Summer flights to Orlando and Key West are now $100 off the next lowest fare. If you’ve been thinking about visiting Key West, grab this fare, as Key West is always expensive, so this great price drop!

Orlando is available over Labor Day. Fare Calendars:

Flights from Chicago to (all flights are roundtrip, including tax):


  • Save up to $100 off typical roundtrip pricing

Travel Dates:

  • To Orlando: Aug. 17-Oct. 19
  • To Key West: July 7-Aug. 27

Sample Screenshots:

Chicago-Orlando: Search Results

Chicago-Orlando: Search Results

Chicago-Orlando: Frontier Booking Page

Chicago-Orlando: Frontier Booking Page

Chicago-Key West: Search Results

Chicago-Key West: Search Results

Chicago-Key West: United Booking Page

Chicago-Key West: United Booking Page Updates

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Featured Image: Pier at the beach in Key West, Florida USA (

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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