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$352+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap 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 March 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Mon 8/37:05 pm
ORD
-
BDS
1 stop30h 40m
SWISS
Wed 8/262:50 pm
BDS
-
ORD
1 stop32h 05m
SWISS
Deal found 3/25$773
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Mon 8/37:05 pm
ORD
-
BDS
1 stop30h 40m
SWISS
Thu 8/2712:15 pm
BDS
-
ORD
1 stop31h 20m
SWISS
Deal found 3/25$778
This TAP AIR PORTUGAL deal was found by Cheapflights users on 3/26. 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.
Sun 11/88:15 pm
ORD
-
BDS
2 stops19h 45m
TAP AIR PORTUGAL
Thu 11/126:20 am
BDS
-
ORD
2 stops40h 10m
TAP AIR PORTUGAL
Deal found 3/26$805
This FlightHub deal was found by Cheapflights users on 3/24. 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.
Sun 9/208:10 pm
ORD
-
BDS
2 stops19h 50m
Multiple Airlines
Sun 9/276:20 am
BDS
-
ORD
2 stops42h 55m
Multiple Airlines
Deal found 3/24$833
This Mytrip deal was found by Cheapflights users on 3/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:10 pm
ORD
-
BDS
2 stops35h 20m
Turkish Airlines
Sun 9/276:20 am
BDS
-
ORD
2 stops42h 55m
Turkish Airlines
Deal found 3/24$837
This oojo deal was found by Cheapflights users on 3/27. 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.
Mon 8/33:00 pm
ORD
-
BDS
2 stops34h 05m
ITA Airways
Wed 8/266:20 am
BDS
-
ORD
1 stop13h 50m
ITA Airways
Deal found 3/27$862
This KLM deal was found by Cheapflights users on 3/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:30 am
ORD
-
BDS
2 stops20h 00m
KLM
Wed 8/266:20 am
BDS
-
ORD
2 stops24h 37m
KLM
Deal found 3/27$885
This Gotogate deal was found by Cheapflights users on 3/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:10 pm
ORD
-
BDS
2 stops39h 15m
Turkish Airlines
Sun 9/276:20 am
BDS
-
ORD
2 stops42h 55m
Turkish Airlines
Deal found 3/26$910
This Gotogate deal was found by Cheapflights users on 3/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:25 am
ORD
-
BDS
2 stops20h 05m
Multiple Airlines
Sun 9/276:20 am
BDS
-
ORD
2 stops42h 55m
Multiple Airlines
Deal found 3/26$919
This Booking.com deal was found by Cheapflights users on 3/27. 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.
Tue 9/111:25 am
ORD
-
BDS
2 stops24h 00m
Multiple Airlines
Wed 9/163:15 pm
BDS
-
ORD
2 stops25h 25m
Multiple Airlines
Deal found 3/27$954
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Sat 5/910:30 pm
ORD
-
BDS
2 stops40h 00m
Multiple Airlines
Sat 5/169:25 pm
BDS
-
ORD
1 stop23h 35m
Multiple Airlines
Deal found 3/25$994

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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$773
(Kiwi.com)

One-way from

$352
(Kiwi.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
One-way flight 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 March 28, 2026.
Use the filters below to find and compare flights from Chicago to Brindisi that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 8/3

3:00 pm-8:05 am

2 stops34h 05m

Brindisi Papola Casale

Thu 8/27

6:20 am-1:10 pm

1 stop13h 50m

$862
Quickest round-trip

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 8/3

11:30 am-2:30 pm

2 stops20h 00m

Brindisi Papola Casale

Wed 8/26

6:20 am-11:57 pm

2 stops24h 37m

$885

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 5/9

10:30 pm-9:30 pm

2 stops40h 00m

Brindisi Papola Casale

Sat 5/16

9:25 pm-2:00 pm

1 stop23h 35m

$994

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 4/10

7:25 pm-7:35 am

3 stops29h 10m

Brindisi Papola Casale

Sun 4/19

12:00 pm-5:35 am

3 stops24h 35m

$1,035

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/2

11:25 am-11:00 pm

2 stops52h 35m

Brindisi Papola Casale

Wed 10/28

3:20 pm-7:25 pm

2 stops34h 05m

$1,038

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 9/20

6:00 pm-2:30 pm

2 stops37h 30m

Brindisi Papola Casale

Sun 9/27

6:20 am-8:56 am

3 stops33h 36m

$1,213

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 9/19

6:05 pm-2:30 pm

2 stops37h 25m

Brindisi Papola Casale

Sun 9/27

6:20 am-8:56 am

3 stops33h 36m

$1,293

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 6/4

11:25 am-6:25 pm

2 stops48h 00m

Brindisi Papola Casale

Sun 6/14

6:20 am-9:40 am

2 stops34h 20m

$1,297
Cheapest one-way

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 9/20

4:55 pm-12:35 am

1 stop24h 40m

$394

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 9/17

9:00 pm-7:35 am

2 stops27h 35m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 11 resultsSorted by cheapest first
1
2
  • 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, February is the cheapest month in which you can book a flight from Chicago to Brindisi (average of $529). Flying from Chicago to Brindisi in June is currently the most expensive (average of $1,116). 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.

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?

    ITA Airways can get you from Chicago to Brindisi in just under 34h 05m. 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 $608, 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, February is the cheapest month in which you can book a flight from Chicago to Brindisi (average of $529). Flying from Chicago to Brindisi in June is currently the most expensive (average of $1,116). 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?

Book flights to Brindisi if you plan to visit one of these locations
Gallipoli

Browse thousands of different options on Cheapflights for your next trip

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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

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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$608Average$993FlexibilityNo cancel feeOn-time81%
SWISSCheapest$877Average$1,054FlexibilityNo cancel feeOn-time79%

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