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R2 126+ 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 3/6. 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 25 — May 21
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 20 April 2025.

Cheapest airline

United Airlines

Good round-trip deal

R5 683 or less

Good one-way deal

R1 929 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of R24 921).
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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 20 April 2025.

Thu 25/919:50ORD - JNB
1 stop31h 45mTurkish Airlines
Fri 24/1017:55JNB - ORD
1 stop31h 00mTurkish Airlines
Deal found 20/4R17 380
Fri 26/910:15ORD - CPT
1 stop21h 20mEthiopian Air
Sat 11/1013:50CPT - ORD
2 stops25h 25mEthiopian Air
Deal found 19/4R17 757
Mon 5/57:10ORD - JNB
2 stops34h 05mMultiple Airlines
Fri 9/517:00JNB - ORD
2 stops27h 04mMultiple Airlines
Deal found 18/4R17 907
Thu 25/910:15ORD - JNB
1 stop19h 50mEthiopian Air
Fri 24/108:20JNB - ORD
2 stops30h 55mEthiopian Air
Deal found 20/4R18 603
Sat 3/57:10ORD - JNB
2 stops34h 05mKenya Airways
Mon 5/51:15JNB - ORD
2 stops47h 14mKenya Airways
Deal found 20/4R18 716
Sat 13/923:45ORD - CPT
1 stop29h 05mTurkish Airlines
Wed 24/916:35CPT - ORD
1 stop24h 05mTurkish Airlines
Deal found 19/4R18 923
Mon 5/521:15ORD - JNB
1 stop26h 45mBritish Airways
Wed 21/521:15JNB - ORD
2 stops27h 19mBritish Airways
Deal found 19/4R19 017
Wed 7/521:15ORD - CPT
1 stop30h 45mBritish Airways
Wed 21/57:00CPT - ORD
2 stops35h 45mBritish Airways
Deal found 20/4R19 562
Sat 6/919:20ORD - JNB
1 stop31h 20mQatar Airways
Tue 16/916:50JNB - ORD
2 stops53h 15mQatar Airways
Deal found 19/4R19 882
Sat 3/515:40ORD - JNB
1 stop19h 05mUnited Airlines
Tue 6/510:25JNB - ORD
2 stops30h 19mUnited Airlines
Deal found 20/4R20 653
Sat 13/923:45ORD - CPT
2 stops31h 50mMultiple Airlines
Wed 24/916:35CPT - ORD
1 stop24h 05mMultiple Airlines
Deal found 19/4R21 236
Tue 6/514:20ORD - JNB
1 stop36h 00mSWISS
Sun 18/519:35JNB - ORD
1 stop27h 20mSWISS
Deal found 19/4R21 312

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 20 April 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

Thu 25/9

19:50-10:35

1 stop31h 45m

Johannesburg OR Tambo

Fri 24/10

17:55-17:55

1 stop31h 00m

R17 380

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Fri 26/9

10:15-14:35

1 stop21h 20m

Cape Town Intl

Sat 11/10

13:50-8:15

2 stops25h 25m

R17 757

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 5/5

7:10-0:15

2 stops34h 05m

Johannesburg OR Tambo

Fri 9/5

17:00-13:04

2 stops27h 04m

R17 907

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 25/9

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Fri 24/10

8:20-8:15

2 stops30h 55m

R18 603

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 3/5

7:10-0:15

2 stops34h 05m

Johannesburg OR Tambo

Mon 5/5

1:15-17:29

2 stops47h 14m

R18 716

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sat 13/9

23:45-11:50

1 stop29h 05m

Cape Town Intl

Wed 24/9

16:35-9:40

1 stop24h 05m

R18 923

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 5/5

21:15-7:00

1 stop26h 45m

Johannesburg OR Tambo

Wed 21/5

21:15-17:34

2 stops27h 19m

R19 017

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 7/5

21:15-11:00

1 stop30h 45m

Cape Town Intl

Wed 21/5

7:00-11:45

2 stops35h 45m

R19 562

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 6/9

19:20-9:40

1 stop31h 20m

Johannesburg OR Tambo

Tue 16/9

16:50-15:05

2 stops53h 15m

R19 882

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sat 3/5

15:40-17:45

1 stop19h 05m

Johannesburg OR Tambo

Tue 6/5

10:25-9:44

2 stops30h 19m

R20 653

Flights are sorted by cheapest return flights first.

Deals found on 19/4

Showing 1-10 of 57 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 OR Tambo. Price data was last updated on 18 April 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 897). Flying from Chicago in July will prove the most costly (average of R24 284). 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 (1 678 flights per day), Detroit (1 164 flights per day) and Los Angeles (663 flights per day).

Wichita Eisenhower National

Wichita Eisenhower National

From R174

Addis Ababa Bole

Addis Ababa Bole

From R788

Doha Hamad Intl

Doha Hamad Intl

From R1 376

Calgary

Calgary

From R103

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 929. Explore other affordable destinations below.

Calgary

Calgary

From R103

Wichita Eisenhower National

Wichita Eisenhower National

From R174

Seattle/Tacoma Intl

Seattle/Tacoma Intl

From R219

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
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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
3 201 reviews
Emirates
8,0
Very Good
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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
7 920 reviews
Emirates
8,0
Very Good
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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
1 331 reviews
Emirates
8,0
Very Good
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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
1 582 reviews
Emirates
8,0
Very Good
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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
3 554 reviews
Emirates
8,0
Very Good
3 201 reviews
Check prices

Overall

8,0

Food

7,8

Crew

8,3

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.

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Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from St. Louis

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 20 April 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, Mumbai are the top choices made by travellers year-round.

  • 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 R16 496 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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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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