American Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $180
United Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $160
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.
All airports
American Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $180
United Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $160
The airlines on the Orlando — Chicago route each fly on specific days: American Airlines and United Airlines fly every day except Sunday.
We couldn't find any special offers for flights from Orlando to Chicago
Flight costs from Orlando to Chicago climb toward the middle of the period, then start to drop. By choosing the right dates, you can save noticeably.
Prices rise from October 2026 to December 2026 (+148%), then decline from December 2026 to March 2027 (20%). The cheapest tickets are in October 2026–November 2026 (averaging $54), while the priciest are in December 2026–March 2027 ($115).
For savings, plan your flight for October 2026–November 2026 — you could save up to 53%. Try to avoid December 2026–March 2027 when possible: prices are at their highest then.
Price spread on this route is 37.7%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.
In different months, ticket prices from Orlando to Chicago vary: minimum — $51 (October 2026), maximum — $127 (December 2026). Typically, the flight costs $84–$102.
Orlando — Chicago
11/05/2026
Departure
Direct flight
AA1615
starting at $227
Orlando — Chicago
11/25/2026
Departure
Direct flight
AA1782
starting at $263
Orlando — Chicago
10/22/2026
Departure
Direct flight
AA1645
starting at $225
Orlando — Chicago
10/30/2026
Departure
Direct flight
UA454
starting at $231
Orlando — Chicago
10/30/2026
Departure
Direct flight
WN693
starting at $277
Orlando — Chicago
10/27/2026
Departure
Direct flight
AA1661
starting at $279
Orlando — Chicago
10/23/2026
Departure
Direct flight
UA1621
starting at $300
Orlando — Chicago
10/28/2026
Departure
Direct flight
AA1782
starting at $369
Orlando — Chicago
12/02/2026
Departure
Direct flight
UA2070
starting at $283
Orlando — Chicago
01/05/2027
Departure
Direct flight
UA2475
starting at $289
starting at $225
starting at $231
starting at $277
starting at $60
starting at $69
The route Orlando — Chicago is served by many carriers — 5 in total, including American Airlines, United Airlines, Southwest Airlines, Allegiant Air, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $60) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
The cheapest flight ticket from Orlando to Chicago according to data for the last 48 hours costs $60
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: October, November, March.
The fastest flights from Orlando to Chicago start from 2 hours 44 minutes in the air.
The following airlines operate direct flights on the route Orlando — Chicago: American Airlines, United Airlines, Southwest Airlines
The cheapest one-way flight from Orlando to Chicago departs on 10/28/2026, is operated by Allegiant Air and costs $60
The cheapest roundtrip flight from Orlando to Chicago departs on 11/06/2026, is operated by Allegiant Air and costs $132
Fastest flight from Orlando to Chicago takes 2h 44m
There are direct flights on this route 4 days a week: Tu, We, Th, and Fr
The distance between Orlando and Chicago is 1587km (984 miles). The average flight duration is 3h 7m. There are 143 direct flights from Orlando to Chicago. The time difference between Orlando and Chicago is 1h. Flights from Orlando begin at 6:30 AM. The latest flight from Orlando departs at 10:55 PM
