Cheap flights Orlando — Chicago (ORL — CHI)

Good to know - Cheap tickets Orlando — Chicago

Cheapest flight found $20
Minimal flight time 2h 21m
Flight distance 1587 km
Most popular airline American Airlines

Airfare Orlando – Chicago by month

Here you can find out in what months how much a ticket Orlando – Chicago costs to buy cheap plane tickets.

Month One-way Round-trip
September 2026
July 2026
May 2026
April 2026
March 2026
February 2026
January 2026
December 2025
November 2025
October 2025
September 2025
August 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Orlando — Chicago

Departure Arrival Flight days Flight Airlines Flight time Airports
06:00 07:59 daily AA938 American Airlines 2h 59m Orlando International Airport — O'Hare International Airport Select dates
06:14 08:15 mon, thu, sat AA938 American Airlines 3h 1m Orlando International Airport — O'Hare International Airport Select dates
06:35 08:32 mon, fri F93853 Frontier (Manteo the Red Wolf Livery) 2h 57m Orlando International Airport — Chicago Midway International Airport Select dates
06:40 08:45 thu AA1585 American Airlines 3h 5m Orlando International Airport — O'Hare International Airport Select dates
06:40 08:54 tue, wed AA1585 American Airlines 3h 14m Orlando International Airport — O'Hare International Airport Select dates
06:42 08:56 mon, thu, fri, sat, sun AA1585 American Airlines 3h 14m Orlando International Airport — O'Hare International Airport Select dates
06:55 08:45 thu, fri, sun WN1464 Southwest Airlines 2h 50m Orlando International Airport — Chicago Midway International Airport Select dates
07:00 08:50 sun WN1464 Southwest Airlines 2h 50m Orlando International Airport — Chicago Midway International Airport Select dates
07:05 08:55 sat WN1464 Southwest Airlines 2h 50m Orlando International Airport — Chicago Midway International Airport Select dates
07:15 09:21 mon, thu, fri, sat, sun UA1097 United Airlines 3h 6m Orlando International Airport — O'Hare International Airport Select dates
All routes

Flights Orlando — Chicago

The selection of cheap flights Orlando — Chicago

Here you can find and purchase the cheapest flights Orlando — Chicago from $20 and Orlando — Chicago — Orlando from $31.

The price of the flight Orlando — Chicago (United States) — Orlando from $31 (round-trip).

The average price of the flight Orlando — Chicago (United States) — Orlando $188 (round-trip).

Low cost flights Orlando — Chicago (ORL — CHI)

The distance between Orlando and Chicago 986 miles (or 1587 kilometres).

The time difference between Orlando and Chicago is 1 h.

Minimal flight time from Orlando to Chicago 2h 21m.

LowCostClub always do a comparison of airfares Orlando — Chicago with several airlines (include American Airlines, Frontier (Manteo the Red Wolf Livery), Southwest Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Orlando — Chicago. Last week, for instance, the cheapest round-trip prices stood at $31 while the cheapest one-way price that was available within the last week cost $20

Routes from nearby cities to Chicago

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to Chicago is from Fort Lauderdale. The cheapest airfare can be purchased with a flight from Miami from $20. The nearest airports from Orlando with a flight to Chicago are in Jacksonville.

Popular International routes from Orlando

Popular routes from Chicago

If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:

Popular domestic routes from Orlando

FAQ about Orlando — Chicago

Yes, they do: AA938, F93853, AA1585, WN1464, UA1097, G42970, WN4535, G41311, WN8828, AA2835, WN3701, WN3624, WN2972, UA561, WN3346, WN626, UA2207, AA913, G41335, AA2966, WN519, WN1021, UA2475, WN1747, AA3076, WN275, UA2426, UA714, WN3643, WN1350, WN2094, AA3071, AA2779, AA3031, WN1345, WN3714, F92791, WN2299, G42840, WN1673, WN1550, UA1828, WN966, WN3221, AA1109, WN549, UA2000, AA3253, AA2202, AA1782, AA1150, AA576, NK897, WN3274, Y42154, F91457, NK623, 5X1327, WN3328, DL8922

Yes, you can fly from Orlando to Chicago. Orlando has 4 airports (Orlando Sanford International Airport, Walt Disney World, Orlando Executive, Orlando International Airport) for flights. American Airlines, Frontier (Manteo the Red Wolf Livery), Southwest Airlines, United Airlines, Allegiant Air, Spirit Airlines, Volaris, UPS, Delta Air Lines depart from Orlando on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Aer Lingus, Aeromexico, Air Canada Express, Air France, Alaska Airlines, AlphaSky, Amazon Air, Amerijet International, Arajet, Avelo Airlines, avianca, British Airways, Cargojet Airways, Contour Aviation, Copa Airlines, DHL, Emirates, FedEx, GlobalX, Iberia, Icelandair, Jet Linx Aviation, JetBlue (Retro Livery), MSC Air Cargo, NetJets, Phoenix Air, Porter, Porter Airlines Canada, Slate Aviation, Sun Country Airlines, Virgin Atlantic, Viva (Raiders Livery), WestJet.

A direct flight lasts an average of 2h 21m, during which time the aircraft covers a distance of 1587 km.

The price of flights Orlando — Chicago starts from $20.

Planes fly Orlando — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Orlando — Orlando Sanford International Airport, Walt Disney World, Orlando Executive, Orlando International Airport. In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport.

The following flights fly between Orlando and Chicago: AA938, AA938, F93853, AA1585, AA1585, AA1585, WN1464, WN1464, WN1464, UA1097, F93853, WN1464, UA1097, UA1097, G42970, WN4535, G41311, F93853, WN8828, AA2835, WN3701, WN3624, WN2972, WN2972, UA561, WN3346, WN1464, WN626, UA2207, UA2207, UA2207, AA913, UA2207, UA2207, UA2207, G41335, AA2966, WN519, WN1021, UA2475, WN1021, UA2475, F93853, WN1747, AA3076, WN275, UA2426, UA2426, UA714, WN3643, F93853, WN1350, WN2094, AA3071, AA2779, WN1350, AA3031, WN1345, WN3714, F92791, WN2299, F93853, G42840, WN1747, F93853, WN3714, WN1673, WN1550, UA1828, UA1828, F92791, WN1550, WN966, WN3221, WN3221, AA1109, AA1109, WN549, WN549, WN549, UA2000, WN549, AA3253, WN549, WN549, WN3221, AA2202, AA2202, AA1782, AA1150, AA576, AA1782, NK897, WN3274, Y42154, WN2094, F91457, WN2094, NK623, 5X1327, 5X1327, 5X1327, 5X1327, WN2094, F91457, WN3328, WN3221, DL8922

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Orlando — Chicago flight deals.

The following airlines have direct flights Orlando — Chicago: American Airlines, Frontier (Manteo the Red Wolf Livery), Southwest Airlines, United Airlines, Allegiant Air, Spirit Airlines, Volaris, UPS, Delta Air Lines.

All the following airlines flights Orlando — Chicago: Aer Lingus, Aeromexico, Air Canada Express, Air France, Alaska Airlines, Allegiant Air, AlphaSky, Amazon Air, American Airlines, Amerijet International, Arajet, Avelo Airlines, avianca, British Airways, Cargojet Airways, Contour Aviation, Copa Airlines, Delta Air Lines, DHL, Emirates, FedEx, Frontier (Manteo the Red Wolf Livery), GlobalX, Iberia, Icelandair, Jet Linx Aviation, JetBlue (Retro Livery), MSC Air Cargo, NetJets, Phoenix Air, Porter, Porter Airlines Canada, Slate Aviation, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Airlines, UPS, Virgin Atlantic, Viva (Raiders Livery), Volaris, WestJet.

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