Can I fly direct from Orlando to Chicago?

Yes, direct flights are available from Orlando to Chicago. Historically, approximately 49.7% of all flights on this route have been direct. For flights that include a stopover, travelers typically experience one stop. This indicates that nearly half of the available options offer a non-stop journey.

What's the flight time from Orlando to Chicago?

A direct flight from Orlando to Chicago typically takes 3 hours and 8 minutes. This corresponds to a median flight time of 188 minutes for non-stop journeys. Flights with one stop, however, have a significantly longer median duration of 8 hours and 2 minutes, or 482 minutes. The distance covered on this route is approximately 1595 kilometers.

How often do Orlando to Chicago flight prices drop?

Historically, flight prices for the Orlando to Chicago route are classified as frequent in terms of price drops. This suggests that travelers can often find opportunities to secure better deals. The route consistently shows price fluctuations, indicating regular chances for savings across the trailing 30 days.

Flights From Orlando

To Chicago

Cheap Flights from Orlando to Chicago

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Deals from

Orlando

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

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 Orlando to Chicago

Explore current cheapest deals departing from Orlando to Chicago

2026-10-21 – 2026-10-28
ORL - Chicago
68% AI deal score
$111
$91
Round trip
2026-09-11 – 2026-09-25
ORL - Chicago
47% AI deal score
$95
$93
Round trip
2026-09-14 – 2026-09-25
ORL - Chicago
47% AI deal score
$96
$96
Round trip
2026-10-02 – 2026-10-05
ORL - Chicago
66% AI deal score
$111
$98
Round trip
2026-10-21 – 2026-10-26
ORL - Chicago
66% AI deal score
$114
$99
Round trip
2026-09-14 – 2026-09-21
ORL - Chicago
49% AI deal score
$106
$101
Round trip
2026-10-23 – 2026-10-28
ORL - Chicago
49% AI deal score
$114
$107
Round trip
2026-12-07 – 2026-12-14
ORL - Chicago
68% AI deal score
$137
$109
Round trip
2026-10-14 – 2026-10-28
ORL - Chicago
46% AI deal score
$96
$110
Round trip
2026-09-11 – 2026-10-05
ORL - Chicago
45% AI deal score
$91
$110
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. This indicates that finding cheap flights from Orlando to Chicago at the lowest end of the spectrum may require some flexibility or advance planning. Overall, fares for this route typically range from $101 to $323, with a median price of $158. Current fares are significantly above the typical level, suggesting higher prices than usual for this route.

A typical journey from Orlando to Chicago takes about 3h 8m, including connections. This median duration reflects the overall travel time you can expect for this route. Given that a meaningful share of itineraries are non-stop, the actual flight time for direct services is also 3h 8m, while connecting flights have a significantly longer median duration of 14h 44m.

When is the cheapest time to fly from Orlando to Chicago? The most affordable months to fly this route are typically September, with a median fare of $99, followed closely by October at $101, and August at $106. These months offer the lowest median prices, making them ideal for budget-conscious travelers.

For flights from Orlando to Chicago, a meaningful share are non-stop, while the rest connect once. Specifically, 49.7% of recent fares are for direct flights from Orlando to Chicago. For itineraries that include connections, the typical number of stopovers is 1. This mix means you have options for both direct and connecting services, depending on your preference for speed versus potential cost savings.

How much is a round trip from Orlando to Chicago

Regular price: $93 - $188

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

The regular price range for flights from Orlando to Chicago is $93 to $188. The current lowest deal is $84 with Allegiant Air, for travel from Oct 23-Oct 28.

now $84

Low $93

High $188

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

Allegiant Air

Frontier Airlines

Southwest Airlines

Last-minute flights going from Orlando to Chicago

Sat, Aug 1

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$383

$254

One-way

Tue, Aug 4

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$343

$223

One-way

Wed, Aug 5

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$251

$186

One-way

Thu, Aug 6

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$253

$187

One-way

Sat, Aug 8

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$259

$159

One-way

Sat, Aug 8

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$285

$182

One-way

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

2 nights

Aug 1 - Aug 3

$383 → $254

34%

5 nights

Aug 26 - Aug 31

$261 → $135

48%

4 nights

Aug 20 - Aug 24

$268 → $144

46%

3 nights

Aug 4 - Aug 7

$343 → $223

35%

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 for this route.

📅 Best time to fly

August is historically the cheapest month to fly.

Historically, August is the cheapest month to fly from Orlando to Chicago, with a median price of $115.

⏱️ Flight duration

Direct flights take 3h 8m.

Direct flights from Orlando to Chicago typically take 3 hours and 8 minutes.

✈️ Airlines & availability

Direct flights are available from 3 airlines.

Allegiant Air, Frontier Airlines, and Southwest Airlines offer direct flights on this route.

🏆 Airline highlight

Allegiant Air offers deals from $84.

Allegiant Air recently offered a flight from Orlando Sanford International to Chicago Rockford International for $84.

🎯 Booking tip

Deals are frequent on this route.

Deals on flights from Orlando to Chicago are frequent, appearing often over a 30-day window.

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 ~$84

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

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

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$84

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 rail or car)

💸 Flights from ~$158

Business & First Class Flight Deals to Chicago

78% AI deal score

$1,913

$1,094

Save $819

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Orlando to Chicago 60+ days in advance typically yields the lowest prices, with an average of $132. Prices tend to increase significantly closer to departure. For instance, flights booked 28-59 days out average $177, while those booked within 0-6 days of travel can average as high as $497. Planning ahead by at least 60 days can result in substantial savings.

Based on historical data across the trailing quarter, a good price for a flight from Orlando to Chicago is around $101. The median price for this route has been $158. While 75% of prices are typically $323 or less, aiming for a price at or below $101 is considered a good 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 offers relatively low prices, with a median of $106. The annual median price for this route is $158, indicating that these months offer notable savings compared to the yearly average.

Related routes

More routes from Orlando

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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: $93 - $188

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

The regular price range for flights from Orlando to Chicago is $93 to $188. The current lowest deal is $84 with Allegiant Air, for travel from Oct 23-Oct 28.

now $84

Low $93

High $188

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