Find flights
Airlines

R2 042+ 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 12/5. 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
Apr 2 — Apr 91
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 28 March 2025.

Cheapest airline

United Airlines

Good round-trip deal

R5 508 or less

Good one-way deal

R1 870 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of R24 153).
Search Deals
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a 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 28 March 2025.

Sun 4/510:15ORD - JNB
1 stop26h 55mEthiopian Air
Sun 11/58:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 27/3R16 426
Wed 7/511:25ORD - JNB
1 stop40h 10mTurkish Airlines
Fri 23/517:55JNB - ORD
1 stop22h 45mTurkish Airlines
Deal found 28/3R16 899
Wed 30/47:10ORD - JNB
2 stops25h 40mMultiple Airlines
Wed 7/512:10JNB - ORD
2 stops36h 19mMultiple Airlines
Deal found 27/3R17 866
Sun 7/919:50ORD - CPT
1 stop33h 00mTurkish Airlines
Sun 14/916:35CPT - ORD
1 stop36h 25mTurkish Airlines
Deal found 27/3R18 704
Wed 7/57:00ORD - JNB
2 stops25h 50mKenya Airways
Tue 13/51:15JNB - ORD
2 stops47h 14mKenya Airways
Deal found 27/3R19 670
Tue 29/411:15ORD - JNB
2 stops23h 30mUnited Airlines
Wed 7/521:20JNB - ORD
1 stop21h 28mUnited Airlines
Deal found 27/3R19 944
Sun 4/510:15ORD - CPT
1 stop43h 45mEthiopian Air
Sun 11/513:50CPT - ORD
2 stops25h 25mEthiopian Air
Deal found 26/3R19 980
Thu 15/520:30ORD - CPT
1 stop31h 30mAmerican Airlines
Tue 20/518:55CPT - ORD
1 stop28h 00mAmerican Airlines
Deal found 26/3R20 400
Sat 13/923:45ORD - DUR
2 stops30h 30mTurkish Airlines
Sun 21/914:45DUR - ORD
2 stops38h 15mTurkish Airlines
Deal found 27/3R20 892
Wed 7/520:15ORD - JNB
2 stops30h 05mSWISS
Sat 17/513:00JNB - ORD
2 stops54h 45mSWISS
Deal found 28/3R20 892
Sun 11/520:30ORD - JNB
1 stop29h 55mAmerican Airlines
Sun 18/521:15JNB - ORD
1 stop25h 40mAmerican Airlines
Deal found 26/3R21 038
Tue 27/519:10ORD - CPT
1 stop32h 50mBritish Airways
Wed 4/618:55CPT - ORD
1 stop26h 00mBritish Airways
Deal found 27/3R21 621

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 28 March 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 4/5

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Sun 11/5

8:20-8:15

2 stops30h 55m

R16 426

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 7/5

11:25-10:35

1 stop40h 10m

Johannesburg OR Tambo

Fri 23/5

17:55-9:40

1 stop22h 45m

R16 899

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 30/4

7:10-15:50

2 stops25h 40m

Johannesburg OR Tambo

Wed 7/5

12:10-17:29

2 stops36h 19m

R17 866

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 7/9

19:50-11:50

1 stop33h 00m

Cape Town Intl

Sun 14/9

16:35-22:00

1 stop36h 25m

R18 704

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 7/5

7:00-15:50

2 stops25h 50m

Johannesburg OR Tambo

Tue 13/5

1:15-17:29

2 stops47h 14m

R19 670

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Tue 29/4

11:15-17:45

2 stops23h 30m

Johannesburg OR Tambo

Wed 7/5

21:20-11:48

1 stop21h 28m

R19 944

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 4/5

10:15-13:00

1 stop43h 45m

Cape Town Intl

Sun 11/5

13:50-8:15

2 stops25h 25m

R19 980

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Thu 15/5

20:30-11:00

1 stop31h 30m

Cape Town Intl

Tue 20/5

18:55-15:55

1 stop28h 00m

R20 400

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 7/5

20:15-9:20

2 stops30h 05m

Johannesburg OR Tambo

Sat 17/5

13:00-15:55

2 stops57h 55m

R20 892

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Sat 13/9

23:45-13:15

2 stops30h 30m

Durban King Shaka Intl

Sun 21/9

14:45-22:00

2 stops38h 15m

R20 892

Flights are sorted by cheapest return flights first.

Deals found on 27/3

Showing 1-10 of 50 results
1
2
3
...
5

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 21 March 2025.

Booking 54 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, November is the cheapest month in which you can book a flight from Chicago (average of R14 438). Flying from Chicago in July will prove the most costly (average of R23 535). 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: Johannesburg.

United Airlines

United Airlines

From R972

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1 024 flights per day), Detroit (682 flights per day) and Orlando (489 flights per day).

Wichita Eisenhower National

Wichita Eisenhower National

From R174

Frankfurt am Main

Frankfurt am Main

From R776

Amsterdam Schiphol

Amsterdam Schiphol

From R635

Doha Hamad Intl

Doha Hamad Intl

From R1 376

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Calgary, with prices starting at R1 870. Explore other affordable destinations below.

Calgary

Calgary

From R103

Detroit

Detroit

From R104

Wichita Eisenhower National

Wichita Eisenhower National

From R174

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.
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Emirates
8,0
Very Good
3 190 reviews
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Delta
8,0
Very Good
7 897 reviews
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
KLM
7,8
Good
1 321 reviews
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
SWISS
7,5
Good
1 570 reviews
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Qatar Airways
7,4
Good
3 538 reviews
Emirates
8,0
Very Good
3 190 reviews
Check prices

Food

7,8

Crew

8,3

Overall

8,0

Entertainment

8,2

Comfort

8,0

Boarding

8,1

Reviews

1 / 20
4,0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Los Angeles
Direct flights from Miami
Direct flights from Atlanta
Direct flights from Orlando
Direct flights from Las Vegas
Direct flights from Boston
Direct flights from Denver
Direct flights from Seattle
Direct flights from San Francisco
Direct flights from Honolulu
Direct flights from Minneapolis
Direct flights from Charlotte
Direct flights from Nashville
Direct flights from Austin
Direct flights from Tampa
Direct flights from Fort Lauderdale
Direct flights from Fargo
Direct flights from Philadelphia
Direct flights from Memphis
Direct flights from Salt Lake City
Direct flights from New Orleans
Direct flights from Omaha
Direct flights from Portland
Direct flights from San Diego
Direct flights from St. Louis
Direct flights from Anchorage
Direct flights from Indianapolis
Direct flights from Des Moines
Direct flights from Little Rock
Direct flights from Oklahoma City

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 28 March 2025.

  • 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, Barcelona-El Prat Airport. While Atlanta, Boston, Athens are the top choices made by travellers year-round.

  • What is the cheapest airport to fly out of Chicago?

    Chicago O'Hare Intl airport offers the cheapest routes to Cape Town from R15 733. Chicago Midway airport is a great option if you're flying to Johannesburg from R29 369. Our top recommendation is to be generally flexible with your dates of travel for the best rates.

  • What is the cheapest month to fly from Chicago?

    November 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 Johannesburg from R15 733 round trip
    Travel from Chicago to Cape Town from R17 702 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.

See more FAQs

Fly with Cheapflights

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.

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.