R1 539+ 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 11/3. 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
Feb 22 — Mar 11
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 23 January 2026.

Good round-trip deal

R8 472 or less

Good one-way deal

R805 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 23 January 2026.

Mon 16/218:30
ORD
-
CPT
1 stop29h 35m
American Airlines
Tue 3/318:55
CPT
-
ORD
1 stop28h 30m
American Airlines
Deal found 21/1R13 819
Mon 2/320:35
ORD
-
JNB
1 stop29h 50m
American Airlines
Wed 18/319:35
JNB
-
ORD
1 stop27h 50m
American Airlines
Deal found 21/1R13 819
Mon 2/320:35
ORD
-
CPT
1 stop31h 35m
American Airlines
Wed 11/320:35
CPT
-
ORD
1 stop26h 50m
American Airlines
Deal found 22/1R13 835
Fri 24/422:35
ORD
-
CPT
1 stop29h 25m
American Airlines
Mon 27/418:50
CPT
-
ORD
1 stop24h 30m
American Airlines
Deal found 21/1R13 852
Sat 18/421:15
ORD
-
JNB
1 stop29h 10m
American Airlines
Mon 27/419:25
JNB
-
ORD
1 stop23h 55m
American Airlines
Deal found 21/1R13 852
Sun 19/421:15
ORD
-
JNB
1 stop29h 10m
British Airways
Thu 30/421:15
JNB
-
ORD
1 stop25h 40m
British Airways
Deal found 21/1R13 868
Tue 7/421:15
ORD
-
JNB
1 stop26h 45m
Multiple Airlines
Wed 22/421:15
JNB
-
ORD
1 stop23h 35m
Multiple Airlines
Deal found 22/1R13 933
Mon 2/318:30
ORD
-
CPT
1 stop33h 40m
British Airways
Wed 1/418:50
CPT
-
ORD
1 stop26h 00m
British Airways
Deal found 22/1R13 997
Tue 7/419:05
ORD
-
JNB
1 stop28h 55m
British Airways
Thu 23/421:15
JNB
-
ORD
1 stop22h 05m
British Airways
Deal found 22/1R13 997
Mon 23/217:10
ORD
-
JNB
1 stop33h 15m
British Airways
Mon 2/322:00
JNB
-
ORD
1 stop23h 50m
British Airways
Deal found 20/1R14 030
Wed 8/422:35
ORD
-
JNB
1 stop27h 50m
Iberia
Thu 23/421:15
JNB
-
ORD
1 stop22h 05m
Iberia
Deal found 22/1R14 046
Wed 4/321:45
ORD
-
JNB
1 stop25h 50m
British Airways
Sun 8/322:00
JNB
-
ORD
1 stop28h 45m
British Airways
Deal found 20/1R14 078

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 23 January 2026. 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

Tue 7/4

19:05-7:00

1 stop28h 55m

Johannesburg OR Tambo

Thu 23/4

21:15-12:20

1 stop22h 05m

R13 997

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 4/3

21:45-7:35

1 stop25h 50m

Johannesburg OR Tambo

Sun 8/3

22:00-19:45

1 stop28h 45m

R14 078

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 10/5

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 24/5

14:30-8:15

2 stops24h 45m

R15 844

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 15/4

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Wed 20/5

8:20-8:15

2 stops30h 55m

R16 330

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 9/3

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Fri 20/3

14:30-8:40

2 stops25h 10m

R16 460

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 3/5

10:15-14:35

1 stop21h 20m

Cape Town Intl

Sat 9/5

13:50-8:15

2 stops25h 25m

R17 173

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 7/3

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sat 14/3

14:30-8:40

2 stops25h 10m

R17 481

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 13/4

19:50-11:50

1 stop33h 00m

Cape Town Intl

Thu 16/4

16:35-9:40

1 stop24h 05m

R18 598

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 9/4

11:25-10:30

1 stop40h 05m

Johannesburg OR Tambo

Fri 24/4

18:00-9:40

1 stop22h 40m

R19 003

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 20/5

10:15-14:35

1 stop21h 20m

Cape Town Intl

Fri 29/5

13:50-8:15

2 stops25h 25m

R19 117

Flights are sorted by cheapest return flights first.

Deals found on 21/1

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 Cape Town. Price data was last updated on 16 January 2026.

Booking 60 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 R12 556). Flying from Chicago in July will prove the most costly (average of R22 649). 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 (1 490 flights per day), Detroit (978 flights per day) and Toronto (848 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 486
Fort Lauderdale
Fort Lauderdale
From R2 631
New York
New York
From R804
Dublin
Dublin
From R5 917

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 R804. Explore other affordable destinations below.

New York
New York
From R804
Fort Lauderdale
Fort Lauderdale
From R2 631
Raleigh-Durham
Raleigh-Durham
From R3 486
Miami
Miami
From R3 625

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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 23 January 2026.

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

    The most selected flight destinations from Chicago for the current month are Atlanta, Ahmedabad, Mumbai. While Atlanta, Boston, Ahmedabad 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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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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