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

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Cheap Flights from MDW to EYW starting at $202 One Way, $327 Round Trip

Prices starting at $327 for return flights and $202 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, Sep 23 - Wed, Sep 30
MDW
Chicago
EYW
Key West
$327 Roundtrip, found 6 days ago
$327
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 23 from Chicago to Key West, returning Wed, Sep 30, priced at $327 found 6 days ago
Fri, Sep 11 - Tue, Sep 15
MDW
Chicago
EYW
Key West
$344 Roundtrip, found 5 days ago
$344
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Sep 11 from Chicago to Key West, returning Tue, Sep 15, priced at $344 found 5 days ago
Fri, Sep 11 - Tue, Sep 15
MDW
Chicago
EYW
Key West
$371 Roundtrip, found 5 days ago
$371
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Sep 11 from Chicago to Key West, returning Tue, Sep 15, priced at $371 found 5 days ago
Wed, Aug 26 - Wed, Sep 2
MDW
Chicago
EYW
Key West
$374 Roundtrip, found 5 days ago
$374
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 26 from Chicago to Key West, returning Wed, Sep 2, priced at $374 found 5 days ago
Sat, Oct 10 - Tue, Oct 13
MDW
Chicago
EYW
Key West
$404 Roundtrip, found 6 days ago
$404
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 10 from Chicago to Key West, returning Tue, Oct 13, priced at $404 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
$203 nightly
The price is $229 total per night from Sep 2 to Sep 3
$229 total
Sep 2 - Sep 3
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! (1,235 reviews)
"The property itself was very nice and well kept. The maintenance and cleaning staff were very creepy men and made me feel very uncomfortable during my stay. It’s something to think about if you are solo traveling. The area was nice, amenities were great, but I would not return here."

Reviewed on Aug 17, 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
$118 nightly
The price is $133 total per night from Aug 30 to Aug 31
$133 total
Aug 30 - Aug 31
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
$152 nightly
The price is $171 total per night from Sep 7 to Sep 8
$171 total
Sep 7 - Sep 8
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! (1,082 reviews)
"Maintenance was in need of improvement after two calls to repair a closet door that was falling off they fixed it by just removing the entire door. Keys didn’t work. To unlock door. Walked to desk they reprogrammed them. Walked back to room and still unable to get into the room. Had to wait for a ..."

Reviewed on Aug 17, 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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 ...
8.8/10 Excellent! (3,533 reviews)
"I definitely won’t stay there again. Just due to the staff. They really had no idea what they are doing from check in to check out. I gave up trying to get hangers after the 4th request. We were out of body wash it took a forever to get and I was already showered by the time it arrived. I requested ..."

Reviewed on Aug 17, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$136 nightly
The price is $153 total per night from Aug 18 to Aug 19
$153 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Sep 1 to Sep 2
$225 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9/10 Wonderful! (1,856 reviews)
"Love love love this hotel."

Reviewed on Aug 17, 2026

Havana Cabana at 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.

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
$152 nightly
The price is $171 total per night from Sep 7 to Sep 8
$171 total
Sep 7 - Sep 8
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! (1,082 reviews)
"Maintenance was in need of improvement after two calls to repair a closet door that was falling off they fixed it by just removing the entire door. Keys didn’t work. To unlock door. Walked to desk they reprogrammed them. Walked back to room and still unable to get into the room. Had to wait for a ..."

Reviewed on Aug 17, 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
$118 nightly
The price is $133 total per night from Aug 30 to Aug 31
$133 total
Aug 30 - Aug 31
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
$145 nightly
The price is $163 total per night from Aug 18 to Aug 19
$163 total
Aug 18 - Aug 19
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! (1,006 reviews)
"The staff was friendly, the place is nice.very laid back."

Reviewed on Aug 17, 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
$155 nightly
The price is $175 total per night from Sep 1 to Sep 2
$175 total
Sep 1 - Sep 2
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! (1,381 reviews)
"Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location."

Reviewed on Aug 14, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$124 nightly
The price is $140 total per night from Aug 30 to Aug 31
$140 total
Aug 30 - Aug 31
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)
"The room itself was very nice, clean, and comfortable, and the location was great because it was very close to everything. My main disappointment was that the listing mentioned a shared area, but when we arrived, it was under construction. There appeared to be a new pool that was already filled with ..."

Reviewed on Aug 13, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$131 nightly
The price is $144 total per night from Aug 26 to Aug 27
$144 total
Aug 26 - Aug 27
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! (1,086 reviews)
"Room was clean. However, I felt the room doors were not very secured. My room was next to the alley, and I noticed that that back fence was never locked. Anyone could just walk in from outside. Don't get me wrong, the area was pretty quiet - not sketchy at all. The place is beautiful, breakfast was ..."

Reviewed on Aug 17, 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
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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 ...
8.8/10 Excellent! (3,533 reviews)
"I definitely won’t stay there again. Just due to the staff. They really had no idea what they are doing from check in to check out. I gave up trying to get hangers after the 4th request. We were out of body wash it took a forever to get and I was already showered by the time it arrived. I requested ..."

Reviewed on Aug 17, 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
$166 nightly
The price is $187 total per night from Sep 1 to Sep 2
$187 total
Sep 1 - Sep 2
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! (2,626 reviews)

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

Travelers say...
"Our stay was amazing! The property was very taken care of and loved all the amenities the hotel offered! Will definitely be booking again for our yearly trip!"

Reviewed on Aug 17, 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
$200 nightly
The price is $225 total per night from Sep 1 to Sep 2
$225 total
Sep 1 - Sep 2
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! (1,838 reviews)
"The room was clean and smells clean. Staffs are very helpful and greeted me enthusiastically. It was a place that I was expecting to be in and relax after a long drive. The pool was nice, heated and relaxing. Highly recommended."

Reviewed on Aug 17, 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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