$138-$301 — Chicago to Orlando & Key West (R/T)

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.

Fly.com Fare Calendars:

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

Savings:

  • 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: Fly.com Search Results

Chicago-Orlando: Fly.com Search Results

Chicago-Orlando: Frontier Booking Page

Chicago-Orlando: Frontier Booking Page

Chicago-Key West: Fly.com Search Results

Chicago-Key West: Fly.com Search Results

Chicago-Key West: United Booking Page

Chicago-Key West: United Booking Page

Fly.com Updates

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Featured Image: Pier at the beach in Key West, Florida USA (Shutterstock.com)

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