* All fares below were last found on: Jan 22, 2019 and 7:32:43 PM.
Fares are round trip, Fares incl. all fuel surcharges, our service fees and taxes.
Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking.
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Book your flights from Orlando to Chicago and save big on airfares. Decorated with miles of beautiful beaches, world class museums and amazing parks, city of Chicago would certainly spoil you for choices. Third most populous city in United States, Chicago certainly deserves a place on your travel itinerary. Spend a romantic evening with your loved one at North Avenue Beach and explore more than 30,000 marine species at the famous Shedd Aquarium. Don’t forget to pamper yourself with the best of brands and cuisines at the Magnificent Mile.
United Airlines, US Airways, American Airlines and JetBlue Airways are some of the major airlines that offer flights from Orlando to Chicago. Take advantage of exclusive deals on flights to Chicago and save more to splurge on a vacation. It takes about three hours and forty five minutes excluding the layover time to cover the destined 987 miles on flights from Orlando to Chicago and although there are plenty of entertainment options provided by the carriers, it’s always a good idea to carry a nice book with you.