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$346+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 27, 2026.

This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 pm
ORD
-
BDS
2 stops20h 45m
Multiple Airlines
Wed 9/1610:10 am
BDS
-
ORD
2 stops33h 30m
Multiple Airlines
Deal found 7/26$761
This lol.travel deal was found by Cheapflights users on 7/22. 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.
Sun 8/163:00 pm
ORD
-
BDS
1 stop16h 30m
ITA Airways
Sat 8/227:10 pm
BDS
-
ORD
1 stop25h 00m
ITA Airways
Deal found 7/22$765
This Mytrip deal was found by Cheapflights users on 7/24. 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.
Tue 9/811:25 am
ORD
-
BDS
2 stops28h 35m
Multiple Airlines
Tue 9/157:45 am
BDS
-
ORD
2 stops32h 55m
Multiple Airlines
Deal found 7/24$781
This ITA Airways deal was found by Cheapflights users on 7/24. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/273:00 pm
ORD
-
BDS
1 stop16h 30m
ITA Airways
Mon 8/247:10 pm
BDS
-
ORD
1 stop25h 00m
ITA Airways
Deal found 7/24$787

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 27, 2026.

Round-trip from

$761
(Trip.com)

One-way from

$330
(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 27, 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

Tue 9/8

3:00 pm-2:30 pm

1 stop16h 30m

Brindisi Papola Casale

Tue 9/15

6:20 am-1:10 pm

1 stop13h 50m

$967

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 8/16

7:05 pm-7:05 pm

1 stop17h 00m

Brindisi Papola Casale

Sun 8/23

2:50 pm-3:55 pm

1 stop32h 05m

$1,046

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sun 8/16

7:25 pm-7:35 pm

2 stops17h 10m

Brindisi Papola Casale

Sat 8/22

4:55 pm-9:20 pm

3 stops35h 25m

$1,103

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Mon 8/24

5:00 pm-5:50 pm

1 stop17h 50m

Brindisi Papola Casale

Thu 8/27

8:35 pm-1:50 pm

1 stop24h 15m

$1,193

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

Sun 8/16

6:00 pm-7:35 pm

2 stops18h 35m

Brindisi Papola Casale

Sun 8/23

4:55 pm-9:25 pm

3 stops35h 30m

$1,257
Cheapest one-way

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Fri 8/14

7:25 pm-6:45 pm

2 stops16h 20m

$436

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Sat 8/1

6:05 pm-7:00 am

2 stops29h 55m

$482

ChicagoBrindisi

ORD - BDS

ORDBDS

Chicago O'Hare Intl

Wed 8/12

9:40 pm-5:00 pm

1 stop12h 20m

$534

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 17 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.

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 July 27, 2026.
Read reviews from past customers who have flown SWISS 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
2,018 reviews

Boarding

7.7

Crew

8.3

Comfort

7.4

Food

7.1

Entertainment

6.8

Overall

7.5

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2026

LAX - ZRH

I want the first option as an entree no more I ordered the Meat it was horrible. The aspect and the taste. First time on Swiss airlines ‘s Business class was surprise on the mediocre of the food. The seats are not as comfortable as in Emirates Brrtish airlines and Iberia airlines The service was ok not great The vanity xase is a joke Only socks, toothpaste and toothbrush. I just choose Swiss air because it was a direct flight. Next time I will rather have a flight nonstop that flying again with this company. I am a frequent flyer traveling 4 or 5 times a intraoceanic flight.but I do not think to flight for the moment again with Swiss. Great disappointment
SWISS
7.5
Good
2,018 reviews
SWISS
7.5
Good
2,018 reviews

Boarding

7.7

Crew

8.3

Comfort

7.4

Food

7.1

Entertainment

6.8

Overall

7.5

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2026

LAX - ZRH

I want the first option as an entree no more I ordered the Meat it was horrible. The aspect and the taste. First time on Swiss airlines ‘s Business class was surprise on the mediocre of the food. The seats are not as comfortable as in Emirates Brrtish airlines and Iberia airlines The service was ok not great The vanity xase is a joke Only socks, toothpaste and toothbrush. I just choose Swiss air because it was a direct flight. Next time I will rather have a flight nonstop that flying again with this company. I am a frequent flyer traveling 4 or 5 times a intraoceanic flight.but I do not think to flight for the moment again with Swiss. Great disappointment

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 and SWISS can get you from Chicago to Brindisi in just under 17h. Your travel time can differ by up to 20h 30m. 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.

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

    ITA Airways, at $608, 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

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Alternative routes for Chicago to Brindisi

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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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$608Average$993FlexibilityNo cancel feeOn-time81%

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