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R2 143+ 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 13/9. 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
Aug 16 — Aug 231
1 adult

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 11 August 2025.

Good round-trip deal

R5 232 or less

Good one-way deal

R3 649 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

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 11 August 2025.

Wed 24/923:45ORD - CPT
1 stop29h 05mTurkish Airlines
Wed 1/1016:35CPT - ORD
1 stop24h 05mTurkish Airlines
Deal found 10/8R16 822
Wed 17/97:00ORD - JNB
2 stops34h 25mMultiple Airlines
Sun 28/917:00JNB - ORD
2 stops26h 10mMultiple Airlines
Deal found 10/8R16 875
Sat 23/810:15ORD - CPT
1 stop21h 20mEthiopian Air
Wed 10/914:35CPT - ORD
2 stops24h 40mEthiopian Air
Deal found 9/8R17 176
Wed 3/923:45ORD - CPT
1 stop29h 05mTurkish Airlines
Thu 18/916:35CPT - ORD
1 stop24h 05mTurkish Airlines
Deal found 10/8R17 282
Wed 17/910:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 8/108:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 9/8R17 318
Wed 26/117:30ORD - JNB
2 stops43h 25mKenya Airways
Sun 7/1217:00JNB - ORD
2 stops32h 36mKenya Airways
Deal found 10/8R17 335
Wed 24/910:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 1/108:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 10/8R17 459
Wed 22/1010:15ORD - JNB
1 stop26h 55mEthiopian Air
Mon 10/1114:30JNB - ORD
2 stops25h 10mEthiopian Air
Deal found 10/8R17 477
Thu 18/910:15ORD - JNB
1 stop26h 55mEthiopian Air
Thu 9/108:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 9/8R17 530
Mon 25/810:15ORD - CPT
1 stop21h 20mEthiopian Air
Wed 10/914:35CPT - ORD
2 stops24h 40mEthiopian Air
Deal found 9/8R17 583
Wed 10/923:45ORD - JNB
1 stop27h 50mTurkish Airlines
Fri 10/1017:55JNB - ORD
1 stop31h 00mTurkish Airlines
Deal found 9/8R17 654
Sat 6/923:45ORD - JNB
1 stop27h 50mTurkish Airlines
Tue 16/917:50JNB - ORD
1 stop22h 50mTurkish Airlines
Deal found 10/8R17 690

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 11 August 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

Wed 24/9

23:45-11:50

1 stop29h 05m

Cape Town Intl

Wed 1/10

16:35-9:40

1 stop24h 05m

R16 822

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 17/9

7:00-0:25

2 stops34h 25m

Johannesburg OR Tambo

Sun 28/9

17:00-12:10

2 stops26h 10m

R16 875

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 23/8

10:15-14:35

1 stop21h 20m

Cape Town Intl

Wed 10/9

14:35-8:15

2 stops24h 40m

R17 176

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 3/9

23:45-11:50

1 stop29h 05m

Cape Town Intl

Thu 18/9

16:35-9:40

1 stop24h 05m

R17 282

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 17/9

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Wed 8/10

8:20-8:15

2 stops30h 55m

R17 318

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 26/11

7:30-10:55

2 stops43h 25m

Johannesburg OR Tambo

Sun 7/12

17:00-17:36

2 stops32h 36m

R17 335

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 24/9

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Wed 1/10

8:20-8:15

2 stops30h 55m

R17 459

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 22/10

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Mon 10/11

14:30-7:40

2 stops25h 10m

R17 477

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 18/9

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Thu 9/10

8:20-8:15

2 stops30h 55m

R17 530

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 25/8

10:15-14:35

1 stop21h 20m

Cape Town Intl

Wed 10/9

14:35-8:15

2 stops24h 40m

R17 583

Flights are sorted by cheapest return flights first.

Deals found on 10/8

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 8 August 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 458). Flying from Chicago in July will prove the most costly (average of R27 057). 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 (885 flights per day), Toronto (872 flights per day) and Los Angeles (685 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R217
London
London
From R1 336
Amsterdam Schiphol
Amsterdam Schiphol
From R1 171
Reykjavik
Reykjavik
From R206

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Reykjavik, with prices starting at R3 649. Explore other affordable destinations below.

Reykjavik
Reykjavik
From R206
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R217
Miami
Miami
From R224

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 594 507 searches.
See what other customers who have flown with Singapore Airlines, Delta, andKLM from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered
Singapore Airlines
8,1
Very Good
1 346 reviews
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered
Delta
8,0
Very Good
7 979 reviews
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered
KLM
7,8
Good
1 381 reviews
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered
Qatar Airways
7,4
Good
3 604 reviews
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered
Virgin Atlantic
7,4
Good
657 reviews
Singapore Airlines
8,1
Very Good
1 346 reviews
Check prices

Comfort

8,0

Boarding

8,2

Crew

8,6

Overall

8,1

Food

7,7

Entertainment

8,0

Reviews

1 / 20
10,0
Excellent

Anonymous,Jul 2025

DAD - SIN

Person in front laid back his seat. I’m quite tall found it difficult to sit straight lucky seat next to me was empty was able to stretch my legs. Eating my meal was difficult also as seat remained lowered

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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 11 August 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, Athens. While Atlanta, Boston, Mumbai 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 R17 176 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

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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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