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$835+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
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 July 20, 2026.

This oojo deal was found by Cheapflights users on 7/16. 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.
Wed 9/303:00 pm
ORD
-
BDS
1 stop16h 30m
ITA Airways
Fri 10/166:20 am
BDS
-
ORD
1 stop13h 50m
ITA Airways
Deal found 7/16$835
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/234:55 pm
ORD
-
BDS
1 stop22h 00m
Multiple Airlines
Thu 10/112:35 pm
BDS
-
ORD
2 stops39h 50m
Multiple Airlines
Deal found 7/17$839
This Mytrip deal was found by Cheapflights users on 7/16. 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.
Wed 9/308:45 am
ORD
-
BDS
3 stops30h 25m
Multiple Airlines
Fri 10/1610:00 pm
BDS
-
ORD
2 stops25h 10m
Multiple Airlines
Deal found 7/16$852
This Gotogate deal was found by Cheapflights users on 7/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:00 pm
ORD
-
BDS
1 stop25h 00m
ITA Airways
Thu 10/111:15 am
BDS
-
ORD
1 stop32h 55m
ITA Airways
Deal found 7/17$864
This oojo deal was found by Cheapflights users on 7/15. 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 9/33:00 pm
ORD
-
BDS
1 stop20h 25m
ITA Airways
Wed 9/164:55 pm
BDS
-
ORD
1 stop27h 15m
ITA Airways
Deal found 7/15$881
This Mytrip deal was found by Cheapflights users on 7/16. 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 8/307:25 pm
ORD
-
BDS
3 stops29h 40m
Multiple Airlines
Sun 9/611:35 pm
BDS
-
ORD
2 stops21h 25m
Multiple Airlines
Deal found 7/16$889
This Trip.com deal was found by Cheapflights users on 7/16. 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.
Sun 8/303:00 pm
ORD
-
BDS
1 stop25h 00m
ITA Airways
Sun 9/66:20 am
BDS
-
ORD
1 stop13h 50m
ITA Airways
Deal found 7/16$896

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 July 20, 2026.

Round-trip from

$835
(oojo)

One-way from

$441
(Kiwi.com)
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 July 20, 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
Quickest round-trip

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Wed 9/30

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

Fri 10/16

6:20 am-1:10 pm

1 stop13h 50m

$835

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/23

6:00 pm-2:30 pm

2 stops37h 30m

Brindisi Papola Casale

Thu 8/27

4:55 pm-4:00 pm

2 stops30h 05m

$977

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/2

3:00 pm-4:10 pm

1 stop18h 10m

Brindisi Papola Casale

Sun 8/9

6:20 am-1:10 pm

1 stop13h 50m

$1,084

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/23

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

Thu 8/27

6:20 am-1:10 pm

1 stop13h 50m

$1,233

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 9/4

8:10 pm-2:30 pm

2 stops59h 20m

Brindisi Papola Casale

Mon 9/14

3:15 pm-9:40 am

2 stops49h 25m

$1,248

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 9/4

6:45 pm-8:55 am

2 stops31h 10m

Brindisi Papola Casale

Mon 9/14

7:55 pm-12:35 pm

1 stop23h 40m

$1,285

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/2

9:45 pm-5:50 pm

2 stops37h 05m

Brindisi Papola Casale

Sun 8/9

8:35 pm-12:30 pm

1 stop22h 55m

$1,387

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 8/24

5:29 pm-5:50 pm

2 stops17h 21m

Brindisi Papola Casale

Thu 8/27

8:35 pm-6:15 pm

1 stop28h 40m

$1,412

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

Sorted by cheapest first

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

No data available for this route at this time. Please check back soon.

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 1 airline has 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 and TAP AIR PORTUGAL can get you from Chicago to Brindisi in just under 16h 30m. Your travel time can differ by up to 21h. The distance between Chicago and Brindisi is about 5084 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

See more FAQs

Traveling to a place near Brindisi?

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

Top airline flying from Chicago to Brindisi

Discover the top airline 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 July 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$608Average$993FlexibilityNo cancel feeOn-time81%

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