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Cheap Flights from MDW to EYW

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Amazing MDW to EYW Flight Deals

The cheapest flights to Key West Intl. found within the past 7 days were $382. Prices and availability subject to change. Additional terms may apply.

Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$382

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$398

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Sun, Feb 9 - Fri, Feb 14

Chicago (MDW)

to

Key West (EYW)

$432

roundtrip

found 5 days ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$450

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$466

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Jan 14 - Thu, Jan 16

Chicago (MDW)

to

Key West (EYW)

$474

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$480

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$496

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$500

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$530

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Mon, Oct 12 - Sat, Oct 17

Chicago (MDW)

to

Key West (EYW)

$538

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$540

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Tue, Mar 31 - Fri, Apr 3

Chicago (MDW)

to

Key West (EYW)

$546

roundtrip

found 6 days ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$548

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$550

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$551

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$571

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$574

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$578

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Feb 20 - Thu, Feb 27

Chicago (MDW)

to

Key West (EYW)

$582

roundtrip

found 6 days ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$598

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$603

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$606

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$621

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$628

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$632

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$633

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$637

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Thu, Jan 9 - Mon, Jan 13

Chicago (MDW)

to

Key West (EYW)

$643

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$653

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$682

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$683

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$697

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$698

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$713

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$723

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$733

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$450

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$466

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$480

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$496

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Dec 31 - Tue, Jan 7

Chicago (MDW)

to

Key West (EYW)

$632

roundtrip

found 19 hours ago

Open MDW to EYW flights search result page
Tue, Jan 14 - Thu, Jan 16

Chicago (MDW)

to

Key West (EYW)

$474

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Thu, Jan 9 - Mon, Jan 13

Chicago (MDW)

to

Key West (EYW)

$643

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Sun, Feb 9 - Fri, Feb 14

Chicago (MDW)

to

Key West (EYW)

$432

roundtrip

found 5 days ago

Open MDW to EYW flights search result page
Thu, Feb 20 - Thu, Feb 27

Chicago (MDW)

to

Key West (EYW)

$582

roundtrip

found 6 days ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$637

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$682

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$697

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Wed, Feb 5 - Sun, Feb 9

Chicago (MDW)

to

Key West (EYW)

$698

roundtrip

found 11 hours ago

Open MDW to EYW flights search result page
Tue, Mar 31 - Fri, Apr 3

Chicago (MDW)

to

Key West (EYW)

$546

roundtrip

found 6 days ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$500

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$550

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Fri, Apr 17 - Tue, Apr 21

Chicago (MDW)

to

Key West (EYW)

$551

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$540

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$571

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$574

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$603

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 9 - Sun, Jul 12

Chicago (MDW)

to

Key West (EYW)

$606

roundtrip

found 4 days ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$621

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$633

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$653

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$683

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$713

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$723

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Jul 23 - Sun, Jul 26

Chicago (MDW)

to

Key West (EYW)

$733

roundtrip

found 22 hours ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$382

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$398

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$530

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Mon, Oct 12 - Sat, Oct 17

Chicago (MDW)

to

Key West (EYW)

$538

roundtrip

found 3 days ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$548

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$578

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$598

roundtrip

found 1 day ago

Open MDW to EYW flights search result page
Thu, Oct 29 - Mon, Nov 2

Chicago (MDW)

to

Key West (EYW)

$628

roundtrip

found 1 day ago

Open MDW to EYW flights search result page

Best Key West Intl. Flight and Hotel Packages

Key West Intl. flight + hotel packages - economy flights

Save $130
Villas Key West
3.5 out of 5.0

Thu, Jan 30 - Sun, Feb 2

Midway Intl. - Key West Intl.

Old price

$1,556

The price now is $1,426 per person
Flight + Hotel
Villas Key West
Save $258
Oceans Edge Key West Resort, Hotel & Marina
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,301

The price now is $1,044 per person
Flight + Hotel
Oceans Edge Key West Resort, Hotel & Marina
Save $315
Hyatt Centric Key West Resort and Spa
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,623

The price now is $1,307 per person
Flight + Hotel
Hyatt Centric Key West Resort and Spa
Save $169
Fairfield Inn and Suites by Marriott Key West
3.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,055

The price now is $886 per person
Flight + Hotel
Fairfield Inn and Suites by Marriott Key West
Save $138
Ibis Bay Beach Resort
2.5 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,066

The price now is $928 per person
Flight + Hotel
Ibis Bay Beach Resort
Save $142
Casa Marina Key West, A Waldorf Astoria Resort
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,329

The price now is $1,187 per person
Flight + Hotel
Casa Marina Key West, A Waldorf Astoria Resort
Save $113
The Chelsea House
2.5 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,072

The price now is $958 per person
Flight + Hotel
The Chelsea House
Save $166
Santa Maria Suites
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,654

The price now is $1,488 per person
Flight + Hotel
Santa Maria Suites
Save $96
Fairfield Inn & Suites Key West at The Keys Collection
3.5 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$998

The price now is $902 per person
Flight + Hotel
Fairfield Inn & Suites Key West at The Keys Collection
Save $138
H2O Suites - Adults Only
3.5 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,440

The price now is $1,302 per person
Flight + Hotel
H2O Suites - Adults Only
Save $233
Ocean Key Resort - A Noble House Resort
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$2,456

The price now is $2,223 per person
Flight + Hotel
Ocean Key Resort - A Noble House Resort
Save $104
Crowne Plaza Key West-La Concha
4.0 out of 5.0

Fri, Jan 10 - Tue, Jan 14

Midway Intl. - Key West Intl.

Old price

$1,177

The price now is $1,073 per person
Flight + Hotel
Crowne Plaza Key West-La Concha

Midway Intl. to Key West Intl. Flight FAQ

Travel FromMidway Intl.
Traveling ToKey West Intl.
Shortest Flight Time hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price$382

Save on your next flight from MDW to EYW when you book through Travelocity. Need a last-minute flight to Key West? Travelocity offers discount airfare no matter when you book, even on popular routes such as Midway Intl. Airport to Key West Intl. Airport. Whether you need a direct or indirect flight, you can trust Travelocity to provide you with the best prices for MDW to EYW flights.

Top Flights from Midway Intl.

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Chicago to Key West Carriers and Route Information

Flight path for flights from Chicago Midway International Airport to Key West International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
EYW - Key West International Airport
Distance:
1,245.00 miles


Top Airlines Servicing MDW - Midway Intl. Airport

Below are the most flown air carriers at Chicago (MDW) airport. Click to see their most popular routes and look for airfare.

Top Airlines Servicing EYW - Key West Intl. Airport

Below are the most flown air carriers at Key West (EYW) airport. Click to see their most popular routes and look for airfare.

Hotels near Key West Intl. Airport (EYW)

Price for 1 night 2 adults*

Havana Cabana at Key West $134

Per night/room

Dec 17 - Dec 18

Reviewed on Nov 14, 2019
See details
 
Havana Cabana at Key West

Havana Cabana at Key West

3420 N. Roosevelt Blvd, Key West, FL
     
    4.5 of 5
    3.5 out of 5.0 Stars

    Best part of staying here was the pool. Staff was great about bringing us out food from the bar and making sure we were doing great.

    Fairfield Inn & Suites Key West at The Keys Collection $134

    Per night/room

    Dec 15 - Dec 16

    Reviewed on May 18, 2019
    See details
     
    Fairfield Inn & Suites Key West at The Keys Collection

    Fairfield Inn & Suites Key West at The Keys Collection

    3852 North Roosevelt Boulevard, Key West, FL
       
      4.3 of 5
      3.5 out of 5.0 Stars

      Very nice very pleasant time there. I was there for training and really didn’t get a chance to see much. The staff was very helpful.

      DoubleTree Resort by Hilton Grand Key - Key West $140

      Per night/room

      Dec 15 - Dec 16

      Reviewed on Aug 12, 2019
      See details
       
      DoubleTree Resort by Hilton Grand Key - Key West

      DoubleTree Resort by Hilton Grand Key - Key West

      3990 S Roosevelt Blvd, Key West, FL
         
        4.2 of 5
        3.5 out of 5.0 Stars

        The property didn’t have much entertainment. I was not too pleased with the decor and room service. The cookies are great and the front desk staff is excellent.

        The Laureate Key West $143

        Per night/room

        Dec 15 - Dec 16

        Reviewed on Nov 13, 2019
        See details
         
        The Laureate Key West

        The Laureate Key West

        3444 N Roosevelt Boulevard, Key West, FL
           
          4.7 of 5
          3.5 out of 5.0 Stars

          Loved the big suite and the bathroom was great. The girl at the desk was very helpful and gave us great tips. Only a snack shop or breakfast bar would have been nice

          See all 624 Properties in Key West Intl.
          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.