Cheap Flights from Orlando (ORL) to Chicago (CHI)

Frequently Asked Questions

• What are the cheapest flights from Orlando to Chicago (ORL-CHI)?

  Based on Trip.com data, Frontier Airlines offers one-way fares as low as US$45 on Cheapest nonstop routes (e.g. MCO to ORD on Sat, May 9), while Frontier Airlines offers Cheapest nonstop round-trips from US$73 departing on Sat, May 2 and returning on Sat, May 9.

• Which airlines offer direct flights from Orlando to Chicago?

  At the moment, you can catch a nonstop flight from Orlando to Chicago with the following airlines, including: Frontier Airlines Spirit Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is a flight from Orlando to Chicago?

  It takes about 3 hours 58 minutes to fly from Orlando to Chicago.

• When is the best time to book flights from Orlando to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Orlando to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How can I find the best deals on flights from Orlando to Chicago?

  To find best deals on flights from Orlando to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, May 9, with one-way flights priced at just US$45.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Frontier Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Orlando to Chicago is October, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Orlando to Chicago on?

  After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Orlando to Chicago on March 16, 2026 with Frontier Airlines, with prices starting at US$50.

• Which airports can I fly to for Chicago from Orlando?

  You can land at any one of the following hubs in Chicago, with Orlando International Airport to O'Hare International Airport (MCO-ORD) is by far the most common option on this route: Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).

• Is there any time difference between Orlando and Chicago?

  The time difference between Chicago and Orlando is 1h.

• How do I change or cancel my ticket from Orlando to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.