Chokoloskee Island Holidays

Photo by Noel Benadom

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Top Flight + Hotel Deals in Chokoloskee Island

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Fort Myers Cape Coral

Courtyard by Marriott Fort Myers Cape Coral

3 out of 5
Price was €413, price is now €356 per person
€356
per person
5 Jun - 7 Jun
found 13 hours ago
Return flight included
Chicago (CHI) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
I enjoyed my stay! Everyone was friendly, room was nice and clean. No issues. Enjoyed the small balcony.

Reviewed on 21 Apr 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was €550, price is now €443 per person
€443
per person
5 Jun - 7 Jun
found 13 hours ago
Return flight included
Chicago (CHI) to Fort Myers (RSW)
9.8/10 Exceptional! (1,167 reviews)
It’s an amazingly relaxing stay. Staff was great. Just one rude bartender at the tiki bar, but we only had him once. The girls were very bubbly & helpful with our drinks. It was great having the kitchen. And we utilized the balcony a lot. The Brew House food was excellent. I believe we ate there 3 times. Would definitely recommend.

Reviewed on 22 Apr 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was €671, price is now €576 per person
€576
per person
5 Jun - 7 Jun
found 13 hours ago
Return flight included
Chicago (CHI) to Fort Myers (RSW)
8.6/10 Excellent! (1,001 reviews)
Likes: Pools and the beach across the road. Free coffee at marina. Our room Well, kept grounds and lots of nature Food at the pool bar was really good and very fast. Dislikes: No ice machine told it was broken Broken elevator Book in room has wrong times when places we’re open and closed not accurate No beach service even though the book says there is. Minimal first aid Door on balcony didn’t close all the way. Gap at the top of slider door Bathroom & bedroom doors squeak really bad Everyday Sewer smell on outside balcony in morning Rented cabana for half a day. No real amenities in the cabana such as a small fridge with waters in it. The only amenity was you had a server come to your cabana and ask if you wanted to order drinks or food. We saw them the first 30 minutes and then after that no service at all. The cushions on the chairs in the cabana did not fit the chairs. We went to two different restaurants while we were there and both had the same menu so really it wasn’t like two different restaurants. Just their names were different. The food was not very good at either restaurants. They have a place to order pizza and a few tables outside of it to sit to eat your pizza if you want or take back to your room. Pizza was not that good

Reviewed on 19 Apr 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was €503, price is now €435 per person
€435
per person
5 Jun - 7 Jun
found 13 hours ago
Return flight included
Chicago (CHI) to Fort Myers (RSW)
9.2/10 Wonderful! (2,408 reviews)
It was a great experience. We will definitely be going back again

Reviewed on 23 Apr 2026

Home2 Suites by Hilton Fort Myers Colonial Blvd

Home2 Suites by Hilton Fort Myers Colonial Blvd

3 out of 5
Price was €428, price is now €379 per person
€379
per person
5 Jun - 7 Jun
found 13 hours ago
Return flight included
Chicago (CHI) to Fort Myers (RSW)
9.4/10 Exceptional! (682 reviews)
I’m always happy with Home 2 , very clean rooms and reasonably priced . The pool was huge and clean. I recommend you try it .

Reviewed on 21 Apr 2026

Top hotels in Chokoloskee Island

Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
9.8/10 Exceptional! (63 reviews)
Had a great time in Chokoloskee, exploring the area by boat. We had our own small boat, and we launched it and kept it at the dock while staying at this beautiful home on the water. We had some great fishing, even though unfamiliar with that part of the water in Florida. It does get shallow, so smaller ...

Reviewed on 31 Mar 2026

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Deep Water Access with a Panoramic View of Chokoloskee Bay
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee FL
9.6/10 Exceptional! (9 reviews)
The property is as advertised. The RV has a few miles on it, but was clean and everything worked. One sleeping area has a great view of the Glades. The porch is covered and also faces the Park. Boat slip has easy access to the Everglades and there is spacious parking for boat trailer and vehicle(s). ...

Reviewed on 24 Mar 2026

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Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL
9.6/10 Exceptional! (133 reviews)
Everything was fantastic. if we had any questions or any concerns, the owner responded right away and helped us out. we would have loved to stay longer, but unfortunately, Weather wasn’t on our side.. the people that were around that place were awesome very friendly polit…

Reviewed on 30 Nov 2025

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Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
See all 206 properties in Chokoloskee Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I cancel my flight booking to Chokoloskee Island due to COVID-19?
Many airlines now provide more flexibility due to COVID-19. Our Customer Service Portal will help you answer most queries about flight changes or cancellations. It's also worth reading through the terms and conditions of your chosen carrier — preferably before purchasing your tickets!
What's the best way to find cheap flights to Chokoloskee Island that have flexible change policies?
We get that things can change from one day to the next, so locking in a flexible airfare with Expedia makes good sense. Just check the "No change fee" box underneath the "Flexible change policies" filter. Your well-priced and flexible flight to Chokoloskee Island is just a few clicks away.
What are some of the general tips for travellers to Chokoloskee Island during the COVID-19 outbreak?
The COVID-19 pandemic has ushered in substantial changes to how we travel. If you're planning an escape to Chokoloskee Island, these tips will help you navigate these new challenges:
  • Investigate the restrictions and rules in both your origin and destination. It may not be possible to travel depending on local circumstances, so remember to check before you lock something in.
  • When you go through airport screening, do not remove your face mask. You will be required to lower it briefly for ID purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be escorted from the terminal.
  • Avoid handing your boarding pass (electronic or paper) directly to a TSA employee. Rather, position the pass on the scanner and then hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will need to be removed from your bag at the X-ray machine for scanning.
  • To minimize handling during screening, place items such as your loose change and phone into your carry-on instead of into the bins.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA employee will need to open and touch your bag for inspection.

Which airlines fly to Chokoloskee Island?
American Airlines operates flights into or near Chokoloskee Island, including 8565 that touch down at Miami Intl. Airport (MIA) each month. Pick your holiday dates and then book your seat early for an unbeatable deal.
How can I find cheap tickets to Chokoloskee Island?
One of the easiest ways to score cheap tickets to Chokoloskee Island is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The lowest price for a flight to Chokoloskee Island in the last seven days was . Booking ahead of time will usually help you get an even better deal.
How much is a flight to Chokoloskee Island?
You could have scored a round-trip flight to Chokoloskee Island from anywhere between and in the last seven days. For one-way journeys leaving from (), the lowest price during this time was just .
What are the most popular airports to fly into in Chokoloskee Island?
Chokoloskee Island's main entry point is Miami Intl. Airport (MIA). Get your amazing adventure underway by securing a ticket on one of the 13184 flights per month to this destination.
When is the cheapest time to fly to Chokoloskee Island?
If you'd prefer to spend your holiday savings enjoying Chokoloskee Island rather than on flying there, jet off early in the week. The cheapest day to travel is generally Tuesday, with Monday a close second. With many people keeping their travel to weekends, Saturday often has the costliest ticket prices.
How much is a plane ticket to Chokoloskee Island?
In the last seven days, plane fares to Chokoloskee Island fluctuated between and . Prices tend to rise over time, so pick up a cheap flight today.
Which airlines with flights to Chokoloskee Island employ COVID-19 cleanliness policies?
In an effort to minimize contact between travellers and cabin crew during the ongoing COVID-19 pandemic, the majority of airlines have taken social distancing and other precautionary measures to the skies. They include:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

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