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Guadeloupe

$320+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PTP
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
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Cheap flight deals from Chicago to Guadeloupe

Keep the following information in mind while searching for Chicago to Guadeloupe flight deals. Data was last updated August 28, 2025.

Round-trip from

$685
(Booking.com)

One-way from

$320
(American Airlines)
From Chicago (CHI) to Guadeloupe
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One-way flight from Chicago (CHI) to Guadeloupe
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Find 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 August 28, 2025.

This Booking.com deal was found by Cheapflights users on 8/28. 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.
Wed 12/38:15 pmORD - PTP
2 stops39h 55mAir Canada
Mon 12/83:10 pmPTP - ORD
2 stops23h 51mAir Canada
Deal found 8/28$685
This Priceline deal was found by Cheapflights users on 8/28. 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 12/412:50 pmORD - PTP
1 stop23h 20mAir Canada
Mon 12/83:10 pmPTP - ORD
2 stops30h 20mAir Canada
Deal found 8/28$711
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 12/298:45 pmORD - PTP
2 stops40h 26mAmerican Airlines
Sat 1/34:11 pmPTP - ORD
1 stop18h 36mAmerican Airlines
Deal found 8/27$1,312
This Air Canada deal was found by Cheapflights users on 8/27. 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 12/288:15 pmORD - PTP
2 stops15h 55mAir Canada
Thu 1/13:10 pmPTP - ORD
2 stops18h 55mAir Canada
Deal found 8/27$1,697
This Priceline deal was found by Cheapflights users on 8/27. 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.
Sun 12/281:13 pmORD - PTP
2 stops22h 57mAir Canada
Fri 1/23:10 pmPTP - ORD
2 stops23h 51mAir Canada
Deal found 8/27$1,763
This Trip.com deal was found by Cheapflights users on 8/27. 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 12/284:15 pmMDW - PTP
2 stops42h 35mAir Transat
Fri 1/22:00 pmPTP - MDW
2 stops23h 50mAir Transat
Deal found 8/27$2,297

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 August 28, 2025.
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

Wed 12/3

8:15 pm-2:10 pm

2 stops39h 55m

Pointe-à-Pitre Le Raizet

Mon 12/8

3:10 pm-1:01 pm

2 stops23h 51m

$685

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Thu 12/4

12:50 pm-2:10 pm

1 stop23h 20m

Pointe-à-Pitre Le Raizet

Mon 12/8

3:10 pm-7:30 pm

2 stops30h 20m

$711

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Tue 2/17

7:15 am-2:10 pm

1 stop28h 55m

Pointe-à-Pitre Le Raizet

Thu 2/19

3:10 pm-7:30 pm

2 stops30h 20m

$952

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Sun 12/28

4:15 pm-12:50 pm

2 stops42h 35m

Pointe-à-Pitre Le Raizet

Fri 1/2

2:00 pm-11:50 am

2 stops23h 50m

$2,297

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Wed 12/17

7:00 am-4:39 pm

1 stop7h 39m

$320

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Tue 12/23

8:50 pm-3:11 pm

2 stops16h 21m

$326

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Wed 12/17

10:18 am-5:00 pm

3 stops28h 42m

$552

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Fri 12/26

8:35 pm-3:11 pm

1 stop16h 36m

$595

ChicagoPointe-à-Pitre

MDW - PTP

MDWPTP

Chicago Midway

Sat 12/27

12:45 pm-12:50 pm

2 stops22h 05m

$653

ChicagoPointe-à-Pitre

ORD - PTP

ORDPTP

Chicago O'Hare Intl

Thu 12/25

7:05 pm-3:00 pm

3 stops41h 55m

$700

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/27

Showing 1-10 of 20 results
1
2

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.

Reviews of airlines servicing Guadeloupe

Get insights into the airlines that provide service to Guadeloupe. 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 Guadeloupe. Reviews last updated August 28, 2025.
Get a feel of what it's like to fly with American Airlines from Chicago to Guadeloupe by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Food

6.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Food

6.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 39h 55m. Fly via Air Canada or Air Transat to get the fastest option. Airlines will cover a distance of 2364 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.

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