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R2 088+ 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 17/2. 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
gen 22 — gen 291
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 17 gennaio 2025.

Cheapest airline

United Airlines
On average, United Airlines currently has the cheapest one-way flight from Chicago.

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 17 gennaio 2025.

mer 5/211:55ORD - JNB
1 stop38h 50mTurkish Airlines
mer 19/219:05JNB - ORD
1 stop23h 05mTurkish Airlines
Deal found 16/1R15 498
sab 15/314:10ORD - JNB
1 stop35h 25mEtihad Airways
mer 26/310:00JNB - ORD
1 stop30h 25mEtihad Airways
Deal found 16/1R16 701
mar 25/27:05ORD - JNB
2 stops24h 55mMultiple Airlines
mar 4/31:15JNB - ORD
2 stops44h 04mMultiple Airlines
Deal found 16/1R16 927
mar 4/27:10ORD - JNB
2 stops33h 05mKenya Airways
mar 11/21:15JNB - ORD
2 stops42h 46mKenya Airways
Deal found 17/1R16 946
dom 2/320:30ORD - DUR
2 stops34h 10mMultiple Airlines
dom 9/38:40DUR - ORD
2 stops33h 30mMultiple Airlines
Deal found 16/1R18 112
dom 2/320:30ORD - PLZ
2 stops38h 30mMultiple Airlines
dom 9/319:40PLZ - ORD
2 stops46h 30mMultiple Airlines
Deal found 15/1R18 375
gio 13/310:15ORD - JNB
1 stop19h 55mEthiopian Air
mer 19/38:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 15/1R18 639
lun 3/320:30ORD - CPT
1 stop31h 30mTurkish Airlines
lun 10/317:15CPT - ORD
1 stop24h 55mTurkish Airlines
Deal found 17/1R18 770
mer 5/321:45ORD - CPT
1 stop30h 25mMultiple Airlines
gio 13/322:00CPT - ORD
1 stop26h 40mMultiple Airlines
Deal found 17/1R18 977
dom 2/318:26ORD - CPT
1 stop29h 34mAmerican Airlines
dom 9/320:55CPT - ORD
1 stop25h 00mAmerican Airlines
Deal found 16/1R19 015
dom 2/317:00ORD - CPT
1 stop33h 20mBritish Airways
dom 9/318:45CPT - ORD
1 stop29h 55mBritish Airways
Deal found 16/1R19 184
dom 11/510:15ORD - CPT
1 stop43h 45mEthiopian Air
mer 4/614:35CPT - ORD
2 stops24h 30mEthiopian Air
Deal found 16/1R19 410

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

Fly to

Any airport

Route

Depart

Return

Price

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mer 5/2

11:55-10:45

1 stop38h 50m

Johannesburg OR Tambo

mer 19/2

19:05-10:10

1 stop23h 05m

R15 498

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

lun 3/3

7:05-0:15

2 stops33h 10m

Johannesburg OR Tambo

lun 10/3

8:40-17:43

2 stops40h 03m

R16 871

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mar 25/2

6:00-16:00

2 stops26h 00m

Johannesburg OR Tambo

mer 5/3

17:00-13:19

2 stops28h 19m

R16 927

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

mer 19/3

14:10-8:35

1 stop35h 25m

Johannesburg OR Tambo

lun 31/3

9:55-8:55

1 stop30h 00m

R17 491

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

dom 2/3

20:30-14:40

2 stops34h 10m

Durban King Shaka Intl

dom 9/3

8:40-10:10

2 stops33h 30m

R18 112

ChicagoPort Elizabeth

ORD - PLZ

ORDPLZ

Chicago O'Hare Intl

dom 2/3

20:30-19:00

2 stops38h 30m

Port Elizabeth

dom 9/3

19:40-11:10

2 stops46h 30m

R18 375

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

gio 13/3

10:15-13:10

1 stop19h 55m

Johannesburg OR Tambo

mer 19/3

8:20-8:40

2 stops31h 20m

R18 639

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

lun 3/3

20:30-12:00

1 stop31h 30m

Cape Town Intl

lun 10/3

17:15-11:10

1 stop24h 55m

R18 770

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

mer 5/3

21:45-12:10

1 stop30h 25m

Cape Town Intl

gio 13/3

22:00-17:40

1 stop26h 40m

R18 977

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

dom 2/3

18:26-8:00

1 stop29h 34m

Cape Town Intl

dom 9/3

20:55-14:55

1 stop25h 00m

R19 015

Flights are sorted by cheapest return flights first.

Deals found on 16/1

Showing 1-10 of 50 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 10 January 2025.

Booking 37 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, February is the cheapest month in which you can book a flight from Chicago (average of R14 238). Flying from Chicago in July will prove the most costly (average of R24 225). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

8,0
Very Good
8 513 reviews
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

8,0
Very Good
9 684 reviews
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7,8
Good
1 339 reviews
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7,5
Good
3 752 reviews
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

7,5
Good
664 reviews
8,0
Very Good
8 513 reviews

Boarding

8,2

Food

7,3

Overall

8,0

Entertainment

7,9

Comfort

8,0

Crew

8,6

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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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 17 gennaio 2025.
  • What are the most popular destinations to fly to from Chicago?

    The most selected flight destinations from Chicago for the current month are Ahmedabad, Mumbai, Atlanta. While Atlanta, Boston, Athens 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 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 234 round trip
    Travel from Chicago to Cape Town from R17 059 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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