R1 744+ 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 24/11. 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
Dec 5 — Dec 121
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 5 November 2025.

Good round-trip deal

R17 560 or less

Good one-way deal

R866 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 5 November 2025.

Mon 9/220:20ORD - CPT
1 stop31h 30mTurkish Airlines
Fri 13/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 3/11R16 131
Tue 13/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Tue 3/219:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 3/11R16 131
Sat 10/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
Tue 10/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 2/11R16 532
Sun 8/211:50ORD - JNB
1 stop39h 00mTurkish Airlines
Mon 16/219:05JNB - ORD
1 stop31h 20mTurkish Airlines
Deal found 3/11R16 532
Sat 18/48:00ORD - JNB
2 stops33h 15mMultiple Airlines
Sun 26/41:15JNB - ORD
2 stops47h 26mMultiple Airlines
Deal found 4/11R16 724
Tue 24/218:25ORD - JNB
2 stops37h 25mMultiple Airlines
Tue 10/317:00JNB - ORD
2 stops26h 44mMultiple Airlines
Deal found 3/11R16 829
Wed 18/312:50ORD - CPT
1 stop40h 00mTurkish Airlines
Mon 23/317:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 3/11R16 863
Tue 24/220:20ORD - JNB
1 stop30h 30mTurkish Airlines
Tue 10/319:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 3/11R16 863
Fri 23/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
Sun 1/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 4/11R16 898
Fri 28/1111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Fri 5/1219:05JNB - ORD
1 stop23h 00mTurkish Airlines
Deal found 4/11R16 898
Tue 20/120:20ORD - CPT
1 stop31h 30mTurkish Airlines
Tue 27/117:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 5/11R16 951
Tue 31/37:30ORD - JNB
2 stops25h 20mKenya Airways
Tue 21/412:10JNB - ORD
2 stops36h 31mKenya Airways
Deal found 2/11R17 003

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 5 November 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

Wed 1/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Tue 7/4

14:30-8:15

2 stops24h 45m

R18 293

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

R18 381

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 4/3

13:10-8:20

1 stop35h 10m

Johannesburg OR Tambo

Sun 8/3

9:50-7:35

1 stop29h 45m

R18 677

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 4/12

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sat 13/12

14:30-7:40

2 stops25h 10m

R19 287

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 16/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

Thu 19/3

17:15-19:25

1 stop33h 10m

R19 427

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 21/3

21:20-11:50

1 stop31h 30m

Cape Town Intl

Sun 29/3

16:40-9:40

1 stop24h 00m

R19 828

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 16/3

10:15-14:35

1 stop21h 20m

Cape Town Intl

Thu 19/3

13:50-8:40

2 stops25h 50m

R20 177

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 15/11

14:39-16:10

1 stop17h 31m

Cape Town Intl

Thu 27/11

20:50-10:45

1 stop21h 55m

R21 485

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 16/11

11:19-19:15

1 stop23h 56m

Cape Town Intl

Thu 27/11

21:30-16:03

1 stop26h 33m

R21 485

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 15/11

8:48-16:10

1 stop23h 22m

Cape Town Intl

Wed 26/11

20:50-10:45

1 stop21h 55m

R21 485

Flights are sorted by cheapest return flights first.

Deals found on 4/11

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 31 October 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, January is the cheapest month in which you can book a flight from Chicago (average of R13 358). Flying from Chicago in July will prove the most costly (average of R26 647). 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 (1 417 flights per day), Detroit (1 014 flights per day) and Los Angeles (643 flights per day).

Orlando
Orlando
From R2 573
New York
New York
From R866
Dublin
Dublin
From R6 369
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 990

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 R866. Explore other affordable destinations below.

New York
New York
From R866
Orlando
Orlando
From R2 573
Miami
Miami
From R3 902
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 990

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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 5 November 2025.

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

    The most selected flight destinations from Chicago for the current month are Atlanta, Boston, 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 R16 131 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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