

Thu 5/1119:45 -

1 stop30h 40m

Deal found 14/9R24 116

Sat 31/1017:00 -

3 stops34h 20m

Wed 25/1118:30 -

3 stops29h 50m

Deal found 13/9R28 627

Thu 29/1021:40 -

2 stops31h 53m

Thu 5/116:04 -

2 stops42h 36m

Deal found 14/9R17 186

Sat 31/1015:05 -

2 stops26h 40m

Wed 25/117:00 -

2 stops27h 35m

Deal found 13/9R17 640

Sat 10/109:45 -

1 stop36h 55m

Sat 17/1012:38 -

2 stops36h 42m

Deal found 12/9R18 695

Wed 14/1020:15 -

2 stops33h 18m

Thu 14/110:35 -

2 stops38h 05m

Deal found 14/9R19 734

Sat 31/1021:20 -

2 stops28h 40m

Wed 25/119:30 -

2 stops28h 30m

Deal found 13/9R23 856

Sat 10/1015:05 -

3 stops31h 00m

Sat 17/1016:26 -

2 stops28h 34m

Deal found 12/9R25 349

Fri 23/1023:15 -

2 stops30h 18m

Fri 30/109:29 -

2 stops26h 41m

Deal found 11/9R24 245

Sat 10/1021:55 -

1 stop31h 38m

Sat 17/106:04 -

1 stop30h 36m

Deal found 12/9R22 769

Sat 10/1023:15 -

2 stops30h 18m

Sat 17/1010:12 -

2 stops26h 28m

Deal found 12/9R24 245

Wed 14/1021:55 -

1 stop31h 38m

Thu 5/1111:38 -

2 stops37h 02m

Deal found 14/9R26 258

Fri 16/1023:15 -

2 stops30h 18m

Fri 30/106:04 -

1 stop30h 06m

Deal found 12/9R26 306

Wed 18/1123:59 -

2 stops29h 34m

Tue 15/127:05 -

2 stops30h 55m

Deal found 11/9R26 874

Find flight deals to Chicago

Return from	R15 222
One-way from	R9 899
Popular in	January
Cheapest in	November
Average price	R18 046

Ethiopian Air
14/10-7/11
3 total stops
57h 20m total
Johannesburg to Chicago

Search Deals

Qatar Airways
5/11-31/12
1 total stop
26h 10m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R929 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (R421 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

Thu 5/11

13:45-17:43

2 stops35h 58m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R12 399

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 17/12

18:50-10:00

1 stop23h 10m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R12 691

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Wed 16/12

18:50-10:00

1 stop23h 10m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R13 453

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Sun 29/11

18:50-12:59

3 stops50h 09m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R14 995

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Wed 25/11

21:20-22:54

1 stop33h 34m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R15 531

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Mon 23/11

9:50-7:02

2 stops53h 12m

Chicago Midway

Wed 31/12

0:00-8:00

Nonstop0h 00m

R15 693

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 17/12

19:35-19:15

1 stop31h 40m

Chicago O'Hare Intl

Wed 31/12

0:00-8:00

Nonstop0h 00m

R16 407

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

R17 137

JohannesburgChicago

JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl

JNBORD

Johannesburg OR Tambo

Thu 29/10

21:40-23:57

2 stops33h 17m

Chicago O'Hare Intl

Thu 5/11

12:00-8:40

2 stops36h 40m

R17 186

JohannesburgChicago

JNB Johannesburg OR Tambo - MDW Chicago Midway

JNBMDW

Johannesburg OR Tambo

Thu 29/10

21:40-22:33

2 stops31h 53m

Chicago Midway

Thu 5/11

6:04-8:40

2 stops42h 36m

R17 186

Flights are sorted by cheapest return flights first.

Deals found on 12/9

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 27 hours 31 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,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

1 580 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

1 580 reviews

KLM

7,8

Good

1 580 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

3 733 reviews

KLM

7,8

Good

1 580 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

4 469 reviews

KLM

7,8

Good

1 580 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

10 213 reviews

KLM

7,8

Good

1 580 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

1 533 reviews

KLM

7,8

Good

1 580 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 047, while return flights cost around R6 209.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R6 209, however they can be found for as little as R6 209.
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 (22 hours 4 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

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 899+ 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 5/11. 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 15 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 15 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 15 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 15 September 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 15 September 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 15 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 15 September 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 15 September 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 27 hours 31 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,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 15 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 15 September 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 15 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 15 September 2026.