R1 575+ 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 10/1. 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 — CPT
Jan 18 — Jan 251
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 19 December 2025.

Good round-trip deal

R16 870 or less

Good one-way deal

R832 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 19 December 2025.

Thu 7/57:30ORD - JNB
2 stops25h 20mKenya Airways
Sat 23/512:10JNB - ORD
2 stops31h 31mKenya Airways
Deal found 17/12R15 966
Sun 15/27:00ORD - JNB
2 stops24h 50mKenya Airways
Sun 22/217:00JNB - ORD
2 stops28h 29mKenya Airways
Deal found 18/12R16 050
Mon 23/310:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 1/414:30JNB - ORD
2 stops24h 45mEthiopian Air
Deal found 18/12R16 201
Sun 1/27:01ORD - JNB
2 stops24h 49mKenya Airways
Sun 8/212:05JNB - ORD
2 stops37h 40mKenya Airways
Deal found 18/12R16 218
Sat 14/314:00ORD - JNB
2 stops42h 50mMultiple Airlines
Sun 22/317:00JNB - ORD
2 stops31h 10mMultiple Airlines
Deal found 18/12R16 335
Tue 20/17:00ORD - JNB
2 stops33h 25mKenya Airways
Tue 10/217:00JNB - ORD
2 stops28h 14mKenya Airways
Deal found 18/12R16 419
Tue 13/17:00ORD - JNB
2 stops43h 55mKenya Airways
Tue 3/212:05JNB - ORD
2 stops33h 09mKenya Airways
Deal found 17/12R16 502
Sat 31/114:30ORD - JNB
2 stops41h 20mMultiple Airlines
Sat 7/217:00JNB - ORD
2 stops32h 45mMultiple Airlines
Deal found 17/12R16 754
Thu 19/218:25ORD - JNB
2 stops46h 00mMultiple Airlines
Tue 24/25:25JNB - ORD
2 stops40h 04mMultiple Airlines
Deal found 18/12R16 804
Wed 11/310:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 25/38:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 17/12R17 139
Thu 19/29:45ORD - JNB
1 stop26h 25mEthiopian Air
Tue 24/214:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 18/12R17 307
Sun 1/29:45ORD - JNB
1 stop26h 25mEthiopian Air
Sun 8/214:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 18/12R17 407

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 19 December 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

Cape Town

Route

Depart

Return

Price

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 19/2

18:25-0:25

2 stops46h 00m

Johannesburg OR Tambo

Tue 24/2

5:25-13:29

2 stops40h 04m

R16 804

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 11/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Wed 25/3

8:20-8:40

2 stops31h 20m

R17 139

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 22/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sat 28/3

8:20-8:15

2 stops30h 55m

R17 307

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 19/2

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Tue 24/2

14:30-7:40

2 stops25h 10m

R17 307

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 21/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sat 28/3

8:20-8:15

2 stops30h 55m

R17 742

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 19/2

11:50-10:50

1 stop39h 00m

Johannesburg OR Tambo

Tue 24/2

19:10-10:05

1 stop22h 55m

R18 345

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 13/1

11:50-10:50

1 stop39h 00m

Johannesburg OR Tambo

Tue 3/2

19:10-18:25

1 stop31h 15m

R18 345

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 26/4

8:20-8:15

2 stops30h 55m

R18 496

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 31/1

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sat 21/2

8:20-7:40

2 stops31h 20m

R18 731

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 15/1

18:25-0:25

2 stops46h 00m

Johannesburg OR Tambo

Sat 31/1

17:00-13:14

2 stops28h 14m

R18 915

Flights are sorted by cheapest return flights first.

Deals found on 16/12

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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 Cape Town. Price data was last updated on 12 December 2025.

Booking 77 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, January is the cheapest month in which you can book a flight from Chicago (average of R13 068). Flying from Chicago in July will prove the most costly (average of R23 422). 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: Toronto (798 flights per day), London (640 flights per day) and New York (634 flights per day).

Fort Lauderdale
Fort Lauderdale
From R2 721
Orlando
Orlando
From R2 472
New York
New York
From R832
Dublin
Dublin
From R6 119

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 R832. Explore other affordable destinations below.

New York
New York
From R832
Orlando
Orlando
From R2 472
Fort Lauderdale
Fort Lauderdale
From R2 721
Miami
Miami
From R3 749

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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 19 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?

    January 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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