$300+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDS
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Brindisi with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Brindisi
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to BrindisiExplore 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 6, 2026.
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 6, 2026.
This oojo deal was found by Cheapflights users on 7/2. 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.
Tue 8/183:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Tue 8/256:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$708
This ITA Airways deal was found by Cheapflights users on 7/5. 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.
Wed 8/193:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Wed 8/266:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/5![ITA Airways logo]()
$716
This lol.travel deal was found by Cheapflights users on 7/5. 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 8/233:00 pm
ORD
- BDS
1 stop20h 25m
ITA Airways
Sat 8/293:15 pm
BDS
- ORD
1 stop28h 55m
ITA Airways
Deal found 7/5![ITA Airways logo]()
$732
This ITA Airways deal was found by Cheapflights users on 7/2. 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.
Sun 8/163:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Sun 8/236:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$760
Best flights from Chicago to BrindisiDiscover carefully curated flight deals from Chicago to Brindisi that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
Discover carefully curated flight deals from Chicago to Brindisi that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
This ITA Airways deal was found by Cheapflights users on 7/3. 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.
Sun 8/163:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Sun 8/236:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/3![ITA Airways logo]()
$762
This Mytrip deal was found by Cheapflights users on 7/1. 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 stops20h 45m
Multiple Airlines
Sat 8/228:20 am
BDS
- ORD
2 stops20h 05m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$883
This ITA Airways deal was found by Cheapflights users on 7/1. 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.
Sat 8/153:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Sat 8/226:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$803
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/3. 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 7/266:00 pm
ORD
- BDS
2 stops37h 30m
TAP AIR PORTUGAL
Sun 8/911:15 am
BDS
- ORD
3 stops29h 56m
TAP AIR PORTUGAL
Deal found 7/3![TAP AIR PORTUGAL logo]()
$1,983
This ITA Airways deal was found by Cheapflights users on 7/3. 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.
Sun 8/23:00 pm
ORD
- BDS
1 stop12h 30m
ITA Airways
Sun 8/96:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/3![ITA Airways logo]()
$994
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/5. 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.
Wed 8/1911:01 am
ORD
- BDS
3 stops28h 59m
Multiple Airlines
Wed 8/264:55 pm
BDS
- ORD
2 stops26h 45m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$1,227
This ITA Airways deal was found by Cheapflights users on 7/2. 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.
Sun 7/263:00 pm
ORD
- BDS
2 stops34h 05m
ITA Airways
Sun 8/96:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$1,060
This ITA Airways deal was found by Cheapflights users on 7/5. 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.
Sun 10/113:00 pm
ORD
- BDS
1 stop12h 30m
ITA Airways
Thu 10/157:10 pm
BDS
- ORD
1 stop25h 00m
ITA Airways
Deal found 7/5![ITA Airways logo]()
$1,173
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/6. 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 8/26:00 pm
ORD
- BDS
2 stops37h 30m
TAP AIR PORTUGAL
Sun 8/911:15 am
BDS
- ORD
3 stops29h 56m
TAP AIR PORTUGAL
Deal found 7/6![TAP AIR PORTUGAL logo]()
$2,131
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/3. 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 8/26:00 pm
ORD
- BDS
2 stops22h 00m
Multiple Airlines
Sun 8/911:15 am
BDS
- ORD
3 stops28h 37m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$1,983
Last-minute flights from Chicago to BrindisiDiscover last-minute flight deals from Chicago to Brindisi. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Brindisi. Data last updated July 6, 2026 and is based on user searches.
This ITA Airways deal was found by Cheapflights users on 7/2. 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.
Sun 8/163:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Sun 8/236:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$760
This oojo deal was found by Cheapflights users on 7/2. 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.
Tue 8/183:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Tue 8/256:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$708
This ITA Airways deal was found by Cheapflights users on 7/5. 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.
Wed 8/193:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Wed 8/266:20 am
BDS
- ORD
1 stop13h 50m
ITA Airways
Deal found 7/5![ITA Airways logo]()
$716
This lol.travel deal was found by Cheapflights users on 7/5. 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 8/233:00 pm
ORD
- BDS
1 stop20h 25m
ITA Airways
Sat 8/293:15 pm
BDS
- ORD
1 stop28h 55m
ITA Airways
Deal found 7/5![ITA Airways logo]()
$732
One-way flights from Chicago to BrindisiSearch for one-way flight options from Chicago to Brindisi. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
Search for one-way flight options from Chicago to Brindisi. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Mytrip deal was found by Cheapflights users on 7/4. 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 7/207:25 pm
ORD
- BDS
2 stops17h 20m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/247:25 pm
ORD
- BDS
2 stops18h 30m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/257:25 pm
ORD
- BDS
3 stops43h 05m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 12/316:30 pm
ORD
- BDS
3 stops30h 20m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$383
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:00 pm
ORD
- BDS
1 stop18h 00m
Aer Lingus
Deal found 7/6![Aer Lingus logo]()
$528
This Booking.com deal was found by Cheapflights users on 7/4. 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.
Mon 7/203:00 pm
ORD
- BDS
1 stop12h 30m
ITA Airways
Deal found 7/4![ITA Airways logo]()
$535
This Flightnetwork deal was found by Cheapflights users on 7/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:00 pm
ORD
- BDS
1 stop16h 30m
ITA Airways
Deal found 7/4![ITA Airways logo]()
$550
This Flightnetwork deal was found by Cheapflights users on 7/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 pm
ORD
- BDS
2 stops39h 05m
TAP AIR PORTUGAL
Deal found 7/1![TAP AIR PORTUGAL logo]()
$586
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 6, 2026.
Round-trip from | $708 (oojo) |
|---|---|
One-way from | $300 (Mytrip) |
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 6, 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
Cheapest round-trip
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 8/16
3:00 pm-2:30 pm
1 stop16h 30m
Brindisi Papola Casale
Sun 8/23
6:20 am-1:10 pm
1 stop13h 50m
$762
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sat 8/15
3:00 pm-2:30 pm
1 stop16h 30m
Brindisi Papola Casale
Sat 8/22
6:20 am-1:10 pm
1 stop13h 50m
$803
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sat 8/15
7:25 pm-11:10 pm
2 stops20h 45m
Brindisi Papola Casale
Sat 8/22
8:20 am-9:25 pm
2 stops20h 05m
$883
Quickest round-trip
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 8/2
3:00 pm-10:30 am
1 stop12h 30m
Brindisi Papola Casale
Sun 8/9
6:20 am-1:10 pm
1 stop13h 50m
$994
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
$1,060
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 10/11
3:00 pm-10:30 am
1 stop12h 30m
Brindisi Papola Casale
Thu 10/15
7:10 pm-1:10 pm
1 stop25h 00m
$1,173
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Wed 8/19
11:01 am-11:00 pm
3 stops28h 59m
Brindisi Papola Casale
Wed 8/26
4:55 pm-12:40 pm
2 stops26h 45m
$1,227
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 7/26
6:00 pm-2:30 pm
2 stops37h 30m
Brindisi Papola Casale
Sun 8/9
11:15 am-10:11 am
3 stops29h 56m
$1,983
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 8/2
6:00 pm-11:00 pm
2 stops22h 00m
Brindisi Papola Casale
Sun 8/9
11:15 am-8:52 am
3 stops28h 37m
$1,983
ChicagoBrindisi
ORD - BDS
ORDBDS
Chicago O'Hare Intl
Sun 8/2
6:00 pm-2:30 pm
2 stops37h 30m
Brindisi Papola Casale
Sun 8/9
11:15 am-10:11 am
3 stops29h 56m
$2,131
Showing 1-10 of 20 resultsSorted 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.
CHI-BDS
ORD-BDS
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
CHI-BDS
ORD-BDS
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.
Traveling to a place near Brindisi?
Book flights to Brindisi if you plan to visit one of these locationsGallipoli
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Other flights to Brindisi
Explore flights to Brindisi departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 6, 2026.
Complete your trip
Complete your trip to Brindisi by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chicago to Brindisi, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Brindisi flights
Browse other Chicago and Brindisi flight options. Last updated on July 6, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$608 | Average$993 | FlexibilityNo cancel fee | On-time81% |