Chicago to Orlando flights in December 2026 from $107 MDW, ORD, RFD → MCO, SFB
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO), Orlando Sanford International Airport (SFB)
For departures in December 2026, the cheapest return found recently is $206 with Frontier Airlines, 1 Dec – 4 Dec, found 2 days ago. The cheapest one-way found recently is $107 with Frontier Airlines, 22 Dec, found 2 days ago.
Return
In December 2026, the cheapest return fare on each of 4 departure dates is usually $195 to $264. Across all 15 departure dates we hold on this route, it is usually $183 to $305. Of the 3 months with enough return fares to compare, 1 is usually cheaper than December 2026.
Cheapest return found recently
$206
1 Dec – 4 Dec · Frontier Airlines
Chicago Midway International Airport (MDW) → Orlando International Airport (MCO)
out 1 stop, back 1 stop
found 2 days ago
Cheapest we hold, of any age
$160
11 Dec – 13 Dec · Frontier Airlines
O'Hare International Airport (ORD) → Orlando International Airport (MCO)
out 1 stop, back nonstop
found 8 days ago
The cheapest dates in December 2026
| Dates | From | Airline | Stops | Found | |
|---|---|---|---|---|---|
| 11 Dec – 13 Dec | $160 | Frontier Airlines | out 1 stop, back nonstop | found 8 days ago | See prices for these dates |
| 1 Dec – 4 Dec | $206 | Frontier Airlines | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 3 Dec – 6 Dec | $256 | Frontier Airlines | out nonstop, back 1 stop | found 7 days ago | See prices for these dates |
| 24 Dec – 28 Dec | $287 | Frontier Airlines | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
Every date we hold
4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 1 Dec – 4 Dec | $206 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 3 Dec – 6 Dec | $256 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out nonstop, back 1 stop | found 7 days ago | See prices for these dates |
| 11 Dec – 13 Dec | $160 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 8 days ago | See prices for these dates |
| 24 Dec – 28 Dec | $287 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
Which month looks cheapest?
January 2027 is the cheapest month — from $134.
One-way
In December 2026, the cheapest one-way fare on each of 9 departure dates is usually $101 to $123. Across all 14 departure dates we hold on this route, it is usually $100 to $128. Of the 2 months with enough one-way fares to compare, December 2026 is usually the most expensive.
Cheapest one-way found recently
$107
22 Dec · Frontier Airlines
Chicago Midway International Airport (MDW) → Orlando International Airport (MCO)
1 stop
found 2 days ago
Cheapest we hold, of any age
$93
11 Dec · Frontier Airlines
O'Hare International Airport (ORD) → Orlando International Airport (MCO)
1 stop
found 4 days ago
The cheapest dates in December 2026
| Dates | From | Airline | Stops | Found | |
|---|---|---|---|---|---|
| 11 Dec | $93 | Frontier Airlines | 1 stop | found 4 days ago | Open this trip |
| 30 Dec | $96 | Frontier Airlines | 1 stop | found 6 days ago | Open this trip |
| 23 Dec | $101 | Frontier Airlines | 1 stop | found 6 days ago | Open this trip |
| 22 Dec | $107 | Frontier Airlines | 1 stop | found 2 days ago | Open this trip |
| 25 Dec | $116 | Frontier Airlines | nonstop | found 6 days ago | Open this trip |
Every date we hold
9 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 11 Dec | $93 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found 4 days ago | Open this trip |
| 21 Dec | $130 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | nonstop | found 2 days ago | Open this trip |
| 22 Dec | $107 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | 1 stop | found 2 days ago | Open this trip |
| 23 Dec | $101 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found 6 days ago | Open this trip |
| 24 Dec | $136 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | 1 stop | found 4 days ago | Open this trip |
| 25 Dec | $116 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | nonstop | found 6 days ago | Open this trip |
| 29 Dec | $116 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | 1 stop | found 3 days ago | Open this trip |
| 30 Dec | $96 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found 6 days ago | Open this trip |
| 31 Dec | $123 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found 6 days ago | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $81.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work