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Guadeloupe

$324+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PTP
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Chicago to Guadeloupe

Cheapest flights from Chicago to Guadeloupe
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 February 20, 2026.

This Priceline deal was found by Cheapflights users on 2/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:50 pm
ORD
-
PTP
1 stop23h 30m
Air Canada
Thu 3/192:20 pm
PTP
-
ORD
1 stop21h 50m
Air Canada
Deal found 2/18$621
This Air Canada deal was found by Cheapflights users on 2/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:45 am
ORD
-
PTP
1 stop27h 55m
Air Canada
Fri 5/222:40 pm
PTP
-
ORD
2 stops25h 15m
Air Canada
Deal found 2/18$673
This Booking.com deal was found by Cheapflights users on 2/17. 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.
Sat 5/99:55 am
ORD
-
PTP
2 stops26h 45m
Air Canada
Fri 5/222:40 pm
PTP
-
ORD
1 stop20h 38m
Air Canada
Deal found 2/17$676
This Air Canada deal was found by Cheapflights users on 2/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:20 pm
ORD
-
PTP
2 stops40h 20m
Air Canada
Fri 5/222:40 pm
PTP
-
ORD
1 stop30h 28m
Air Canada
Deal found 2/18$698
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:00 am
ORD
-
PTP
1 stop7h 46m
American Airlines
Wed 3/252:36 pm
PTP
-
ORD
1 stop9h 41m
American Airlines
Deal found 2/16$717
This Mytrip deal was found by Cheapflights users on 2/17. 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 3/1911:00 am
MDW
-
PTP
3 stops25h 20m
Multiple Airlines
Thu 3/262:20 pm
PTP
-
MDW
3 stops28h 34m
Multiple Airlines
Deal found 2/17$1,298
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:07 pm
MDW
-
PTP
2 stops17h 58m
Delta
Thu 3/264:35 pm
PTP
-
MDW
2 stops20h 54m
Delta
Deal found 2/17$1,398
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/164:30 pm
MDW
-
PTP
2 stops19h 40m
Delta
Sat 5/234:35 pm
PTP
-
MDW
2 stops23h 51m
Delta
Deal found 2/18$1,402
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:07 pm
MDW
-
PTP
2 stops18h 03m
Delta
Thu 4/94:35 pm
PTP
-
MDW
2 stops25h 47m
Delta
Deal found 2/16$2,050

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 February 20, 2026.

Round-trip from

$621
(Priceline)

One-way from

$324
(Booking.com)
From Chicago (CHI) to Guadeloupe
Search Deals
One-way flight from Chicago (CHI) to Guadeloupe
Search Deals

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 February 20, 2026.
Use the filters below to find and compare flights from Chicago to Guadeloupe that are best for you.

Fly from

Chicago

Fly to

Guadeloupe

Route

Depart

Return

Price

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Thu 3/12

12:50 pm-1:20 pm

1 stop23h 30m

Pointe-à-Pitre Le Raizet

Thu 3/19

2:20 pm-11:10 am

1 stop21h 50m

$621

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Sat 5/16

8:45 am-1:40 pm

1 stop27h 55m

Pointe-à-Pitre Le Raizet

Fri 5/22

2:40 pm-2:55 pm

2 stops25h 15m

$673

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Sat 5/9

9:55 am-1:40 pm

2 stops26h 45m

Pointe-à-Pitre Le Raizet

Fri 5/22

2:40 pm-10:18 am

1 stop20h 38m

$676

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Fri 5/15

8:20 pm-1:40 pm

2 stops40h 20m

Pointe-à-Pitre Le Raizet

Fri 5/22

2:40 pm-8:08 pm

1 stop30h 28m

$698

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Mon 5/18

5:35 pm-1:40 pm

2 stops43h 05m

Pointe-à-Pitre Le Raizet

Fri 5/22

2:40 pm-10:18 am

1 stop20h 38m

$698

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Thu 3/19

11:00 am-1:20 pm

3 stops25h 20m

Pointe-à-Pitre Le Raizet

Thu 3/26

2:20 pm-5:54 pm

3 stops28h 34m

$1,298

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Thu 3/19

6:07 pm-1:05 pm

2 stops17h 58m

Pointe-à-Pitre Le Raizet

Thu 3/26

4:35 pm-12:29 pm

2 stops20h 54m

$1,398

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Sat 5/16

4:30 pm-1:10 pm

2 stops19h 40m

Pointe-à-Pitre Le Raizet

Sat 5/23

4:35 pm-3:26 pm

2 stops23h 51m

$1,402

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Thu 4/2

6:07 pm-1:10 pm

2 stops18h 03m

Pointe-à-Pitre Le Raizet

Thu 4/9

4:35 pm-5:22 pm

2 stops25h 47m

$2,050

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Fri 4/24

4:15 pm-1:10 pm

2 stops43h 55m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 21 results
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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.
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
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 Guadeloupe. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Guadeloupe?

    There are many flights that can get you from Chicago to Guadeloupe in 17h 58m. Fly via Air Canada or Delta to get the fastest option. Airlines will cover a distance of 2349 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Chicago to Guadeloupe that include hotel bookings?

    Yes. In addition to deals on Chicago to Guadeloupe flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Guadeloupe?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Guadeloupe.

  • Can I find deals for business class flights from Chicago to Guadeloupe?

    Yes. Cheapflights offers flight deals from Chicago to Guadeloupe 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 Guadeloupe

See prices for flight routes from nearby airports that may be better suited for you.
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