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$251+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$637
(FlightHub)

One-way from

$251
(Kiwi.com)
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 August 20, 2025.

This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:10 pmORD - BDS
2 stops36h 20mMultiple Airlines
Tue 11/189:20 amBDS - ORD
2 stops36h 40mMultiple Airlines
Deal found 8/20$637
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:30 pmORD - BDS
2 stops20h 20mMultiple Airlines
Fri 11/710:20 pmBDS - ORD
2 stops26h 00mMultiple Airlines
Deal found 8/20$660
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:15 pmORD - BDS
2 stops43h 45mMultiple Airlines
Fri 12/53:20 pmBDS - ORD
2 stops54h 40mMultiple Airlines
Deal found 8/20$669
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:30 pmORD - BDS
2 stops19h 45mMultiple Airlines
Sun 11/96:10 amBDS - ORD
2 stops18h 10mMultiple Airlines
Deal found 8/20$703
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Mon 10/1311:25 amORD - BDS
2 stops19h 30mMultiple Airlines
Mon 10/206:20 amBDS - ORD
2 stops22h 40mMultiple Airlines
Deal found 8/18$741
This Gotogate deal was found by Cheapflights users on 8/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:50 pmORD - BDS
1 stop12h 15mSWISS
Fri 11/78:00 pmBDS - ORD
1 stop27h 20mSWISS
Deal found 8/20$751
This oojo deal was found by Cheapflights users on 8/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:50 amORD - BDS
2 stops19h 40mMultiple Airlines
Sat 11/83:20 pmBDS - ORD
2 stops25h 45mMultiple Airlines
Deal found 8/20$768
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 10/37:50 pmORD - BDS
2 stops19h 55mMultiple Airlines
Fri 10/1010:40 amBDS - ORD
2 stops30h 00mMultiple Airlines
Deal found 8/19$776
This lol.travel deal was found by Cheapflights users on 8/18. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:05 pmORD - BDS
1 stop11h 55mSWISS
Mon 10/207:55 pmBDS - ORD
1 stop27h 00mSWISS
Deal found 8/18$778
This oojo deal was found by Cheapflights users on 8/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:45 pmORD - BDS
2 stops27h 40mMultiple Airlines
Thu 10/23:15 pmBDS - ORD
2 stops25h 25mMultiple Airlines
Deal found 8/20$816

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 August 20, 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

Wed 11/5

7:10 pm-2:30 pm

2 stops36h 20m

Brindisi Papola Casale

Tue 11/18

9:20 am-3:00 pm

2 stops36h 40m

$637

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 10/31

7:30 pm-9:50 pm

2 stops20h 20m

Brindisi Papola Casale

Fri 11/7

10:20 pm-5:20 pm

2 stops26h 00m

$660

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 11/28

8:15 pm-11:00 pm

2 stops43h 45m

Brindisi Papola Casale

Fri 12/5

3:20 pm-3:00 pm

2 stops54h 40m

$669

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Tue 11/4

6:30 pm-9:15 pm

2 stops19h 45m

Brindisi Papola Casale

Sun 11/9

6:10 am-5:20 pm

2 stops18h 10m

$703

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 10/13

11:25 am-1:55 pm

2 stops19h 30m

Brindisi Papola Casale

Mon 10/20

6:20 am-10:00 pm

2 stops22h 40m

$741

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 10/31

7:50 pm-2:05 pm

1 stop12h 15m

Brindisi Papola Casale

Fri 11/7

8:00 pm-4:20 pm

1 stop27h 20m

$751

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Wed 11/5

11:50 am-2:30 pm

2 stops19h 40m

Brindisi Papola Casale

Sat 11/8

3:20 pm-10:05 am

2 stops25h 45m

$768

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 10/3

7:50 pm-10:45 pm

2 stops19h 55m

Brindisi Papola Casale

Fri 10/10

10:40 am-9:40 am

2 stops30h 00m

$776

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 10/13

7:05 pm-2:00 pm

1 stop11h 55m

Brindisi Papola Casale

Mon 10/20

7:55 pm-3:55 pm

1 stop27h 00m

$778

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 9/27

7:50 pm-11:00 pm

2 stops20h 10m

Brindisi Papola Casale

Thu 10/2

3:15 pm-9:40 am

2 stops25h 25m

$816

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 17 results
1
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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 time of day to fly from CHI to BDS?

Find hourly flight availability from Chicago to Brindisi. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

It’s typically best to fly out from Chicago to Brindisi in the afternoon. Doing so could potentially save you 30% on the flight price compared to flying at noon, which is usually more expensive.

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 August 20, 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
7.6
Good
1,699 reviews

Overall

7.6

Comfort

7.4

Entertainment

6.8

Crew

8.3

Food

7.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Yvette,Nov 2024

BOS - ZRH

Food was not very good and the options were poor. The seat wasn't very comfortable. I would not choose to fly on this airline again. Their website was also difficult to navigate.
SWISS
7.6
Good
1,699 reviews
SWISS
7.6
Good
1,699 reviews

Overall

7.6

Comfort

7.4

Entertainment

6.8

Crew

8.3

Food

7.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Yvette,Nov 2024

BOS - ZRH

Food was not very good and the options were poor. The seat wasn't very comfortable. I would not choose to fly on this airline again. Their website was also difficult to navigate.
ITA Airways
6.7
Okay
1,021 reviews
SWISS
7.6
Good
1,699 reviews

Overall

7.6

Comfort

7.4

Entertainment

6.8

Crew

8.3

Food

7.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Yvette,Nov 2024

BOS - ZRH

Food was not very good and the options were poor. The seat wasn't very comfortable. I would not choose to fly on this airline again. Their website was also difficult to navigate.

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.

  • What is the cheapest airline to fly from Chicago to Brindisi round-trip?

    SWISS, at $1,008, was found to be the cheapest airline from Chicago to Brindisi..

  • 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
O'Hare Intl to Brindisi flights
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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$1,008Average$1,574FlexibilityNo cancel feeOn-time79%

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