Can I fly direct from Orlando to Chicago?

Yes, direct flights from Orlando to Chicago are available. Historically, approximately 49.7% of flights on this route have been direct. For journeys that include stopovers, travelers typically experience one stop. This indicates a good availability of non-stop options for this route.

What's the flight time from Orlando to Chicago?

A direct flight from Orlando to Chicago typically takes 3 hours and 8 minutes, covering a distance of 1595 kilometers. For flights with one stop, the median travel time is considerably longer, averaging 8 hours and 2 minutes. Travelers seeking the quickest journey should prioritize direct flight options.

How often do Orlando to Chicago flight prices drop?

Prices for flights from Orlando to Chicago are classified as dropping frequently. This indicates that travelers on this route often see fluctuations that can lead to opportunities for savings. Historically, this route has shown consistent price changes, suggesting that monitoring fares can be beneficial for securing a good deal.

Flights From Orlando

To Chicago

Cheap Flights from Orlando to Chicago

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Deals from

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 Orlando to Chicago

Explore current cheapest deals departing from Orlando to Chicago

2026-11-06 – 2026-11-11
ORL - Chicago
69% AI deal score
$106
$84
Round trip
2026-11-13 – 2026-11-16
ORL - Chicago
66% AI deal score
$112
$99
Round trip
2026-11-07 – 2026-11-11
ORL - Chicago
44% AI deal score
$100
$105
Round trip
2026-10-30 – 2026-11-11
ORL - Chicago
46% AI deal score
$91
$105
Round trip
2026-11-06 – 2026-11-09
ORL - Chicago
47% AI deal score
$108
$106
Round trip
2026-12-03 – 2026-12-08
ORL - Chicago
49% AI deal score
$123
$106
Round trip
2026-12-04 – 2026-12-07
ORL - Chicago
48% AI deal score
$122
$110
Round trip
2026-10-09 – 2026-10-20
ORL - Chicago
44% AI deal score
$91
$112
Round trip
2026-10-16 – 2026-11-11
ORL - Chicago
45% AI deal score
$87
$112
Round trip
2026-10-23 – 2026-11-11
ORL - Chicago
45% AI deal score
$87
$112
Round trip

Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

Right now, only 1% of recent fares from Orlando to Chicago are classified as a good price. Fares for this route typically range from $101–$323, with a median of $158. Current fares are significantly above the typical level for this route. New deals appear almost daily, suggesting opportunities for better pricing may arise.

For travelers seeking cheap flights from Orlando to Chicago, the cheapest time to fly is typically in September, with a median fare of $99. October also offers competitive pricing, with a median fare of $101. Following closely, August presents a median fare of $106, making these months the most budget-friendly options for this journey.

The journey from Orlando to Chicago covers a distance of 1595 km, classifying it as a medium-haul flight. This distance means you are looking at a flight that is neither short nor extremely long, offering a balanced travel experience.

A typical journey from Orlando to Chicago takes about 3h 8m, including connections. While a meaningful share of itineraries are non-stop, the rest typically connect once. This median duration accounts for both direct flights from Orlando to Chicago and those with a single stopover, providing a realistic expectation for your travel time.

How much is a round trip from Orlando to Chicago

Regular price: $77 - $186

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

The regular price range for flights from Orlando to Chicago is $77 to $186. The current lowest deal is $105 with Allegiant Air, for travel from Oct 30-Nov 11.

now $105

Low $77

High $186

The cheapest time to fly from Orlando to Chicago

The cheapest month to fly from Orlando to Chicago is August, with a median price of $115. The most expensive month is March, with a median price of $660. Prices are generally lower from February to November.

August

Cheapest

Flights from $115

March

Most Expensive

Flights from $660

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Orlando to Chicago

Frontier Airlines

Allegiant Air

Last-minute flights going from Orlando to Chicago

Wed, Sep 16

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$381

$279

One-way

Mon, Sep 21

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$336

$243

One-way

Fri, Sep 25

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$317

$229

One-way

Fri, Sep 25

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$319

$239

One-way

Mon, Sep 28

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$306

$226

One-way

Fri, Oct 2

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$237

$217

One-way

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

7 nights

Sep 18 - Sep 25

$371 → $248

33%

2 nights

Oct 16 - Oct 18

$265 → $162

39%

1 night

Oct 23 - Oct 24

$262 → $164

37%

1 night

Oct 6 - Oct 7

$210 → $114

46%

Popular Airports to fly from Orlando to Chicago

Orlando - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares for Orlando to Chicago are above the typical level at $158.

📅 Best time to fly

September is historically the cheapest month to fly.

Historically, September is the cheapest month to fly from Orlando to Chicago, with a median price of $99.

⏱️ Flight duration

Direct flights average 3h 8m.

Direct flights from Orlando to Chicago typically take 3h 8m, while connecting flights average 14h 44m.

✈️ Airlines & availability

About half of recent flights are direct.

Approximately 49.7% of recent flights on this route are direct, with connecting flights typically having 1 stopover.

🏆 Airline highlight

Frontier Airlines and Allegiant Air offer direct flights.

Frontier Airlines and Allegiant Air are among the airlines offering direct flights on this route.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Orlando to Chicago appear frequently, with a good price share of 1%.

Orlando main airports to depart from

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International offers a budget-friendly option for flights from Orlando to Chicago.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$112

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International is a good option for budget-conscious travelers flying from Orlando to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$96

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car). Requires travel across state lines into Wisconsin.

💸 Flights from ~$128

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From MCO

Elite

Sep 18

Chicago, United States

80% AI deal score

$2,427

$1,503

Save $924

Porter Airlines, +1

Business Class

From MCO

Elite

Sep 19

Chicago, United States

78% AI deal score

$2,353

$1,569

Save $784

Air Transat, +1

Business Class

From MCO

Elite

Sep 18

Chicago, United States

78% AI deal score

$2,337

$1,593

Save $744

Porter Airlines, +1

Business Class

From MCO

Elite

Sep 18

Chicago, United States

78% AI deal score

$2,354

$1,624

Save $730

Porter Airlines, +1

Business Class

From MCO

Elite

Sep 18

Chicago, United States

76% AI deal score

$2,445

$1,804

Save $641

Porter Airlines, +1

Business Class

From MCO

Elite

Dec 22

Chicago, United States

74% AI deal score

$1,308

$883

Save $425

From MCO

Elite

Dec 24

Chicago, United States

73% AI deal score

$1,203

$859

Save $344

From MCO

Elite

Dec 25

Chicago, United States

73% AI deal score

$1,216

$859

Save $357

From MCO

Elite

Dec 24

Chicago, United States

73% AI deal score

$1,216

$884

Save $332

From MCO

Elite

Dec 23

Chicago, United States

72% AI deal score

$1,240

$898

Save $342

From MCO

Elite

Oct 01

Chicago, United States

72% AI deal score

$1,330

$959

Save $371

From MCO

Elite

Sep 18

Chicago, United States

71% AI deal score

$2,418

$1,839

Save $579

Porter Airlines, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Orlando to Chicago 60+ days in advance has yielded the lowest average prices, typically around $132. Prices tend to increase significantly closer to the departure date. For instance, flights booked 7-13 days out have an average price of $270, while those booked within 0-6 days of travel average $497. Planning ahead by at least two months can result in substantial savings.

Based on historical data from the trailing 90 days, a good price for a flight from Orlando to Chicago is considered to be $101 or less. The median price for this route has been $158. Prices can vary, with 75% of observed fares being $323 or less. Aiming for a price close to or below $101 will generally secure a favorable deal.

Historically, the cheapest months to fly from Orlando to Chicago are September, with a median price of $99, and October, with a median price of $101. August also shows competitive pricing, with a median of $106. Across the trailing quarter, these months consistently offer prices below the annual median of $158, making them ideal for budget-conscious travelers.

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Flights to Chicago from other cities

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Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

How much is a round trip from Orlando to Chicago

Regular price: $77 - $186

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

The regular price range for flights from Orlando to Chicago is $77 to $186. The current lowest deal is $105 with Allegiant Air, for travel from Oct 30-Nov 11.

now $105

Low $77

High $186

The cheapest time to fly from Orlando to Chicago

August

Cheapest

Flights from $115

March

Most Expensive

Flights from $660

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Orlando to Chicago

Frontier Airlines

Allegiant Air

Last-minute flights going from Orlando to Chicago

Wed, Sep 16

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$381

$279

One-way

Mon, Sep 21

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$336

$243

One-way

Fri, Sep 25

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$317

$229

One-way

Fri, Sep 25

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$319

$239

One-way

Mon, Sep 28

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$306

$226

One-way

Fri, Oct 2

⌛ Last-Minute

SFB - Chicago

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$237

$217

One-way

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

7 nights

Sep 18 - Sep 25

$371 → $248

33%

2 nights

Oct 16 - Oct 18

$265 → $162

39%

1 night

Oct 23 - Oct 24

$262 → $164

37%

1 night

Oct 6 - Oct 7

$210 → $114

46%

Popular Airports to fly from Orlando to Chicago

Orlando - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares for Orlando to Chicago are above the typical level at $158.

📅 Best time to fly

September is historically the cheapest month to fly.

Historically, September is the cheapest month to fly from Orlando to Chicago, with a median price of $99.

⏱️ Flight duration

Direct flights average 3h 8m.

Direct flights from Orlando to Chicago typically take 3h 8m, while connecting flights average 14h 44m.

✈️ Airlines & availability

About half of recent flights are direct.

Approximately 49.7% of recent flights on this route are direct, with connecting flights typically having 1 stopover.

🏆 Airline highlight

Frontier Airlines and Allegiant Air offer direct flights.

Frontier Airlines and Allegiant Air are among the airlines offering direct flights on this route.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Orlando to Chicago appear frequently, with a good price share of 1%.

Orlando main airports to depart from

Orlando Sanford International (SFB)

Cheapest

Orlando Sanford International offers a budget-friendly option for flights from Orlando to Chicago.

📍 ~30 km from Orlando (reachable by car)

💸 Flights from ~$112

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International is a good option for budget-conscious travelers flying from Orlando to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$96

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

Chicago, United States

74% AI deal score

$1,308

$883

Save $425

From MCO

Elite

Dec 24

Chicago, United States

73% AI deal score

$1,203

$859

Save $344

From MCO

Elite

Dec 25

Chicago, United States

73% AI deal score

$1,216

$859

Save $357

From MCO

Elite

Dec 24

Chicago, United States

73% AI deal score

$1,216

$884

Save $332

From MCO

Elite

Dec 23

Chicago, United States

72% AI deal score

$1,240

$898

Save $342

From MCO

Elite

Oct 01

Chicago, United States

72% AI deal score

$1,330

$959

Save $371

From MCO

Elite

Sep 18

Chicago, United States

71% AI deal score

$2,418

$1,839

Save $579

Porter Airlines, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Orlando to Chicago

Today’s best flight deals from Orlando to Chicago

Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

How much is a round trip from Orlando to Chicago

The cheapest time to fly from Orlando to Chicago

Direct flights from Orlando to Chicago

Last-minute flights going from Orlando to Chicago

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

Popular Airports to fly from Orlando to Chicago

Orlando - Chicago route insights

Recent fares are above the typical level.

September is historically the cheapest month to fly.

Direct flights average 3h 8m.

About half of recent flights are direct.

Frontier Airlines and Allegiant Air offer direct flights.

Deals appear frequently on this route.

Orlando main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 18

Sep 19

Sep 18

Sep 18

Sep 18

Dec 22

Dec 24

Dec 25

Dec 24

Dec 23

Oct 01

Sep 18

Frequently Asked Questions About Flights to Chicago

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

How much should a flight from Orlando to Chicago cost?

When is the cheapest time of year to fly from Orlando to Chicago?

Can I fly direct from Orlando to Chicago?

What's the flight time from Orlando to Chicago?

How often do Orlando to Chicago flight prices drop?

Related routes

More routes from Orlando

Flights to Chicago from other cities

Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

How much is a round trip from Orlando to Chicago

The cheapest time to fly from Orlando to Chicago

Direct flights from Orlando to Chicago

Last-minute flights going from Orlando to Chicago

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

Popular Airports to fly from Orlando to Chicago

Orlando - Chicago route insights

Recent fares are above the typical level.

September is historically the cheapest month to fly.

Direct flights average 3h 8m.

About half of recent flights are direct.

Frontier Airlines and Allegiant Air offer direct flights.

Deals appear frequently on this route.

Orlando main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 18

Sep 19

Sep 18

Sep 18

Sep 18

Dec 22

Dec 24

Dec 25

Dec 24

Dec 23

Oct 01

Sep 18

Frequently Asked Questions About Flights to Chicago

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

How much should a flight from Orlando to Chicago cost?

When is the cheapest time of year to fly from Orlando to Chicago?