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R2 184+ 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 1/5. 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 — JNB
May 5 — May 121
1 adult
1 adult, Economy, 0 bags

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 5 April 2026. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 6/9

20:10-11:50

1 stop32h 40m

Cape Town Intl

Thu 24/9

16:35-9:40

1 stop24h 05m

R16 559

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 15/9

9:00-9:00

2 stops41h 00m

Johannesburg OR Tambo

Tue 22/9

12:40-15:05

1 stop33h 25m

R24 449

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Wed 9/9

19:20-10:35

2 stops32h 15m

Durban King Shaka Intl

Sun 13/9

17:00-15:05

2 stops53h 05m

R25 296

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Thu 17/9

19:20-10:35

2 stops32h 15m

Durban King Shaka Intl

Mon 21/9

11:15-15:05

2 stops34h 50m

R25 313

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 2/9

10:15-14:35

1 stop21h 20m

Cape Town Intl

Sun 13/9

13:50-8:15

2 stops25h 25m

R25 719

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Fri 11/9

20:35-16:40

1 stop37h 05m

Cape Town Intl

Wed 23/9

20:00-15:45

1 stop26h 45m

R26 159

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Fri 5/6

20:10-13:15

2 stops34h 05m

Durban King Shaka Intl

Fri 12/6

14:45-9:40

2 stops25h 55m

R26 938

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Fri 11/9

20:35-11:30

1 stop31h 55m

Cape Town Intl

Sat 26/9

20:00-15:45

1 stop26h 45m

R27 006

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Thu 10/9

20:35-11:30

1 stop31h 55m

Cape Town Intl

Sat 26/9

20:00-15:45

1 stop26h 45m

R27 023

ChicagoPort Elizabeth

ORD - PLZ

ORDPLZ

Chicago O'Hare Intl

Sat 16/5

11:25-18:20

2 stops47h 55m

Port Elizabeth

Sat 23/5

13:30-9:40

2 stops27h 10m

R27 209

Flights are sorted by cheapest return flights first.

Deals found on 1/4

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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 OR Tambo. Price data was last updated on 3 April 2026.

Booking 21 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 R12 749). Flying from Chicago in July will prove the most costly (average of R20 352). 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: Detroit (1 020 flights per day), New York (906 flights per day) and Toronto (756 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 643
Fort Lauderdale
Fort Lauderdale
From R2 750
Dublin
Dublin
From R6 184
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 845

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Fort Lauderdale, with prices starting at R2 750. Explore other affordable destinations below.

Fort Lauderdale
Fort Lauderdale
From R2 750
Raleigh-Durham
Raleigh-Durham
From R3 643
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 845
Dublin
Dublin
From R6 184

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 Ethiopian Air from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Ethiopian Air
7,2
Good
994 reviews
Check prices

Food

6,9

Crew

7,6

Boarding

7,2

Overall

7,2

Entertainment

6,7

Comfort

7,1

Reviews

1 / 20
8,0
Excellent

Anonymous,Mar 2026

JRO - SGN

For a business class flight, you’d expect the boarding process to be far better than it was. Besides that, it’s was a good experience.
Ethiopian Air
7,2
Good
994 reviews
Ethiopian Air
7,2
Good
994 reviews
Check prices

Food

6,9

Crew

7,6

Boarding

7,2

Overall

7,2

Entertainment

6,7

Comfort

7,1

Reviews

1 / 20
8,0
Excellent

Anonymous,Mar 2026

JRO - SGN

For a business class flight, you’d expect the boarding process to be far better than it was. Besides that, it’s was a good experience.

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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 5 April 2026.

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

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

  • What is the cheapest month to fly from Chicago?

    February 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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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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