RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → MCO
Chicago to Orlando
Best fare, round trip
$145
−28%
below its usual $200
you keep $55
GoodFound
- Depart
- Mon 16 Nov
- Return
- Mon 23 Nov
- Stay
- 7 nights
- Flight
- Nonstop · 3h
- Airline
Frontier Airlines
Most of this route’s monthly lows fall between $175 and $202. The drop beats 74% of measured fares on the board, over 5 observed months.
Cached fare — the booking search re-prices live before you pay.
United StatesOrlandoThe theme parks are the point, and the fare war they create is the cheapest way into Florida.Best windowFeb–Apr · Oct–NovAirportsOrlando (MCO) · Sanford (SFB)Every route into OrlandoFare seasonality
When this route gets cheap.
Fares bottom out in November around $145 and peak in February near $293, 102% dearer, across the 5 months we track. The cheapest itinerary we are tracking flies Frontier Airlines nonstop and takes about 3 hours outbound, on a 7-night trip. At $145 for 1,601 km each way, that works out to about $45 per 1,000 km flown. That is about the $41 per 1,000 km typical of short-haul fares here. Across the 7 departure cities we track at a similar distance from Orlando, this fare ranks 5th — 48% above the $98 from Dallas. The best time to be in Orlando: Feb–Apr · Oct–Nov.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 4% lower than when tracking began on 8 Aug — $207 then versus $198 now, across 18 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $118, on 11 Sep.
Cached day-level data for this route is sparse — 12 of 111 days priced, from 81 tracked fares. The days below are shown as found, with no cheapest-day or below-median call.
October 2026
November 2026
Sunday 1 November: $150. Compare fares from this day.234Thursday 5 November: $264. Compare fares from this day.6Saturday 7 November: $205. Compare fares from this day.891011Thursday 12 November: $235. Compare fares from this day.Friday 13 November: $164. Compare fares from this day.Saturday 14 November: $161. Compare fares from this day.15Monday 16 November: $145. Compare fares from this day.17181920212223242526Friday 27 November: $369. Compare fares from this day.282930
December 2026
12345678910111213141516171819202122232425262728293031
January 2027
1234567Friday 8 January: $198. Compare fares from this day.9101112131415161718192021222324252627Thursday 28 January: $185. Compare fares from this day.293031
Cached fares · checked 13 Oct 2026
Cheapest in Nov, around $145
28% below the $200 typical fare
$175Oct, below the usual price. Compare October fares.$145Nov, the cheapest month. Compare November fares.$202Dec, around the usual price. Compare December fares.$185Jan ’27, below the usual price. Compare January fares.$293Feb, above the usual price. Compare February fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Orlando, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Orlando (MCO) · Sanford (SFB)
- Flight time
- ≈3 hours outbound
- Distance
- ≈1,601 km each way
- Typical price
- $200 round-trip (seasonal median)
- Airlines on the board
- Frontier Airlines
- Itineraries
- Nonstop available
- Best months to visit
- Feb–Apr · Oct–Nov
Good to know
CHI → MCO, answered.
Is $145 a good price for Chicago to Orlando?
Yes — the seasonal median for this route is around $200 round-trip. At $145 you're 28% below that, which we rate good for this route.
What is the cheapest month to fly from Chicago to Orlando?
Across 5 months of cached-fare history, Nov comes out cheapest on this route. The best months to actually be in Orlando are Feb–Apr · Oct–Nov — when those overlap, that's your window.
How far in advance should I book CHI → Orlando?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. What we can measure is which month is cheap: across 5 months of cached fares, Nov comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to Orlando?
Yes — the current board includes nonstop fares (Frontier Airlines). The outbound leg runs around 3 hours.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Orlando?
Lock the flight first — then compare stays for 16–23 Nov · 7 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → MCO drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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