$313+ Cheap flights from Chicago (CHI) to Azores
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
Mar 11 — Mar 181
1 adult, Economy
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Find cheap flights from Chicago to Azores 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
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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 Azores
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Cheapest flights from Chicago to AzoresExplore the most affordable flight options available from Chicago to Azores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
Explore the most affordable flight options available from Chicago to Azores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
This oojo deal was found by Cheapflights users on 2/7. 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 11/47:00 pm
ORD
- PDL
1 stop23h 45m
TAP AIR PORTUGAL
Wed 11/116:35 am
PDL
- ORD
1 stop13h 25m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$575
This Gotogate deal was found by Cheapflights users on 2/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:10 pm
ORD
- PDL
1 stop32h 00m
TAP AIR PORTUGAL
Thu 3/127:25 pm
PDL
- ORD
1 stop25h 00m
TAP AIR PORTUGAL
Deal found 2/5![TAP AIR PORTUGAL logo]()
$580
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:51 pm
ORD
- PDL
2 stops18h 44m
Multiple Airlines
Tue 3/106:30 am
PDL
- ORD
2 stops22h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$611
This oojo deal was found by Cheapflights users on 2/7. 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.
Fri 10/166:00 pm
ORD
- PDL
1 stop16h 00m
TAP AIR PORTUGAL
Sun 11/16:30 am
PDL
- ORD
1 stop13h 30m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$615
This FlightHub deal was found by Cheapflights users on 2/7. 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.
Sun 3/89:25 pm
ORD
- PDL
1 stop30h 50m
TAP AIR PORTUGAL
Sun 3/156:30 am
PDL
- ORD
1 stop13h 15m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$665
This oojo deal was found by Cheapflights users on 2/8. 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.
Sun 5/106:00 pm
ORD
- PDL
1 stop24h 45m
TAP AIR PORTUGAL
Sat 5/166:30 am
PDL
- ORD
1 stop14h 45m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$670
This FlightHub deal was found by Cheapflights users on 2/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 pm
ORD
- PDL
1 stop15h 20m
TAP AIR PORTUGAL
Fri 5/156:30 am
PDL
- ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 2/6![TAP AIR PORTUGAL logo]()
$680
This oojo deal was found by Cheapflights users on 2/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 pm
ORD
- PDL
1 stop15h 20m
TAP AIR PORTUGAL
Sat 5/166:30 am
PDL
- ORD
1 stop14h 45m
TAP AIR PORTUGAL
Deal found 2/6![TAP AIR PORTUGAL logo]()
$691
This BusinessClass deal was found by Cheapflights users on 2/9. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/117:10 pm
ORD
- PDL
1 stop18h 25m
TAP AIR PORTUGAL
Tue 2/177:25 pm
PDL
- ORD
1 stop24h 35m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$695
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/117:10 pm
ORD
- PDL
1 stop18h 25m
TAP AIR PORTUGAL
Fri 2/206:30 am
PDL
- ORD
1 stop13h 55m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$701
This oojo deal was found by Cheapflights users on 2/7. 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.
Mon 3/910:00 am
ORD
- TER
1 stop16h 15m
Multiple Airlines
Mon 3/161:50 pm
TER
- ORD
2 stops24h 20m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$798
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:25 am
MDW
- PDL
3 stops32h 20m
Multiple Airlines
Sun 5/316:30 am
PDL
- MDW
3 stops32h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$799
Best flights from Chicago to AzoresDiscover carefully curated flight deals from Chicago to Azores that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
Discover carefully curated flight deals from Chicago to Azores that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
This oojo deal was found by Cheapflights users on 2/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 pm
ORD
- PDL
1 stop15h 20m
TAP AIR PORTUGAL
Sat 5/166:30 am
PDL
- ORD
1 stop14h 45m
TAP AIR PORTUGAL
Deal found 2/6![TAP AIR PORTUGAL logo]()
$691
This Mytrip deal was found by Cheapflights users on 2/8. 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 4/199:50 am
ORD
- PDL
2 stops32h 55m
Multiple Airlines
Sun 4/263:25 pm
PDL
- ORD
2 stops33h 00m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$782
This United Airlines deal was found by Cheapflights users on 2/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:00 am
ORD
- PDL
2 stops17h 40m
United Airlines
Mon 5/1811:00 am
PDL
- ORD
2 stops13h 22m
United Airlines
Deal found 2/6![United Airlines logo]()
$822
This Air Canada deal was found by Cheapflights users on 2/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:58 pm
ORD
- PDL
2 stops31h 22m
Air Canada
Fri 8/289:35 am
PDL
- ORD
2 stops27h 15m
Air Canada
Deal found 2/7![Air Canada logo]()
$827
This oojo deal was found by Cheapflights users on 2/7. 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.
Mon 3/910:00 am
ORD
- TER
1 stop16h 15m
Multiple Airlines
Mon 3/161:50 pm
TER
- ORD
2 stops24h 20m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$798
This oojo deal was found by Cheapflights users on 2/8. 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.
Sun 7/266:00 pm
ORD
- PDL
1 stop24h 45m
TAP AIR PORTUGAL
Sun 8/26:30 am
PDL
- ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$803
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:25 am
MDW
- PDL
3 stops32h 20m
Multiple Airlines
Sun 5/316:30 am
PDL
- MDW
3 stops32h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$799
This FlightHub deal was found by Cheapflights users on 2/8. 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.
Sun 4/196:00 pm
ORD
- PDL
1 stop16h 00m
TAP AIR PORTUGAL
Sun 4/267:40 pm
PDL
- ORD
2 stops41h 01m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$820
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Thu 7/237:45 pm
ORD
- PDL
1 stop18h 05m
TAP AIR PORTUGAL
Sun 8/26:30 am
PDL
- ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$822
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 4/157:30 am
MDW
- PDL
2 stops21h 15m
Multiple Airlines
Sun 4/195:30 pm
PDL
- MDW
1 stop24h 30m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$866
This Cheapflightsfares deal was found by Cheapflights users on 2/7. 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.
Sat 8/16:15 pm
ORD
- PDL
1 stop19h 35m
TAP AIR PORTUGAL
Sat 8/86:30 am
PDL
- ORD
1 stop14h 45m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$822
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Thu 5/2810:25 am
MDW
- PDL
1 stop15h 15m
Multiple Airlines
Tue 6/27:40 pm
PDL
- MDW
2 stops43h 00m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$883
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Sat 8/16:15 pm
ORD
- PDL
1 stop19h 35m
TAP AIR PORTUGAL
Sun 8/96:30 am
PDL
- ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$822
This oojo deal was found by Cheapflights users on 2/8. 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 7/237:45 pm
ORD
- PDL
1 stop18h 05m
TAP AIR PORTUGAL
Sat 8/17:35 pm
PDL
- ORD
1 stop25h 25m
TAP AIR PORTUGAL
Deal found 2/8![TAP AIR PORTUGAL logo]()
$823
This FlightHub deal was found by Cheapflights users on 2/7. 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.
Sat 7/186:15 pm
ORD
- PDL
1 stop34h 30m
TAP AIR PORTUGAL
Sun 7/266:30 am
PDL
- ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$827
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Thu 5/1410:25 am
MDW
- PDL
1 stop15h 15m
Multiple Airlines
Tue 5/197:40 pm
PDL
- MDW
2 stops43h 00m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$1,029
This FlightHub deal was found by Cheapflights users on 2/7. 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 4/156:00 pm
ORD
- PDL
1 stop19h 50m
TAP AIR PORTUGAL
Sun 4/193:25 pm
PDL
- ORD
2 stops45h 16m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$828
This Mytrip deal was found by Cheapflights users on 2/8. 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 5/1010:25 am
MDW
- PDL
3 stops23h 35m
Multiple Airlines
Sat 5/169:50 pm
PDL
- MDW
3 stops24h 00m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$1,037
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Sun 8/210:25 am
MDW
- PDL
1 stop17h 15m
Multiple Airlines
Sat 8/810:00 am
PDL
- MDW
2 stops13h 31m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$1,061
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Sun 7/2610:25 am
MDW
- PDL
1 stop17h 15m
Multiple Airlines
Sat 8/810:00 am
PDL
- MDW
2 stops13h 31m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$1,061
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Sun 7/2610:25 am
MDW
- PDL
1 stop17h 15m
Multiple Airlines
Mon 8/310:00 am
PDL
- MDW
2 stops13h 31m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$1,064
This FlightHub deal was found by Cheapflights users on 2/7. 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.
Mon 3/91:09 pm
ORD
- TER
2 stops41h 51m
TAP AIR PORTUGAL
Mon 3/1612:35 pm
TER
- ORD
2 stops38h 39m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$1,104
This Mytrip deal was found by Cheapflights users on 2/8. 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 3/2510:00 am
ORD
- TER
2 stops33h 15m
Multiple Airlines
Wed 4/111:10 am
TER
- ORD
3 stops25h 50m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$1,074
This Mytrip deal was found by Cheapflights users on 2/7. 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 6/198:45 am
ORD
- HOR
3 stops29h 45m
Multiple Airlines
Fri 6/2610:25 am
HOR
- ORD
2 stops28h 51m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$1,304
This TAP AIR PORTUGAL deal was found by Cheapflights users on 2/5. 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.
Sun 4/266:00 pm
ORD
- HOR
1 stop17h 55m
TAP AIR PORTUGAL
Thu 4/3010:25 am
HOR
- ORD
1 stop34h 35m
TAP AIR PORTUGAL
Deal found 2/5![TAP AIR PORTUGAL logo]()
$1,479
Last-minute flights from Chicago to AzoresDiscover last-minute flight deals from Chicago to Azores. Data last updated February 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Azores. Data last updated February 9, 2026 and is based on user searches.
This BusinessClass deal was found by Cheapflights users on 2/9. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/117:10 pm
ORD
- PDL
1 stop18h 25m
TAP AIR PORTUGAL
Tue 2/177:25 pm
PDL
- ORD
1 stop24h 35m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$695
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/117:10 pm
ORD
- PDL
1 stop18h 25m
TAP AIR PORTUGAL
Fri 2/206:30 am
PDL
- ORD
1 stop13h 55m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$701
This TAP AIR PORTUGAL deal was found by Cheapflights users on 2/9. 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 2/117:10 pm
ORD
- PDL
1 stop18h 25m
TAP AIR PORTUGAL
Thu 2/197:25 pm
PDL
- ORD
1 stop25h 00m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$733
This Mytrip deal was found by Cheapflights users on 2/7. 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 2/1610:00 am
ORD
- PDL
3 stops25h 30m
Multiple Airlines
Mon 2/238:00 pm
PDL
- ORD
2 stops22h 10m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$721
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:51 pm
ORD
- PDL
2 stops18h 44m
Multiple Airlines
Tue 3/106:30 am
PDL
- ORD
2 stops22h 10m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$611
This Gotogate deal was found by Cheapflights users on 2/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:10 pm
ORD
- PDL
1 stop32h 00m
TAP AIR PORTUGAL
Thu 3/127:25 pm
PDL
- ORD
1 stop25h 00m
TAP AIR PORTUGAL
Deal found 2/5![TAP AIR PORTUGAL logo]()
$580
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:25 pm
ORD
- PDL
1 stop30h 50m
TAP AIR PORTUGAL
Sun 3/156:30 am
PDL
- ORD
1 stop13h 15m
TAP AIR PORTUGAL
Deal found 2/6![TAP AIR PORTUGAL logo]()
$665
This oojo deal was found by Cheapflights users on 2/7. 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.
Mon 3/910:00 am
ORD
- TER
1 stop16h 15m
Multiple Airlines
Mon 3/161:50 pm
TER
- ORD
2 stops24h 20m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$798
This FlightHub deal was found by Cheapflights users on 2/7. 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.
Mon 3/91:09 pm
ORD
- TER
2 stops41h 51m
TAP AIR PORTUGAL
Mon 3/1612:35 pm
TER
- ORD
2 stops38h 39m
TAP AIR PORTUGAL
Deal found 2/7![TAP AIR PORTUGAL logo]()
$1,104
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:01 pm
ORD
- PDL
2 stops25h 44m
Multiple Airlines
Mon 3/237:25 pm
PDL
- ORD
2 stops32h 57m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$735
This Mytrip deal was found by Cheapflights users on 2/8. 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 3/2510:00 am
ORD
- TER
2 stops33h 15m
Multiple Airlines
Wed 4/111:10 am
TER
- ORD
3 stops25h 50m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$1,074
This oojo deal was found by Cheapflights users on 2/8. 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.
Mon 3/306:20 pm
ORD
- PDL
1 stop31h 00m
Multiple Airlines
Mon 4/66:05 pm
PDL
- ORD
1 stop20h 05m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$736
One-way flights from Chicago to AzoresSearch for one-way flight options from Chicago to Azores. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
Search for one-way flight options from Chicago to Azores. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 4/156:31 am
ORD
- PDL
2 stops31h 19m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Tue 4/79:06 am
ORD
- PDL
3 stops24h 34m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 4/157:30 am
MDW
- PDL
2 stops35h 15m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 3/156:10 pm
ORD
- PDL
3 stops44h 25m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$372
This Mytrip deal was found by Cheapflights users on 2/8. 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 6/129:55 am
ORD
- PDL
1 stop18h 40m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 3/157:30 am
MDW
- PDL
2 stops31h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Tue 4/74:15 pm
MDW
- PDL
3 stops45h 35m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$409
This SmartFares deal was found by Cheapflights users on 2/9. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:25 pm
ORD
- PDL
1 stop17h 10m
TAP AIR PORTUGAL
Deal found 2/9![TAP AIR PORTUGAL logo]()
$442
This KAYAK deal was found by Cheapflights users on 2/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/147:35 pm
ORD
- PDL
2 stops32h 30m
WestJet
Deal found 2/8![WestJet logo]()
$467
This oojo deal was found by Cheapflights users on 2/8. 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 5/198:31 am
ORD
- PDL
2 stops16h 49m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 8/29:30 am
MDW
- PDL
2 stops17h 40m
WestJet
Deal found 2/9![WestJet logo]()
$535
Find flight deals from Chicago to Azores
Keep the following information in mind while searching for Chicago to Azores flight deals. Data was last updated February 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $575 (oojo) |
One-way from | $313 (Kiwi.com) |
Popular in | May |
Cheapest in | January |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Azores 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 February 9, 2026.
Use the filters below to find and compare flights from Chicago to Azores that are best for you.
Fly from
Chicago
Fly to
Azores
Route
Depart
Return
Price
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sat 5/9
6:15 pm-2:35 pm
1 stop15h 20m
Ponta Delgada Nordela
Sat 5/16
6:30 am-4:15 pm
1 stop14h 45m
$691
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sun 4/19
9:50 am-11:45 pm
2 stops32h 55m
Ponta Delgada Nordela
Sun 4/26
3:25 pm-7:25 pm
2 stops33h 00m
$782
ChicagoLajes
ORD - TER
ORDTER
Chicago O'Hare Intl
Mon 3/9
10:00 am-6:15 am
1 stop16h 15m
Lajes
Mon 3/16
1:50 pm-10:10 am
2 stops24h 20m
$798
ChicagoPonta Delgada
MDW - PDL
MDWPDL
Chicago Midway
Sun 5/24
10:25 am-11:45 pm
3 stops32h 20m
Ponta Delgada Nordela
Sun 5/31
6:30 am-9:40 am
3 stops32h 10m
$799
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sun 7/26
6:00 pm-11:45 pm
1 stop24h 45m
Ponta Delgada Nordela
Sun 8/2
6:30 am-4:00 pm
1 stop14h 30m
$803
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sun 4/19
6:00 pm-3:00 pm
1 stop16h 00m
Ponta Delgada Nordela
Sun 4/26
7:40 pm-7:41 am
2 stops41h 01m
$820
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sun 5/10
10:00 am-8:40 am
2 stops17h 40m
Ponta Delgada Nordela
Mon 5/18
11:00 am-7:22 pm
2 stops13h 22m
$822
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Thu 7/23
7:45 pm-6:50 pm
1 stop18h 05m
Ponta Delgada Nordela
Sun 8/2
6:30 am-4:00 pm
1 stop14h 30m
$822
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sat 8/1
6:15 pm-6:50 pm
1 stop19h 35m
Ponta Delgada Nordela
Sat 8/8
6:30 am-4:15 pm
1 stop14h 45m
$822
ChicagoPonta Delgada
ORD - PDL
ORDPDL
Chicago O'Hare Intl
Sat 8/1
6:15 pm-6:50 pm
1 stop19h 35m
Ponta Delgada Nordela
Sun 8/9
6:30 am-4:00 pm
1 stop14h 30m
$822
Showing 1-10 of 36 results
Best time to book a flight from Chicago to Azores
Have a flexible travel schedule? Discover the best time to fly to Azores from Chicago with our price prediction graph.
ORD-PDL
ORD-TER
MDW-PDL
ORD-HOR
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 Azores
CHI-PTAC
ORD-PDL
ORD-TER
MDW-PDL
ORD-HOR
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Azores
Get insights into the airlines that provide service to Azores. 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 Azores. Reviews last updated February 9, 2026.
Read reviews from past customers who have flown United Airlines and TAP AIR PORTUGAL from Chicago to Azores. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Chicago to Azores. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Azores
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Complete your trip
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Chicago and Azores flights
Browse other Chicago and Azores flight options. Last updated on February 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Azores
Discover the top 2 airlines that operate flights from Chicago to Azores. 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 February 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$550 | Average$921 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$716 | Average$1,201 | FlexibilityNo cancel fee | On-time69% |