What percentage of Chicago to Orlando flights are direct?

In the trailing 90 days, approximately 24.2% of flights from Chicago to Orlando were direct. For travelers with connecting flights, the median number of stopovers was 2. 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?

The typical direct flight from Chicago to Orlando takes approximately 2 hours and 53 minutes, covering a distance of 1620 kilometers. Flights with one stop, however, have a significantly longer median duration of 10 hours and 36 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 one with frequent price changes. Monitoring prices can help travelers identify opportune moments to book, potentially leading to better deals. Historically, prices on this route have shown enough fluctuation to warrant active tracking.

Flights From Chicago

To Orlando

Cheap Flights from Chicago to Orlando

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Chicago to Orlando

Explore current cheapest deals departing from Chicago to Orlando

2026-12-05 – 2026-12-09
CHI - Orlando
85% AI deal score
$534
$110
Round trip
2027-01-09 – 2027-01-20
CHI - Orlando
78% AI deal score
$199
$112
Round trip
2027-01-23 – 2027-01-27
CHI - Orlando
80% AI deal score
$232
$113
Round trip
2027-01-09 – 2027-01-13
CHI - Orlando
80% AI deal score
$224
$113
Round trip
2027-01-09 – 2027-01-14
CHI - Orlando
80% AI deal score
$225
$114
Round trip
2026-11-09 – 2026-11-11
CHI - Orlando
82% AI deal score
$239
$117
Round trip
2026-12-21 – 2026-12-22
CHI - Orlando
86% AI deal score
$546
$117
Round trip
2026-12-02 – 2026-12-05
CHI - Orlando
81% AI deal score
$299
$118
Round trip
2026-12-14 – 2026-12-24
CHI - Orlando
78% AI deal score
$251
$118
Round trip
2026-12-15 – 2026-12-24
CHI - Orlando
79% AI deal score
$260
$118
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 shows that May is typically the cheapest month to fly, with a median fare of $149. Other budget-friendly options include August, with a median fare of $344, and July, where the median fare is $349. Planning your trip around these months could lead to significant savings.

Fares for flights from Chicago to Orlando typically range from $310–$681, with a median of $431. Right now, current fares are near the typical level, indicating a stable pricing environment. Approximately 27% of recent fares were classified as a good price, suggesting that opportunities for savings are available if you monitor prices.

When considering how long is the flight from Chicago to Orlando, a typical journey, including connections, takes about 2h 53m. However, most itineraries connect at least once, with connecting flights having a median duration of 18h 54m and typically involving 2 stopovers. Only 24.2% of recent fares were for direct flights from Chicago to Orlando, so you will likely encounter a connecting itinerary.

The route from Chicago to Orlando covers a distance of 1620 kilometers, classifying it as a medium-haul flight. This distance means you can expect a journey that is longer than a short domestic hop but shorter than an international or transcontinental flight. New deals for this route appear almost daily, so setting up a price alert can help you catch favorable pricing as it emerges.

How much is a round trip from Chicago to Orlando

Regular price: $163 - $608

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

The regular price range for this route is typically between $163 and $608. The current lowest deal is $115 with Frontier Airlines, for travel from December 15 to December 23.

now $115

Low $163

High $608

The cheapest time to fly from Chicago to Orlando

The cheapest month to fly from Chicago to Orlando is May, with a median price of $149. The most expensive month is April, with a median price of $914. Prices are generally lower from May to December.

May

Cheapest

Flights from $149

April

Most Expensive

Flights from $914

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

Tue, Oct 27

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$475

$274

One-way

Tue, Oct 27

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$481

$312

One-way

Tue, Oct 27

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$480

$321

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$267

$242

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$481

$287

One-way

Thu, Oct 29

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$463

$287

One-way

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

3 nights

Dec 5 - Dec 8

$535 → $123

77%

4 nights

Dec 5 - Dec 9

$534 → $123

77%

1 night

Dec 5 - Dec 6

$535 → $130

76%

1 night

Dec 8 - Dec 9

$535 → $131

76%

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

💸 Price insights

Recent fares are near the typical level.

Recent fares for Chicago to Orlando are near the typical level of $431.

📅 Best time to fly

May is historically the cheapest month to fly.

Historically, May is the cheapest month to fly from Chicago to Orlando, with a median price of $149.

⏱️ Flight duration

Direct flights take 2h 53m.

Direct flights from Chicago to Orlando typically take 2h 53m, while connecting flights average 18h 54m.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Connecting flights make up 75.8% of options, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines has a recent deal for $115.

Frontier Airlines recently offered a deal for $115 from Chicago to Orlando (Dec 15-Dec 23).

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Chicago to Orlando appear frequently, typically within a 30-day window.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

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

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$80

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a good option for flights from Chicago to Orlando, with prices from $100.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$100

Airports nearby Orlando used as alternative

Tampa International (TPA)

Tampa International (TPA) is a major international hub offering a wide variety of carriers for your trip.

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

💸 Flights from ~$161

Business & First Class Flight Deals to Orlando

69% AI deal score

$1,107

$878

Save $229

Frequently Asked Questions About Flights to Orlando

Historically, the lowest prices for flights from Chicago to Orlando are found when booking 28-59 days in advance. During this period, the average price is around $455. Booking within 0-6 days of departure typically sees prices rise significantly, with an average of $770. Even booking 60+ days out tends to be more expensive, averaging $623, indicating that the sweet spot for savings is within that one-to-two-month window.

Across the trailing quarter, a good price for a flight from Chicago to Orlando is considered to be $310 or less. The median price for this route over the same 90-day period was $431. Prices can go up to $681 or more for the higher end of the market.

Historically, May has been the cheapest month to fly from Chicago to Orlando, with a median price of $149. Other relatively inexpensive months include August and July, with median prices of $344 and $349, respectively. The annual median price for this route is $431, so flying in May offers significant savings compared to the yearly average.

Related routes

More routes from Chicago

Flights from Chicago to Paris Flights from Chicago to Philadelphia Flights from Chicago to Phoenix Flights from Chicago to Pittsburgh Flights from Chicago to Portland Flights from Chicago to Prague Flights from Chicago to Puerto Vallarta Flights from Chicago to Pune Flights from Chicago to Punta Cana Flights from Chicago to Raleigh Flights from Chicago to Reykjavik Flights from Chicago to West Palm Beach

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: $163 - $608

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

The regular price range for this route is typically between $163 and $608. The current lowest deal is $115 with Frontier Airlines, for travel from December 15 to December 23.

now $115

Low $163

High $608

The cheapest time to fly from Chicago to Orlando

The cheapest month to fly from Chicago to Orlando is May, with a median price of $149. The most expensive month is April, with a median price of $914. Prices are generally lower from May to December.

May

Cheapest

Flights from $149

April

Most Expensive

Flights from $914

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec