R1 444+ 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 25/1. 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
Feb 13 — Feb 201
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 14 January 2026.

Good round-trip deal

R8 582 or less

Good one-way deal

R815 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 14 January 2026.

Thu 29/114:50
ORD
-
JNB
1 stop20h 10m
Virgin Atlantic
Wed 11/221:55
JNB
-
ORD
1 stop26h 54m
Virgin Atlantic
Deal found 14/1R12 078
Thu 29/112:48
MDW
-
JNB
1 stop22h 12m
Virgin Atlantic
Wed 11/221:55
JNB
-
MDW
1 stop32h 36m
Virgin Atlantic
Deal found 14/1R12 176
Mon 26/116:35
ORD
-
CPT
1 stop18h 40m
Virgin Atlantic
Sun 8/221:30
CPT
-
ORD
1 stop27h 25m
Virgin Atlantic
Deal found 12/1R12 193
Mon 26/112:48
MDW
-
CPT
1 stop22h 27m
Virgin Atlantic
Sun 8/221:30
CPT
-
MDW
1 stop27h 59m
Virgin Atlantic
Deal found 12/1R12 307
Mon 26/110:35
ORD
-
CPT
2 stops24h 40m
Delta
Sun 8/221:30
CPT
-
ORD
1 stop20h 35m
Delta
Deal found 12/1R12 373
Thu 29/19:55
ORD
-
JNB
1 stop25h 05m
Delta
Wed 11/221:55
JNB
-
ORD
2 stops26h 19m
Delta
Deal found 14/1R12 389
Wed 28/114:50
ORD
-
CPT
1 stop20h 25m
Delta
Tue 10/221:30
CPT
-
ORD
1 stop27h 25m
Delta
Deal found 12/1R12 537
Fri 13/211:18
ORD
-
JNB
1 stop23h 42m
Delta
Tue 5/521:55
JNB
-
ORD
1 stop30h 35m
Delta
Deal found 13/1R12 537
Tue 27/112:48
MDW
-
JNB
1 stop22h 12m
Delta
Sun 8/221:55
JNB
-
MDW
1 stop27h 34m
Delta
Deal found 13/1R12 537
Wed 28/112:48
MDW
-
CPT
1 stop22h 27m
Delta
Fri 13/221:30
CPT
-
MDW
1 stop25h 51m
Delta
Deal found 13/1R12 537
Sat 31/113:55
ORD
-
CPT
2 stops21h 20m
Delta
Tue 10/221:30
CPT
-
ORD
1 stop20h 35m
Delta
Deal found 13/1R12 619
Thu 29/113:49
MDW
-
CPT
2 stops21h 26m
Delta
Thu 12/221:30
CPT
-
MDW
2 stops23h 35m
Delta
Deal found 13/1R12 619

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 14 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

MDW - JNB

MDWJNB

Chicago Midway

Thu 29/1

12:48-19:00

1 stop22h 12m

Johannesburg OR Tambo

Wed 11/2

21:55-22:31

1 stop32h 36m

R12 176

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 26/1

13:58-19:15

2 stops21h 17m

Cape Town Intl

Sun 8/2

21:30-13:26

2 stops23h 56m

R12 373

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 28/1

7:05-19:15

1 stop28h 10m

Cape Town Intl

Sun 8/2

21:30-13:40

1 stop24h 10m

R12 537

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 3/2

14:50-19:00

1 stop20h 10m

Johannesburg OR Tambo

Wed 11/2

21:55-16:49

1 stop26h 54m

R12 537

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Fri 30/1

6:00-19:00

1 stop29h 00m

Johannesburg OR Tambo

Wed 11/2

21:55-11:59

1 stop22h 04m

R12 537

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Tue 3/2

10:48-19:00

1 stop24h 12m

Johannesburg OR Tambo

Wed 11/2

21:55-17:45

1 stop27h 50m

R12 537

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 9/2

7:10-19:15

2 stops28h 05m

Cape Town Intl

Tue 17/2

21:30-17:06

2 stops27h 36m

R12 619

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 17/2

12:05-19:00

2 stops22h 55m

Johannesburg OR Tambo

Thu 7/5

21:55-19:01

1 stop28h 06m

R12 619

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Fri 30/1

11:15-19:00

1 stop23h 45m

Johannesburg OR Tambo

Sun 8/2

21:55-16:30

2 stops26h 35m

R12 619

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Thu 29/1

9:33-19:00

2 stops25h 27m

Johannesburg OR Tambo

Wed 11/2

21:55-11:59

1 stop22h 04m

R12 619

Flights are sorted by cheapest return flights first.

Deals found on 12/1

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 9 January 2026.

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 R12 718). Flying from Chicago in July will prove the most costly (average of R22 941). 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 (1 531 flights per day), Detroit (968 flights per day) and Toronto (830 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 531
Fort Lauderdale
Fort Lauderdale
From R2 665
Orlando
Orlando
From R2 421
New York
New York
From R815

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 R815. Explore other affordable destinations below.

New York
New York
From R815
Orlando
Orlando
From R2 421
Fort Lauderdale
Fort Lauderdale
From R2 665
Raleigh-Durham
Raleigh-Durham
From R3 531

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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 14 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 Ahmedabad, Atlanta, 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.

  • Where are the cheapest places to fly to from Chicago?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to Cape Town from R12 537 round trip

  • 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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