Find cheap flights from Chicago to Key West starting at $92.
Book one-way or return flights from Chicago to Key West from as little as $92. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- ORD08:253h 14mDirectEYW12:39Tue, Apr 30|Chicago - Key West|American Airlines$92$18550% OFF50% OFF$185$92
- ORD05:078h 18m1 stopEYW14:25Wed, Jul 3|Chicago - Key West|American Airlines$106$18543% OFF43% OFF$185$106
- ORD09:556h 30m1 stopEYW17:25Wed, May 8|Chicago - Key West|American Airlines$106$18543% OFF43% OFF$185$106
- ORD07:056h 1m1 stopEYW14:06Wed, Jun 26|Chicago - Key West|American Airlines$106$106
- ORD07:007h 54m1 stopEYW15:54Tue, Jul 9|Chicago - Key West|American Airlines$106$106
- ORD15:236h 19m1 stopEYW22:42Sat, May 4|Chicago - Key West|American Airlines$107$107
- ORD06:025h 59m1 stopEYW13:01Tue, Jun 11|Chicago - Key West|American Airlines$107$107
- ORD09:555h 10m1 stopEYW16:05Sun, Apr 28|Chicago - Key West|American Airlines$127$127
- ORD10:583h 5mDirectEYW15:03Tue, Apr 30|Chicago - Key West|United Airlines$127$127
- ORD18:4019h 10m1 stopEYW14:50Fri, May 10|Chicago - Key West|Spirit Airlines$134$134
- CHI13:003h 5mDirectEYW14:00Sat, May 4|Chicago - Key West|American AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Searching for the best last minute flight from Chicago to Key West? Find one-way or return flights that are affordable and fit your itinerary.
Trip.com monitors the ticket fares of flights from Chicago to Key West. Stay updated on price trends and snag the best deals for your upcoming trip.
View airlines operating flights from Chicago to Key West. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Find more flights and airlines
Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Key West.
- CheapestORD08:253h 14mDirectEYW12:39O'Hare International Airport - Key West International AirportTue, Apr 30American Airlines$92
- MDW06:208h 5m1 transferEYW15:25Midway International Airport - Key West International AirportWed, Jun 26Frontier Airlines$151
- RFD08:369h 59m1 transferEYW19:35Chicago Rockford International Airport - Key West International AirportFri, May 24Allegiant Air$327
- RFD08:369h 59m1 transferEYW19:35Chicago Rockford International Airport - Key West International AirportFri, May 24Allegiant Air$327Find More Flights
Frequently Asked Questions
How to find a cheap flight from Chicago to Key West
Cheapest nonstop flight price | $91 |
---|---|
Cheapest round-trip ticket price | $303 |
Off-season for travel | April |
Peak season for travel | July |
Flight distance | 2,001.04km |
Average flight time | 3 hours 9 minutes |
Popular airline | American Airlines |
Plan Your Trip Around Key West
Popular Flights
Popular Flights from Chicago
- Chicago to Taipei Flights
- Chicago to Hong Kong Flights
- Chicago to Shanghai Flights
- Chicago to Seoul Flights
- Chicago to Tokyo Flights
- Chicago to Bangkok Flights
- Chicago to New York Flights
- Chicago to Manila Flights
- Chicago to Beijing Flights
- Chicago to Atlanta Flights
- Chicago to Orlando Flights
- Chicago to Dallas Flights
- Flights from O'Hare International Airport to Jiamusi
- Flights from O'Hare International Airport to Butuan
- Flights from O'Hare International Airport to Okayama
- Flights from O'Hare International Airport to Hanamaki
- Flights from O'Hare International Airport to Taichung
- Flights from O'Hare International Airport to Bhuj
- Flights from Chicago to Guangzhou Baiyun International Airport
- Flights from Chicago to Changchun Longjia International Airport
- Flights from Chicago to Chiayi Airport
- Flights from Chicago to DDG Airport
- Flights from Chicago to Zhangjiajie Hehua Airport
- Flights from Chicago to Meilan International Airport
- Flights from O'Hare International Airport to Rajkot International Airport
- Flights from Midway International Airport to Taipei Songshan Airport
- Flights from Midway International Airport to Taiwan Taoyuan International Airport
- Flights from O'Hare International Airport to Taipei Songshan Airport
- Flights from O'Hare International Airport to Taiwan Taoyuan International Airport
- Flights from Midway International Airport to Hong Kong International Airport
Recommended Hotels in Key West
- Hotels near James Coleman Gallery Key West
- Hotels near The Home Depot
- Hotels near USCGC Ingham Maritime Museum
- Hotels near South Beach
- Hotels near DE LA Gallery
- Hotels near Gallery On Greene
- Hotels near Diamonds International
- Hotels near Key West Lighthouse Sunset Experience
- Hotels near La Naturelle
- Hotels near Audubon House & Tropical Gardens
- Hotels near The Cabaret At La Te Da
- Hotels near Conch Jewelers
- Hotels near Solaya - Spiritual Guidance, Psychic, Tarot Card Reader
- Hotels near Cornish Memorial A.M.E. Zion Church
- Hotels near Wreckers Sloop Mary
- Hotels near Archeo Gallery
- Hotels near Key West
- Hotels near Tucker's Provisions
- Hotels near Dog Beach
- Hotels near Florida Keys Historical Military Memorial
- Hotels near Fort East Martello Museum
- Hotels near Nancy Forrester's Secret Garden
- Hotels near Sails to Rails Museum Key West
- Hotels near The Wine Cottage on Eaton
- Hotels near SunShine Scooters, Inc.
- Hotels near Simonton Street Beach
- Hotels near Yankee Freedom- Dry Tortugas National Park Museum
- Hotels near A & B Marina
- Hotels near Fort Zachary Taylor Historic State Park Beach
- Hotels near Savlen Gallery
Popular Flights to Key West
- Tampa to Key West Flights
- London to Key West Flights
- Orlando to Key West Flights
- Fort Lauderdale to Key West Flights
- Houston to Key West Flights
- Tallahassee to Key West Flights
- New York to Key West Flights
- Hong Kong to Key West Flights
- Cancun to Key West Flights
- Oklahoma City to Key West Flights
- Mcallen to Key West Flights
- Dusseldorf to Key West Flights
- Flights from Hong Kong International Airport to Key West
- Flights from Taiwan Taoyuan International Airport to Key West
- Flights from Narita International Airport to Key West
- Flights from Shanghai Pudong International Airport to Key West
- Flights from Ngurah Rai Airport to Key West
- Flights from Ninoy Aquino International Airport to Key West
- Flights from Auckland to Key West International Airport
- Flights from Tokyo to Key West International Airport
- Flights from Frankfurt to Key West International Airport
- Flights from Honolulu to Key West International Airport
- Flights from Sydney to Key West International Airport
- Flights from Melbourne to Key West International Airport
- Flights from Tampa International Airport to Key West International Airport
- Flights from St. Pete-Clearwater International Airport to Key West International Airport
- Flights from London Heathrow Airport to Key West International Airport
- Flights from London City Airport to Key West International Airport
- Flights from London Gatwick Airport to Key West International Airport
- Flights from London Stansted Airport to Key West International Airport
Recommended Routes
- Los Angeles to New York Flights
- New York to Los Angeles Flights
- San Francisco to Los Angeles Flights
- San Francisco to Las Vegas Flights
- Los Angeles to Las Vegas Flights
- Los Angeles to Honolulu Flights
- Las Vegas to San Francisco Flights
- Las Vegas to Los Angeles Flights
- San Francisco to New York Flights
- Los Angeles to San Francisco Flights
- New York to Orlando Flights
- New York to San Francisco Flights
- Flights from Los Angeles International Airport to Knoxville
- Flights from Los Angeles International Airport to Page
- Flights from Los Angeles International Airport to El Paso
- Flights from Los Angeles International Airport to Wausau
- Flights from Los Angeles International Airport to Traverse City
- Flights from Los Angeles International Airport to Memphis
- Flights from Honolulu to Brunswick Golden Isles Airport
- Flights from Honolulu to Aspen-Pitkin County Airport
- Flights from Honolulu to Corpus Christi International Airport
- Flights from Honolulu to Bismarck Municipal Airport
- Flights from Honolulu to Ted Stevens Anchorage International Airport
- Flights from Honolulu to Bishop International Airport
- Flights from Los Angeles International Airport to Newark Liberty International Airport
- Flights from Los Angeles International Airport to John F. Kennedy International Airport
- Flights from Los Angeles International Airport to Stewart Airport
- Flights from Los Angeles International Airport to New York LaGuardia Airport
- Flights from Ontario International Airport to New York LaGuardia Airport
- Flights from Ontario International Airport to Newark Liberty International Airport
About
Site Operator: Trip.com Travel Singapore Pte. Ltd.