Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Orlando to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Orlando to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The Orlando — Chicago route is served by multiple airlines, including Allegiant Air, United Airlines, and Frontier Airlines. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $99, and depending on season and promotions, even better deals may appear. With our service, you can easily compare available options and book tickets that match your plans. The variety of carriers allows flexible choices and comfortable travel without overpaying.
Orlando — Chicago
06/06/2026
Departure
Direct flight
G41306
starting at $99
Orlando — Chicago
11/05/2026
Departure
Direct flight
UA2683
starting at $100
Orlando — Chicago
07/04/2026
Departure
Direct flight
G41272
starting at $102
Orlando — Chicago
06/05/2026
Departure
Direct flight
G42939
starting at $110
Orlando — Chicago
06/10/2026
Departure
Direct flight
G42934
starting at $117
Orlando — Chicago
06/10/2026
Departure
Direct flight
F92791
starting at $121
Orlando — Chicago
07/17/2026
Departure
Direct flight
G42930
starting at $121
Orlando — Chicago
06/01/2026
Departure
Direct flight
G41239
starting at $126
Orlando — Chicago
06/07/2026
Departure
Direct flight
UA1839
starting at $134
Orlando — Chicago
06/08/2026
Departure
Direct flight
UA2475
starting at $134
There are most likely no direct flights on the Orlando — Chicago route
The cheapest flight ticket from Orlando to Chicago according to data for the last 48 hours costs $99
Often the best time to buy tickets from Orlando to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Orlando to Chicago can be found flying in these months: June, November, July.
The fastest flights from Orlando to Chicago start from 2 hours 43 minutes in the air.
The following airlines operate direct flights on the route Orlando — Chicago: Allegiant Air, United Airlines, Frontier Airlines
In different months, ticket prices from Orlando to Chicago vary: minimum — $99 (June 2026), maximum — $102 (July 2026). Typically, the flight costs $100–$202.
On the Orlando — Chicago route, ticket prices are stable. Whichever month you choose, the difference will be minimal.
There is a slight difference: it's a bit cheaper in June 2026–July 2026 (averaging $100) and slightly more in July 2026–November 2026 ($101). But overall, the difference is small.
On this route, you don't need to target specific months — prices are stable. The difference between the cheapest and most expensive period is only 1%. Book whenever it's convenient.
Monthly price variation is just 1.2%. Ticket costs on this route are among the most predictable.
We couldn't find any special offers for flights from Orlando to Chicago
The cheapest one-way flight from Orlando to Chicago departs on 06/06/2026, is operated by Allegiant Air and costs $99
The cheapest roundtrip flight from Orlando to Chicago departs on 06/03/2026, is operated by Allegiant Air and costs $141
Fastest flight from Orlando to Chicago takes 2h 43m
There are direct flights on this route 6 days a week: Su, Mo, We, Th, Fr, and Sa
The distance between Orlando and Chicago is 1587km (984 miles). The time difference between Orlando and Chicago is 1h