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R2 048+ 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 18/3. 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
mar 5 — mar 121
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 febbraio 2025.

Cheapest airline

United Airlines

Good round-trip deal

R5 573 or less

Good one-way deal

R1 632 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of R24 440).
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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 28 febbraio 2025.

mer 2/410:15ORD - CPT
1 stop21h 20mEthiopian Air
mer 9/414:35CPT - ORD
2 stops24h 30mEthiopian Air
Deal found 27/2R15 790
gio 20/310:15ORD - JNB
1 stop26h 45mEthiopian Air
sab 5/48:20JNB - ORD
2 stops30h 45mEthiopian Air
Deal found 28/2R16 602
gio 10/47:35ORD - JNB
2 stops25h 15mMultiple Airlines
gio 24/417:00JNB - ORD
2 stops27h 10mMultiple Airlines
Deal found 27/2R17 561
sab 5/47:35ORD - JNB
2 stops33h 40mKenya Airways
mar 15/417:00JNB - ORD
2 stops27h 10mKenya Airways
Deal found 27/2R17 801
gio 15/519:50ORD - JNB
1 stop31h 45mTurkish Airlines
ven 30/517:55JNB - ORD
1 stop22h 45mTurkish Airlines
Deal found 26/2R18 114
mar 22/419:50ORD - CPT
1 stop33h 00mTurkish Airlines
mar 6/516:35CPT - ORD
1 stop24h 05mTurkish Airlines
Deal found 27/2R18 557
lun 14/413:55ORD - JNB
1 stop35h 25mEtihad Airways
lun 21/49:50JNB - ORD
1 stop29h 55mEtihad Airways
Deal found 27/2R18 908
mar 29/416:55ORD - JNB
1 stop31h 05mAmerican Airlines
mer 7/521:15JNB - ORD
1 stop21h 30mAmerican Airlines
Deal found 28/2R19 922
dom 20/47:45ORD - JNB
2 stops27h 00mUnited Airlines
lun 28/415:05JNB - ORD
2 stops25h 40mUnited Airlines
Deal found 27/2R20 346
dom 18/519:05ORD - JNB
1 stop31h 15mSWISS
mer 21/519:35JNB - ORD
1 stop23h 35mSWISS
Deal found 27/2R20 402
ven 16/522:25ORD - CPT
1 stop29h 35mAmerican Airlines
sab 7/618:55CPT - ORD
1 stop29h 05mAmerican Airlines
Deal found 27/2R20 549
sab 14/621:15ORD - CPT
1 stop30h 45mBritish Airways
lun 23/69:00CPT - ORD
2 stops37h 55mBritish Airways
Deal found 26/2R20 678

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

Fly to

OR Tambo

Route

Depart

Return

Price

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

mer 2/4

10:15-14:35

1 stop21h 20m

Cape Town Intl

mer 9/4

14:35-8:05

2 stops24h 30m

R15 790

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

gio 20/3

10:15-20:00

1 stop26h 45m

Johannesburg OR Tambo

sab 5/4

8:20-8:05

2 stops30h 45m

R16 602

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

gio 10/4

7:35-15:50

2 stops25h 15m

Johannesburg OR Tambo

gio 24/4

17:00-13:10

2 stops27h 10m

R17 561

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

sab 5/4

7:35-0:15

2 stops33h 40m

Johannesburg OR Tambo

mar 15/4

17:00-13:10

2 stops27h 10m

R17 801

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

gio 15/5

19:50-10:35

1 stop31h 45m

Johannesburg OR Tambo

ven 30/5

17:55-9:40

1 stop22h 45m

R18 114

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

mar 22/4

19:50-11:50

1 stop33h 00m

Cape Town Intl

mar 6/5

16:35-9:40

1 stop24h 05m

R18 557

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

lun 14/4

13:55-8:20

1 stop35h 25m

Johannesburg OR Tambo

lun 21/4

9:50-8:45

1 stop29h 55m

R18 908

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mar 29/4

16:55-7:00

1 stop31h 05m

Johannesburg OR Tambo

mer 7/5

21:15-11:45

1 stop21h 30m

R19 922

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

dom 20/4

7:45-17:45

2 stops27h 00m

Johannesburg OR Tambo

lun 28/4

15:05-9:45

2 stops25h 40m

R20 346

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

dom 18/5

19:05-9:20

1 stop31h 15m

Johannesburg OR Tambo

mer 21/5

19:35-12:10

1 stop23h 35m

R20 402

Flights are sorted by cheapest return flights first.

Deals found on 28/2

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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 25 February 2025.

Booking 62 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, September is the cheapest month in which you can book a flight from Chicago (average of R14 111). Flying from Chicago in July will prove the most costly (average of R23 796). 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 (1 231 flights per day), Detroit (854 flights per day) and Toronto (692 flights per day).

Wichita Eisenhower National

Wichita Eisenhower National

From R174

Calgary

Calgary

From R103

Washington, D.C.

Washington, D.C.

From R88

Doha Hamad Intl

Doha Hamad Intl

From R584

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Washington, D.C., with prices starting at R1 632. Explore other affordable destinations below.

Washington, D.C.

Washington, D.C.

From R88

Calgary

Calgary

From R103

Detroit

Detroit

From R104

Wichita Eisenhower National

Wichita Eisenhower National

From R174

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
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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
8,1
Very Good
3 251 reviews
Emirates
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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
8 138 reviews
Emirates
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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
1 328 reviews
Emirates
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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.

Austrian Airlines
7,5
Good
770 reviews
Emirates
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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
1 565 reviews
Emirates
8,1
Very Good
3 251 reviews
Check prices

Boarding

8,1

Food

7,8

Entertainment

8,2

Crew

8,3

Comfort

8,0

Overall

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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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 febbraio 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, Mumbai, Ahmedabad. While Atlanta, Boston, Athens are the top choices made by travellers year-round.

  • What is the cheapest month to fly from Chicago?

    September 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 366 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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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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