R1 382+ 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 3/3. 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
Mar 3 — Mar 101
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 1 February 2026.

Good round-trip deal

R16 185 or less

Good one-way deal

R779 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 1 February 2026.

Wed 18/36:45
ORD
-
JNB
2 stops34h 40m
Multiple Airlines
Tue 31/312:10
JNB
-
ORD
2 stops36h 00m
Multiple Airlines
Deal found 31/1R14 016
Mon 13/46:04
ORD
-
JNB
2 stops26h 46m
Kenya Airways
Thu 7/517:00
JNB
-
ORD
2 stops35h 36m
Kenya Airways
Deal found 30/1R14 032
Mon 2/37:00
ORD
-
JNB
2 stops24h 50m
Kenya Airways
Tue 10/317:00
JNB
-
ORD
2 stops26h 57m
Kenya Airways
Deal found 31/1R15 414
Fri 20/26:04
ORD
-
JNB
2 stops25h 46m
Multiple Airlines
Tue 10/317:00
JNB
-
ORD
2 stops25h 54m
Multiple Airlines
Deal found 30/1R15 478
Wed 4/36:04
ORD
-
JNB
2 stops25h 46m
Multiple Airlines
Tue 31/317:00
JNB
-
ORD
2 stops26h 57m
Multiple Airlines
Deal found 30/1R15 623
Mon 2/39:45
ORD
-
JNB
1 stop26h 25m
Ethiopian Air
Tue 10/314:30
JNB
-
ORD
2 stops25h 10m
Ethiopian Air
Deal found 31/1R15 671
Sun 26/411:25
ORD
-
CPT
1 stop41h 25m
Turkish Airlines
Wed 6/516:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 30/1R15 703
Thu 5/39:45
ORD
-
JNB
1 stop26h 25m
Ethiopian Air
Tue 10/314:30
JNB
-
ORD
2 stops25h 10m
Ethiopian Air
Deal found 1/2R15 816
Tue 24/312:20
ORD
-
JNB
2 stops44h 30m
Multiple Airlines
Thu 2/417:00
JNB
-
ORD
2 stops31h 10m
Multiple Airlines
Deal found 30/1R16 009
Thu 9/410:15
ORD
-
JNB
1 stop26h 55m
Ethiopian Air
Tue 28/48:20
JNB
-
ORD
2 stops30h 55m
Ethiopian Air
Deal found 30/1R16 041
Thu 5/39:45
ORD
-
JNB
1 stop26h 25m
Ethiopian Air
Tue 17/314:30
JNB
-
ORD
2 stops25h 10m
Ethiopian Air
Deal found 31/1R16 089
Sun 22/211:50
ORD
-
CPT
1 stop40h 00m
Turkish Airlines
Tue 10/317:15
CPT
-
ORD
1 stop33h 10m
Turkish Airlines
Deal found 31/1R16 330

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 1 February 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

Wed 18/3

6:45-0:25

2 stops34h 40m

Johannesburg OR Tambo

Tue 31/3

12:10-17:10

2 stops36h 00m

R14 016

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 5/3

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Tue 10/3

14:30-8:40

2 stops25h 10m

R15 816

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 24/3

12:20-15:50

2 stops44h 30m

Johannesburg OR Tambo

Thu 2/4

17:00-17:10

2 stops31h 10m

R16 009

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 26/4

10:15-14:35

1 stop21h 20m

Cape Town Intl

Wed 6/5

13:50-8:15

2 stops25h 25m

R16 700

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 4/3

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sun 8/3

8:20-7:40

2 stops31h 20m

R16 989

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 13/4

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Thu 7/5

22:50-8:15

2 stops40h 25m

R17 230

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 4/5

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Wed 20/5

8:20-8:15

2 stops30h 55m

R17 343

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 6/5

10:15-14:35

1 stop21h 20m

Cape Town Intl

Sat 16/5

13:50-8:15

2 stops25h 25m

R17 391

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 19/4

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Mon 27/4

22:50-8:15

2 stops40h 25m

R17 568

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 18/4

10:15-14:35

1 stop21h 20m

Cape Town Intl

Tue 28/4

13:50-8:15

2 stops25h 25m

R17 600

Flights are sorted by cheapest return flights first.

Deals found on 31/1

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 23 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 489). Flying from Chicago in July will prove the most costly (average of R22 470). 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 (1 388 flights per day), Detroit (954 flights per day) and Toronto (732 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 458
Fort Lauderdale
Fort Lauderdale
From R2 611
New York
New York
From R779
Dublin
Dublin
From R5 870

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 R779. Explore other affordable destinations below.

New York
New York
From R779
Fort Lauderdale
Fort Lauderdale
From R2 611
Raleigh-Durham
Raleigh-Durham
From R3 458
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 599

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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 1 February 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, Boston. 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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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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