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R12 165+ 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 27/11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jul 22 — Jul 291
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

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 22 June 2026.

Wed 28/1018:50
JNB
-
ORD
1 stop23h 10m
Turkish Airlines
Tue 10/1111:45
ORD
-
JNB
1 stop39h 15m
Turkish Airlines
Deal found 17/6R15 815
Tue 21/722:00
JNB
-
ORD
1 stop31h 06m
United Airlines
Tue 25/810:35
ORD
-
JNB
1 stop24h 55m
United Airlines
Deal found 17/6R16 653
Mon 7/99:45
JNB
-
ORD
1 stop29h 50m
Etihad Airways
Wed 3/313:10
ORD
-
JNB
1 stop35h 10m
Etihad Airways
Deal found 18/6R16 834
Tue 14/718:50
JNB
-
ORD
2 stops28h 20m
Multiple Airlines
Wed 28/416:20
ORD
-
JNB
1 stop22h 00m
Multiple Airlines
Deal found 19/6R17 212
Wed 18/1120:10
JNB
-
MDW
2 stops34h 00m
Virgin Atlantic
Thu 21/113:05
MDW
-
JNB
2 stops35h 15m
Virgin Atlantic
Deal found 19/6R17 212
Wed 28/1021:40
JNB
-
ORD
2 stops31h 05m
Virgin Atlantic
Tue 10/1115:00
ORD
-
JNB
2 stops33h 20m
Virgin Atlantic
Deal found 21/6R17 228
Tue 21/718:50
JNB
-
ORD
1 stop27h 20m
Multiple Airlines
Tue 25/816:20
ORD
-
JNB
1 stop22h 00m
Multiple Airlines
Deal found 19/6R17 278
Tue 21/723:15
JNB
-
ORD
2 stops27h 15m
KLM
Tue 25/816:20
ORD
-
JNB
1 stop22h 00m
KLM
Deal found 19/6R17 376
Mon 3/819:00
JNB
-
ORD
2 stops29h 02m
United Airlines
Tue 1/97:30
ORD
-
JNB
2 stops28h 00m
United Airlines
Deal found 19/6R17 409
Tue 21/723:15
JNB
-
MDW
2 stops30h 00m
Delta
Tue 28/76:00
MDW
-
JNB
1 stop30h 40m
Delta
Deal found 21/6R18 264
Tue 21/723:15
JNB
-
MDW
2 stops30h 00m
Delta
Tue 25/89:59
MDW
-
JNB
2 stops28h 21m
Delta
Deal found 19/6R19 431
Thu 3/920:15
JNB
-
MDW
2 stops33h 21m
Virgin Atlantic
Sun 13/910:48
MDW
-
JNB
1 stop25h 52m
Virgin Atlantic
Deal found 22/6R20 352

Find flight deals to Chicago

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 594 507 searches and data was last updated on 22 June 2026.

Return from

R15 815

One-way from

R12 165

Popular in

January

Cheapest in

February

Average price

R18 741
Turkish Airlines
  • Turkish Airlines
  • 28/10-10/11
  • 2 total stops
  • 62h 25m total
  • Johannesburg to Chicago
Search Deals
Etihad Airways
  • Etihad Airways
  • 27/11
  • 1 total stop
  • 30h 05m total
  • Johannesburg to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (R1 280 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (R473 potential savings vs. average return price).
Search Deals
Average for return flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 594 507 searches and data was last updated on 22 June 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Wed 18/11

20:10-22:10

2 stops34h 00m

Chicago Midway

Thu 21/1

13:05-8:20

2 stops35h 15m

R17 212

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 21/7

23:15-19:30

2 stops27h 15m

Chicago O'Hare Intl

Tue 25/8

16:20-21:20

1 stop22h 00m

R17 376

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 28/10

21:40-18:32

2 stops27h 52m

Chicago O'Hare Intl

Tue 10/11

15:35-8:20

2 stops32h 45m

R17 393

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 3/8

22:00-16:52

2 stops25h 52m

Chicago O'Hare Intl

Tue 1/9

7:05-18:30

1 stop28h 25m

R17 491

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 21/7

23:15-22:15

2 stops30h 00m

Chicago Midway

Tue 28/7

9:19-19:40

2 stops27h 21m

R18 264

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Wed 18/11

23:55-18:37

2 stops26h 42m

Chicago Midway

Thu 21/1

10:35-19:00

1 stop24h 25m

R18 264
Fastest return journey

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 7/9

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Wed 3/3

12:15-22:00

2 stops25h 45m

R18 691

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 7/9

17:00-12:25

2 stops26h 25m

Chicago O'Hare Intl

Wed 3/3

6:00-10:55

2 stops44h 55m

R19 645

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 4/8

19:00-12:55

1 stop24h 55m

Chicago O'Hare Intl

Wed 2/9

12:40-18:30

2 stops22h 50m

R19 645

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 4/8

19:00-12:55

1 stop24h 55m

Chicago O'Hare Intl

Tue 1/9

12:16-18:30

1 stop23h 14m

R19 645

Flights are sorted by cheapest return flights first.

Deals found on 21/6

Showing 1-10 of 35 resultsSorted by cheapest first
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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.
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

How long is the flight to Chicago?

On average, a flight from Johannesburg to Chicago takes 23 hours 26 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 KLM, British Airways and United Airlines.

United Airlines
United Airlines
From R15 258
KLM
KLM
From R16 606
British Airways
British Airways
From R16 193
Qatar Airways
Qatar Airways
From R16 751

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Johannesburg to Chicago are Etihad Airways, Turkish Airlines and Ethiopian Air.

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.

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 67 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 insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 22 June 2026.
Get a feel of what it's like to fly with Emirates,KLM, 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.
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf
Emirates
8,1
Very Good
3 593 reviews
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf
KLM
7,8
Good
1 530 reviews
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf
United Airlines
7,4
Good
9 874 reviews
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf
Etihad Airways
7,3
Good
1 459 reviews
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf
British Airways
6,7
Okay
8 064 reviews
Emirates
8,1
Very Good
3 593 reviews
Check prices

Crew

8,4

Comfort

8,0

Entertainment

8,2

Food

7,9

Boarding

8,1

Overall

8,1

Reviews

1 / 20
2,0
Mediocre

Anonymous,Apr 2026

DXB - MIA

Flight was cancelled due to the war in the Gulf

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 209, while return flights cost around R9 518.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around R9 518, however they can be found for as little as R9 518.

  • 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 54 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

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Airports serving Chicago

Book a flight to or from one of these Chicago airports.
Flights to Midway
Flights to O'Hare Intl
Flights from Midway
Flights from O'Hare Intl

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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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