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Cheap flights from Chicago to anywhere

Fly from Chicago to anywhere in the world.

CHI — CPT
Dec 11 — Dec 181
1 adult

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 2024. In the last 7 days, Cheapflights users made a total of 655 463 searches

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Any airport

Route

Depart

Return

Price

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 20/1

18:45-10:20

2 stops31h 35m

Johannesburg OR Tambo

Mon 27/1

19:25-17:38

2 stops30h 13m

R16 664

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 19/1

11:55-10:55

1 stop39h 00m

Johannesburg OR Tambo

Sun 26/1

19:05-10:10

1 stop23h 05m

R16 736

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 20/1

7:05-16:00

2 stops24h 55m

Johannesburg OR Tambo

Sun 9/2

1:15-9:55

2 stops40h 40m

R16 754

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 2/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sat 12/4

8:20-8:05

2 stops30h 45m

R16 989

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 19/1

18:30-16:00

2 stops37h 30m

Johannesburg OR Tambo

Sat 25/1

1:15-9:55

2 stops40h 40m

R17 423

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 15/1

21:45-10:20

1 stop28h 35m

Johannesburg OR Tambo

Wed 22/1

19:25-13:55

1 stop26h 30m

R17 585

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Wed 29/1

11:55-13:30

2 stops41h 35m

Durban King Shaka Intl

Wed 5/2

16:05-10:10

2 stops26h 05m

R17 694

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Sun 19/1

11:55-14:40

2 stops42h 45m

Durban King Shaka Intl

Sun 26/1

8:40-10:10

2 stops33h 30m

R18 850

ChicagoPort Elizabeth

ORD - PLZ

ORDPLZ

Chicago O'Hare Intl

Sun 19/1

11:55-19:00

2 stops47h 05m

Port Elizabeth

Sun 26/1

8:40-10:10

2 stops33h 30m

R18 923

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 22/3

14:10-8:35

1 stop35h 25m

Johannesburg OR Tambo

Wed 26/3

10:00-9:25

1 stop30h 25m

R19 013

Flights are sorted by cheapest return flights first.

Deals found on 5/12

Showing 1-10 of 55 results
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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 2024.

Cheapest airline

United Airlines
On average, United Airlines currently has the cheapest one-way flight from Chicago.
Search Deals

Find flights from Chicago

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 2024.

Mon 20/118:45ORD - JNB
2 stops31h 35mAmerican Airlines
Mon 27/119:25JNB - ORD
2 stops30h 13mAmerican Airlines
Deal found 6/12R16 664
Sun 19/111:55ORD - JNB
1 stop39h 00mTurkish Airlines
Sun 26/119:05JNB - ORD
1 stop23h 05mTurkish Airlines
Deal found 4/12R16 736
Mon 20/17:05ORD - JNB
2 stops24h 55mKenya Airways
Sun 9/21:15JNB - ORD
2 stops40h 40mKenya Airways
Deal found 6/12R16 754
Wed 2/410:15ORD - JNB
1 stop19h 50mEthiopian Air
Sat 12/48:20JNB - ORD
2 stops30h 45mEthiopian Air
Deal found 4/12R16 989
Sun 19/118:30ORD - JNB
2 stops37h 30mMultiple Airlines
Sat 25/11:15JNB - ORD
2 stops40h 40mMultiple Airlines
Deal found 4/12R17 423
Wed 15/121:45ORD - JNB
1 stop28h 35mBritish Airways
Wed 22/119:25JNB - ORD
1 stop26h 30mBritish Airways
Deal found 5/12R17 585
Wed 29/111:55ORD - DUR
2 stops41h 35mTurkish Airlines
Wed 5/216:05DUR - ORD
2 stops26h 05mTurkish Airlines
Deal found 5/12R17 694
Sun 19/111:55ORD - DUR
2 stops42h 45mMultiple Airlines
Sun 26/18:40DUR - ORD
2 stops33h 30mMultiple Airlines
Deal found 5/12R18 850
Sun 19/111:55ORD - PLZ
2 stops47h 05mMultiple Airlines
Sun 26/18:40PLZ - ORD
2 stops33h 30mMultiple Airlines
Deal found 5/12R18 923
Sat 22/314:10ORD - JNB
1 stop35h 25mEtihad Airways
Wed 26/310:00JNB - ORD
1 stop30h 25mEtihad Airways
Deal found 5/12R19 013
Thu 27/214:03ORD - JNB
2 stops23h 57mKLM
Thu 6/323:55JNB - ORD
2 stops26h 30mKLM
Deal found 5/12R20 278
Thu 27/214:08MDW - JNB
2 stops23h 52mKLM
Thu 6/323:55JNB - MDW
2 stops25h 52mKLM
Deal found 5/12R20 278

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 22 November 2024.

Booking 29 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, February is the cheapest month in which you can book a flight from Chicago (average of R16 754). Flying from Chicago in July will prove the most costly (average of R27 526). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

When flying from Chicago check dates and pricing for the following: United Airlines. As it departs for the following popular destinations: Cape Town.