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$732+ Cheap flights from Chicago (CHI) to Brindisi (BDS)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Feb 18 — Feb 251
Wed 2/18
Wed 2/25
1 adult, Economy
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Cheap flight deals from Chicago to Brindisi

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Brindisi (BDS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$732
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Brindisi Papola Casale flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Brindisi Papola Casale flights.
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From Chicago (CHI) to Brindisi Papola Casale
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Find flight deals from Chicago to Brindisi

Cheapest flights from Chicago to Brindisi
Explore the most affordable flight options available from Chicago to Brindisi. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 19, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:00 pm
ORD
-
BDS
1 stop17h 45m
Multiple Airlines
Sun 4/269:25 pm
BDS
-
ORD
2 stops27h 50m
Multiple Airlines
Deal found 1/18$732
This Cheapflightsfares deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:05 pm
ORD
-
BDS
1 stop17h 00m
SWISS
Sun 4/267:55 pm
BDS
-
ORD
1 stop23h 40m
SWISS
Deal found 1/18$741
This oojo deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:25 am
ORD
-
BDS
2 stops28h 35m
Multiple Airlines
Sat 5/211:15 am
BDS
-
ORD
2 stops29h 25m
Multiple Airlines
Deal found 1/18$768
This Cheapflightsfares deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:05 pm
ORD
-
BDS
1 stop11h 55m
SWISS
Sat 5/29:45 am
BDS
-
ORD
1 stop13h 10m
SWISS
Deal found 1/18$782
This Cheapflightsfares deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:30 pm
ORD
-
BDS
2 stops28h 45m
Lufthansa
Sat 5/210:55 am
BDS
-
ORD
1 stop14h 20m
Lufthansa
Deal found 1/18$823
This Trip.com deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:40 pm
ORD
-
BDS
2 stops18h 20m
Multiple Airlines
Tue 6/96:20 am
BDS
-
ORD
2 stops20h 35m
Multiple Airlines
Deal found 1/18$869
This TAP AIR PORTUGAL deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/238:15 pm
ORD
-
BDS
2 stops19h 45m
TAP AIR PORTUGAL
Tue 1/273:20 pm
BDS
-
ORD
2 stops30h 40m
TAP AIR PORTUGAL
Deal found 1/18$890
This Turkish Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2311:50 am
ORD
-
BDS
2 stops28h 10m
Turkish Airlines
Tue 1/276:10 am
BDS
-
ORD
2 stops34h 55m
Turkish Airlines
Deal found 1/17$1,024
This Expedia deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:25 pm
ORD
-
BDS
2 stops20h 35m
Multiple Airlines
Sun 6/146:20 am
BDS
-
ORD
2 stops22h 05m
Multiple Airlines
Deal found 1/17$1,100

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Brindisi that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 19, 2026.
Use the filters below to find and compare flights from Chicago to Brindisi that are best for you.

Fly from

Chicago

Fly to

Brindisi

Route

Depart

Return

Price

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 4/19

9:00 pm-9:45 pm

1 stop17h 45m

Brindisi Papola Casale

Sun 4/26

9:25 pm-6:15 pm

2 stops27h 50m

$732

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 4/19

7:05 pm-7:05 pm

1 stop17h 00m

Brindisi Papola Casale

Sun 4/26

7:55 pm-12:35 pm

1 stop23h 40m

$741

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

11:25 am-11:00 pm

2 stops28h 35m

Brindisi Papola Casale

Sat 5/2

11:15 am-9:40 am

2 stops29h 25m

$768

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

7:05 pm-2:00 pm

1 stop11h 55m

Brindisi Papola Casale

Sat 5/2

9:45 am-3:55 pm

1 stop13h 10m

$782

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

10:30 pm-10:15 am

2 stops28h 45m

Brindisi Papola Casale

Sat 5/2

10:55 am-6:15 pm

1 stop14h 20m

$823

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Tue 5/26

9:40 pm-11:00 pm

2 stops18h 20m

Brindisi Papola Casale

Tue 6/9

6:20 am-7:55 pm

2 stops20h 35m

$869

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Tue 6/9

7:25 pm-11:00 pm

2 stops20h 35m

Brindisi Papola Casale

Sun 6/14

6:20 am-9:25 pm

2 stops22h 05m

$1,100

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 6/12

3:00 pm-10:30 am

1 stop12h 30m

Brindisi Papola Casale

Fri 6/26

6:20 am-1:10 pm

1 stop13h 50m

$1,152

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 6/12

7:25 pm-10:30 am

2 stops32h 05m

Brindisi Papola Casale

Fri 6/26

11:15 am-9:25 pm

2 stops17h 10m

$1,173

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 6/19

8:10 pm-2:30 pm

2 stops35h 20m

Brindisi Papola Casale

Sat 6/27

6:20 am-10:05 pm

2 stops22h 45m

$1,180

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

  • Most accurate provider: When it comes to deals on Chicago-Brindisi flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Brindisi flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Brindisi flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Brindisi flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Brindisi flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Brindisi

Have a flexible travel schedule? Discover the best time to fly to Brindisi from Chicago with our price prediction graph.
Estimated round-trip 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Brindisi

What is the cheapest month to book a flight from Chicago to Brindisi?

Currently, March is the cheapest month in which you can book a flight from Chicago to Brindisi (average of $609). Flying from Chicago to Brindisi in May is currently the most expensive (average of $1,222). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Brindisi

Get insights into the airlines that provide service to Brindisi. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Brindisi. Reviews last updated January 19, 2026.
Read reviews from past customers who have flown SWISS and ITA Airways from Chicago to Brindisi. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.5
Good
1,854 reviews

Entertainment

6.8

Boarding

7.7

Overall

7.5

Comfort

7.4

Crew

8.3

Food

7.1

Reviews

1 / 20
10.0
Excellent

Henriette,Dec 2025

ZRH - JNB

The flight was good but again my luggage was delayed. The 2nd time now. I know it us at the airlines fault but maybe there have to be more control on which luggage on on which plane. Especially if a flight has been delayed.
SWISS
7.5
Good
1,854 reviews
SWISS
7.5
Good
1,854 reviews

Entertainment

6.8

Boarding

7.7

Overall

7.5

Comfort

7.4

Crew

8.3

Food

7.1

Reviews

1 / 20
10.0
Excellent

Henriette,Dec 2025

ZRH - JNB

The flight was good but again my luggage was delayed. The 2nd time now. I know it us at the airlines fault but maybe there have to be more control on which luggage on on which plane. Especially if a flight has been delayed.
ITA Airways
6.7
Okay
1,129 reviews
SWISS
7.5
Good
1,854 reviews

Entertainment

6.8

Boarding

7.7

Overall

7.5

Comfort

7.4

Crew

8.3

Food

7.1

Reviews

1 / 20
10.0
Excellent

Henriette,Dec 2025

ZRH - JNB

The flight was good but again my luggage was delayed. The 2nd time now. I know it us at the airlines fault but maybe there have to be more control on which luggage on on which plane. Especially if a flight has been delayed.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Brindisi. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Brindisi from Chicago?

    Brindisi Papola Casale (BDS) is the airport you will fly into if you book a flight from Chicago to Brindisi. You should not have trouble finding flights to Papola Casale from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Brindisi airport from Chicago. It is only a 1.9 mi journey from Papola Casale (BDS) to Brindisi’s city center.

  • How long is the flight from Chicago to Brindisi?

    SWISS can get you from Chicago to Brindisi in just under 17h. Your travel time can differ by up to . The distance between Chicago and Brindisi is about 5084 mi.

  • What are the cheapest airlines flying from Chicago to Brindisi round-trip?

    ITA Airways, at $726, was found to be the cheapest airline from Chicago to Brindisi. An alternate airline flying to your destination would be SWISS.

  • Can I find deals for flights from Chicago to Brindisi that include hotel bookings?

    Yes. In addition to deals on Chicago to Brindisi flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Brindisi?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Brindisi.

  • Can I find deals for business class flights from Chicago to Brindisi?

    Yes. Cheapflights offers flight deals from Chicago to Brindisi by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Brindisi?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Brindisi (average of $609). Flying from Chicago to Brindisi in May is currently the most expensive (average of $1,222). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Brindisi?

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Gallipoli

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Alternative routes for Chicago to Brindisi

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Bari flights
Midway to Bari flights
O'Hare Intl to Brindisi flights

Top 2 airlines flying from Chicago to Brindisi

Discover the top 2 airlines that operate flights from Chicago to Brindisi. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$726Average$993FlexibilityNo cancel feeOn-time81%
SWISSCheapest$985Average$1,480FlexibilityNo cancel feeOn-time79%

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