Can I fly direct from Orlando to Chicago?

Yes, direct flights from Orlando to Chicago are available. Historically, approximately 21.8% of flights on this route have been direct. For flights with stopovers, the median number of stopovers observed was 2. This indicates that while direct options exist, connecting flights are also common for this route.

What's the flight time from Orlando to Chicago?

The median flight time for a direct flight from Orlando to Chicago is 3 hours and 8 minutes, covering a distance of 1595 kilometers. For flights with one stop, the median duration increases significantly to 8 hours and 59 minutes. Travelers should consider these differences when planning their journey.

How often do Orlando to Chicago flight prices drop?

Historically, flight prices for the Orlando to Chicago route have shown frequent drops. This suggests that travelers may have regular opportunities to find deals. Keeping an eye on price fluctuations can be beneficial for securing a more favorable fare on this route.

Flights From Orlando

To Chicago

Cheap Flights from Orlando to Chicago

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

Deals from

Orlando

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

Prices updated today

485 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Nov 2, 2026.)

Today’s best flight deals from Orlando to Chicago

Explore current cheapest deals departing from Orlando to Chicago

2027-01-28 – 2027-01-31
ORL - Chicago
46% AI deal score
$100
$106
Round trip
2027-01-14 – 2027-01-25
ORL - Chicago
45% AI deal score
$87
$111
Round trip
2027-01-14 – 2027-01-31
ORL - Chicago
45% AI deal score
$85
$111
Round trip
2027-02-25 – 2027-03-01
ORL - Chicago
44% AI deal score
$105
$111
Round trip
2027-02-25 – 2027-03-02
ORL - Chicago
44% AI deal score
$104
$111
Round trip
2026-12-03 – 2026-12-05
ORL - Chicago
46% AI deal score
$118
$115
Round trip
2026-11-10 – 2026-11-11
ORL - Chicago
77% AI deal score
$253
$117
Round trip
2027-02-25 – 2027-02-27
ORL - Chicago
79% AI deal score
$202
$118
Round trip
2027-02-27 – 2027-03-01
ORL - Chicago
76% AI deal score
$177
$118
Round trip
2027-02-27 – 2027-03-02
ORL - Chicago
76% AI deal score
$177
$118
Round trip

Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

Right now, 4% of recent fares for flights from Orlando to Chicago are classified as a good price. Fares for this route typically range from $283 to $580, with a median price of $389. Current fares are near the typical level, and new deals appear almost daily for this route.

When looking for cheap flights from Orlando to Chicago, the data indicates that January is typically the most affordable month, with a median fare of $184. Other cost-effective months include August, where the median fare is $294, and November, with a median fare of $367.

A typical journey from Orlando to Chicago takes about 3h 8m, including connections. Most itineraries connect at least once, with the median connecting journey taking 15h 32m. For the direct flights from Orlando to Chicago, the median flight time is also 3h 8m.

The distance between Orlando and Chicago is 1595 kilometers. This makes it a medium-haul route, indicating a moderate travel distance that typically involves several hours in the air.

How much is a round trip from Orlando to Chicago

Regular price: $83 - $212

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

The regular price range for flights from Orlando to Chicago is between $83 and $212. The current lowest deal is $111 with Frontier Airlines, for travel from Feb 25-Mar 2.

now $111

Low $83

High $212

The cheapest time to fly from Orlando to Chicago

The cheapest month to fly from Orlando to Chicago is January, with a median price of $184. The most expensive month is September, with a median price of $439. Prices are generally lower from January to November.

January

Cheapest

Flights from $184

September

Most Expensive

Flights from $439

Jan

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Orlando to Chicago

Frontier Airlines

Allegiant Air

Last-minute flights going from Orlando to Chicago

Tue, Nov 3

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$267

$194

One-way

Sat, Nov 7

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$238

$214

One-way

Tue, Nov 10

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$253

$117

One-way

Tue, Nov 10

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$253

$206

One-way

Fri, Nov 13

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$205

$169

One-way

Fri, Nov 13

⌛ Last-Minute

MCO - Chicago

Orlando (MCO) - Chicago (ORD)

Frontier Airlines

$205

$194

One-way

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

1 night

Nov 10 - Nov 11

$247 → $117

53%

1 night

Dec 4 - Dec 5

$249 → $133

47%

3 nights

Dec 10 - Dec 13

$247 → $140

43%

1 night

Dec 2 - Dec 3

$232 → $133

43%

Popular Airports to fly from Orlando to Chicago

Orlando - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Orlando to Chicago are near the typical level for this route.

📅 Best time to fly

January is historically cheapest at $184

Historically, January is the cheapest month to fly from Orlando to Chicago, with a median price of $184.

⏱️ Flight duration

Direct flights take 3h 8m

Direct flights from Orlando to Chicago typically take 3h 8m, while connecting flights average 15h 32m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 78.2% of recent deals, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines has offered 2 direct flight deals from Orlando to Chicago recently.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Orlando to Chicago are frequent, appearing often in the last 30 days.

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 ~$90

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International is a major gateway to Chicago, offering many flight options from Orlando.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$62

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by rail or car)

💸 Flights from ~$93

Business & First Class Flight Deals to Chicago

67% AI deal score

$1,169

$924

Save $245

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from Orlando to Chicago are found when booking 28-59 days in advance. During this period, the average price was $410. Booking within 0-6 days of departure typically saw prices around $655, while booking 7-13 days out averaged $608. Prices generally increase closer to the departure date, so planning ahead can lead to savings.

Based on historical data across the trailing quarter, a good price for a flight from Orlando to Chicago is considered to be $283 or less. The median price for this route was $389. Prices can vary, with 75% of observed prices being $580 or less. Travelers aiming for a budget-friendly trip should target prices at or below the $283 threshold.

Historically, January has been the cheapest month to fly from Orlando to Chicago, with a median price of $184. August also offered lower prices, with a median of $294. The annual median price for this route was $389, indicating that certain months offer significant savings compared to the yearly average.

Related routes

More routes from Orlando

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Flights to Chicago from other cities

Flights from Louisville to Chicago Flights from Philadelphia to Chicago Flights from Phoenix to Chicago Flights from Pittsburgh to Chicago Flights from Portland to Chicago Flights from Prague to Chicago Flights from Raleigh to Chicago Flights from Reno to Chicago Flights from Reykjavik to Chicago Flights from Sacramento to Chicago Flights from San Antonio to Chicago Flights from San Diego to Chicago

Orlando to Chicago: Overview

Insights for flights from Orlando to Chicago

The distance between Orlando and Chicago is 1595 kilometers. This makes it a medium-haul route, indicating a moderate travel distance that typically involves several hours in the air.

How much is a round trip from Orlando to Chicago

Regular price: $83 - $212

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

The regular price range for flights from Orlando to Chicago is between $83 and $212. The current lowest deal is $111 with Frontier Airlines, for travel from Feb 25-Mar 2.

now $111

Low $83

High $212

The cheapest time to fly from Orlando to Chicago

January

Cheapest

Flights from $184

September

Most Expensive

Flights from $439

Jan

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec