Cheap flights from MDW to EYW (Midway Intl. to Key West Intl.)

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Cheap Flights from MDW to EYW starting at $325 One Way, $366 Round Trip

Prices starting at $366 for return flights and $325 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.

Wed, Feb 3 - Wed, Feb 10
MDW
Chicago
EYW
Key West
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 3 from Chicago to Key West, returning Wed, Feb 10, priced at $366 found 1 day ago
Wed, Feb 3 - Wed, Feb 10
MDW
Chicago
EYW
Key West
$424 Roundtrip, found 1 day ago
$424
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 3 from Chicago to Key West, returning Wed, Feb 10, priced at $424 found 1 day ago
Wed, Feb 10 - Sun, Feb 14
MDW
Chicago
EYW
Key West
$459 Roundtrip, found 1 day ago
$459
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 10 from Chicago to Key West, returning Sun, Feb 14, priced at $459 found 1 day ago
Wed, Feb 3 - Wed, Feb 10
MDW
Chicago
EYW
Key West
$476 Roundtrip, found 1 day ago
$476
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 3 from Chicago to Key West, returning Wed, Feb 10, priced at $476 found 1 day ago
Wed, Feb 10 - Sun, Feb 14
MDW
Chicago
EYW
Key West
$487 Roundtrip, found 1 day ago
$487
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 10 from Chicago to Key West, returning Sun, Feb 14, priced at $487 found 1 day 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
$232 nightly
The price is $261 total per night from Oct 26 to Oct 27
$261 total
Oct 26 - Oct 27
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 ...
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
$169 nightly
The price is $190 total per night from Oct 6 to Oct 7
$190 total
Oct 6 - Oct 7
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 ...
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
$153 nightly
The price is $172 total per night from Oct 11 to Oct 12
$172 total
Oct 11 - Oct 12
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 ...
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$265 nightly
The price is $298 total per night from Oct 6 to Oct 7
$298 total
Oct 6 - Oct 7
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,788 reviews)
"The staff were friendly and extremely helpful. The shuttle provided an excellent means for transportation to Duval Street as well as the ferry. The beaches in Key West are not the greatest so if your decision is based on proximity to the beach, it may not be worthwhile. The pool at the resort was ..."

Reviewed on Oct 5, 2026

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
$168 nightly
The price is $189 total per night from Oct 6 to Oct 7
$189 total
Oct 6 - Oct 7
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 ...
8.6/10 Excellent! (2,713 reviews)
"Great rooms and property. But the elevators need work. slow and only one wroking."

Reviewed on Oct 5, 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$185 nightly
The price is $208 total per night from Oct 6 to Oct 7
$208 total
Oct 6 - Oct 7
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,588 reviews)
"I like the location, they do not have a clean beach!"

Reviewed on Oct 5, 2026

Beachside Resort & Residences
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
$153 nightly
The price is $172 total per night from Oct 11 to Oct 12
$172 total
Oct 11 - Oct 12
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 ...
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
$169 nightly
The price is $190 total per night from Oct 6 to Oct 7
$190 total
Oct 6 - Oct 7
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 ...
Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$171 nightly
The price is $192 total per night from Oct 6 to Oct 7
$192 total
Oct 6 - Oct 7
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! (1,005 reviews)
"I feel like this is a hidden gem in key west. Its hidden in a neighborhood close to all the action. Beautiful pool, our room was clean and I mean it smelt clean that was nice. They also accommodated an early check in for me. It was a great experience I will definitely be back. I have zero ..."

Reviewed on Oct 4, 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
$169 nightly
The price is $190 total per night from Oct 6 to Oct 7
$190 total
Oct 6 - Oct 7
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! (1,384 reviews)
"Great location. Third stay here. Will return again Rooms are small but clean fresh coffee every morning."

Reviewed on Oct 3, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$122 nightly
The price is $137 total per night from Oct 6 to Oct 7
$137 total
Oct 6 - Oct 7
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! (1,000 reviews)
"Pool was not accessible, disappointing 😑 😒"

Reviewed on Sep 30, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$147 nightly
The price is $162 total per night from Oct 14 to Oct 15
$162 total
Oct 14 - Oct 15
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 ...
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
$247 nightly
The price is $278 total per night from Oct 11 to Oct 12
$278 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this spa 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 ...
8.6/10 Excellent! (3,618 reviews)
"The resort itself was nice and most of the staff was super nice! But we paid way too much money for us not to be aware that the big pool was closed for the week and on top of it they ran a power washer for 3 days which sounded like it was inside of or room! It ran from 9-5 only turning off for about ..."

Reviewed on Oct 4, 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$168 nightly
The price is $189 total per night from Oct 6 to Oct 7
$189 total
Oct 6 - Oct 7
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 ...
8.6/10 Excellent! (2,713 reviews)

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

Travelers say...
"Great rooms and property. But the elevators need work. slow and only one wroking."

Reviewed on Oct 5, 2026

Blue Flamingo Resort Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$178 nightly
The price is $201 total per night from Oct 12 to Oct 13
$201 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,802 reviews)
"This was our second time to stay here and this place never disappoints. Staff is wonderful too"

Reviewed on Oct 3, 2026

Hilton Key West Resort & Marina
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.

MDW to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
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

Frequently asked questions

What is the shortest flight from Chicago Airport to Key West Intl. Airport (EYW)?
Treat yourself to an in-flight vino and settle into your seat with a gripping book or movie. With the journey from Chicago to Key West taking 3 hours and 49 minutes, there's plenty of time to relax and enjoy the experience.
How many hours flight from Chicago Airport to Key West Intl. Airport (EYW)?
The flight from MDW to Key West Intl. Airport (EYW) takes an average of 3 hours and 53 minutes. A few good movies, some podcasts and a decent snooze will help make time zip by.
What airlines have the most flights from Chicago Airport to EYW?
You'll have to make one or more stopovers if you need to get from MDW to EYW. For now, there are no airlines that offer direct flights on this route.

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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