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Cheap flights Chicago — Orlando

Chicago (CHI, US) Orlando (ORL, US)
from $71 1 587 km ~2h 22m 6 flights found 4 airlines cheapest on Wednesday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $71 on 08.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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December 2026
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January 2027
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Prices found for 19 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
15 Nov 2026, Sun
Allegiant Air G4 499
19:30
RFD Chicago Rockford International Airport
23:50
MCO Orlando International Airport
4h 20m 1 stop
Kiwi.com
$107
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 2945
21:55
MDW Chicago Midway International Airport
03:00
MCO Orlando International Airport
5h 5m Direct
Farehutz
$145
View this ticket
Route characteristics
Distance
1 587 km
Flight time
2h 22m
Time difference
+1h
Minimum price
from $71 (08.12.2026)
Average price
$105
Maximum price
$134
Departures per week
1
Cheapest day
Wednesday
Departure airports (3)
MDW Chicago Midway International Airport ORD O'Hare International Airport RFD Chicago Rockford International Airport
Arrival airports (2)
MCO Orlando International Airport SFB Orlando Sanford International Airport
Airlines (4)
G4 Allegiant Air F9 Frontier Airlines WN Southwest Airlines AA American Airlines
Agencies (5)
Trip.com Kiwi.com Farera Farehutz Tickets
Airlines — cheapest prices 4
Allegiant Air
Allegiant Air
Low-cost 2 flights · 2 days
$103
Frontier Airlines
Frontier Airlines
Low-cost 2 flights · 2 days
$112
Southwest Airlines
Southwest Airlines
Low-cost 1 flights · 1 days
$145
American Airlines
American Airlines
1 flights · 1 days
$188
Where to buy tickets 5
Trip.com
2 tickets · 2 days
from $103
Kiwi.com
1 tickets · 1 days
from $107
Farera
1 tickets · 1 days
from $112
Farehutz
1 tickets · 1 days
from $145
Tickets
1 tickets · 1 days
from $188
Airports

From — Chicago (3)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport
  • RFD Chicago Rockford International Airport

To — Orlando (2)

  • MCO Orlando International Airport
  • SFB Orlando Sanford International Airport
Other destinations from Chicago
Las Vegas
US · Hub
Denver
US · Hub
Nashville
US
Fort Lauderdale
US
Minneapolis
US · Hub
St Louis
US
Atlanta
US · Hub
Philadelphia
US · Hub
Tampa
US
Phoenix
US
New Orleans
US
Baltimore
US
Frequently asked questions about the route Chicago — Orlando
How long is the flight from Chicago to Orlando?
Approximate flight time — 2h 22m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Chicago to Orlando?
The straight-line distance — 1 587 km.
How much do flights from Chicago to Orlando cost?
The minimum price over 3 months — from $71 on 08.12.2026.
What is the average ticket price?
The average price — $105. Range: $71 — $134.
What is the time difference between Chicago and Orlando?
The difference — +1h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport), ORD (O'Hare International Airport), RFD (Chicago Rockford International Airport).
To which airports in Orlando do flights arrive?
To Orlando: MCO (Orlando International Airport), SFB (Orlando Sanford International Airport).
Which airlines fly this route?
This route is served by 4 airlines: Allegiant Air, Frontier Airlines, Southwest Airlines, American Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $145. Total direct flights found: 1.
Which day of the week is cheapest?
The cheapest day of the week — Wednesday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Chicago — Orlando

Flights Chicago — Orlando is a popular route. The straight-line distance is 1 587 km. Flight time 2h 22m. Time difference +1h.

From Chicago (CHI) flights depart from 3 airports: MDW, ORD, RFD. To Orlando (ORL) — 2 arrival airports: MCO, SFB.

4 airlines operate on this route: Allegiant Air, Frontier Airlines, Southwest Airlines, American Airlines.

The minimum price for the next 3 months — from $71 (08.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $105, ranging from $71 to $134. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Wednesday.

Other destinations in United States from Chicago
Denver
US
Las Vegas
US
Nashville
US
Fort Lauderdale
US
Minneapolis
US
St Louis
US
Atlanta
US
Philadelphia
US

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