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$406+ 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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
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 May 29, 2026.

This oojo deal was found by Cheapflights users on 5/27. 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.
Sat 8/153:00 pm
ORD
-
BDS
1 stop20h 25m
ITA Airways
Thu 8/206:20 am
BDS
-
ORD
1 stop13h 50m
ITA Airways
Deal found 5/27$886
This Mytrip deal was found by Cheapflights users on 5/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:25 pm
ORD
-
BDS
2 stops15h 55m
Multiple Airlines
Thu 8/2010:35 pm
BDS
-
ORD
2 stops28h 17m
Multiple Airlines
Deal found 5/27$935
This Orbitz deal was found by Cheapflights users on 5/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 pm
ORD
-
BDS
2 stops46h 00m
TAP AIR PORTUGAL
Sat 9/194:55 pm
BDS
-
ORD
2 stops30h 05m
TAP AIR PORTUGAL
Deal found 5/28$970
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:25 pm
ORD
-
BDS
2 stops18h 35m
Multiple Airlines
Mon 9/146:00 pm
BDS
-
ORD
1 stop27h 25m
Multiple Airlines
Deal found 5/26$983
This Justfly.com deal was found by Cheapflights users on 5/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 pm
ORD
-
BDS
2 stops21h 55m
TAP AIR PORTUGAL
Thu 8/204:55 pm
BDS
-
ORD
2 stops30h 05m
TAP AIR PORTUGAL
Deal found 5/27$999
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:55 pm
ORD
-
BDS
1 stop22h 00m
Multiple Airlines
Tue 9/159:30 am
BDS
-
ORD
2 stops39h 20m
Multiple Airlines
Deal found 5/26$1,005
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Fri 9/119:00 pm
ORD
-
BDS
1 stop18h 00m
Multiple Airlines
Sat 9/1911:15 pm
BDS
-
ORD
2 stops25h 35m
Multiple Airlines
Deal found 5/28$1,021
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:25 pm
ORD
-
BDS
2 stops18h 35m
Multiple Airlines
Thu 9/1010:35 pm
BDS
-
ORD
1 stop22h 25m
Multiple Airlines
Deal found 5/26$1,040
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:25 pm
ORD
-
BDS
2 stops20h 45m
Multiple Airlines
Wed 7/227:30 am
BDS
-
ORD
2 stops20h 55m
Multiple Airlines
Deal found 5/26$1,059
This Mytrip deal was found by Cheapflights users on 5/28. 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.
Thu 9/37:25 pm
ORD
-
BDS
2 stops17h 35m
Multiple Airlines
Wed 9/167:30 am
BDS
-
ORD
2 stops20h 55m
Multiple Airlines
Deal found 5/28$1,061

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 May 29, 2026.

Round-trip from

$886
(oojo)

One-way from

$406
(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 May 29, 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

Fri 9/4

6:00 pm-11:00 pm

2 stops22h 00m

Brindisi Papola Casale

Mon 9/14

4:55 pm-4:00 pm

2 stops54h 05m

$1,097

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 8/15

7:25 pm-11:00 pm

3 stops20h 35m

Brindisi Papola Casale

Thu 8/20

7:30 am-10:05 pm

3 stops45h 35m

$1,129

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 7/26

3:00 pm-8:05 am

2 stops34h 05m

Brindisi Papola Casale

Sun 8/9

6:20 am-1:10 pm

1 stop13h 50m

$1,158

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Wed 7/1

3:00 pm-10:30 am

1 stop12h 30m

Brindisi Papola Casale

Tue 9/15

6:20 am-1:10 pm

1 stop13h 50m

$1,171
Quickest round-trip

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 9/11

2:20 pm-8:45 am

1 stop11h 25m

Brindisi Papola Casale

Sun 9/20

9:35 am-3:55 pm

1 stop13h 20m

$1,192

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/2

2:07 pm-2:30 pm

2 stops17h 23m

Brindisi Papola Casale

Sun 8/9

3:15 pm-4:24 pm

2 stops32h 09m

$1,233

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-3:55 pm

1 stop27h 00m

$1,233

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Thu 9/3

3:00 pm-8:05 am

2 stops34h 05m

Brindisi Papola Casale

Wed 9/16

7:10 pm-1:10 pm

1 stop25h 00m

$1,238

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 7/4

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

Sat 8/15

7:10 pm-1:10 pm

1 stop25h 00m

$1,399
Cheapest one-way

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 7/26

7:25 pm-6:00 pm

3 stops39h 35m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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?

    TAP AIR PORTUGAL, ITA Airways, and KLM can get you from Chicago to Brindisi in just under 17h 23m. Your travel time can differ by up to 16h 42m. 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?

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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

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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$608Average$993FlexibilityNo cancel feeOn-time81%

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