Good to know - Cheap tickets Orlando — Chicago
| Cheapest flight found | $20 |
|---|---|
| Minimal flight time | 2h 33m |
| Flight distance | 1587 km |
| Most popular airline | American Eagle |
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 |
|---|---|---|
| May 2026 | ||
| January 2026 | ||
| December 2025 | ||
| November 2025 | ||
| October 2025 | ||
| September 2025 | ||
| August 2025 | ||
| July 2025 | ||
| June 2025 | ||
| May 2025 | ||
| April 2025 | ||
| March 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 | |
|---|---|---|---|---|---|---|---|
| 06:20 | 08:05 | mon, thu, fri | WN1053 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:22 | fri, sun | F93853 | Frontier (Xavier the Mountain Goat Livery) | 2h 52m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:50 | 08:35 | sun | WN147 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:56 | 09:00 | wed | AA938 | American Eagle | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:05 | daily | AA938 | American Eagle | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:10 | thu, sat | AA938 | American Eagle | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:03 | mon, fri | AA938 | American Eagle | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:10 | 08:55 | tue, wed | WN3591 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:00 | sat | WN147 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:30 | 09:36 | mon, thu, fri, sat, sun | UA1097 | United Express | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
Popular airlines flying Orlando — Chicago
Flight Orlando – Chicago is served by 34 airlines. 7 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Sales of tickets from Orlando to Chicago in the last 48 hours
Dynamics airfare Orlando — Chicago by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Orlando — Chicago
The graph shows that booking flights Orlando — Chicago is best planned for October and flights Orlando — Chicago — Orlando in the month of September.
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).
- Departure city: Orlando
- IATA code of the city of origin: ORL
- Departure airports: Orlando Sanford International Airport, Walt Disney World, Orlando Executive, Orlando International Airport
- Departure country: United States
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Destination country: United States
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 33m.
LowCostClub always do a comparison of airfares Orlando — Chicago with several airlines (include Southwest Airlines, Frontier (Xavier the Mountain Goat Livery), American Eagle). 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
Are there any direct flights Orlando — Chicago?
Yes, they do: WN1053, F93853, WN147, AA938, WN3591, UA1097, WN1570, WN1719, G41242, G41250, WN350, AA2279, AA1842, G41328, WN3255, UA2341, WN2956, G41337, WN1373, UA2207, WN3870, AA1629, WN2409, UA2475, G41277, F93043, WN1164, WN3603, WN3643, AA1163, NK2410, UA1403, AA3031, WN1788, WN1500, G42971, WN1186, AA2142, UA1828, WN1972, AA3232, WN748, AA1247, NK341, WN255, WN3726, NK2343, 5X1327, F92791, WN2634, WN3277
Can we fly from Orlando to Chicago?
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. Southwest Airlines, Frontier (Xavier the Mountain Goat Livery), American Eagle, United Express, Allegiant Air, Spirit Airlines, UPS depart from Orlando on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Horizon, Amazon Air, Amazon Air, Amerijet International, Atlas Air, Avelo Airlines, avianca, British Airways, Contour Aviation, Copa Airlines, Delta Connection, DHL, Emirates, FedEx, GlobalX, Icelandair, Jet Linx Aviation, JetBlue, Kalitta Air, National Airlines, NetJets, Phoenix Air, Porter, Porter Airlines Canada, Slate Aviation, Virgin Atlantic, Viva, Volaris, WestJet.
How long does it take to fly from Orlando to Chicago?
A direct flight lasts an average of 2h 33m, during which time the aircraft covers a distance of 1587 km.
How much do flights Orlando — Chicago cost?
The price of flights Orlando — Chicago starts from $20.
What days does the plane fly Orlando — Chicago?
Planes fly Orlando — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Orlando and Chicago?
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.
What flights are currently flying from Orlando to Chicago?
The following flights fly between Orlando and Chicago: WN1053, F93853, WN147, AA938, AA938, AA938, AA938, WN3591, WN147, UA1097, WN1570, WN1719, F93853, WN1719, G41242, G41250, WN350, AA2279, AA1842, G41328, WN3255, G41250, WN3255, UA2341, WN2956, G41337, WN1373, WN3591, UA2207, UA2207, WN2956, UA2207, WN3870, AA1629, WN2409, WN1373, UA2475, UA2475, WN1373, G41277, F93043, WN1164, F93853, WN3603, F93853, WN3643, AA1163, NK2410, NK2410, UA1403, UA1403, AA3031, WN1788, WN1500, G42971, WN1788, WN1186, AA2142, WN3603, WN1788, UA1828, UA1828, WN3255, F93043, WN1972, AA2142, UA1828, WN1972, F93043, AA3232, WN1972, F93853, WN748, AA1247, AA1247, AA1247, WN748, NK341, WN748, WN255, WN3726, WN3726, NK2343, WN748, 5X1327, 5X1327, F92791, WN2634, WN2634, F92791, WN3726, WN3277
What month is the cheapest to fly from Orlando to Chicago?
High season is considered to be December and the cheapest month is October. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Orlando — Chicago flight deals.
Which airlines direct fly from Orlando to Chicago?
The following airlines have direct flights Orlando — Chicago: Southwest Airlines, Frontier (Xavier the Mountain Goat Livery), American Eagle, United Express, Allegiant Air, Spirit Airlines, UPS.
Which airlines fly from Orlando to Chicago?
All the following airlines flights Orlando — Chicago: ABX Air, Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Horizon, Allegiant Air, Amazon Air, Amazon Air, American Eagle, Amerijet International, Atlas Air, Avelo Airlines, avianca, British Airways, Contour Aviation, Copa Airlines, Delta Connection, DHL, Emirates, FedEx, Frontier (Xavier the Mountain Goat Livery), GlobalX, Icelandair, Jet Linx Aviation, JetBlue, Kalitta Air, National Airlines, NetJets, Phoenix Air, Porter, Porter Airlines Canada, Slate Aviation, Southwest Airlines, Spirit Airlines, United Express, UPS, Virgin Atlantic, Viva, Volaris, WestJet.