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R1 686+ 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 5/12. 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
Dec 14 — Dec 211
1 adult
1 adult, Economy, 0 bags

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 14 November 2025.

Good round-trip deal

R17 151 or less

Good one-way deal

R846 or less
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

Enter your travel dates to find the best prices.

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 14 November 2025.

Wed 11/220:20ORD - CPT
1 stop31h 30mTurkish Airlines
Wed 25/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 11/11R16 556
Sun 1/311:50ORD - CPT
1 stop40h 00mTurkish Airlines
Thu 19/317:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 12/11R16 879
Mon 9/220:20ORD - CPT
1 stop31h 30mTurkish Airlines
Fri 13/217:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 14/11R16 947
Mon 24/119:45ORD - JNB
1 stop26h 25mEthiopian Air
Wed 10/128:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 13/11R17 356
Sun 19/47:30ORD - JNB
2 stops33h 45mMultiple Airlines
Sat 25/417:00JNB - ORD
2 stops26h 50mMultiple Airlines
Deal found 13/11R17 407
Wed 4/37:01ORD - JNB
2 stops33h 24mKenya Airways
Sat 7/31:35JNB - ORD
2 stops42h 09mKenya Airways
Deal found 13/11R17 458
Thu 12/310:15ORD - JNB
1 stop19h 50mEthiopian Air
Wed 25/38:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 13/11R17 475
Thu 29/111:50ORD - CPT
1 stop40h 00mTurkish Airlines
Wed 4/217:15CPT - ORD
1 stop33h 10mTurkish Airlines
Deal found 13/11R17 680
Thu 4/129:45ORD - JNB
1 stop26h 25mEthiopian Air
Wed 17/128:20JNB - ORD
2 stops31h 20mEthiopian Air
Deal found 13/11R17 731
Mon 2/29:45ORD - CPT
1 stop20h 50mEthiopian Air
Sun 15/213:50CPT - ORD
2 stops25h 50mEthiopian Air
Deal found 12/11R17 765
Mon 2/211:50ORD - CPT
1 stop40h 00mTurkish Airlines
Sun 15/217:15CPT - ORD
1 stop24h 50mTurkish Airlines
Deal found 12/11R17 816
Mon 24/117:00ORD - JNB
2 stops43h 55mKenya Airways
Thu 11/1212:05JNB - ORD
2 stops37h 41mKenya Airways
Deal found 14/11R17 918

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 14 November 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

Mon 9/2

20:20-11:50

1 stop31h 30m

Cape Town Intl

Fri 13/2

17:15-18:25

1 stop33h 10m

R16 947

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 9/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

Fri 20/3

17:15-11:05

1 stop24h 50m

R17 680

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 4/3

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Sun 8/3

8:20-7:40

2 stops31h 20m

R17 952

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Wed 18/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

Mon 23/3

17:15-11:05

1 stop24h 50m

R18 310

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 16/3

21:20-11:50

1 stop31h 30m

Cape Town Intl

Thu 19/3

17:15-19:25

1 stop33h 10m

R18 974

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 9/3

12:50-11:50

1 stop40h 00m

Cape Town Intl

Fri 20/3

14:00-11:05

2 stops28h 05m

R19 417

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 16/3

10:15-14:35

1 stop21h 20m

Cape Town Intl

Thu 19/3

13:50-8:40

2 stops25h 50m

R19 707

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 24/1

16:30-19:15

1 stop18h 45m

Cape Town Intl

Mon 2/2

21:30-12:01

1 stop22h 31m

R21 325

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Thu 22/1

10:53-19:15

1 stop24h 22m

Cape Town Intl

Mon 2/2

21:30-9:58

1 stop20h 28m

R21 325

ChicagoCape Town

MDW - CPT

MDWCPT

Chicago Midway

Sat 24/1

10:46-19:15

1 stop24h 29m

Cape Town Intl

Sun 1/2

21:30-17:32

1 stop28h 02m

R21 325

Flights are sorted by cheapest return flights first.

Deals found on 13/11

Showing 1-10 of 60 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 7 November 2025.

Booking 16 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, April is the cheapest month in which you can book a flight from Chicago (average of R14 001). Flying from Chicago in July will prove the most costly (average of R20 661). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1 510 flights per day), Detroit (1 084 flights per day) and Los Angeles (655 flights per day).

Orlando
Orlando
From R2 513
New York
New York
From R846
Dublin
Dublin
From R6 221
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 874

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at R846. Explore other affordable destinations below.

New York
New York
From R846
Orlando
Orlando
From R2 513
Miami
Miami
From R3 812
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 874

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.
See what other customers who have flown with Turkish Airlines and Ethiopian Air from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Turkish Airlines
7,3
Good
4 043 reviews
Check prices

Comfort

7,3

Boarding

7,3

Overall

7,3

Crew

7,7

Entertainment

7,4

Food

7,4

Reviews

1 / 20
6,0
Good

Christina,Sept 2025

DTW - IST

Crew was fine but the plane seemed smaller like the seats were very crammed in for an international flight. I’m a small person and it felt suffocating to me.
Turkish Airlines
7,3
Good
4 043 reviews
Turkish Airlines
7,3
Good
4 043 reviews
Check prices

Comfort

7,3

Boarding

7,3

Overall

7,3

Crew

7,7

Entertainment

7,4

Food

7,4

Reviews

1 / 20
6,0
Good

Christina,Sept 2025

DTW - IST

Crew was fine but the plane seemed smaller like the seats were very crammed in for an international flight. I’m a small person and it felt suffocating to me.
Ethiopian Air
7,2
Good
894 reviews
Turkish Airlines
7,3
Good
4 043 reviews
Check prices

Comfort

7,3

Boarding

7,3

Overall

7,3

Crew

7,7

Entertainment

7,4

Food

7,4

Reviews

1 / 20
6,0
Good

Christina,Sept 2025

DTW - IST

Crew was fine but the plane seemed smaller like the seats were very crammed in for an international flight. I’m a small person and it felt suffocating to me.

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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 14 November 2025.

  • What are the most popular destinations to fly to from Chicago?

    The most selected flight destinations from Chicago for the current month are Mumbai, Atlanta, Ahmedabad. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.

  • What is the cheapest month to fly from Chicago?

    April 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 334 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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