How many flights depart from Orlando Airport to Chicago on average per day?

48 flights are operational daily from Orlando Airport to Chicago as of November 2026. The most popular departure time for this route is 7:00AM, with 45% of flights per day taking off at noon.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Chicago?

Frontier, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Orlando Airport according to our data. Frontier is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Orlando Airport to Chicago on average per week?

337 flights are operational weekly from Orlando Airport to Chicago as of November 2026. The most popular departure day for this route is Sun, with 22% of flights per week taking off on this day.

Which airline has the best punctuality record on Orlando to Chicago flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

How often are flights from Orlando to Chicago delayed?

Historically, on average around 18% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 144 minutes.

What is the cheapest airline that flies from Orlando to Chicago?

Southwest, United Airlines, and JetBlue are the most popular carriers operating from Orlando to Chicago

What is the most punctual flight time for Orlando to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

When did momondo last update prices for flights from Orlando Airport to Chicago?

Prices for flights from Orlando Airport to Chicago refresh daily.

How many operators does momondo search for flights from Orlando Airport to Chicago?

As of November 2026, there are 4 operators available to choose from for flights from Orlando Airport to Chicago.

How old do you have to be to fly from Orlando Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$112 Cheap Flights from Orlando Airport to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Orlando Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:08 pm - 9:45 pmMCO Orlando-ORD Chicago O'Hare Intl

26h 37m1 stop Atlanta Hartsfield-Jackson

1:30 pm - 8:27 pmORD Chicago O'Hare Intl-MCO Orlando

5h 57m1 stop Atlanta Hartsfield-Jackson

$207Frontier

Mon, Jan 4 - Mon, Jan 11

6:04 am - 10:21 pmMCO Orlando-ORD Chicago O'Hare Intl

17h 17m1 stop San Juan Luis Munoz Marin Intl

9:34 pm - 8:53 pmORD Chicago O'Hare Intl-MCO Orlando

22h 19m2 stops Philadelphia Atlanta Hartsfield-Jackson

$207Frontier

Wed, Nov 25 - Mon, Dec 7

9:40 am - 11:33 pmMCO Orlando-ORD Chicago O'Hare Intl

14h 53m1 stop Fort Lauderdale

4:00 pm - 11:27 pmORD Chicago O'Hare Intl-MCO Orlando

6h 27m1 stop Atlanta Hartsfield-Jackson

$231Multiple Airlines

Sun, Dec 6 - Wed, Dec 9

9:40 am - 11:33 pmMCO Orlando-ORD Chicago O'Hare Intl

14h 53m1 stop Fort Lauderdale

4:00 pm - 11:27 pmORD Chicago O'Hare Intl-MCO Orlando

6h 27m1 stop Atlanta Hartsfield-Jackson

$231Multiple Airlines

Thu, Dec 3 - Wed, Dec 9

2:25 pm - 4:25 pmMCO Orlando-MDW Chicago Midway

3h 00mnonstop

4:25 pm - 8:00 pmMDW Chicago Midway-MCO Orlando

2h 35mnonstop

$339Southwest

Tue, Dec 8 - Wed, Dec 9

6:15 am - 8:30 amMCO Orlando-ORD Chicago O'Hare Intl

3h 15mnonstop

3:00 pm - 6:54 pmORD Chicago O'Hare Intl-MCO Orlando

2h 54mnonstop

$339American Airlines

Tue, Dec 15 - Tue, Dec 15

6:06 am - 8:30 amMCO Orlando-ORD Chicago O'Hare Intl

3h 24mnonstop

7:05 pm - 11:06 pmORD Chicago O'Hare Intl-MCO Orlando

3h 01mnonstop

$339American Airlines

Sat, Nov 21 - Mon, Nov 23

3:50 pm - 7:40 pmMCO Orlando-MDW Chicago Midway

4h 50m1 stop Grand Rapids Gerald R. Ford Intl

4:25 pm - 8:00 pmMDW Chicago Midway-MCO Orlando

2h 35mnonstop

$345Southwest

Tue, Dec 8 - Wed, Dec 9

9:22 am - 11:29 amMCO Orlando-ORD Chicago O'Hare Intl

3h 07mnonstop

11:23 am - 3:20 pmORD Chicago O'Hare Intl-MCO Orlando

2h 57mnonstop

$357United Airlines

Fri, Nov 20 - Mon, Nov 23

4:15 pm - 6:33 pmMCO Orlando-ORD Chicago O'Hare Intl

3h 18mnonstop

7:05 am - 10:56 amORD Chicago O'Hare Intl-MCO Orlando

2h 51mnonstop

$357United Airlines

Thu, Dec 24 - Tue, Dec 29

Cheap last minute flights

Enter your travel dates to find the best prices.

2:52 pm - 5:07 pmMCO Orlando-ORD Chicago O'Hare Intl

3h 15mnonstop

10:29 pm - 11:50 amORD Chicago O'Hare Intl-MCO Orlando

12h 21m1 stop Atlanta Hartsfield-Jackson

$224Frontier

Wed, Nov 4 - Sun, Dec 6

9:21 pm - 11:31 pmMCO Orlando-ORD Chicago O'Hare Intl

3h 10mnonstop

10:19 am - 5:24 pmORD Chicago O'Hare Intl-MCO Orlando

6h 05m1 stop Atlanta Hartsfield-Jackson

$235Frontier

Sat, Nov 7 - Sun, Nov 8

9:21 pm - 11:31 pmMCO Orlando-ORD Chicago O'Hare Intl

3h 10mnonstop

7:00 am - 10:24 pmORD Chicago O'Hare Intl-MCO Orlando

14h 24m1 stop Fort Lauderdale

$267Multiple Airlines

Sat, Nov 7 - Thu, Nov 12

11:58 am - 6:30 pmMCO Orlando-ORD Chicago O'Hare Intl

7h 32m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:24 pmORD Chicago O'Hare Intl-MCO Orlando

14h 24m1 stop Fort Lauderdale

$278Multiple Airlines

Sat, Nov 7 - Thu, Nov 12

2:35 pm - 4:35 pmMCO Orlando-MDW Chicago Midway

3h 00mnonstop

2:40 pm - 6:15 pmMDW Chicago Midway-MCO Orlando

2h 35mnonstop

$410Southwest

Wed, Nov 4 - Sun, Dec 6

9:52 am - 11:59 amMCO Orlando-ORD Chicago O'Hare Intl

3h 07mnonstop

4:20 pm - 8:12 pmORD Chicago O'Hare Intl-MCO Orlando

2h 52mnonstop

$411United Airlines

Wed, Nov 4 - Wed, Nov 4

10:54 am - 1:02 pmMCO Orlando-ORD Chicago O'Hare Intl

3h 08mnonstop

9:05 am - 1:01 pmORD Chicago O'Hare Intl-MCO Orlando

2h 56mnonstop

$411United Airlines

Sat, Nov 7 - Tue, Nov 10

6:30 pm - 8:30 pmMCO Orlando-MDW Chicago Midway

3h 00mnonstop

8:10 am - 11:50 amMDW Chicago Midway-MCO Orlando

2h 40mnonstop

$411Southwest

Sat, Nov 7 - Tue, Nov 10

6:18 am - 8:39 amMCO Orlando-ORD Chicago O'Hare Intl

3h 21mnonstop

2:51 pm - 6:41 pmORD Chicago O'Hare Intl-MCO Orlando

2h 50mnonstop

$411American Airlines

Sat, Nov 7 - Sat, Nov 7

7:44 am - 10:00 amMCO Orlando-ORD Chicago O'Hare Intl

3h 16mnonstop

2:51 pm - 6:41 pmORD Chicago O'Hare Intl-MCO Orlando

2h 50mnonstop

$411American Airlines

Wed, Nov 4 - Wed, Nov 4

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Frontier flights from Orlando Airport to Chicago

Our best Frontier deals on Orlando Airport to Chicago flight tickets

Frontier

Nov 25

MCO6:04 amOrlando

17h 17m

1 stop

ORD10:21 pmChicago O'Hare Intl

Dec 7

ORD9:34 pmChicago O'Hare Intl

22h 19m

2 stops

MCO8:53 pmOrlando

$207

Frontier

Dec 4

MCO10:22 pmOrlando

17h 08m

2 stops

ORD2:30 pmChicago O'Hare Intl

Dec 7

ORD10:37 pmChicago O'Hare Intl

14h 10m

1 stop

MCO1:47 pmOrlando

$208

Frontier

Dec 23

MCO7:08 amOrlando

5h 52m

1 stop

ORD12:00 pmChicago O'Hare Intl

Dec 30

ORD4:59 pmChicago O'Hare Intl

6h 14m

1 stop

MCO12:13 amOrlando

$209

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Mon 1/4

8:08 pm-9:45 pm

1 stop26h 37m

Chicago O'Hare Intl

Mon 1/11

1:30 pm-8:27 pm

1 stop5h 57m

$207

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Wed 11/25

6:04 am-10:21 pm

1 stop17h 17m

Chicago O'Hare Intl

Mon 12/7

9:34 pm-8:53 pm

2 stops22h 19m

$207

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Sun 12/6

9:40 am-11:33 pm

1 stop14h 53m

Chicago O'Hare Intl

Wed 12/9

4:00 pm-11:27 pm

1 stop6h 27m

$231

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Thu 12/3

9:40 am-11:33 pm

1 stop14h 53m

Chicago O'Hare Intl

Wed 12/9

4:00 pm-11:27 pm

1 stop6h 27m

$231

Quickest round-trip

OrlandoChicago

MCO Orlando - MDW Chicago Midway

MCOMDW

Orlando

Tue 12/8

2:25 pm-4:25 pm

Nonstop3h 00m

Chicago Midway

Wed 12/9

4:25 pm-8:00 pm

Nonstop2h 35m

$339

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Tue 12/15

6:15 am-8:30 am

Nonstop3h 15m

Chicago O'Hare Intl

Tue 12/15

3:00 pm-6:54 pm

Nonstop2h 54m

$339

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Sat 11/21

6:06 am-8:30 am

Nonstop3h 24m

Chicago O'Hare Intl

Mon 11/23

7:05 pm-11:06 pm

Nonstop3h 01m

$339

OrlandoChicago

MCO Orlando - MDW Chicago Midway

MCOMDW

Orlando

Tue 12/8

3:50 pm-7:40 pm

1 stop4h 50m

Chicago Midway

Wed 12/9

4:25 pm-8:00 pm

Nonstop2h 35m

$345

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Fri 11/20

9:22 am-11:29 am

Nonstop3h 07m

Chicago O'Hare Intl

Mon 11/23

11:23 am-3:20 pm

Nonstop2h 57m

$357

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Thu 12/24

4:15 pm-6:33 pm

Nonstop3h 18m

Chicago O'Hare Intl

Tue 12/29

7:05 am-10:56 am

Nonstop2h 51m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Orlando Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the typical price of a round-trip flight between Orlando Airport and Chicago?

Prices are currently typical for flights on this route.

Typical prices usually range from $120 to $342.
The lowest price recently found on this route was $207.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $175. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Orlando Airport to Chicago during February average around $178.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $344. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $552.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $262. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $560.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices

How far in advance should I book a flight from Orlando Airport to Chicago?

You are more likely to see cheaper flights to Chicago from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $272 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando Airport for as low as $240 on momondo.

What cabin class options are available on Orlando Airport to Chicago flights?

There are 4 cabin classes available to choose from on Orlando Airport to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Orlando Airport to Chicago flight prices changed over time?

As of November 2026, prices for Orlando Airport to Chicago flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Orlando Airport to Chicago (MCO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando Airport to Chicago

Best Price Found	$112
Fastest flight time	2h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Orlando Airport in the past 72 hours is $112. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $207.

The fastest flight from Orlando Airport to Chicago takes 2h 50m

Direct flights go from Orlando Airport to Chicago every day.

There are 3 airports in Chicago. From Orlando Airport there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Orlando Airport to Chicago

How far is Orlando to Chicago by plane?
There are 993.7 mi between Orlando and Chicago. A reasonable flight in good conditions will take 2h 50m.
When did momondo last update prices for flights from Orlando Airport to Chicago?
Prices for flights from Orlando Airport to Chicago refresh daily.
How many operators does momondo search for flights from Orlando Airport to Chicago?
As of November 2026, there are 4 operators available to choose from for flights from Orlando Airport to Chicago.
How old do you have to be to fly from Orlando Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Orlando Airport to Chicago is Airbus A321neo (18.73% of total bookings). The next most popular plane models are Airbus A321-100/200 (11.89%), Boeing 737-800 (11.63%), and Boeing 737-900 (9.26%).
What is the most popular airline from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Orlando Airport to Chicago is Frontier (47% of total bookings). The next most popular airlines are United Airlines (19%), Southwest (17%), and American Airlines (15%).

Best airlines flying from Orlando Airport to Chicago

Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $79	Free Cancellation	Rating 5.5 2,511 reviews	Search Frontier flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,220 reviews	Search Southwest flights
United Airlines	PriceFrom $177	Free Cancellation	Rating 7.3 10,463 reviews	Search United Airlines flights
American Airlines	PriceFrom $184	Free Cancellation	Rating 7.0 12,222 reviews	Search American Airlines flights

Southwest Flights From Orlando Airport to Chicago
Across 37 Southwest flights from Orlando Airport to Chicago this week, the average price was $368, with the best Southwest deals starting from $157 round-trip. 4,220 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Orlando Airport to Chicago
Another popular option for Orlando Airport to Chicago flights is United Airlines (7.3/10, 10,463 ratings). United Airlines flies from Orlando Airport to Chicago around 34 times per week, with deals starting from $177 round-trip and rising to an average price of around $379.

Merrillville

New Buffalo

Hammond

Portage

Lansing

Saint Joseph

Benton Harbor

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

Finding the right flight to Chicago from Orlando is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

All flight searches from Orlando to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Orlando to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Orlando Airport to Chicago from $112

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando Airport to Chicago departing on 12/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from Orlando Airport to Chicago

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How to get the cheapest flight ticket from Orlando Airport to Chicago

What is the typical price of a round-trip flight between Orlando Airport and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Orlando to Chicago flight route?

How far in advance should I book a flight from Orlando Airport to Chicago?

What cabin class options are available on Orlando Airport to Chicago flights?

How have Orlando Airport to Chicago flight prices changed over time?

What is the cheapest airline that flies from Orlando to Chicago?

What airlines fly to Chicago?

How often are flights from Orlando to Chicago delayed?

What is the most punctual flight time for Orlando to Chicago flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Orlando to Chicago flights?

How many flights depart from Orlando Airport to Chicago on average per day?

How many flights depart from Orlando Airport to Chicago on average per week?

When to book flights from Orlando Airport to Chicago

Cheap Orlando Airport to Chicago (MCO to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Orlando Airport to Chicago

Best airlines flying from Orlando Airport to Chicago

Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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