What percentage of Chicago to Orlando flights are direct?

Across the trailing 90 days, approximately 42.3% of flights from Chicago to Orlando have been direct. For journeys that include stopovers, travelers typically experience a median of 2 connections. This indicates that while direct options are available, a significant portion of flights on this route 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 in flight time when planning their journey.

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

Historically, deals for flights from Chicago to Orlando have been frequent. This route is classified as one where price fluctuations occur regularly. Setting a price alert can be beneficial to capture these frequent deals as they emerge, helping travelers secure more favorable fares for their journey.

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 12 days ago

406 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 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
79% AI deal score
$157
$91
Round trip
2026-10-26 – 2026-10-30
CHI - Orlando
77% AI deal score
$157
$96
Round trip
2026-09-09 – 2026-09-11
CHI - Orlando
68% AI deal score
$138
$101
Round trip
2026-10-07 – 2026-10-28
CHI - Orlando
68% AI deal score
$130
$104
Round trip
2026-11-10 – 2026-12-07
CHI - Orlando
50% AI deal score
$117
$106
Round trip
2026-11-02 – 2026-11-06
CHI - Orlando
69% AI deal score
$142
$107
Round trip
2026-11-04 – 2026-11-11
CHI - Orlando
68% AI deal score
$138
$108
Round trip
2026-10-14 – 2026-10-21
CHI - Orlando
74% AI deal score
$152
$110
Round trip
2026-10-14 – 2026-10-28
CHI - Orlando
67% AI deal score
$135
$110
Round trip
2026-09-02 – 2026-10-02
CHI - Orlando
47% AI deal score
$106
$110
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 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. Planning your trip during these months can lead to more favorable prices.

Fares for this route typically range from $130–$599, with a median of $298. Right now, current fares are significantly above the typical level, indicating a less opportune time for booking. Only 18% of recent fares were classified as a good price, suggesting that finding a bargain may require more flexibility or a longer search.

When considering direct flights from Chicago to Orlando, the route has a mixed share of non-stop itineraries. Approximately 42.3% of recent fares were for direct flights. For itineraries that include connections, travelers can expect a typical journey with 2 stopovers. New deals for this route appear almost daily, making it beneficial to monitor prices regularly.

A typical journey from Chicago to Orlando takes about 2h 55m, including both direct and connecting itineraries. This duration reflects the overall travel time you might experience. For non-stop flights, the median flight time is also 2h 55m, while connecting flights have a significantly longer median duration of 16h 38m.

The distance between Chicago and Orlando is approximately 1620 kilometers. This places the route in the medium-haul category, meaning it's a journey that typically involves a few hours in the air, often suitable for a single-day travel plan.

How much is a round trip from Chicago to Orlando

Regular price: $118 - $225

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

The regular price range for flights from Chicago to Orlando is $118 to $225. The current lowest deal is $98 with Allegiant Air for travel from Oct 14-Oct 21.

now $98

Low $118

High $225

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

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$611

$383

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$688

$405

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$559

$405

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$693

$419

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$710

$553

One-way

Fri, Aug 7

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$713

$387

One-way

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

1 night

Aug 14 - Aug 15

$684 → $164

76%

9 nights

Dec 1 - Dec 10

$620 → $214

65%

6 nights

Dec 11 - Dec 17

$638 → $259

59%

3 nights

Aug 12 - Aug 15

$665 → $317

52%

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, with deals around $98.

📅 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 $147.

⏱️ Flight duration

Direct flights average 2h 55m

Direct flights from Chicago to Orlando typically take 2h 55m. Connecting flights average 16h 38m.

✈️ Airlines & availability

42.3% of recent flights are direct

42.3% of recent flights from Chicago to Orlando are direct, with frequent deals available.

🏆 Airline highlight

Allegiant Air offers direct flights

Allegiant Air offers direct flights from Chicago to Orlando, with 1 direct deal recently found.

🎯 Booking tip

Good prices are available 18% of the time

Good prices for flights from Chicago to Orlando are available 18% of the time.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers the cheapest flights from Chicago to Orlando, starting from $66.

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

💸 Flights from ~$66

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a good option for flights to Orlando, offering a budget-friendly choice.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$93

Airports nearby Orlando used as alternative

Tampa International (TPA)

Tampa International is a major international hub, offering a wide variety of carriers for reliable long-haul flights.

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

💸 Flights from ~$114

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 05

Orlando, United States

85% AI deal score

$4,852

$2,049

Save $2,803

Aeroméxico, +1

Business Class

From ORD

Elite

Sep 05

Orlando, United States

85% AI deal score

$4,858

$2,071

Save $2,787

Aeroméxico, +1

Business Class

From MDW

Elite

Oct 06

Orlando, United States

85% AI deal score

$5,054

$2,108

Save $2,946

Aeroméxico, +1

Business Class

From ORD

Elite

Sep 07

Orlando, United States

84% AI deal score

$4,829

$2,089

Save $2,740

Aeroméxico, +1

Business Class

From ORD

Elite

Sep 05

Orlando, United States

84% AI deal score

$4,844

$2,105

Save $2,739

Aeroméxico, +1

Business Class

From MDW

Elite

Oct 06

Orlando, United States

84% AI deal score

$5,115

$2,142

Save $2,973

Aeroméxico, +1

Business Class

From ORD

Elite

Sep 05

Orlando, United States

84% AI deal score

$4,902

$2,161

Save $2,741

Aeroméxico, +1

Business Class

From MDW

Elite

Dec 02

Orlando, United States

82% AI deal score

$1,330

$665

Save $665

From MDW

Orlando, United States

81% AI deal score

$5,306

$2,075

Save $3,231

Aeroméxico, +1

Business Class

Frequently Asked Questions About Flights to Orlando

Historically, the lowest prices for flights from Chicago to Orlando are found by 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 can result in higher prices, with an average of $511, indicating that waiting for the optimal window is beneficial.

Based on historical data across the trailing quarter, a good price for a flight from Chicago to Orlando is typically around $130 or less. The median price for this route has been observed at $298. Prices can go up to $599 or more for the higher end of the market, so aiming for the $130 threshold can help secure a more economical fare.

Historically, September has been the cheapest month to fly from Chicago to Orlando, with a median price of $104. April and May also offer competitive prices, with median fares of $117 and $130 respectively. These months are considerably more affordable than the annual median price of $298 for this route, making them ideal for budget-conscious travelers.

Related routes

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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: $118 - $225

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

The regular price range for flights from Chicago to Orlando is $118 to $225. The current lowest deal is $98 with Allegiant Air for travel from Oct 14-Oct 21.

now $98

Low $118

High $225

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

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$611

$383

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$688

$405

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$559

$405

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$693

$419

One-way

Thu, Aug 6

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$710

$553

One-way

Fri, Aug 7

⌛ Last-Minute

MDW - Orlando

Chicago (MDW) - Orlando (MCO)

$713

$387

One-way

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

1 night

Aug 14 - Aug 15

$684 → $164

76%

9 nights

Dec 1 - Dec 10

$620 → $214

65%

6 nights

Dec 11 - Dec 17

$638 → $259

59%

3 nights

Aug 12 - Aug 15

$665 → $317

52%

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, with deals around $98.

📅 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 $147.

⏱️ Flight duration

Direct flights average 2h 55m

Direct flights from Chicago to Orlando typically take 2h 55m. Connecting flights average 16h 38m.

✈️ Airlines & availability

42.3% of recent flights are direct

42.3% of recent flights from Chicago to Orlando are direct, with frequent deals available.

🏆 Airline highlight

Allegiant Air offers direct flights

Allegiant Air offers direct flights from Chicago to Orlando, with 1 direct deal recently found.

🎯 Booking tip

Good prices are available 18% of the time

Good prices for flights from Chicago to Orlando are available 18% of the time.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers the cheapest flights from Chicago to Orlando, starting from $66.

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

💸 Flights from ~$66

Orlando main airports to arrive at

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International is a good option for flights to Orlando, offering a budget-friendly choice.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$93

Airports nearby Orlando used as alternative

Tampa International (TPA)

Tampa International is a major international hub, offering a wide variety of carriers for reliable long-haul flights.

Orlando, United States

82% AI deal score

$1,330

$665

Save $665

From MDW

Orlando, United States

81% AI deal score

$5,306

$2,075

Save $3,231

Aeroméxico, +1

Business Class

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

May is historically the cheapest month to fly

Direct flights average 2h 55m

42.3% of recent flights are direct

Allegiant Air offers direct flights

Good prices are available 18% of the time

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 05

Sep 05

Oct 06

Sep 07

Sep 05

Oct 06

Sep 05

Dec 02

Dec 02

Oct 06

Sep 05

Sep 05

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

May is historically the cheapest month to fly

Direct flights average 2h 55m

42.3% of recent flights are direct

Allegiant Air offers direct flights

Good prices are available 18% of the time

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 05

Sep 05

Oct 06

Sep 07

Sep 05

Oct 06

Sep 05

Dec 02

Dec 02

Oct 06

Sep 05

Sep 05

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?