$253+ Cheap flights from Chicago (CHI) to Guadeloupe
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PTP
Jun 20 — Jun 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Guadeloupe 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 Guadeloupe
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to GuadeloupeExplore the most affordable flight options available from Chicago to Guadeloupe. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
Explore the most affordable flight options available from Chicago to Guadeloupe. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.
This Travelocity deal was found by Cheapflights users on 5/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/172:00 pm
ORD
- PTP
2 stops46h 15m
Air Canada
Wed 6/242:10 pm
PTP
- ORD
2 stops27h 47m
Air Canada
Deal found 5/19![Air Canada logo]()
$604
This Expedia deal was found by Cheapflights users on 5/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:20 pm
ORD
- PTP
2 stops39h 45m
Air Canada
Sun 6/142:05 pm
PTP
- ORD
1 stop25h 45m
Air Canada
Deal found 5/16![Air Canada logo]()
$605
This Air Canada deal was found by Cheapflights users on 5/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:55 pm
ORD
- PTP
1 stop22h 15m
Air Canada
Sun 12/63:05 pm
PTP
- ORD
1 stop22h 05m
Air Canada
Deal found 5/19![Air Canada logo]()
$691
This Air Canada deal was found by Cheapflights users on 5/16. 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.
Sat 8/811:05 am
ORD
- PTP
1 stop25h 10m
Air Canada
Fri 8/142:10 pm
PTP
- ORD
1 stop21h 06m
Air Canada
Deal found 5/16![Air Canada logo]()
$692
This Air Canada deal was found by Cheapflights users on 5/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:55 pm
ORD
- PTP
1 stop20h 15m
Air Canada
Sun 12/133:05 pm
PTP
- ORD
2 stops19h 55m
Air Canada
Deal found 5/20![Air Canada logo]()
$699
This Mytrip deal was found by Cheapflights users on 5/21. 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 6/1810:25 am
MDW
- PTP
3 stops25h 50m
Multiple Airlines
Thu 6/2510:45 am
PTP
- MDW
3 stops23h 55m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$1,073
This Mytrip deal was found by Cheapflights users on 5/16. 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 8/810:20 am
MDW
- PTP
3 stops25h 55m
Multiple Airlines
Fri 8/142:10 pm
PTP
- MDW
2 stops20h 07m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$1,074
Best flights from Chicago to GuadeloupeDiscover carefully curated flight deals from Chicago to Guadeloupe that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
Discover carefully curated flight deals from Chicago to Guadeloupe that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 21, 2026.
This Travelocity deal was found by Cheapflights users on 5/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/172:00 pm
ORD
- PTP
2 stops46h 15m
Air Canada
Wed 6/242:10 pm
PTP
- ORD
2 stops27h 47m
Air Canada
Deal found 5/19![Air Canada logo]()
$604
This Mytrip deal was found by Cheapflights users on 5/16. 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 6/152:00 pm
ORD
- PTP
2 stops46h 05m
Multiple Airlines
Mon 6/227:15 am
PTP
- ORD
3 stops38h 01m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$905
This FlightHub deal was found by Cheapflights users on 5/16. 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 6/86:22 pm
ORD
- PTP
2 stops41h 43m
Air Canada
Sun 6/142:05 pm
PTP
- ORD
2 stops31h 11m
Air Canada
Deal found 5/16![Air Canada logo]()
$607
This Mytrip deal was found by Cheapflights users on 5/16. 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 6/152:00 pm
ORD
- PTP
2 stops46h 05m
Air Canada
Sun 6/212:10 pm
PTP
- ORD
2 stops29h 42m
Air Canada
Deal found 5/16![Air Canada logo]()
$607
This Mytrip deal was found by Cheapflights users on 5/16. 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 6/85:30 pm
ORD
- PTP
3 stops42h 35m
Multiple Airlines
Sun 6/142:05 pm
PTP
- ORD
2 stops24h 05m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$960
This Mytrip deal was found by Cheapflights users on 5/16. 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 8/87:25 am
ORD
- PTP
3 stops28h 50m
Air Canada
Fri 8/142:10 pm
PTP
- ORD
2 stops24h 00m
Air Canada
Deal found 5/16![Air Canada logo]()
$825
This Mytrip deal was found by Cheapflights users on 5/18. 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.
Sun 8/98:45 am
ORD
- PTP
3 stops35h 30m
Multiple Airlines
Sun 8/162:10 pm
PTP
- ORD
2 stops31h 06m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$1,008
This Mytrip deal was found by Cheapflights users on 5/21. 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 6/1810:25 am
MDW
- PTP
3 stops25h 50m
Multiple Airlines
Thu 6/2510:45 am
PTP
- MDW
3 stops23h 55m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$1,073
This Mytrip deal was found by Cheapflights users on 5/16. 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 8/810:20 am
MDW
- PTP
3 stops25h 55m
Multiple Airlines
Fri 8/142:10 pm
PTP
- MDW
2 stops20h 07m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$1,074
Last-minute flights from Chicago to GuadeloupeDiscover last-minute flight deals from Chicago to Guadeloupe. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Guadeloupe. Data last updated May 21, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 5/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:20 pm
ORD
- PTP
2 stops39h 45m
Air Canada
Sun 6/142:05 pm
PTP
- ORD
1 stop25h 45m
Air Canada
Deal found 5/16![Air Canada logo]()
$605
This Mytrip deal was found by Cheapflights users on 5/16. 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 6/85:30 pm
ORD
- PTP
3 stops42h 35m
Multiple Airlines
Sun 6/142:05 pm
PTP
- ORD
2 stops24h 05m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$960
This Gotogate deal was found by Cheapflights users on 5/16. 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.
Mon 6/156:22 pm
ORD
- PTP
2 stops41h 43m
Air Canada
Sun 6/212:10 pm
PTP
- ORD
1 stop21h 06m
Air Canada
Deal found 5/16![Air Canada logo]()
$749
This Mytrip deal was found by Cheapflights users on 5/16. 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 6/152:00 pm
ORD
- PTP
2 stops46h 05m
Multiple Airlines
Mon 6/227:15 am
PTP
- ORD
3 stops38h 01m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$905
This Travelocity deal was found by Cheapflights users on 5/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/172:00 pm
ORD
- PTP
2 stops46h 15m
Air Canada
Wed 6/242:10 pm
PTP
- ORD
2 stops27h 47m
Air Canada
Deal found 5/19![Air Canada logo]()
$604
This Mytrip deal was found by Cheapflights users on 5/19. 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.
Wed 6/174:37 pm
ORD
- PTP
3 stops21h 23m
Multiple Airlines
Wed 6/242:10 pm
PTP
- ORD
3 stops25h 45m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$1,211
This Mytrip deal was found by Cheapflights users on 5/21. 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 6/1810:25 am
MDW
- PTP
3 stops25h 50m
Multiple Airlines
Thu 6/2510:45 am
PTP
- MDW
3 stops23h 55m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$1,073
One-way flights from Chicago to GuadeloupeSearch for one-way flight options from Chicago to Guadeloupe. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
Search for one-way flight options from Chicago to Guadeloupe. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This FlightHub deal was found by Cheapflights users on 5/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2611:05 am
ORD
- PTP
1 stop25h 00m
Air Canada
Deal found 5/18![Air Canada logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/263:20 pm
MDW
- PTP
3 stops23h 00m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$707
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:33 am
ORD
- PTP
3 stops37h 47m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$831
Find flight deals from Chicago to Guadeloupe
Keep the following information in mind while searching for Chicago to Guadeloupe flight deals. Data was last updated May 21, 2026.
Round-trip from | $604 (Travelocity) |
|---|---|
One-way from | $253 (FlightHub) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Guadeloupe 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 21, 2026.
Use the filters below to find and compare flights from Chicago to Guadeloupe that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Wed 6/17
2:00 pm-1:15 pm
2 stops46h 15m
Pointe-à-Pitre Le Raizet
Wed 6/24
2:10 pm-4:57 pm
2 stops27h 47m
$604
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Mon 6/8
6:22 pm-1:05 pm
2 stops41h 43m
Pointe-à-Pitre Le Raizet
Sun 6/14
2:05 pm-8:16 pm
2 stops31h 11m
$607
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Mon 6/15
2:00 pm-1:05 pm
2 stops46h 05m
Pointe-à-Pitre Le Raizet
Sun 6/21
2:10 pm-6:52 pm
2 stops29h 42m
$607
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Sat 8/8
7:25 am-1:15 pm
3 stops28h 50m
Pointe-à-Pitre Le Raizet
Fri 8/14
2:10 pm-1:10 pm
2 stops24h 00m
$825
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Mon 6/15
2:00 pm-1:05 pm
2 stops46h 05m
Pointe-à-Pitre Le Raizet
Mon 6/22
7:15 am-8:16 pm
3 stops38h 01m
$905
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Mon 6/8
5:30 pm-1:05 pm
3 stops42h 35m
Pointe-à-Pitre Le Raizet
Sun 6/14
2:05 pm-1:10 pm
2 stops24h 05m
$960
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Sun 8/9
8:45 am-9:15 pm
3 stops35h 30m
Pointe-à-Pitre Le Raizet
Sun 8/16
2:10 pm-8:16 pm
2 stops31h 06m
$1,008
ChicagoPointe-à-Pitre
MDW - PTP
MDWPTP
Chicago Midway
Thu 6/18
10:25 am-1:15 pm
3 stops25h 50m
Pointe-à-Pitre Le Raizet
Thu 6/25
10:45 am-9:40 am
3 stops23h 55m
$1,073
Quickest round-trip
ChicagoPointe-à-Pitre
MDW - PTP
MDWPTP
Chicago Midway
Sat 8/8
10:20 am-1:15 pm
3 stops25h 55m
Pointe-à-Pitre Le Raizet
Fri 8/14
2:10 pm-9:17 am
2 stops20h 07m
$1,074
Cheapest one-way
Quickest one-way
ChicagoPointe-à-Pitre
ORD - PTP
ORDPTP
Chicago O'Hare Intl
Tue 5/26
6:22 pm-1:05 pm
2 stops17h 43m
$253
Showing 1-10 of 12 resultsSorted by cheapest first
Best time to book a flight from Chicago to Guadeloupe
Have a flexible travel schedule? Discover the best time to fly to Guadeloupe from Chicago with our price prediction graph.
ORD-PTP
MDW-PTP
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 Guadeloupe
CHI-GP0
ORD-PTP
MDW-PTP
No data available for this route at this time. Please check back soon.
Related info for your journey
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