R1 542+ 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 15/1. 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
Jan 5 — Jan 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 6 December 2025.

Good round-trip deal

R17 063 or less

Good one-way deal

R842 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 6 December 2025.

Tue 3/220:20ORD - JNB
1 stop30h 30mTurkish Airlines
Thu 19/219:10JNB - ORD
1 stop31h 15mTurkish Airlines
Deal found 3/12R14 098
Sun 18/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Sun 25/119:05JNB - ORD
1 stop31h 20mTurkish Airlines
Deal found 4/12R14 166
Sat 31/120:20ORD - JNB
1 stop30h 30mTurkish Airlines
Sat 21/219:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 3/12R14 488
Sat 18/411:25ORD - JNB
1 stop40h 10mTurkish Airlines
Mon 27/418:00JNB - ORD
1 stop22h 40mTurkish Airlines
Deal found 4/12R14 556
Tue 20/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Tue 10/219:10JNB - ORD
1 stop31h 15mTurkish Airlines
Deal found 4/12R14 827
Mon 26/120:20ORD - JNB
1 stop30h 30mTurkish Airlines
Mon 16/219:05JNB - ORD
1 stop31h 20mTurkish Airlines
Deal found 5/12R14 844
Fri 23/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Fri 30/119:05JNB - ORD
1 stop31h 20mTurkish Airlines
Deal found 5/12R14 946
Mon 19/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Mon 26/119:05JNB - ORD
1 stop23h 00mTurkish Airlines
Deal found 5/12R15 064
Thu 15/111:50ORD - JNB
1 stop39h 00mTurkish Airlines
Sat 31/119:10JNB - ORD
1 stop22h 55mTurkish Airlines
Deal found 4/12R15 285
Thu 29/120:20ORD - CPT
1 stop31h 30mTurkish Airlines
Wed 4/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 4/12R16 471
Wed 28/120:20ORD - CPT
1 stop31h 30mTurkish Airlines
Wed 4/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 3/12R16 691
Wed 18/321:20ORD - CPT
1 stop31h 30mTurkish Airlines
Mon 23/317:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 4/12R17 098

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 6 December 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 22/4

11:25-10:35

1 stop40h 10m

Johannesburg OR Tambo

Sun 26/4

18:00-18:15

1 stop31h 15m

R16 505

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 9/3

10:15-14:35

1 stop21h 20m

Cape Town Intl

Wed 18/3

14:35-8:40

2 stops25h 05m

R17 521

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 28/1

9:45-14:35

1 stop20h 50m

Cape Town Intl

Wed 4/2

14:35-7:40

2 stops25h 05m

R17 521

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 20/4

10:15-14:35

1 stop21h 20m

Cape Town Intl

Sun 26/4

13:50-8:15

2 stops25h 25m

R17 521

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/4

7:30-0:15

2 stops33h 45m

Johannesburg OR Tambo

Sun 26/4

17:00-17:41

2 stops31h 41m

R17 538

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/4

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Sun 26/4

14:30-8:15

2 stops24h 45m

R17 860

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Fri 20/3

12:50-10:50

1 stop39h 00m

Johannesburg OR Tambo

Sat 4/4

17:55-9:40

1 stop22h 45m

R18 013

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 14/3

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sat 4/4

14:30-8:15

2 stops24h 45m

R18 199

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 17/1

9:45-14:35

1 stop20h 50m

Cape Town Intl

Thu 22/1

13:50-7:40

2 stops25h 50m

R18 250

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Fri 27/2

9:45-14:35

1 stop20h 50m

Cape Town Intl

Sun 8/3

13:50-8:40

2 stops25h 50m

R18 250

Flights are sorted by cheapest return flights first.

Deals found on 4/12

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 28 November 2025.

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 R13 133). Flying from Chicago in July will prove the most costly (average of R25 570). 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 (1 399 flights per day), Toronto (796 flights per day) and Detroit (786 flights per day).

Fort Lauderdale
Fort Lauderdale
From R1 225
Orlando
Orlando
From R2 500
New York
New York
From R841
Dublin
Dublin
From R6 189

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 R841. Explore other affordable destinations below.

New York
New York
From R841
Fort Lauderdale
Fort Lauderdale
From R1 225
Orlando
Orlando
From R2 500
Miami
Miami
From R3 792

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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 6 December 2025.

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

    The most selected flight destinations from Chicago for the current month are Ahmedabad, Mumbai, Atlanta. 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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