R1 305+ 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 22/2. 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 9 — Feb 161
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 10 January 2026.

Good round-trip deal

R8 637 or less

Good one-way deal

R820 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 10 January 2026.

Sat 24/115:24ORD - CPT
1 stop19h 51mVirgin Atlantic
Fri 6/221:30CPT - ORD
1 stop27h 33mVirgin Atlantic
Deal found 9/1R12 254
Sat 24/110:46MDW - CPT
1 stop24h 29mVirgin Atlantic
Fri 6/221:30CPT - MDW
1 stop32h 52mVirgin Atlantic
Deal found 9/1R12 254
Sat 24/113:55ORD - CPT
2 stops21h 20mDelta
Fri 6/221:30CPT - ORD
2 stops23h 38mDelta
Deal found 9/1R12 469
Sat 31/111:15ORD - CPT
1 stop24h 00mDelta
Fri 13/221:30CPT - ORD
1 stop27h 24mDelta
Deal found 9/1R12 617
Mon 23/29:48ORD - JNB
1 stop25h 12mVirgin Atlantic
Tue 3/321:55JNB - ORD
1 stop29h 24mVirgin Atlantic
Deal found 7/1R12 617
Mon 23/210:49MDW - JNB
1 stop24h 11mDelta
Tue 3/321:55JNB - MDW
1 stop27h 50mDelta
Deal found 7/1R12 617
Sun 1/312:45MDW - CPT
1 stop22h 30mDelta
Tue 24/321:30CPT - MDW
1 stop21h 32mDelta
Deal found 8/1R12 617
Sat 31/110:35ORD - CPT
2 stops24h 40mDelta
Tue 10/221:30CPT - ORD
2 stops23h 43mDelta
Deal found 9/1R12 700
Sat 21/210:36ORD - JNB
2 stops24h 24mDelta
Tue 3/321:55JNB - ORD
2 stops26h 19mDelta
Deal found 7/1R12 700
Wed 4/313:49MDW - CPT
2 stops21h 26mDelta
Mon 23/321:30CPT - MDW
2 stops21h 59mDelta
Deal found 8/1R12 700
Thu 23/411:19ORD - CPT
1 stop23h 31mDelta
Sun 3/520:05CPT - ORD
1 stop32h 25mDelta
Deal found 8/1R12 717
Mon 9/211:15ORD - JNB
1 stop23h 45mVirgin Atlantic
Wed 18/221:55JNB - ORD
1 stop31h 06mVirgin Atlantic
Deal found 8/1R12 717

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 10 January 2026. 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

Sat 24/1

13:55-19:15

2 stops21h 20m

Cape Town Intl

Fri 6/2

21:30-13:49

1 stop24h 19m

R12 469

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 23/2

16:25-22:05

1 stop21h 40m

Johannesburg OR Tambo

Mon 2/3

23:59-13:20

2 stops45h 21m

R12 617

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 31/1

11:15-19:15

1 stop24h 00m

Cape Town Intl

Fri 13/2

21:30-16:54

1 stop27h 24m

R12 617

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/3

10:49-19:15

1 stop24h 26m

Cape Town Intl

Tue 24/3

21:30-16:55

1 stop26h 25m

R12 617

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sun 1/3

10:49-19:15

1 stop24h 26m

Cape Town Intl

Mon 23/3

21:30-12:02

1 stop21h 32m

R12 617

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Mon 2/3

12:45-19:15

1 stop22h 30m

Cape Town Intl

Mon 23/3

21:30-12:02

1 stop21h 32m

R12 617

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 23/2

10:49-19:00

1 stop24h 11m

Johannesburg OR Tambo

Tue 3/3

21:55-18:40

2 stops28h 45m

R12 700

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Wed 4/3

13:49-19:15

2 stops21h 26m

Cape Town Intl

Tue 24/3

21:30-12:29

2 stops21h 59m

R12 700

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 9/2

11:15-19:00

1 stop23h 45m

Johannesburg OR Tambo

Wed 18/2

21:55-21:01

1 stop31h 06m

R12 717

ChicagoJohannesburg

MDW - JNB

MDWJNB

Chicago Midway

Mon 9/2

12:46-19:00

1 stop22h 14m

Johannesburg OR Tambo

Wed 18/2

21:55-11:59

1 stop22h 04m

R12 783

Flights are sorted by cheapest return flights first.

Deals found on 9/1

Showing 1-10 of 57 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 2 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 733). Flying from Chicago in July will prove the most costly (average of R23 088). 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 (1 462 flights per day), Detroit (980 flights per day) and Toronto (802 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 554
Fort Lauderdale
Fort Lauderdale
From R2 682
Orlando
Orlando
From R2 436
New York
New York
From R820

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 R820. Explore other affordable destinations below.

New York
New York
From R820
Orlando
Orlando
From R2 436
Fort Lauderdale
Fort Lauderdale
From R2 682
Phoenix Sky Harbor Intl
Phoenix Sky Harbor Intl
From R3 047

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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 10 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.

  • 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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