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$449+ Cheap flights from Chicago (CHI) to Brindisi (BDS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$799
(oojo)

One-way from

$449
(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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One-way flight 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 8, 2026.

This oojo deal was found by Cheapflights users on 1/8. 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.
Sun 2/228:20 pmORD - BDS
2 stops19h 40mMultiple Airlines
Sun 3/13:20 pmBDS - ORD
2 stops49h 45mMultiple Airlines
Deal found 1/8$799
This oojo deal was found by Cheapflights users on 1/6. 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 amORD - BDS
2 stops20h 05mMultiple Airlines
Sun 5/33:15 pmBDS - ORD
2 stops25h 25mMultiple Airlines
Deal found 1/6$830
This oojo deal was found by Cheapflights users on 1/6. 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 amORD - BDS
2 stops28h 35mMultiple Airlines
Sat 5/211:15 amBDS - ORD
2 stops29h 25mMultiple Airlines
Deal found 1/6$832
This FlightHub deal was found by Cheapflights users on 1/6. 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.
Thu 4/237:05 pmORD - BDS
1 stop17h 00mSWISS
Sat 5/22:50 pmBDS - ORD
1 stop28h 45mSWISS
Deal found 1/6$844
This KAYAK deal was found by Cheapflights users on 1/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:20 pmORD - BDS
1 stop21h 45mSWISS
Sun 5/311:15 amBDS - ORD
2 stops56h 30mSWISS
Deal found 1/6$845
This FlightHub deal was found by Cheapflights users on 1/6. 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.
Sat 5/306:15 pmORD - BDS
2 stops33h 15mMultiple Airlines
Wed 6/106:20 amBDS - ORD
2 stops40h 00mMultiple Airlines
Deal found 1/6$942

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 8, 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 2/22

8:20 pm-11:00 pm

2 stops19h 40m

Brindisi Papola Casale

Sun 3/1

3:20 pm-10:05 am

2 stops49h 45m

$799

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

11:25 am-2:30 pm

2 stops20h 05m

Brindisi Papola Casale

Sun 5/3

3:15 pm-9:40 am

2 stops25h 25m

$830

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

$832

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

2:20 pm-7:05 pm

1 stop21h 45m

Brindisi Papola Casale

Sun 5/3

11:15 am-12:45 pm

2 stops56h 30m

$845

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 4/23

2:20 pm-12:00 pm

1 stop14h 40m

Brindisi Papola Casale

Sat 5/2

8:20 pm-12:45 pm

1 stop23h 25m

$847

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 5/30

6:15 pm-10:30 am

2 stops33h 15m

Brindisi Papola Casale

Wed 6/10

6:20 am-3:20 pm

2 stops40h 00m

$942

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 1/23

8:15 pm-11:00 pm

2 stops43h 45m

Brindisi Papola Casale

Tue 1/27

6:10 am-3:00 pm

2 stops39h 50m

$958

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 6/6

7:25 pm-7:40 am

3 stops29h 15m

$449

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 6/7

9:00 pm-9:45 pm

1 stop17h 45m

$451

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 6/6

3:00 pm-10:30 am

1 stop12h 30m

$807

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

  • 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 $590). 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 8, 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
1,840 reviews

Entertainment

6.8

Boarding

7.7

Food

7.1

Overall

7.5

Comfort

7.4

Crew

8.3

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
1,840 reviews
SWISS
7.5
Good
1,840 reviews

Entertainment

6.8

Boarding

7.7

Food

7.1

Overall

7.5

Comfort

7.4

Crew

8.3

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
1,126 reviews
SWISS
7.5
Good
1,840 reviews

Entertainment

6.8

Boarding

7.7

Food

7.1

Overall

7.5

Comfort

7.4

Crew

8.3

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 21h 45m. 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 $590). 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 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$726Average$993FlexibilityNo cancel feeOn-time81%
SWISSCheapest$1,008Average$1,575FlexibilityNo cancel feeOn-time79%

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