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Book Flights from Chicago to Orlando will help you to find the best deals on flights from Chicago to Orlando. With our search technology, effortlessly searching flight routes across hundreds of airlines has never been easier or more convenient. With, we aim to make it simple and quick to search, select and save on the flights that best suit your needs and budget.

No matter if you are traveling for business or pleasure, we offer a wide range of deals from business class discounts to last minute flight deals to destinations like Orlando. Whether you are planning ahead or looking for last minute tickets, CheapOair has the right flights at the right price. After booking your ticket, explore this page to view blog posts about this destination, learn more about hotels near ORL and read reviews from others who booked their flights with

Frequently Asked Questions - Chicago to Orlando Flights

  • When does the first flight of the day depart from CHI?

    7:45AM United Airlines Flight #2398

  • When does the last flight depart to ORL?

    8:14PM Spirit Airlines Flight #929

  • What is the travel distance between Chicago and Orlando?

    987 miles

  • How many weekly flights are there between CHI to ORL?

    There are 74 weekly flights between CHI and ORL.

  • How many daily flights fly between Chicago and Orlando?

    There are 9 daily flights between CHI and ORL

  • Which is the busiest day in terms of passengers traffic between CHI to ORL?


  • Which is the nearest airport to Orlando, Florida?

    Orlando International Airport

  • Which is the nearest airport to Chicago, Illinois?

    Midway International Airport