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$648+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
janv. 22 — janv. 291
jeu. 1/22
jeu. 1/29
1 adult, Economy
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Cheap flight deals from Chicago to Brindisi

Best flights from Chicago to Brindisi
Discover carefully curated flight deals from Chicago to Brindisi that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated décembre 23, 2025.

This Booking.com deal was found by Cheapflights users on 12/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/67:20 pmORD - BDS
3 stops19h 50mMultiple Airlines
dim. 2/1512:25 pmBDS - ORD
2 stops35h 20mMultiple Airlines
Deal found 12/22$648
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
ven. 2/69:05 pmORD - BDS
2 stops34h 35mSWISS
dim. 2/153:30 pmBDS - ORD
1 stop31h 50mSWISS
Deal found 12/22$706
This Turkish Airlines deal was found by Cheapflights users on 12/20. 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.
mer. 2/48:20 pmORD - BDS
2 stops59h 15mTurkish Airlines
dim. 2/86:10 amBDS - ORD
2 stops34h 55mTurkish Airlines
Deal found 12/20$995
This oojo deal was found by Cheapflights users on 12/21. 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.
dim. 6/73:00 pmORD - BDS
1 stop25h 00mITA Airways
mar. 6/163:15 pmBDS - ORD
1 stop28h 55mITA Airways
Deal found 12/21$1,079
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 6/76:00 pmORD - BDS
2 stops22h 00mMultiple Airlines
mar. 6/163:15 pmBDS - ORD
2 stops31h 45mMultiple Airlines
Deal found 12/21$979
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/313:00 pmORD - BDS
1 stop16h 30mITA Airways
mer. 6/106:20 amBDS - ORD
1 stop13h 50mITA Airways
Deal found 12/21$1,080
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
dim. 5/313:45 pmORD - BDS
1 stop23h 00mMultiple Airlines
mer. 6/107:30 amBDS - ORD
2 stops18h 30mMultiple Airlines
Deal found 12/21$1,060
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 5/313:00 pmORD - BDS
1 stop16h 30mITA Airways
mar. 6/96:20 amBDS - ORD
2 stops17h 42mITA Airways
Deal found 12/21$1,085

Find 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 décembre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$648
(Booking.com)
Provider with most accurate pricing for Chicago (CHI)-Brindisi Papola Casale flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Brindisi Papola Casale flights.
Search Deals
From Chicago (CHI) to Brindisi Papola Casale
Search Deals

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 décembre 23, 2025.
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

ven. 2/6

7:20 pm-10:10 pm

3 stops19h 50m

Brindisi Papola Casale

dim. 2/15

12:25 pm-4:45 pm

2 stops35h 20m

$648

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

ven. 2/6

9:05 pm-2:40 pm

2 stops34h 35m

Brindisi Papola Casale

dim. 2/15

3:30 pm-4:20 pm

1 stop31h 50m

$706

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

dim. 6/7

6:00 pm-11:00 pm

2 stops22h 00m

Brindisi Papola Casale

mar. 6/16

3:15 pm-4:00 pm

2 stops31h 45m

$979

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

mer. 2/4

8:20 pm-2:35 pm

2 stops59h 15m

Brindisi Papola Casale

dim. 2/8

6:10 am-10:05 am

2 stops34h 55m

$995

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

dim. 5/31

3:45 pm-9:45 pm

1 stop23h 00m

Brindisi Papola Casale

mer. 6/10

7:30 am-7:00 pm

2 stops18h 30m

$1,060

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

dim. 6/7

3:00 pm-11:00 pm

1 stop25h 00m

Brindisi Papola Casale

mar. 6/16

3:15 pm-1:10 pm

1 stop28h 55m

$1,079

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

dim. 5/31

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

mer. 6/10

6:20 am-1:10 pm

1 stop13h 50m

$1,080

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

dim. 5/31

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

mar. 6/9

6:20 am-5:02 pm

2 stops17h 42m

$1,085

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

  • 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 $585). 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 décembre 23, 2025.
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
1,817 reviews

Crew

8.3

Entertainment

6.8

Food

7.1

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
SWISS
7.5
Good
1,817 reviews
SWISS
7.5
Good
1,817 reviews

Crew

8.3

Entertainment

6.8

Food

7.1

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.
ITA Airways
6.7
Okay
1,112 reviews
SWISS
7.5
Good
1,817 reviews

Crew

8.3

Entertainment

6.8

Food

7.1

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Katerina,Sep 2025

GVA - ATH

Although the plane was half empty and the flight was late at night, we were not allowed to change seats/ use empty seats to get ourselves more comfortable, or get some proper sleep. It is really frustrating to see lack of flexibility in such a simple need.

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 34h 35m. 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 $585). 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
O'Hare Intl to Brindisi flights
Midway to Bari 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 décembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$726Average$993FlexibilityNo cancel feeOn-time81%
SWISSCheapest$1,008Average$1,575FlexibilityNo cancel feeOn-time79%

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