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

The displayed flights from Orlando to Chicago are round-trip. Airfares are non-warranted and subject to change. The fares comprise base fare, fuel surcharges, airline/airport taxes, and our service fee.

Cheapfaremart takes away the hassles of fare comparison and flight booking from your travel planning. We list fares from ORL to CHI with all the carriers operating on the route. We have invested in the best of travel technology that pulls out the top Chicago airfare deals available with different passenger carriers.

Cheapfaremart is the leading online travel agency approved by the American Society of Travel Agents. We help you find flights by your convenience — search flights by departure or arrival timing or by airlines. So, travel in the time that suits you, and also don’t miss the miles or rewards offered by your favorite travel suppliers.

If you are traveling in a group with size 10 or more, you deserve an additional flight discount. We help corporates, academic, and other institutions to save big on their group flight booking.

1. Orlando International Airport (IATA: MCO, ICAO: KMCO)

 The airport has 176 departure flights to Chicago in a week. Out of those, 61 departs to Chicago/Midway, IL with the leading budget airlines, Southwest. Another low-cost carrier, i.e., Spirit operates 14 flights departing to Chicago/O’Hare, IL in a week. Looking for a full-service airline? American (34), Frontier Airlines (11) and United (56) are the choices available to you.

2. Daytona Beach International Airport (DAB / KDAB)

 Daytona Beach International Airport is a county-owned airport located three miles (5 km) southwest of Daytona Beach. The airport has domestic flights from Daytona Beach, Florida and is 53 miles from Orlando, FL. Do not expect any nonstop flight from DAB to CHI. Connecting flights are available with American Airlines, Jetblue Airways, and United Airlines.

1. O’Hare International Airport

O’Hare International Airport (IATA: ORD, ICAO: KORD, FAA LID: ORD), typically referred to as O’Hare Airport, Chicago O’Hare, or simply O’Hare is an international airport located on the far Northwest Side of Chicago, Illinois, 14 miles (23 km) northwest of the Loop business district. The airport has daily arrivals from Orlando with Spirit Airlines, United Airlines, American Airlines, and Frontier Airlines.

The Chicago Department of Aviation oversees the operation of the airport. O’Hare has non-stop flights to 218 destinations in North America, South America, Europe, Africa, Asia, and Oceania.

2. Chicago Midway International Airport

Chicago Midway International Airport (IATA: MDW, ICAO: KMDW, FAA LID: MDW) is a major commercial airport on the southwest side of Chicago, Illinois, located eight miles (13 km) from the Loop. Established in 1927, Midway served as Chicago’s primary airport until the opening of O’Hare International Airport in 1955.  Chicago is Southwest’s largest focus city. Though many would think that getting a cheap flight ticket to Chicago from Orlando would be easier, it’s not like that. Chicago is a business center and financial hub, so there is always a high demand for air ticket on this route.

The flight time from Orlando to Chicago is 2 hours 21 minutes (approximate). The flight distance between ORL and CHI is 985 miles/1584 km. Take note of the time difference between Chicago and Orlando. Chicago is one hour behind Orlando. You may observe some variation in flight time and distance based on the departure and arrival airport pair.

Note: The flight distance and flight time are tentative. You should check with your airlines to have the precise information.

Practice these simple flight booking hacks to discover cheap flight deals on Chicago flight booking.

1. Be flexible with your date

If you are flexible, you are likely to find the top ORL to Chicago flight deals. Scheduling your flight departure day on a Wednesday or Thursday, you can have the edge over the competition of getting a flight ticket that happens on the weekend.

2. Be flexible with your time

Majority of travelers travel in day hours. Going against the trend, if you opt for a red-eye flight, you have chances to save some cash.

3. Wait for the right season

The best time for getting good deals on flights is winter, especially in January and February. Late November and early December also see dips in pricing for flights. If you are heading in winter, you must add some extra layer as the nights see sub-zero temperature.

4. Don’t wait for unexpected fare drop

Patience pays off. However, it should not stop you from rationale decision-making when you come across any ORL to CHI fare which you understand is far below the average.

Confirm your one-way or round trip flight tickets from Orlando to Chicago now. You may get in touch with us over the phone or chat to see on-demand help in flight booking.