What percentage of Chicago to Orlando flights are direct?

Across the trailing quarter, 42.3% of flights from Chicago to Orlando were direct. For flights that include stopovers, travelers typically experience 2 stopovers on average. This indicates that while direct options are available, a significant portion of routes involve connections. Travelers should consider this when planning their journey.

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

A direct flight from Chicago to Orlando typically takes 2 hours and 55 minutes, or 175 minutes. This covers an approximate distance of 1620 kilometers. Flights with one stopover, however, have a significantly longer median duration, averaging 8 hours and 52 minutes, which is 532 minutes. Travelers should account for these differences when choosing their flight option.

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

Historically, prices for flights from Chicago to Orlando have shown frequent fluctuations. This route is classified as one with frequent price changes across the trailing 30 days. Setting a price alert can be beneficial for travelers seeking to secure a good deal. Given the dynamic nature of pricing for this route, an alert can help identify opportune booking moments.

Flights From Chicago

To Orlando

Cheap Flights from Chicago to Orlando

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Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Orlando

Explore current cheapest deals departing from Chicago to Orlando

2026-11-11 – 2026-11-13
CHI - Orlando
78% AI deal score
$137
$84
Round trip
2026-12-04 – 2026-12-06
CHI - Orlando
49% AI deal score
$126
$114
Round trip
2026-12-02 – 2026-12-09
CHI - Orlando
82% AI deal score
$298
$114
Round trip
2026-10-16 – 2026-10-23
CHI - Orlando
68% AI deal score
$143
$115
Round trip
2026-10-05 – 2026-10-07
CHI - Orlando
68% AI deal score
$154
$116
Round trip
2026-10-21 – 2026-10-30
CHI - Orlando
66% AI deal score
$135
$116
Round trip
2026-12-03 – 2026-12-06
CHI - Orlando
48% AI deal score
$124
$116
Round trip
2026-11-11 – 2026-11-14
CHI - Orlando
65% AI deal score
$137
$118
Round trip
2026-10-28 – 2026-10-31
CHI - Orlando
65% AI deal score
$141
$119
Round trip
2026-12-08 – 2026-12-15
CHI - Orlando
82% AI deal score
$309
$120
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 September is typically the most affordable month to fly, with a median fare of $104. Other budget-friendly options include April, with a median fare of $117, and May, where the median fare is $130. These months offer the best opportunities for lower prices on this route.

Right now, fares for flights from Chicago to Orlando typically range from $130 to $599, with a median price of $298. Current fares are significantly above the typical level for this route. Only 18% of recent fares were classified as a good price, indicating that finding a low fare may require some flexibility or advance planning. New deals appear almost daily for this route, so setting up a price alert could be beneficial.

When flying from Chicago to Orlando, 42.3% of recent fares are for direct flights. This means you'll find a meaningful share of non-stop options. For itineraries that do include connections, the typical number of stopovers is 2. If you prioritize non-stop travel, it's advisable to check flight details carefully.

A typical journey from Chicago to Orlando takes about 2h 55m, including both direct and connecting itineraries. For non-stop flights, the median duration is also 2h 55m. However, if your itinerary includes connections, the median journey time extends significantly to 16h 38m, so factoring in layover times is important when planning your trip.

The flight route from Chicago to Orlando covers a distance of 1620 kilometers. This classifies it as a medium-haul flight, meaning it's too far for a short hop but not a long-distance international journey. You can expect a flight experience typical of routes within this distance category.

How much is a round trip from Chicago to Orlando

Regular price: $108 - $226

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

The regular price range for this route is between $108 and $226. The current lowest deal is $83 with Allegiant Air, for travel from Nov 11-Nov 13.

now $83

Low $108

High $226

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 $147. The most expensive month 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

Sun, Oct 4

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (MCO)

Allegiant Air

$393

$174

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$144

$121

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$268

$137

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$109

$125

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$125

$126

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$133

$131

One-way

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

3 nights

Dec 5 - Dec 8

$553 → $166

70%

5 nights

Dec 7 - Dec 12

$548 → $173

68%

4 nights

Dec 15 - Dec 19

$568 → $193

66%

2 nights

Dec 17 - Dec 19

$574 → $225

61%

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

💸 Price insights

Recent fares are below the typical level

Recent fares for Chicago to Orlando are below the typical level, with a median of $298.

📅 Best time to fly

Fly in September for the lowest prices

Historically, September offers the lowest median prices at $104 for this route.

⏱️ Flight duration

Direct flights average 2h 55m

Nonstop flights from Chicago to Orlando typically take 2 hours and 55 minutes.

✈️ Airlines & availability

42.3% of recent flights are direct

Historically, 42.3% of flights on this route have been direct, with frequent deals.

🏆 Airline highlight

Allegiant Air offers direct flights

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

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Chicago to Orlando are frequent, appearing within 30 days.

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 ~$110

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights to Orlando, located closer to the city.

📍 ~14 km from Chicago (reachable by car or public transport)

💸 Flights from ~$151

O Hare International (ORD)

O Hare International provides another choice for travelers flying from Chicago to Orlando.

📍 ~25 km from Chicago (reachable by car or public transport)

💸 Flights from ~$135

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a good option for travelers looking for potentially cheaper flights to Orlando.

📍 ~30 km from Orlando city center (reachable by car)

💸 Flights from ~$110

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 ~$131

Business & First Class Flight Deals to Orlando

Discover luxury on the budget with premium cabin class on flights from Chicago to Orlando.

Elite

Best Elite deals to Orlando

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Sep 28

Orlando, United States

86% AI deal score

$3,249

$746

Save $2,503

From ORD

Elite

Sep 19

Orlando, United States

82% AI deal score

$5,333

$2,638

Save $2,695

Air Canada, +1

Business Class

From MDW

Elite

Dec 08

Orlando, United States

79% AI deal score

$1,591

$859

Save $732

From ORD

Elite

Sep 15

Orlando, United States

78% AI deal score

$1,469

$909

Save $560

From ORD

Elite

Oct 13

Orlando, United States

77% AI deal score

$1,371

$872

Save $499

From MDW

Elite

Sep 14

Orlando, United States

77% AI deal score

$1,402

$909

Save $493

From ORD

Elite

Sep 18

Orlando, United States

77% AI deal score

$1,604

$979

Save $625

From MDW

Elite

Nov 15

Orlando, United States

76% AI deal score

$1,323

$859

Save $464

From ORD

Elite

Oct 20

Orlando, United States

76% AI deal score

$1,354

$887

Save $467

From ORD

Elite

Oct 21

Orlando, United States

76% AI deal score

$1,354

$888

Save $466

From ORD

Elite

Oct 15

Orlando, United States

76% AI deal score

$1,369

$893

Save $476

From ORD

Elite

Oct 21

Orlando, United States

76% AI deal score

$1,385

$907

Save $478

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 significantly, averaging $700. Even booking 60+ days out tends to be more expensive, with an average price of $511. Planning within the 14-27 day window generally offers the best value.

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 over the same period was $298. Travelers should aim for prices at or below the $130 threshold to secure a particularly favorable deal. Prices can go up to $599 or more for the higher end of the market.

Historically, September has been the cheapest month to fly from Chicago to Orlando, with a median price of $104. April also offers competitive prices, with a median of $117. May follows as another affordable option, with a median price of $130. These months typically present better value compared to the annual median price 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: $108 - $226

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

The regular price range for this route is between $108 and $226. The current lowest deal is $83 with Allegiant Air, for travel from Nov 11-Nov 13.

now $83

Low $108

High $226

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

Direct flights from Chicago to Orlando

Allegiant Air

Frontier Airlines

Last-minute flights going from Chicago to Orlando

Sun, Oct 4

⌛ Last-Minute

RFD - Orlando

Chicago (RFD) - Orlando (MCO)

Allegiant Air

$393

$174

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$144

$121

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$268

$137

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$109

$125

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$125

$126

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Orlando

Chicago (ORD) - Orlando (MCO)

Frontier Airlines

$133

$131

One-way

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

3 nights

Dec 5 - Dec 8

$553 → $166

70%

5 nights

Dec 7 - Dec 12

$548 → $173

68%

4 nights

Dec 15 - Dec 19

$568 → $193

66%

2 nights

Dec 17 - Dec 19

$574 → $225

61%

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

💸 Price insights

Recent fares are below the typical level

Recent fares for Chicago to Orlando are below the typical level, with a median of $298.

📅 Best time to fly

Fly in September for the lowest prices

Historically, September offers the lowest median prices at $104 for this route.

⏱️ Flight duration

Direct flights average 2h 55m

Nonstop flights from Chicago to Orlando typically take 2 hours and 55 minutes.

✈️ Airlines & availability

42.3% of recent flights are direct

Historically, 42.3% of flights on this route have been direct, with frequent deals.

🏆 Airline highlight

Allegiant Air offers direct flights

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

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Chicago to Orlando are frequent, appearing within 30 days.

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 ~$110

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights to Orlando, located closer to the city.

📍 ~14 km from Chicago (reachable by car or public transport)

💸 Flights from ~$151

O Hare International (ORD)

O Hare International provides another choice for travelers flying from Chicago to Orlando.

📍 ~25 km from Chicago (reachable by car or public transport)

💸 Flights from ~$135

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a good option for travelers looking for potentially cheaper flights to Orlando.

📍 ~30 km from Orlando city center (reachable by car)

💸 Flights from ~$110

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 ~$131

Business & First Class Flight Deals to Orlando

Discover luxury on the budget with premium cabin class on flights from Chicago to Orlando.

Elite

Best Elite deals to Orlando

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Sep 28

Orlando, United States

86% AI deal score

$3,249

$746

Save $2,503

From ORD

Elite

Sep 19

Orlando, United States

82% AI deal score

$5,333

$2,638

Save $2,695

Air Canada, +1

Business Class

From MDW

Elite

Dec 08

Orlando, United States

79% AI deal score

$1,591

$859

Save $732

From ORD

Elite

Sep 15

Orlando, United States

78% AI deal score

$1,469

$909

Save $560

From ORD

Elite

Oct 13

Orlando, United States

77% AI deal score

$1,371

$872

Save $499

From MDW

Elite

Sep 14

Orlando, United States

77% AI deal score

$1,402

$909

Save $493

From ORD

Elite

Sep 18

Orlando, United States

77% AI deal score

$1,604

$979

Save $625

From MDW

Elite

Nov 15

Orlando, United States

76% AI deal score

$1,323

$859

Save $464

From ORD

Elite

Oct 20

Orlando, United States

76% AI deal score

$1,354

$887

Save $467

From ORD

Elite

Oct 21

Orlando, United States

76% AI deal score

$1,354

$888

Save $466

From ORD

Elite

Oct 15

Orlando, United States

76% AI deal score

$1,369

$893

Save $476

From ORD

Elite

Oct 21

Orlando, United States

76% AI deal score

$1,385

$907

Save $478

Frequently Asked Questions About Flights to Orlando

Cheap Flights from Chicago to Orlando

Today’s best flight deals from Chicago to Orlando

Chicago to Orlando: Overview

Insights for flights from Chicago to Orlando

How much is a round trip from Chicago to Orlando

The cheapest time to fly from Chicago to Orlando

Direct flights from Chicago to Orlando

Last-minute flights going from Chicago to Orlando

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

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

Recent fares are below the typical level

Fly in September for the lowest prices

Direct flights average 2h 55m

42.3% of recent flights are direct

Allegiant Air offers direct flights

Deals are frequent for this route

Chicago main airports to depart from

Orlando main airports to arrive at

Airports nearby Orlando used as alternative

Business & First Class Flight Deals to Orlando

Best Elite deals to Orlando

Sep 28

Sep 19

Dec 08

Sep 15

Oct 13

Sep 14

Sep 18

Nov 15

Oct 20

Oct 21

Oct 15

Oct 21

Frequently Asked Questions About Flights to Orlando

How early should I book Chicago to Orlando flights to get the cheapest price?

How much should a flight from Chicago to Orlando cost?

What's the cheapest month to fly from Chicago to Orlando?

What percentage of Chicago to Orlando flights are direct?

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

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

Related routes

More routes from Chicago

Flights to Orlando from other cities

Chicago to Orlando: Overview

Insights for flights from Chicago to Orlando

How much is a round trip from Chicago to Orlando

The cheapest time to fly from Chicago to Orlando

Direct flights from Chicago to Orlando

Last-minute flights going from Chicago to Orlando

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

Popular Airports to fly from Chicago to Orlando

Chicago - Orlando route insights

Recent fares are below the typical level

Fly in September for the lowest prices

Direct flights average 2h 55m

42.3% of recent flights are direct

Allegiant Air offers direct flights

Deals are frequent for this route

Chicago main airports to depart from

Orlando main airports to arrive at

Airports nearby Orlando used as alternative

Business & First Class Flight Deals to Orlando

Best Elite deals to Orlando

Sep 28

Sep 19

Dec 08

Sep 15

Oct 13

Sep 14

Sep 18

Nov 15

Oct 20

Oct 21

Oct 15

Oct 21

Frequently Asked Questions About Flights to Orlando

How early should I book Chicago to Orlando flights to get the cheapest price?

How much should a flight from Chicago to Orlando cost?

What's the cheapest month to fly from Chicago to Orlando?