Good to know - Cheap tickets Orlando — Chicago
| Cheapest flight found | $20 |
|---|---|
| Minimal flight time | 2h 33m |
| 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 |
|---|---|---|
| May 2026 | ||
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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 | mon, tue, wed, thu, fri, sun | AA938 | American Airlines | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:05 | 08:07 | sat | F93043 | Frontier (Buck the Pronghorn Livery) | 3h 2m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:20 | 08:10 | tue, wed | WN3724 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:25 | 08:15 | sun | WN3716 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:14 | sat | G42963 | Allegiant Air | 2h 44m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 06:30 | 08:12 | sat | G42970 | Allegiant Air | 2h 42m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 06:30 | 08:30 | sat | AA938 | American Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:35 | 08:20 | mon, thu, fri | WN3716 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:40 | 08:25 | sat | WN3716 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:22 | mon, thu, fri, sun | UA2673 | United Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
Popular airlines flying Orlando — Chicago
Flight Orlando – Chicago is served by 31 airlines. 8 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
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 July and flights Orlando — Chicago — Orlando in the month of October.
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 $38.
The price of the flight Orlando — Chicago (United States) — Orlando from $38 (round-trip).
The average price of the flight Orlando — Chicago (United States) — Orlando $191 (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 American Airlines, Frontier (Buck the Pronghorn 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 $38 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: AA938, F93043, WN3724, WN3716, G42963, G42970, UA2673, NK1114, G41250, AA465, WN805, WN3255, UA2341, WN4852, WN2549, UA2207, AA1629, UA3922, UA3903, UA2475, SY8718, WN1164, NK1369, WN3643, AA1163, UA1403, AA3031, G42971, G42949, WN4028, WN1788, NK2190, WN1320, WN6551, UA1828, AA2153, G42941, WN4791, AA1247, WN579, WN255, WN3726, 5X1327, F92791, UA3904
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. American Airlines, Frontier (Buck the Pronghorn Livery), Southwest Airlines, Allegiant Air, United Airlines, Spirit Airlines, Sun Country Airlines, UPS depart from Orlando on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through 21 Air, Aer Lingus, Aeromexico, Air Canada Express, Air France, Alaska SkyWest, 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, Porter, Porter Airlines Canada, TAP Air Portugal, 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: AA938, F93043, WN3724, WN3716, G42963, G42970, AA938, WN3716, WN3716, UA2673, UA2673, WN3716, F93043, NK1114, G41250, AA465, WN805, WN3255, WN3255, UA2341, UA2341, WN4852, WN2549, UA2207, WN2549, UA2207, WN4852, AA1629, WN2549, UA3922, UA3903, UA2475, SY8718, WN1164, F93043, WN4852, F93043, NK1369, WN3643, AA1163, UA1403, NK1114, AA3031, AA3031, G42971, G42949, WN4028, WN1788, NK2190, WN1320, NK1114, WN6551, UA1828, UA1828, UA1828, UA1828, UA1828, UA1828, UA1828, WN3255, NK2190, WN3724, AA2153, G42941, WN3724, WN4791, WN3724, NK1114, WN4791, AA1247, WN579, AA1247, WN255, WN3726, WN3726, NK1114, 5X1327, F92791, NK1369, NK2190, WN3726, UA3904
What month is the cheapest to fly from Orlando to Chicago?
High season is considered to be December and the cheapest month is July. 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: American Airlines, Frontier (Buck the Pronghorn Livery), Southwest Airlines, Allegiant Air, United Airlines, Spirit Airlines, Sun Country Airlines, UPS.
Which airlines fly from Orlando to Chicago?
All the following airlines flights Orlando — Chicago: 21 Air, Aer Lingus, Aeromexico, Air Canada Express, Air France, Alaska SkyWest, Allegiant Air, American Airlines, Amerijet International, Atlas Air, Avelo Airlines, Avianca, British Airways, Contour Aviation, Copa Airlines, Delta Connection, DHL, Emirates, FedEx, Frontier (Buck the Pronghorn Livery), GlobalX, Icelandair, Jet Linx Aviation, JetBlue, Kalitta Air, National Airlines, NetJets, Porter, Porter Airlines Canada, Southwest Airlines, Spirit Airlines, Sun Country Airlines, TAP Air Portugal, United Airlines, UPS, Virgin Atlantic, Viva, Volaris, WestJet.