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R1 546+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 20/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — JNB
Jan 29 — Feb 51
1 adult
1 adult, Economy, 0 bags

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 30 December 2025.

Good round-trip deal

R8 696 or less

Good one-way deal

R826 or less
Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 30 December 2025.

Sun 1/36:04ORD - JNB
2 stops25h 46mMultiple Airlines
Sun 8/317:00JNB - ORD
2 stops25h 49mMultiple Airlines
Deal found 30/12R15 382
Tue 13/19:45ORD - JNB
1 stop26h 25mEthiopian Air
Thu 2/48:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 30/12R16 063
Mon 2/320:20ORD - CPT
1 stop31h 30mTurkish Airlines
Wed 11/317:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 29/12R16 113
Wed 22/48:31ORD - JNB
2 stops24h 19mMultiple Airlines
Thu 7/517:00JNB - ORD
2 stops27h 16mMultiple Airlines
Deal found 30/12R16 130
Mon 9/218:50ORD - JNB
2 stops39h 50mQatar Airways
Wed 18/212:45JNB - ORD
1 stop33h 45mQatar Airways
Deal found 30/12R16 180
Wed 15/47:00ORD - JNB
2 stops25h 50mKenya Airways
Tue 21/412:10JNB - ORD
2 stops31h 21mKenya Airways
Deal found 29/12R16 213
Sun 1/320:20ORD - CPT
1 stop31h 30mTurkish Airlines
Tue 10/317:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 28/12R16 429
Wed 15/48:31ORD - JNB
2 stops24h 19mMultiple Airlines
Thu 30/417:00JNB - ORD
2 stops28h 20mMultiple Airlines
Deal found 30/12R16 429
Tue 20/17:00ORD - JNB
2 stops24h 50mKenya Airways
Tue 10/217:00JNB - ORD
2 stops28h 14mKenya Airways
Deal found 30/12R16 462
Tue 20/17:00ORD - JNB
2 stops43h 55mKenya Airways
Sat 28/217:00JNB - ORD
2 stops32h 43mKenya Airways
Deal found 29/12R16 479
Thu 29/118:25ORD - JNB
2 stops37h 25mKenya Airways
Thu 5/217:00JNB - ORD
2 stops28h 14mKenya Airways
Deal found 30/12R16 579
Thu 9/419:50ORD - CPT
1 stop33h 00mTurkish Airlines
Wed 15/416:35CPT - ORD
1 stop24h 05mTurkish Airlines
Deal found 29/12R16 596

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 30 December 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/4

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Thu 7/5

14:30-8:15

2 stops24h 45m

R16 063

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 2/3

20:20-11:50

1 stop31h 30m

Cape Town Intl

Wed 11/3

17:15-11:05

1 stop24h 50m

R16 113

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Tue 3/3

20:20-11:50

1 stop31h 30m

Cape Town Intl

Tue 10/3

17:15-19:25

1 stop33h 10m

R16 113

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/4

8:31-15:50

2 stops24h 19m

Johannesburg OR Tambo

Thu 7/5

17:00-13:16

2 stops27h 16m

R16 130

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 18/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

Mon 23/3

17:15-19:25

1 stop33h 10m

R16 729

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 18/4

19:20-9:40

2 stops31h 20m

Johannesburg OR Tambo

Mon 27/4

11:55-15:00

1 stop34h 05m

R16 828

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 24/3

17:50-15:50

2 stops39h 00m

Johannesburg OR Tambo

Tue 31/3

12:10-17:10

2 stops36h 00m

R17 277

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 15/4

10:15-14:35

1 stop21h 20m

Cape Town Intl

Thu 30/4

13:50-8:15

2 stops25h 25m

R17 394

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 19/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 3/5

14:30-8:15

2 stops24h 45m

R17 543

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 26/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 10/5

14:30-8:15

2 stops24h 45m

R17 543

Flights are sorted by cheapest return flights first.

Deals found on 28/12

Showing 1-10 of 60 results
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from 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.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a return flight from Chicago to OR Tambo. Price data was last updated on 26 December 2025.

Booking 16 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago?

Currently, April is the cheapest month in which you can book a flight from Chicago (average of R13 636). Flying from Chicago in July will prove the most costly (average of R20 171). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (924 flights per day), Orlando (826 flights per day) and New York (768 flights per day).

Fort Lauderdale
Fort Lauderdale
From R2 701
Orlando
Orlando
From R2 453
New York
New York
From R826
Dublin
Dublin
From R6 073

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at R826. Explore other affordable destinations below.

New York
New York
From R826
Orlando
Orlando
From R2 453
Fort Lauderdale
Fort Lauderdale
From R2 701
Phoenix Sky Harbor Intl
Phoenix Sky Harbor Intl
From R3 068

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 594 507 searches.
See what other customers who have flown with Turkish Airlines and Ethiopian Air from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Turkish Airlines
7,3
Good
4 133 reviews
Check prices

Boarding

7,3

Overall

7,3

Entertainment

7,4

Comfort

7,3

Crew

7,8

Food

7,4

Reviews

1 / 20
6,0
Good

Chandra,Nov 2025

ATL - IST

TV was not available in Indigo from Istanbul to Delhi. Seat was not moving back. It was jammed.
Turkish Airlines
7,3
Good
4 133 reviews
Turkish Airlines
7,3
Good
4 133 reviews
Check prices

Boarding

7,3

Overall

7,3

Entertainment

7,4

Comfort

7,3

Crew

7,8

Food

7,4

Reviews

1 / 20
6,0
Good

Chandra,Nov 2025

ATL - IST

TV was not available in Indigo from Istanbul to Delhi. Seat was not moving back. It was jammed.
Ethiopian Air
7,2
Good
923 reviews
Turkish Airlines
7,3
Good
4 133 reviews
Check prices

Boarding

7,3

Overall

7,3

Entertainment

7,4

Comfort

7,3

Crew

7,8

Food

7,4

Reviews

1 / 20
6,0
Good

Chandra,Nov 2025

ATL - IST

TV was not available in Indigo from Istanbul to Delhi. Seat was not moving back. It was jammed.

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 30 December 2025.

  • What are the most popular destinations to fly to from Chicago?

    The most selected flight destinations from Chicago for the current month are Ahmedabad, Mumbai, Atlanta. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.

  • What is the cheapest month to fly from Chicago?

    April is currently the cheapest month to fly from Chicago. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

  • Why should you use Cheapflights to find cheap flight tickets from 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 from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Certainly. Search results for flights from 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 from Chicago become cheaper?

    Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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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 from Chicago?

Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from 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 from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Certainly. Search results for flights from 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 from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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