What percentage of Chicago to Orlando flights are direct?

In the trailing 90 days, approximately 42.3% of flights from Chicago to Orlando have been direct. For flights that include stopovers, travelers typically experience a median of 2 connections. This indicates that while direct options are available, a significant portion of routes involve at least one stop.

How long does it take to fly from Chicago to Orlando?

A direct flight from Chicago to Orlando typically takes about 2 hours and 55 minutes, covering a distance of 1620 kilometers. Flights with one stop, however, have a significantly longer median duration, averaging around 8 hours and 52 minutes. Travelers should consider these differences when planning their journey.

Should I set a price alert for Chicago to Orlando flights?

Yes, setting a price alert for Chicago to Orlando flights is advisable. This route is classified as having frequent price fluctuations. Historically, prices on this route change often, making price alerts a useful tool for tracking deals. This helps travelers identify opportune moments to book their flights.

Flights From Chicago

To Orlando

Cheap Flights from Chicago to Orlando

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Orlando

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to Orlando

Explore current cheapest deals departing from Chicago to Orlando

2026-10-26 – 2026-10-28
CHI - Orlando
81% AI deal score
$163
$83
Round trip
2026-10-28 – 2026-10-30
CHI - Orlando
80% AI deal score
$163
$90
Round trip
2026-11-09 – 2026-11-11
CHI - Orlando
79% AI deal score
$153
$90
Round trip
2026-08-31 – 2026-09-11
CHI - Orlando
73% AI deal score
$119
$90
Round trip
2026-10-14 – 2026-10-30
CHI - Orlando
76% AI deal score
$133
$91
Round trip
2026-08-10 – 2026-08-31
CHI - Orlando
68% AI deal score
$114
$92
Round trip
2026-10-14 – 2026-10-28
CHI - Orlando
76% AI deal score
$136
$92
Round trip
2026-10-19 – 2026-10-21
CHI - Orlando
79% AI deal score
$161
$92
Round trip
2026-08-14 – 2026-09-11
CHI - Orlando
67% AI deal score
$111
$94
Round trip
2026-10-14 – 2026-10-21
CHI - Orlando
77% AI deal score
$152
$96
Round trip

Chicago to Orlando: Overview

Insights for flights from Chicago to Orlando

For travelers looking for cheap flights from Chicago to Orlando, the data indicates that September is typically the cheapest month to fly, with a median fare of $104. Other cost-effective options include April, with a median fare of $117, and May, where the median fare is $130. These months offer the most favorable prices for this route.

Fares for flights from Chicago to Orlando typically range from $130 to $599, with a median of $298. Right now, current fares are above the typical level, and only 18% of recent fares were classified as a good price. New deals appear almost daily for this route, so monitoring prices can be beneficial.

When considering how long is the flight from Chicago to Orlando, a typical journey, including connections, takes about 2h 55m. This route has a mixed share of direct flights, with 42.3% of itineraries being non-stop. For the remaining itineraries that include connections, travelers can expect a median of 2 stopovers.

The distance between Chicago and Orlando is approximately 1620 kilometers, classifying this as a medium-haul route. This distance typically translates to a flight duration that balances convenience with the need for potential connections.

How much is a round trip from Chicago to Orlando

Regular price: $125 - $220

Prices for flights from Chicago to Orlando are currently below the regular range.

The regular price range for flights from Chicago to Orlando is between $125 and $220. The current lowest deal is $84 with Allegiant Air, for travel from Oct 26-Oct 28.

now $84

Low $125

High $220

The cheapest time to fly from Chicago to Orlando

Flights from Chicago to Orlando are cheapest in May, with a median price of $147. The most expensive month to fly is December, with a median price of $1353. Prices are generally lower from January to October.

May

Cheapest

Flights from $147

December

Most Expensive

Flights from $1,353

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Orlando

Allegiant Air

Frontier Airlines

Last-minute flights going from Chicago to Orlando

Mon, Aug 3

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$305

$178

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$117

$113

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$263

$147

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$288

$169

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$341

$175

One-way

Fri, Aug 7

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (SFB)

Allegiant Air

$282

$181

One-way

Biggest price drops on these dates for flights from Chicago to Orlando

3 nights

Dec 24 - Dec 27

$692 → $312

55%

3 nights

Oct 4 - Oct 7

$386 → $177

54%

2 nights

Oct 8 - Oct 10

$385 → $182

53%

5 nights

Oct 11 - Oct 16

$383 → $182

53%

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Orlando are below the typical level of $298.

📅 Best time to fly

Fly in May for the best prices

Historically, May is the cheapest month to fly, with a median price of $147.

⏱️ Flight duration

Direct flights take 2h 55m

The typical direct flight from Chicago to Orlando takes 2 hours and 55 minutes.

✈️ Airlines & availability

42.3% of recent flights are direct

Direct flights are available from Chicago to Orlando, making up 42.3% of recent routes.

🏆 Airline highlight

Allegiant Air offers direct flights

Allegiant Air is one of the airlines providing direct flights on this route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Orlando are frequent, appearing often in the last 30 days.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers the cheapest flights from Chicago to Orlando, making it a budget-friendly option.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$66

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights from Chicago to Orlando due to its closer proximity.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~$156

O Hare International (ORD)

O Hare International provides another option for flights from Chicago to Orlando.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$92

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International Airport is a good option for flights to the Orlando area.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$66

Airports nearby Orlando used as alternative

Tampa International (TPA)

Tampa International is a major international hub offering a wide variety of domestic and international carriers.

📍 ~135 km from Orlando (approximately 1.5 to 2 hours drive depending on I-4 traffic)

💸 Flights from ~$121

Business & First Class Flight Deals to Orlando

78% AI deal score

$1,104

$722

Save $382

Frequently Asked Questions About Flights to Orlando

Historically, the lowest prices for flights from Chicago to Orlando are found when booking 14-27 days in advance. During this period, the average price is around $305. Booking within 0-6 days of departure typically sees prices rise to about $700. Even booking 60+ days out can result in higher average prices, around $511, so planning within the optimal two-to-four-week window is generally recommended.

Across the trailing quarter, a good price for a flight from Chicago to Orlando is considered to be $130 or less. The median price for this route historically stands at $298. Prices can go up significantly, with 75% of flights costing $599 or more. Travelers aiming for the best value should target fares around the $130 threshold.

Historically, September is often the cheapest month to fly from Chicago to Orlando, with a median price of $104. April also offers competitive fares, with a median price of $117. May can also be a good option, showing a median price of $130. These months typically offer prices significantly lower than the annual median of $298 for this route.

Related routes

More routes from Chicago

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Flights to Orlando from other cities

Flights from Charlotte to Orlando Flights from Cincinnati to Orlando Flights from Cleveland to Orlando Flights from Columbus to Orlando Flights from Dallas to Orlando Flights from Dayton to Orlando Flights from Denver to Orlando Flights from Detroit to Orlando Flights from Dubai to Orlando Flights from Dublin to Orlando Flights from Evansville to Orlando Flights from Flint to Orlando

Chicago to Orlando: Overview

Insights for flights from Chicago to Orlando

How much is a round trip from Chicago to Orlando

Regular price: $125 - $220

Prices for flights from Chicago to Orlando are currently below the regular range.

The regular price range for flights from Chicago to Orlando is between $125 and $220. The current lowest deal is $84 with Allegiant Air, for travel from Oct 26-Oct 28.

now $84

Low $125

High $220

The cheapest time to fly from Chicago to Orlando

May

Cheapest

Flights from $147

December

Most Expensive

Flights from $1,353

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec