Find flights
Airlines

R2 726+ Cheap flights from Chicago

CHI — JNB
Sep 26 — Oct 31
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Mon 1/2

20:15-12:05

1 stop31h 50m

Cape Town Intl

Fri 19/2

17:20-10:00

1 stop24h 40m

R18 347

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Thu 11/2

20:15-12:05

1 stop31h 50m

Cape Town Intl

Thu 25/2

17:20-18:20

1 stop33h 00m

R18 347

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Sun 1/11

12:45-23:00

1 stop26h 15m

Cape Town Intl

Tue 10/11

0:55-10:00

1 stop41h 05m

R18 347

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Tue 19/1

11:45-12:05

1 stop40h 20m

Cape Town Intl

Thu 28/1

17:20-10:00

1 stop24h 40m

R18 825

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Wed 20/1

20:15-12:05

1 stop31h 50m

Cape Town Intl

Fri 29/1

17:20-18:20

1 stop33h 00m

R18 825

ChicagoJohannesburg

ORD Chicago O'Hare Intl - JNB Johannesburg OR Tambo

ORDJNB

Chicago O'Hare Intl

Wed 11/11

11:45-11:00

1 stop39h 15m

Johannesburg OR Tambo

Tue 17/11

18:50-18:20

1 stop31h 30m

R18 889

ChicagoCape Town

ORD Chicago O'Hare Intl - CPT Cape Town Intl

ORDCPT

Chicago O'Hare Intl

Wed 20/1

20:15-12:05

1 stop31h 50m

Cape Town Intl

Thu 28/1

14:00-18:20

2 stops36h 20m

R19 240

ChicagoJohannesburg

ORD Chicago O'Hare Intl - JNB Johannesburg OR Tambo

ORDJNB

Chicago O'Hare Intl

Fri 5/2

20:15-22:25

1 stop42h 10m

Johannesburg OR Tambo

Wed 17/2

0:20-18:20

1 stop26h 00m

R19 527

ChicagoJohannesburg

ORD Chicago O'Hare Intl - JNB Johannesburg OR Tambo

ORDJNB

Chicago O'Hare Intl

Sun 11/10

11:25-10:15

1 stop39h 50m

Johannesburg OR Tambo

Sun 18/10

18:00-9:40

1 stop22h 40m

R19 846

ChicagoJohannesburg

ORD Chicago O'Hare Intl - JNB Johannesburg OR Tambo

ORDJNB

Chicago O'Hare Intl

Wed 11/11

9:45-0:05

2 stops30h 20m

Johannesburg OR Tambo

Wed 18/11

14:30-7:40

2 stops25h 10m

R20 961

Flights are sorted by cheapest return flights first.

Deals found on 23/8

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

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 849). Flying from Chicago in December will prove the most costly (average of R30 334). 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 (1 182 flights per day), New York (1 174 flights per day) and Los Angeles (809 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 430
Boston Logan Intl
Boston Logan Intl
From R2 445
Istanbul
Istanbul
From R7 073
Dublin
Dublin
From R8 839

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Boston Logan Intl, with prices starting at R2 445. Explore other affordable destinations below.

Boston Logan Intl
Boston Logan Intl
From R2 445
Raleigh-Durham
Raleigh-Durham
From R3 430
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 561
Istanbul
Istanbul
From R7 073

When is the best time to book a flight from Chicago?

Booking 39 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.

Airline reviews for flights from Chicago

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
1 033 reviews
Check prices

Comfort

7,1

Boarding

7,2

Entertainment

6,7

Food

6,9

Crew

7,5

Overall

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

LFW - ACC

Took too long to serve the refreshments. We sat in transit on the aircraft. It’s hot. They won’t even serve water. That’s not good customer. It’s because we were not in business class? 75% of your customers are in economy. Are we not good enough.
Ethiopian Air
7,2
Good
1 033 reviews
Ethiopian Air
7,2
Good
1 033 reviews
Check prices

Comfort

7,1

Boarding

7,2

Entertainment

6,7

Food

6,9

Crew

7,5

Overall

7,2

Reviews

1 / 20
6,0
Good

Anonymous,Apr 2026

LFW - ACC

Took too long to serve the refreshments. We sat in transit on the aircraft. It’s hot. They won’t even serve water. That’s not good customer. It’s because we were not in business class? 75% of your customers are in economy. Are we not good enough.

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

  • 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, 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 December 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.

See more FAQs

Fly with Cheapflights

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book With Flexibility

Our users can plan ahead with confidence and find flights with no change fees.

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.