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R1 346+ 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 2/3. 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 21 — Mar 281
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 19 February 2026.

Good round-trip deal

R16 134 or less

Good one-way deal

R796 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 19 February 2026.

Wed 15/420:10
ORD
-
CPT
1 stop32h 40m
Turkish Airlines
Wed 22/416:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 18/2R13 395
Tue 14/420:10
ORD
-
CPT
1 stop32h 40m
Turkish Airlines
Tue 21/416:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 17/2R13 764
Sun 8/321:20
ORD
-
CPT
1 stop31h 30m
Turkish Airlines
Thu 9/416:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 15/2R13 780
Wed 4/311:50
ORD
-
JNB
1 stop39h 00m
Turkish Airlines
Tue 10/319:10
JNB
-
ORD
1 stop22h 55m
Turkish Airlines
Deal found 19/2R14 116
Thu 5/311:50
ORD
-
CPT
1 stop40h 00m
Turkish Airlines
Wed 8/416:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 16/2R14 148
Sun 12/420:10
ORD
-
CPT
1 stop32h 40m
Turkish Airlines
Wed 22/416:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 15/2R14 228
Fri 24/411:25
ORD
-
CPT
1 stop41h 25m
Turkish Airlines
Tue 5/516:35
CPT
-
ORD
1 stop32h 40m
Turkish Airlines
Deal found 15/2R14 372
Tue 5/520:10
ORD
-
CPT
1 stop32h 40m
Turkish Airlines
Tue 26/516:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 18/2R14 453
Fri 24/48:31
ORD
-
JNB
2 stops32h 44m
Multiple Airlines
Thu 30/417:00
JNB
-
ORD
2 stops45h 41m
Multiple Airlines
Deal found 18/2R14 485
Wed 22/411:25
ORD
-
CPT
1 stop41h 25m
Turkish Airlines
Tue 16/616:35
CPT
-
ORD
1 stop24h 05m
Turkish Airlines
Deal found 15/2R14 517
Mon 4/520:10
ORD
-
JNB
1 stop31h 20m
Turkish Airlines
Wed 13/518:00
JNB
-
ORD
1 stop31h 15m
Turkish Airlines
Deal found 16/2R14 517
Sun 3/56:04
ORD
-
JNB
2 stops35h 11m
Kenya Airways
Mon 18/512:10
JNB
-
ORD
2 stops31h 11m
Kenya Airways
Deal found 16/2R14 597

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 19 February 2026. 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

Fri 24/4

8:31-15:50

2 stops24h 19m

Johannesburg OR Tambo

Thu 30/4

17:00-7:41

2 stops45h 41m

R14 485

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 12/4

20:10-11:50

1 stop32h 40m

Cape Town Intl

Thu 23/4

16:35-9:40

1 stop24h 05m

R14 837

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 13/4

20:10-11:50

1 stop32h 40m

Cape Town Intl

Thu 23/4

16:35-9:40

1 stop24h 05m

R15 462

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Thu 19/3

12:50-10:50

1 stop39h 00m

Johannesburg OR Tambo

Tue 7/4

17:50-9:40

1 stop22h 50m

R15 638

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 4/3

9:45-20:10

1 stop26h 25m

Johannesburg OR Tambo

Tue 10/3

8:20-8:40

2 stops31h 20m

R15 654

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 10/5

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 24/5

8:20-8:15

2 stops30h 55m

R15 686

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 13/4

11:25-11:50

1 stop41h 25m

Cape Town Intl

Thu 16/4

16:35-9:40

1 stop24h 05m

R15 734

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Thu 23/4

20:10-11:50

1 stop32h 40m

Cape Town Intl

Thu 7/5

9:55-9:40

2 stops30h 45m

R16 023

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 1/4

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Wed 22/4

8:20-8:15

2 stops30h 55m

R16 167

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 6/5

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Fri 22/5

8:20-8:15

2 stops30h 55m

R16 327

Flights are sorted by cheapest return flights first.

Deals found on 17/2

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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 18 February 2026.

Booking 21 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 R12 290). Flying from Chicago in July will prove the most costly (average of R19 356). 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 (1 411 flights per day), Detroit (992 flights per day) and Toronto (828 flights per day).

Raleigh-Durham
Raleigh-Durham
From R3 448
Fort Lauderdale
Fort Lauderdale
From R2 602
New York
New York
From R796
Dublin
Dublin
From R5 852

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 R796. Explore other affordable destinations below.

New York
New York
From R796
Fort Lauderdale
Fort Lauderdale
From R2 602
Raleigh-Durham
Raleigh-Durham
From R3 448
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From R4 585

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 Ethiopian Air from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Ethiopian Air
7,2
Good
962 reviews
Check prices

Crew

7,6

Entertainment

6,7

Overall

7,2

Comfort

7,1

Food

6,9

Boarding

7,2

Reviews

1 / 20
2,0
Mediocre

Samith,Feb 2026

JNB - ADD

Boarding experience was unprofessional and disorganized. Food was okay. Had to call cabin crew 4 times for a glass of water. Cabin crew carried themselves with an attitude. After landing in Jeddah, one of my baggage never came and I have been contacting Ethiopian Airlines for the past 5 days. Either no response or always saying there's no updates. Would not recommend especially if you're trying to avoid getting your baggage lost.
Ethiopian Air
7,2
Good
962 reviews
Ethiopian Air
7,2
Good
962 reviews
Check prices

Crew

7,6

Entertainment

6,7

Overall

7,2

Comfort

7,1

Food

6,9

Boarding

7,2

Reviews

1 / 20
2,0
Mediocre

Samith,Feb 2026

JNB - ADD

Boarding experience was unprofessional and disorganized. Food was okay. Had to call cabin crew 4 times for a glass of water. Cabin crew carried themselves with an attitude. After landing in Jeddah, one of my baggage never came and I have been contacting Ethiopian Airlines for the past 5 days. Either no response or always saying there's no updates. Would not recommend especially if you're trying to avoid getting your baggage lost.

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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 19 February 2026.

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

    The most selected flight destinations from Chicago for the current month are Atlanta, Ahmedabad, Boston. While Atlanta, Boston, Ahmedabad 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 R14 116 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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