R1 662+ Cheap flights from Chicago

CHI — JNB
Nov 25 — Dec 21
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Mon 16/11

13:20-17:25

1 stop5h 05m

Denver Intl

Wed 31/12

0:00-1:00

Nonstop0h 00m

R1 762

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Tue 1/12

17:30-23:49

1 stop7h 19m

Denver Intl

Wed 31/12

0:00-1:00

Nonstop0h 00m

R1 828

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Thu 19/11

5:55-12:26

1 stop5h 31m

Boston Logan Intl

Wed 31/12

0:00-23:00

Nonstop0h 00m

R1 845

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Fri 20/11

5:55-7:45

Nonstop2h 50m

Denver Intl

Wed 31/12

0:00-1:00

Nonstop0h 00m

R1 895

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Sat 5/12

11:05-17:40

2 stops7h 35m

Denver Intl

Wed 31/12

0:00-1:00

Nonstop0h 00m

R1 912

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Mon 30/11

14:37-22:25

1 stop6h 48m

Boston Logan Intl

Wed 31/12

0:00-23:00

Nonstop0h 00m

R1 945

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sun 22/11

5:00-11:07

1 stop5h 07m

Boston Logan Intl

Wed 31/12

0:00-23:00

Nonstop0h 00m

R1 945

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sun 6/12

7:00-12:27

1 stop4h 27m

Boston Logan Intl

Wed 31/12

0:00-23:00

Nonstop0h 00m

R1 945

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 18/11

7:00-12:25

1 stop4h 25m

Boston Logan Intl

Wed 31/12

0:00-23:00

Nonstop0h 00m

R1 945

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Wed 25/11

18:30-20:20

Nonstop2h 50m

Denver Intl

Wed 31/12

0:00-1:00

Nonstop0h 00m

R2 028

Flights are sorted by cheapest return flights first.

Deals found on 26/10

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 R17 087). Flying from Chicago in December will prove the most costly (average of R30 468). 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: Qatar Airways. As it departs for the following popular destinations: Johannesburg.

Qatar Airways
Qatar Airways
From R21 812

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1 448 flights per day), Orlando (881 flights per day) and Detroit (842 flights per day).

Istanbul
Istanbul
From R16 248
Raleigh-Durham
Raleigh-Durham
From R3 577
Addis Ababa Bole
Addis Ababa Bole
From R15 180
Boston Logan Intl
Boston Logan Intl
From R2 640

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 640. Explore other affordable destinations below.

Boston Logan Intl
Boston Logan Intl
From R2 640
Raleigh-Durham
Raleigh-Durham
From R3 577
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 757
Mexico City Benito Juarez
Mexico City Benito Juarez
From R8 125

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

Booking 38 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.

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 Atlanta, Boston, Ahmedabad. While Atlanta, Boston, Mumbai 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.