Cheap flights from RFD to EYW (Greater Rockford to Key West Intl.)

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Cheap Flights from RFD to EYW starting at $188 One Way, $401 Round Trip

Prices starting at $401 for return flights and $188 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 3 - Tue, Nov 10
RFD
Rockford
EYW
Key West
$401 Roundtrip, found 5 days ago
$401
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Nov 3 from Rockford to Key West, returning Tue, Nov 10, priced at $401 found 5 days ago
Fri, May 15 - Sat, May 23
RFD
Rockford
EYW
Key West
$427 Roundtrip, found 6 days ago
$427
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Rockford to Key West, returning Sat, May 23, priced at $427 found 6 days ago
Tue, Nov 3 - Tue, Nov 10
RFD
Rockford
EYW
Key West
$491 Roundtrip, found 5 days ago
$491
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Nov 3 from Rockford to Key West, returning Tue, Nov 10, priced at $491 found 5 days ago
Fri, May 15 - Sat, May 23
RFD
Rockford
EYW
Key West
$519 Roundtrip, found 6 days ago
$519
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Rockford to Key West, returning Sat, May 23, priced at $519 found 6 days ago
Fri, May 15 - Sat, May 23
RFD
Rockford
EYW
Key West
$539 Roundtrip, found 6 days ago
$539
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 15 from Rockford to Key West, returning Sat, May 23, priced at $539 found 6 days ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$387 nightly
The price is $436 total per night from Jun 6 to Jun 7
$436 total
Jun 6 - Jun 7
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,071 reviews)
The place was beautiful just too loud by being next to the airport.....

Reviewed on May 7, 2026

Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$209 nightly
The price is $235 total per night from May 10 to May 11
$235 total
May 10 - May 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,357 reviews)
Staff are mostly friendly and helpful (Sam at the front desk was awesome, as were all the shuttle drivers). Room was spotless. Pool area was a little nasty as people left their areas with half eaten food and beverages. Found chicken bone in the pool. Breakfast is super boring and tasteless. Lunch ...

Reviewed on May 7, 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$185 nightly
The price is $208 total per night from May 31 to Jun 1
$208 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,016 reviews)
Booked a balcony room two months ago. Our balcony was on the ground floor next to laundry exhaust and within 50 feet of the dumpsters, piles of tile, equipment, etc. Kept the blinds pulled for two days..

Reviewed on May 7, 2026

DoubleTree Resort by Hilton Grand Key - Key West
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.

Hotels In Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$211 nightly
The price is $237 total per night from May 10 to May 11
$237 total
May 10 - May 11
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,203 reviews)
This place is trying really hard to be hip. It was a little too much of a party vibe for me, but for those who are into live music and avocado toast and lawn games and a couple of onsite bar options, you all would really like this place. Two pools (one was full of kids, the other had more adults), ...

Reviewed on May 7, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
$260 nightly
The price is $292 total per night from May 10 to May 11
$292 total
May 10 - May 11
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,809 reviews)
Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.

Reviewed on May 7, 2026

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$283 nightly
The price is $319 total per night from May 25 to May 26
$319 total
May 25 - May 26
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,287 reviews)
We have visited Key West several times....Southernmost was by far the hotel we have stayed at. Location is perfect!!!!

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses
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.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$185 nightly
The price is $208 total per night from May 31 to Jun 1
$208 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,016 reviews)
Booked a balcony room two months ago. Our balcony was on the ground floor next to laundry exhaust and within 50 feet of the dumpsters, piles of tile, equipment, etc. Kept the blinds pulled for two days..

Reviewed on May 7, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$209 nightly
The price is $235 total per night from May 10 to May 11
$235 total
May 10 - May 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,357 reviews)
Staff are mostly friendly and helpful (Sam at the front desk was awesome, as were all the shuttle drivers). Room was spotless. Pool area was a little nasty as people left their areas with half eaten food and beverages. Found chicken bone in the pool. Breakfast is super boring and tasteless. Lunch ...

Reviewed on May 7, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$173 nightly
The price is $195 total per night from May 17 to May 18
$195 total
May 17 - May 18
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,010 reviews)
We very much enjoyed our stay - the pool, hot tub and bar area especially, but the bed was disappointing - not comfortable and a nightly battle with too small fitted sheets. In a great location for access to the ferry terminal (recommend Dry Tortugas National Park trip) and dinner at Cafe Sole! Old ...

Reviewed on May 7, 2026

Eden House
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.

Low Priced Key West Hotels

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$194 nightly
The price is $218 total per night from Jun 2 to Jun 3
$218 total
Jun 2 - Jun 3
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,328 reviews)
Very nice place to stay. The breakfast was good, pools were nicely kept very clean and always towels available. The best part was the use of the beach, great chairs and towels provided. The area was very quiet and comfortable

Reviewed on May 6, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$164 nightly
The price is $185 total per night from May 10 to May 11
$185 total
May 10 - May 11
Total with taxes and fees
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,004 reviews)
Easy check in and check out. Friendly staff, newly renovated rooms, very clean! Accessible to tourist spots!

Reviewed on May 4, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$211 nightly
The price is $234 total per night from May 12 to May 13
$234 total
May 12 - May 13
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,033 reviews)
The breakfast was more than adequate mainly continental but the air con was maybe a bit loud

Reviewed on May 6, 2026

Duval House
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.

Family Friendly Hotels in Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$283 nightly
The price is $319 total per night from May 25 to May 26
$319 total
May 25 - May 26
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,287 reviews)
We have visited Key West several times....Southernmost was by far the hotel we have stayed at. Location is perfect!!!!

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Duval Street and Smathers Beach ...
8.4/10 Very Good! (999 reviews)

Families like: Outdoor pool, babysitting, close to beach, bicycle rentals

Travelers say...
This is a beautiful resort full of amenities! Margaritas when you arrive, smoothies at the pool each day around noon, free airport and old town shuttles so we didn’t need to Uber anywhere, also coffee/water/cookies in the lobby daily. The beach is an easy walk across the street. The hotel is super ...

Reviewed on Apr 19, 2026

Get rates
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$211 nightly
The price is $237 total per night from May 10 to May 11
$237 total
May 10 - May 11
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,203 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
This place is trying really hard to be hip. It was a little too much of a party vibe for me, but for those who are into live music and avocado toast and lawn games and a couple of onsite bar options, you all would really like this place. Two pools (one was full of kids, the other had more adults), ...

Reviewed on May 7, 2026

Blue Flamingo Resort Key West
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.

RFD to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
RFD Address & GPS
Address:
2 Airport Cir
Rockford IL, 61109
United States
IATA Code:
RFD
Longitude:
-89.095372
Latitude:
42.201748
Time Zone:
America/Chicago
EYW Address & GPS
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA Code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time Zone:
America/New_York

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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