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, Etihad Airways is rated the highest out of the airlines that fly to Chicago.

What is the cheapest airport to fly to in Chicago?

Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost R1 421, while return flights cost around R4 220.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around R10 335, however they can be found for as little as R4 220.

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 46 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).

R10 632+ Cheap Flights to Chicago, Illinois

Flights to Chicago in 2025

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 17 December 2025.

Thu 25/1222:00JNB - ORD

1 stop22h 05mUnited Airlines

Sat 24/18:54ORD - JNB

2 stops25h 41mUnited Airlines

Deal found 15/12R15 680

Sat 27/1221:55JNB - ORD

1 stop29h 04mVirgin Atlantic

Thu 22/114:50ORD - JNB

1 stop20h 10mVirgin Atlantic

Deal found 15/12R15 831

Fri 26/1219:45JNB - ORD

1 stop23h 25mUnited Airlines

Fri 23/114:27ORD - JNB

1 stop20h 08mUnited Airlines

Deal found 15/12R15 948

Wed 24/1219:45JNB - ORD

2 stops44h 02mUnited Airlines

Mon 19/114:00ORD - JNB

2 stops20h 35mUnited Airlines

Deal found 15/12R16 049

Thu 25/1222:00JNB - ORD

1 stop22h 05mUnited Airlines

Tue 20/116:05ORD - JNB

1 stop33h 25mUnited Airlines

Deal found 15/12R16 082

Fri 26/1219:45JNB - ORD

1 stop23h 25mUnited Airlines

Tue 27/118:25ORD - JNB

1 stop31h 05mUnited Airlines

Deal found 15/12R16 283

Sat 27/128:20JNB - ORD

2 stops31h 20mEthiopian Air

Thu 22/19:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 15/12R16 367

Thu 25/1220:15JNB - ORD

2 stops47h 03mAir Canada

Mon 19/115:35ORD - JNB

2 stops58h 55mAir Canada

Deal found 15/12R16 451

Thu 25/1220:15JNB - ORD

2 stops47h 03mAir Canada

Thu 22/118:28ORD - JNB

2 stops52h 37mAir Canada

Deal found 15/12R16 585

Thu 25/1220:15JNB - ORD

2 stops47h 03mAir Canada

Wed 21/112:50ORD - JNB

2 stops36h 40mAir Canada

Deal found 15/12R16 887

Wed 24/1219:45JNB - ORD

1 stop23h 25mUnited Airlines

Wed 21/116:15ORD - JNB

1 stop18h 20mUnited Airlines

Deal found 15/12R16 904

Wed 24/1219:45JNB - ORD

2 stops51h 25mAir Canada

Sat 24/17:15ORD - JNB

2 stops43h 15mAir Canada

Deal found 15/12R16 938

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 17 December 2025.

Tue 24/319:10JNB - ORD

1 stop31h 15mTurkish Airlines

Wed 15/411:25ORD - JNB

1 stop40h 10mTurkish Airlines

Deal found 16/12R14 422

Mon 2/29:50JNB - ORD

2 stops41h 46mEtihad Airways

Wed 18/26:04ORD - JNB

2 stops42h 16mEtihad Airways

Deal found 16/12R15 378

Thu 16/48:20JNB - ORD

2 stops30h 55mEthiopian Air

Mon 11/510:15ORD - JNB

1 stop19h 50mEthiopian Air

Deal found 16/12R15 579

Thu 5/319:35JNB - ORD

2 stops26h 25mBritish Airways

Mon 9/316:19ORD - JNB

2 stops32h 16mBritish Airways

Deal found 16/12R16 602

Fri 30/122:00JNB - ORD

2 stops31h 26mUnited Airlines

Fri 6/214:27ORD - JNB

1 stop20h 08mUnited Airlines

Deal found 15/12R16 652

Thu 29/121:30JNB - MDW

2 stops29h 06mDelta

Thu 5/212:48MDW - JNB

1 stop22h 12mDelta

Deal found 15/12R16 904

Thu 16/417:55JNB - ORD

1 stop22h 45mTurkish Airlines

Mon 11/511:25ORD - JNB

1 stop40h 10mTurkish Airlines

Deal found 16/12R14 422

Thu 5/314:30JNB - ORD

2 stops25h 10mEthiopian Air

Mon 9/310:15ORD - JNB

1 stop19h 50mEthiopian Air

Deal found 15/12R15 730

Tue 24/322:00JNB - MDW

2 stops27h 40mDelta

Wed 15/49:30MDW - JNB

2 stops27h 10mDelta

Deal found 16/12R16 921

Thu 5/319:10JNB - ORD

1 stop31h 15mTurkish Airlines

Mon 9/312:50ORD - JNB

1 stop39h 00mTurkish Airlines

Deal found 14/12R15 411

Tue 3/214:30JNB - ORD

2 stops25h 10mEthiopian Air

Sat 7/29:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 16/12R15 931

Thu 16/423:15JNB - MDW

2 stops25h 50mDelta

Mon 11/513:00MDW - JNB

2 stops23h 40mDelta

Deal found 15/12R20 442

Fri 30/119:20JNB - MDW

2 stops28h 56mDelta

Sat 14/26:00MDW - JNB

1 stop29h 00mDelta

Deal found 14/12R117 942

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 17 December 2025 and is based on user searches.

Wed 24/1219:45JNB - ORD

2 stops44h 02mUnited Airlines

Mon 19/114:00ORD - JNB

2 stops20h 35mUnited Airlines

Deal found 15/12R16 049

Thu 25/1222:00JNB - ORD

1 stop22h 05mUnited Airlines

Sat 24/18:54ORD - JNB

2 stops25h 41mUnited Airlines

Deal found 15/12R15 680

Thu 25/1222:00JNB - ORD

1 stop22h 05mUnited Airlines

Tue 20/116:05ORD - JNB

1 stop33h 25mUnited Airlines

Deal found 15/12R16 082

Fri 26/1222:00JNB - ORD

1 stop22h 05mUnited Airlines

Sat 3/115:53ORD - JNB

1 stop18h 42mUnited Airlines

Deal found 17/12R15 713

Fri 26/1219:45JNB - ORD

1 stop23h 25mUnited Airlines

Wed 21/113:00ORD - JNB

2 stops21h 35mUnited Airlines

Deal found 15/12R15 948

Sat 27/1221:55JNB - ORD

1 stop29h 04mVirgin Atlantic

Thu 22/114:50ORD - JNB

1 stop20h 10mVirgin Atlantic

Deal found 15/12R15 831

Thu 29/18:20JNB - ORD

2 stops31h 20mEthiopian Air

Thu 5/29:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 15/12R13 902

Thu 29/119:10JNB - ORD

1 stop22h 55mTurkish Airlines

Thu 5/220:20ORD - JNB

1 stop30h 30mTurkish Airlines

Deal found 15/12R14 523

Thu 29/121:30JNB - MDW

2 stops29h 06mDelta

Thu 5/29:53MDW - JNB

2 stops25h 07mDelta

Deal found 15/12R16 904

Fri 30/119:05JNB - ORD

1 stop31h 20mTurkish Airlines

Sat 14/220:20ORD - JNB

1 stop30h 30mTurkish Airlines

Deal found 14/12R14 674

Fri 30/122:00JNB - ORD

2 stops29h 15mAmerican Airlines

Sat 14/221:00ORD - JNB

2 stops29h 25mAmerican Airlines

Deal found 14/12R15 864

Fri 30/119:20JNB - MDW

2 stops28h 18mMultiple Airlines

Sat 14/211:45MDW - JNB

2 stops26h 20mMultiple Airlines

Deal found 14/12R18 195

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 17 December 2025.

Fri 1/511:55JNB - ORD

1 stop33h 55mQatar Airways

Deal found 17/12R10 632

Tue 23/129:50JNB - ORD

1 stop29h 45mEtihad Airways

Deal found 14/12R11 219

Wed 21/19:50JNB - ORD

1 stop29h 45mEtihad Airways

Deal found 15/12R11 336

Thu 22/117:00JNB - ORD

2 stops33h 29mMultiple Airlines

Deal found 14/12R11 471

Fri 30/119:05JNB - ORD

1 stop31h 20mTurkish Airlines

Deal found 16/12R11 521

Wed 21/119:45JNB - MDW

3 stops56h 07mMultiple Airlines

Deal found 15/12R11 739

Wed 24/1223:00JNB - ORD

3 stops45h 57mMultiple Airlines

Deal found 14/12R11 856

Wed 21/120:30JNB - ORD

3 stops35h 16mMultiple Airlines

Deal found 15/12R11 974

Thu 22/117:00JNB - MDW

3 stops34h 52mMultiple Airlines

Deal found 14/12R12 007

Thu 30/40:45JNB - ORD

3 stops44h 30mMultiple Airlines

Deal found 17/12R12 041

Mon 22/129:50JNB - ORD

1 stop29h 45mEtihad Airways

Deal found 14/12R12 175

Tue 23/1217:00JNB - ORD

2 stops27h 57mMultiple Airlines

Deal found 14/12R12 728

Find flight deals to Chicago

Return from	R13 399
One-way from	R10 632
Popular in	January
Cheapest in	February
Average price	R20 023

Etihad Airways
2/2-18/2
2 total stops
64h 55m total
Johannesburg to Chicago

Search Deals

Qatar Airways
1/5
1 total stop
33h 55m total
Johannesburg to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (R835 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (R210 potential savings vs. average return price).

Search Deals

Average for return flights in December 2025

Search Deals

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 24/3

19:10-19:25

1 stop31h 15m

Chicago O'Hare Intl

Wed 15/4

11:25-10:35

1 stop40h 10m

R14 422

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 16/4

17:55-9:40

1 stop22h 45m

Chicago O'Hare Intl

Mon 11/5

11:25-10:35

1 stop40h 10m

R14 422

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 2/2

9:50-19:36

2 stops41h 46m

Chicago O'Hare Intl

Wed 18/2

6:04-8:20

2 stops42h 16m

R15 378

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 5/3

19:10-18:25

1 stop31h 15m

Chicago O'Hare Intl

Mon 9/3

12:50-10:50

1 stop39h 00m

R15 411

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 16/4

8:20-8:15

2 stops30h 55m

Chicago O'Hare Intl

Mon 11/5

10:15-13:05

1 stop19h 50m

R15 579

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 5/3

14:30-7:40

2 stops25h 10m

Chicago O'Hare Intl

Mon 9/3

10:15-13:05

1 stop19h 50m

R15 730

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 3/2

14:30-7:40

2 stops25h 10m

Chicago O'Hare Intl

Sat 7/2

9:45-20:10

1 stop26h 25m

R15 931

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 5/3

19:35-14:00

2 stops26h 25m

Chicago O'Hare Intl

Mon 9/3

16:19-7:35

2 stops32h 16m

R16 602

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 30/1

22:00-21:26

2 stops31h 26m

Chicago O'Hare Intl

Fri 6/2

14:27-18:35

1 stop20h 08m

R16 652

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 29/1

21:30-18:36

2 stops29h 06m

Chicago Midway

Thu 5/2

12:48-19:00

1 stop22h 12m

R16 904

Flights are sorted by cheapest return flights first.

Deals found on 17/12

Showing 1-10 of 30 results

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

When is the best time to book a flight to Chicago?

The best time to book flights to Chicago is 69 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.

How long is the flight to Chicago?

On average, a flight from Johannesburg to Chicago takes 24 hours 7 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.

When is the cheapest time to fly to Chicago?

Users looking for the lowest fares to Chicago should consider flying on Tuesday evenings, when prices are typically cheapest. Budget-minded travellers will want to avoid Monday afternoons, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Johannesburg to Chicago are British Airways, KLM and Turkish Airlines.

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

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).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM, Etihad Airways, 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

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

KLM

7,7

Good

1 430 reviews

KLM

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

Etihad Airways

7,4

Good

1 332 reviews

KLM

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

United Airlines

7,4

Good

9 091 reviews

KLM

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

Turkish Airlines

7,3

Good

4 105 reviews

KLM

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

British Airways

6,7

Okay

7 585 reviews

KLM

7,7

Good

1 430 reviews

Check prices

Reviews

1 / 20

8,0

Excellent

Anonymous,Dec 2025

YYC - AMS

Not literally sitting in the very last row in the middle

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, Etihad Airways is rated the highest out of the airlines that fly to Chicago.
What is the cheapest airport to fly to in Chicago?
Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost R1 421, while return flights cost around R4 220.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around R10 335, however they can be found for as little as R4 220.
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 46 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 serving Chicago

Flights to Midway

Flights to O'Hare Intl

Flights from Midway

Flights from O'Hare Intl

Most traveled routes by our users

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Frankfurt am Main Airport to Johannesburg OR Tambo Airport flights

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East London to New York flights

Port Elizabeth to Bloemfontein flights

South Africa to South Korea flights

Johannesburg OR Tambo Airport to Cape Town flights

Nairobi to Dar Es Salaam flights

South Africa to Chania flights

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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R10 632+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

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 17 December 2025.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 17 December 2025.

Find flight deals to Chicago

Find the latest flights to Chicago in 2025, 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 17 December 2025.

Return from

One-way from

Popular in

Cheapest in

Average price

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

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Johannesburg to Chicago. Price data was last updated on 12 December 2025.

How long is the flight to Chicago?

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return from Johannesburg to Chicago. Price data was last updated on 16 December 2024.

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with KLM, Etihad Airways, 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

Book a flight to or from one of these Chicago airports.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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 17 December 2025.