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, Frontier Airlines, and Southwest Airlines. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $46, 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
10/07/2026
Departure
Direct flight
G41344
starting at $46
Orlando — Chicago
11/14/2026
Departure
Direct flight
F92791
starting at $81
Orlando — Chicago
09/10/2026
Departure
Direct flight
F91349
starting at $95
Orlando — Chicago
09/10/2026
Departure
Direct flight
F93043
starting at $95
Orlando — Chicago
09/09/2026
Departure
Direct flight
F92791
starting at $105
Orlando — Chicago
11/24/2026
Departure
Direct flight
F91457
starting at $131
Orlando — Chicago
12/31/2026
Departure
Direct flight
F91349
starting at $137
Orlando — Chicago
09/06/2026
Departure
Direct flight
F92791
starting at $152
Orlando — Chicago
12/31/2026
Departure
Direct flight
F91457
starting at $163
Orlando — Chicago
11/27/2026
Departure
Direct flight
G42923
starting at $168
There are most likely no direct flights on the Orlando — Chicago route
Orlando International Airport (MCO) is the region’s primary international gateway and a major hub for both legacy and low-cost carriers, so fares can range from budget-friendly to premium depending on season. It sits about 13 miles (20 km) southeast of downtown Orlando, with shuttle services, ride-shares and taxis typically taking 20–30 minutes and costing roughly $30–$60; the SunRail plus shuttle options can be cheaper but add transfer time. Orlando Sanford (SFB) serves more low-cost and leisure-focused airlines and is farther north, around 30–40 minutes from central Orlando by car. MCO offers more nonstop choices and amenities; SFB can be quieter and less expensive but has fewer transport links and longer transfers to the city.
Chicago is served mainly by O'Hare International (ORD) and Midway (MDW), with ORD typically functioning as the city’s large international and domestic hub—favored by major network carriers—while MDW generally handles more domestic and budget-oriented flights. O’Hare sits about 17–20 miles northwest of downtown; travel by CTA Blue Line usually takes 45–60 minutes and can be cheaper than airport shuttles or taxis, which commonly run 30–60 minutes depending on traffic. Midway is roughly 10 miles southwest and is often quicker to reach from the Loop, with the CTA Orange Line taking about 25–35 minutes and lower fares than private rides. O’Hare offers extensive international connections and plentiful amenities but can be busy and spread out; Midway can be more compact and easier to navigate for domestic trips but has fewer nonstop long-haul options. Both airports provide ride-hailing, shuttle, and car-rental services, with regional commuter and bus links for budget-conscious travelers.
The cheapest one-way flight from Orlando to Chicago departs on 10/07/2026, is operated by Allegiant Air and costs $46
The cheapest roundtrip flight from Orlando to Chicago departs on 09/29/2026, is operated by Frontier Airlines and costs $146
Fastest flight from Orlando to Chicago takes
There are direct flights on this route 6 days a week: Su, Tu, We, Th, Fr, and Sa
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
The cheapest flight ticket from Orlando to Chicago according to data for the last 48 hours costs $46
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: September, November, December.
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: Allegiant Air, Frontier Airlines
In different months, ticket prices from Orlando to Chicago vary: minimum — $80 (September 2026), maximum — $137 (December 2026). Typically, the flight costs $100–$219.
Tickets from Orlando to Chicago are getting more expensive each month. From September 2026 to December 2026, the increase reached 71%, with prices now at $137. It's unlikely to get cheaper than the current level.
The most significant price increase was from September 2026 to December 2026 — up 71%. The best time to fly is September 2026–November 2026, when the average price is $81. In November 2026–December 2026, tickets cost around $109.
Given the rising prices, it's best not to delay your purchase. Flying in September 2026–November 2026 can save you up to 26% compared to the most expensive months.
Price variation across months on this route is 26.8%. Your choice of departure month significantly affects the total flight cost.
