Cheap Flights from Orlando to Chicago from $50

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 $50 on Cheapest nonstop routes (e.g. MCO to ORD on Wed, Sep 23), while Frontier Airlines offers Cheapest nonstop round-trips from $98 departing on Tue, Sep 15 and returning on Tue, Sep 22.

• 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 American Airlines United Airlines Allegiant Air Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?

  It takes around 3 hours 36 minutes to fly from Orlando (ORL) to Chicago (CHI).

• 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 many flights are there per week from Orlando to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 100 flight per week flying from Orlando to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA2279 (09:01) American Airlines: S/M/T/W/T/F/S -- AA938 (06:35) United Airlines: S/M/T/W/T/F/S -- UA1801 (07:50)

• 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 Wed, Sep 23, with one-way flights priced at just $50.
  · 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 August flight calendar, it's currently cheapest to fly from Orlando to Chicago on August 24, 2026 with Frontier Airlines, with prices starting at $101.

• 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: O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) 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.

• What is the average cost of a one-way flight from Orlando to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Orlando to Chicago is $171. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Orlando to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Orlando to Chicago is $273. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Orlando to Chicago on Trip.com?

  Enter Orlando and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

• Are there budget airlines on the Orlando to Chicago route?

  Frontier Airlines and Allegiant Airare the most popular budget airlines flying from Orlando to Chicago. Check baggage, seat and payment fees before comparing the final price.