
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $111 (Kiwi.com) |
One-way from | $51 (CheapOair) |
Popular in | March |
Cheapest in | September |
Average price | $318 |
Good round-trip deal | $178 or less |
Good one-way deal | $98 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Fri 5/8
8:35 pm-12:10 am
Nonstop2h 35m
Orlando
Wed 5/13
10:15 am-12:10 pm
Nonstop2h 55m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 4/17
4:15 pm-12:40 am
1 stop7h 25m
Orlando
Mon 4/20
9:55 pm-12:50 pm
2 stops15h 55m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 5/1
4:15 pm-12:40 am
1 stop7h 25m
Orlando
Tue 5/5
9:10 pm-12:50 pm
2 stops16h 40m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 5/9
1:55 pm-10:20 pm
1 stop7h 25m
Orlando
Tue 5/12
9:10 pm-12:50 pm
2 stops16h 40m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 4/14
7:45 am-11:20 am
Nonstop2h 35m
Orlando
Mon 4/20
10:10 pm-12:05 am
Nonstop2h 55m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 4/14
11:55 am-10:20 pm
2 stops9h 25m
Orlando
Sat 4/18
7:15 am-3:30 pm
2 stops9h 15m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 5/13
11:55 am-10:20 pm
2 stops9h 25m
Orlando
Mon 5/18
6:55 am-3:30 pm
2 stops9h 35m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sat 3/21
6:50 pm-12:15 am
1 stop4h 25m
Orlando
Wed 3/25
7:15 am-9:15 am
Nonstop3h 00m
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 3/12
7:50 am-1:05 pm
1 stop4h 15m
Orlando
Sun 3/15
10:55 pm-12:50 am
Nonstop2h 55m
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Mon 4/6
2:40 pm-8:55 pm
1 stop5h 15m
Orlando
Sun 4/12
10:55 pm-12:50 pm
2 stops14h 55m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Orlando Airport, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Chicago to Orlando Airport (average of $58). Flying from Chicago to Orlando Airport in June is currently the most expensive (average of $113). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
One of the essential ways to save on airfare from Chicago to Orlando Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 14% on airfare.
Travelers seeking maximum savings on their Chicago to Orlando Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to MCO are scheduled on a Monday (77 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (16 on average).
About 16% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 148 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Food
Boarding
Overall
Comfort
Entertainment
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$165 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$521 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$343 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$166 | Average$331 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$167 | Average$348 | FlexibilityNo cancel fee | On-time69% |