R1 715+ 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 25/11. 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
nov. 21 — nov. 281
1 adult
1 adult, Economy

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 22 octubre 2025.

Good round-trip deal

R17 446 or less

Good one-way deal

R1 620 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 22 octubre 2025.

mar. 18/1111:50ORD - JNB
1 stop39h 00mTurkish Airlines
jue. 4/1219:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 20/10R16 425
mar. 27/120:20ORD - JNB
1 stop30h 30mTurkish Airlines
mar. 31/317:55JNB - ORD
1 stop22h 45mTurkish Airlines
Deal found 20/10R16 564
sáb. 18/48:00ORD - JNB
2 stops33h 15mMultiple Airlines
dom. 26/41:15JNB - ORD
2 stops47h 26mMultiple Airlines
Deal found 21/10R16 616
mar. 18/1118:33ORD - JNB
2 stops37h 17mMultiple Airlines
mié. 3/121:35JNB - ORD
2 stops48h 11mMultiple Airlines
Deal found 20/10R16 719
jue. 29/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
mié. 4/217:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 20/10R16 754
jue. 15/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
sáb. 31/119:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 21/10R16 754
vie. 30/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
sáb. 14/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 21/10R16 806
mar. 13/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
sáb. 24/117:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 20/10R16 823
lun. 17/1120:20ORD - JNB
1 stop30h 30mTurkish Airlines
mié. 3/1219:05JNB - ORD
1 stop23h 00mTurkish Airlines
Deal found 20/10R16 823
lun. 3/117:00ORD - JNB
2 stops33h 25mKenya Airways
lun. 17/111:35JNB - ORD
2 stops43h 04mKenya Airways
Deal found 20/10R16 841
lun. 10/1111:50ORD - JNB
1 stop39h 00mTurkish Airlines
lun. 17/1119:05JNB - ORD
1 stop31h 20mTurkish Airlines
Deal found 20/10R16 893
lun. 3/119:45ORD - CPT
1 stop20h 50mEthiopian Air
dom. 16/1113:50CPT - ORD
2 stops25h 50mEthiopian Air
Deal found 20/10R16 962

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

Fly to

Cape Town

Route

Depart

Return

Price

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

dom. 15/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

dom. 22/3

17:15-19:25

1 stop33h 10m

R16 754

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

jue. 5/3

20:20-10:50

1 stop30h 30m

Johannesburg OR Tambo

dom. 15/3

19:05-11:05

1 stop23h 00m

R16 754

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mié. 4/3

7:30-15:50

2 stops24h 20m

Johannesburg OR Tambo

sáb. 7/3

1:35-16:37

2 stops47h 02m

R17 759

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

jue. 2/4

19:50-11:50

1 stop33h 00m

Cape Town Intl

jue. 9/4

16:40-18:15

1 stop32h 35m

R17 863

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

dom. 23/11

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

sáb. 29/11

8:20-7:40

2 stops31h 20m

R18 054

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

dom. 15/3

10:15-13:00

1 stop43h 45m

Cape Town Intl

dom. 22/3

13:50-8:40

2 stops25h 50m

R18 313

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

mié. 18/3

21:20-11:50

1 stop31h 30m

Cape Town Intl

lun. 23/3

14:00-11:05

2 stops28h 05m

R18 521

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

lun. 16/3

21:20-11:50

1 stop31h 30m

Cape Town Intl

jue. 19/3

17:15-19:25

1 stop33h 10m

R18 591

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mié. 4/3

20:20-10:50

1 stop30h 30m

Johannesburg OR Tambo

dom. 8/3

19:05-11:05

1 stop23h 00m

R18 591

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

jue. 6/11

9:45-13:00

1 stop43h 15m

Cape Town Intl

sáb. 15/11

13:50-7:40

2 stops25h 50m

R18 920

Flights are sorted by cheapest return flights first.

Deals found on 21/10

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 17 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 220). Flying from Chicago in July will prove the most costly (average of R26 474). 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 (1 398 flights per day), Detroit (994 flights per day) and Atlanta (632 flights per day).

Orlando
Orlando
From R2 556
Dublin
Dublin
From R6 328
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 958
Austin Bergstrom
Austin Bergstrom
From R17 446

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 R1 204. Explore other affordable destinations below.

New York
New York
From R1 204
Boston Logan Intl
Boston Logan Intl
From R1 325
Orlando
Orlando
From R2 556
Miami
Miami
From R3 877

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Direct flights from New Orleans
Direct flights from Portland
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Direct flights from Little Rock
Direct flights from Anchorage
Direct flights from Indianapolis
Direct flights from Des Moines

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 22 octubre 2025.

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

    The most selected flight destinations from Chicago for the current month are Boston, Atlanta, Ahmedabad. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.

  • What are the cheapest airlines flying from Chicago to anywhere?

    Looking at our data, Turkish Airlines, Ethiopian Air, and United Airlines have been found to have the cheapest prices from Chicago. Here are some options available: Turkish Airlines flights from Chicago to Johannesburg OR Tambo (R14 660). Ethiopian Air flights from Chicago to Johannesburg OR Tambo (R15 423). United Airlines flights from Chicago to Johannesburg OR Tambo (R16 933).

  • 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 754 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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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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