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R1 576+ 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 11/1. 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 16 — Jan 231
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 17 December 2025.

Good round-trip deal

R16 887 or less

Good one-way deal

R833 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

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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 17 December 2025.

Thu 7/57:30ORD - JNB
2 stops25h 20mKenya Airways
Sat 23/512:10JNB - ORD
2 stops31h 31mKenya Airways
Deal found 17/12R15 982
Fri 13/37:00ORD - JNB
2 stops34h 25mKenya Airways
Sun 22/312:05JNB - ORD
2 stops36h 05mKenya Airways
Deal found 16/12R16 065
Wed 1/410:15ORD - JNB
1 stop26h 55mEthiopian Air
Wed 8/414:30JNB - ORD
2 stops24h 45mEthiopian Air
Deal found 15/12R16 351
Tue 20/17:00ORD - JNB
2 stops43h 55mKenya Airways
Tue 10/217:00JNB - ORD
2 stops32h 45mKenya Airways
Deal found 16/12R16 518
Wed 4/39:45ORD - JNB
1 stop26h 25mEthiopian Air
Wed 25/314:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 15/12R16 585
Sat 31/114:30ORD - JNB
2 stops41h 20mMultiple Airlines
Sat 7/217:00JNB - ORD
2 stops32h 45mMultiple Airlines
Deal found 17/12R16 770
Fri 20/310:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 1/48:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 15/12R16 988
Sun 8/29:45ORD - JNB
1 stop26h 25mEthiopian Air
Tue 17/214:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 14/12R17 072
Sat 7/312:51ORD - JNB
2 stops42h 59mMultiple Airlines
Sun 12/417:00JNB - ORD
2 stops35h 33mMultiple Airlines
Deal found 16/12R17 088
Wed 11/310:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 25/38:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 17/12R17 156
Fri 30/19:45ORD - JNB
1 stop26h 25mEthiopian Air
Tue 3/214:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 15/12R17 306
Thu 7/510:15ORD - JNB
1 stop19h 50mEthiopian Air
Sat 23/58:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 17/12R17 323

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 17 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

Sun 26/4

8:20-8:15

2 stops30h 55m

R17 675

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 22/2

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sun 1/3

14:30-7:40

2 stops25h 10m

R17 675

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 16/2

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Wed 25/2

14:30-7:40

2 stops25h 10m

R17 675

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Fri 13/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sat 21/3

8:20-8:40

2 stops31h 20m

R18 011

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Fri 30/1

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Fri 6/2

8:20-7:40

2 stops31h 20m

R18 011

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 21/2

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sun 1/3

14:30-7:40

2 stops25h 10m

R18 514

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 11/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Fri 20/3

14:30-8:40

2 stops25h 10m

R18 514

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Fri 30/1

20:20-13:30

2 stops33h 10m

Durban King Shaka Intl

Fri 6/2

16:00-10:05

2 stops26h 05m

R19 168

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 4/5

10:15-14:35

1 stop21h 20m

Cape Town Intl

Thu 7/5

13:50-8:15

2 stops25h 25m

R19 403

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

15:20-11:05

2 stops26h 45m

R19 755

Flights are sorted by cheapest return flights first.

Deals found on 15/12

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 12 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 751). Flying from Chicago in July will prove the most costly (average of R20 342). 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: New York (1 315 flights per day), Detroit (812 flights per day) and Toronto (726 flights per day).

Fort Lauderdale
Fort Lauderdale
From R2 724
Orlando
Orlando
From R2 474
New York
New York
From R833
Dublin
Dublin
From R6 125

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 R833. Explore other affordable destinations below.

New York
New York
From R833
Orlando
Orlando
From R2 474
Fort Lauderdale
Fort Lauderdale
From R2 724
Miami
Miami
From R3 753

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
4 105 reviews
Check prices

Overall

7,3

Entertainment

7,4

Boarding

7,3

Crew

7,8

Comfort

7,3

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
4 105 reviews
Turkish Airlines
7,3
Good
4 105 reviews
Check prices

Overall

7,3

Entertainment

7,4

Boarding

7,3

Crew

7,8

Comfort

7,3

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
911 reviews
Turkish Airlines
7,3
Good
4 105 reviews
Check prices

Overall

7,3

Entertainment

7,4

Boarding

7,3

Crew

7,8

Comfort

7,3

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 17 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, Athens 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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