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

Tuesday 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.

How often are flights from Orlando to Chicago delayed?

Historically, on average around 16% 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 156 minutes.

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

41 flights are operational daily from Orlando Airport to Chicago as of February 2026. The most popular departure time for this route is 2:00PM, with 56% of flights per day taking off in the afternoon.

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 10% of their flights experiencing any sort of delay.

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

Southwest, Frontier, and Spirit Airlines are the most popular carriers operating from Orlando to Chicago

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

289 flights are operational weekly from Orlando Airport to Chicago as of February 2026. The most popular departure day for this route is Sun, with 23% of flights per week taking off on this day.

What airlines fly to Chicago?

Frontier, Spirit Airlines and American 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 35% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 February 2026, there are 6 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.

$51 Cheap Flights from Orlando Airport to Chicago in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

8:20 am - 10:46 am

MCO

ORD

3h 26mnonstop

10:44 am - 2:34 pm

ORD

MCO

2h 50mnonstop

$78Multiple Airlines

Thu, Feb 26 - Tue, Mar 10

3:39 pm - 5:46 pm

MCO

ORD

3h 07mnonstop

10:44 am - 2:34 pm

ORD

MCO

2h 50mnonstop

$81Spirit Airlines

Thu, Mar 5 - Tue, Mar 10

6:41 am - 9:06 am

MCO

ORD

3h 25mnonstop

10:44 am - 2:34 pm

ORD

MCO

2h 50mnonstop

$82Multiple Airlines

Fri, Mar 6 - Tue, Mar 10

4:05 pm - 6:13 pm

MCO

MDW

3h 08mnonstop

11:19 am - 3:04 pm

MDW

MCO

2h 45mnonstop

$84Frontier

Tue, Mar 10 - Wed, Mar 11

1:33 pm - 3:52 pm

MCO

ORD

3h 19mnonstop

10:44 am - 2:34 pm

ORD

MCO

2h 50mnonstop

$84Multiple Airlines

Wed, Feb 25 - Sat, Feb 28

9:51 pm - 11:51 pm

MCO

MDW

3h 00mnonstop

8:00 am - 11:49 am

MDW

MCO

2h 49mnonstop

$85Frontier

Fri, Mar 6 - Sun, Mar 8

6:48 pm - 8:53 pm

MCO

MDW

3h 05mnonstop

8:00 am - 11:49 am

MDW

MCO

2h 49mnonstop

$86Frontier

Fri, Mar 6 - Sun, Mar 8

5:34 pm - 7:47 pm

MCO

ORD

3h 13mnonstop

12:44 pm - 4:31 pm

ORD

MCO

2h 47mnonstop

$86Spirit Airlines

Thu, Mar 5 - Mon, Mar 9

7:00 am - 9:15 am

MCO

ORD

3h 15mnonstop

10:25 am - 2:21 pm

ORD

MCO

2h 56mnonstop

$87Frontier

Thu, May 14 - Sun, May 17

6:05 am - 8:04 am

MCO

MDW

2h 59mnonstop

9:14 am - 1:03 pm

MDW

MCO

2h 49mnonstop

$87Frontier

Thu, May 7 - Sun, May 10

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets

Spirit Airlines

Mar 5

MCO3:39 pmOrlando

3h 07m

ORD5:46 pmChicago O'Hare Intl

Mar 10

ORD10:44 amChicago O'Hare Intl

2h 50m

MCO2:34 pmOrlando

$81

Spirit Airlines

Mar 5

MCO5:34 pmOrlando

3h 13m

ORD7:47 pmChicago O'Hare Intl

Mar 9

ORD12:44 pmChicago O'Hare Intl

2h 47m

MCO4:31 pmOrlando

$86

Spirit Airlines

Feb 12

MCO5:34 pmOrlando

3h 13m

ORD7:47 pmChicago O'Hare Intl

Feb 17

ORD10:44 amChicago O'Hare Intl

2h 50m

MCO2:34 pmOrlando

$89

Frontier flights from Orlando Airport to Chicago

Our best Frontier deals on Orlando Airport to Chicago flight tickets

Frontier

Mar 10

MCO4:05 pmOrlando

3h 08m

MDW6:13 pmChicago Midway

Mar 11

MDW11:19 amChicago Midway

2h 45m

MCO3:04 pmOrlando

$84

Frontier

Mar 6

MCO9:51 pmOrlando

3h 00m

MDW11:51 pmChicago Midway

Mar 8

MDW8:00 amChicago Midway

2h 49m

MCO11:49 amOrlando

$85

Frontier

Mar 6

MCO6:48 pmOrlando

3h 05m

MDW8:53 pmChicago Midway

Mar 8

MDW8:00 amChicago Midway

2h 49m

MCO11:49 amOrlando

$86

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 2/26

8:20 am-10:46 am

Nonstop3h 26m

Chicago O'Hare Intl

Tue 3/10

10:44 am-2:34 pm

Nonstop2h 50m

$78

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 3/5

3:39 pm-5:46 pm

Nonstop3h 07m

Chicago O'Hare Intl

Tue 3/10

10:44 am-2:34 pm

Nonstop2h 50m

$81

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 3/6

6:41 am-9:06 am

Nonstop3h 25m

Chicago O'Hare Intl

Tue 3/10

10:44 am-2:34 pm

Nonstop2h 50m

$82

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/10

4:05 pm-6:13 pm

Nonstop3h 08m

Chicago Midway

Wed 3/11

11:19 am-3:04 pm

Nonstop2h 45m

$84

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 2/25

1:33 pm-3:52 pm

Nonstop3h 19m

Chicago O'Hare Intl

Sat 2/28

10:44 am-2:34 pm

Nonstop2h 50m

$84

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/6

9:51 pm-11:51 pm

Nonstop3h 00m

Chicago Midway

Sun 3/8

8:00 am-11:49 am

Nonstop2h 49m

$85

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 3/6

6:48 pm-8:53 pm

Nonstop3h 05m

Chicago Midway

Sun 3/8

8:00 am-11:49 am

Nonstop2h 49m

$86

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 3/5

5:34 pm-7:47 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 3/9

12:44 pm-4:31 pm

Nonstop2h 47m

$86

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 5/14

7:00 am-9:15 am

Nonstop3h 15m

Chicago O'Hare Intl

Sun 5/17

10:25 am-2:21 pm

Nonstop2h 56m

$87

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 5/7

6:05 am-8:04 am

Nonstop2h 59m

Chicago Midway

Sun 5/10

9:14 am-1:03 pm

Nonstop2h 49m

$87

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 cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $136. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Orlando Airport to Chicago during September average around $154.

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 $236. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $455.

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 $217. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $447.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices

How far in advance should I book a flight 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 $212 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 $164 on momondo.

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

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

Can stopping save me money on Orlando Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Orlando Airport to Chicago.

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

As of February 2026, prices for Orlando Airport to Chicago flights are approximately 31% 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	$101
Fastest flight time	2h 45m
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 $101. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $110.

The fastest flight from Orlando Airport to Chicago takes 2h 45m

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 O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

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 45m.
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 February 2026, there are 6 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 (18.29% of total bookings). The next most popular plane models are Airbus A320 (sharklets) (11.61%), Airbus A320neo (10.78%), and Airbus A321 (sharklets) (10.71%).
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 (43% of total bookings). The next most popular airlines are Spirit Airlines (20%), Southwest (13%), and American Airlines (13%).

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 $63	Free Cancellation	Rating 5.7 3,052 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $72	Free Cancellation	Rating 6.3 8,430 reviews	Search Spirit Airlines flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 8,172 reviews	Search Delta flights
United Airlines	PriceFrom $154	Free Cancellation	Rating 7.4 9,254 reviews	Search United Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.2 11,249 reviews	Search American Airlines flights

Southwest Flights From Orlando Airport to Chicago
Across 52 Southwest flights from Orlando Airport to Chicago this week, the average price was $265, with the best Southwest deals starting from $157 round-trip. 4,280 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 (7.4/10, 9,254 ratings). United Airlines flies from Orlando Airport to Chicago around 27 times per week, with deals starting from $154 round-trip and rising to an average price of around $305.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Tue 3/10

Tue 3/17

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Orlando Airport

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Orlando Airport to Chicago from $50

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 5/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Orlando Airport to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets

Frontier flights from Orlando Airport to Chicago

Our best Frontier deals on Orlando Airport to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

See travel insights to Chicago from

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

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 $217. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $447.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices

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

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

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

Can stopping save me money on Orlando Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Orlando Airport to Chicago.

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

As of February 2026, prices for Orlando Airport to Chicago flights are approximately 31% more expensive when compared to flights at the same time last year.

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

Southwest, Frontier, and Spirit Airlines are the most popular carriers operating from Orlando to Chicago

What airlines fly to Chicago?

How often are flights from Orlando to Chicago delayed?

Historically, on average around 16% 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 156 minutes.

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.

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

Tuesday 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.

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 10% of their flights experiencing any sort of delay.

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

41 flights are operational daily from Orlando Airport to Chicago as of February 2026. The most popular departure time for this route is 2:00PM, with 56% of flights per day taking off in the afternoon.

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

289 flights are operational weekly from Orlando Airport to Chicago as of February 2026. The most popular departure day for this route is Sun, with 23% of flights per week taking off on this day.

When to book flights from Orlando Airport to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Orlando to Chicago by plane?

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

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

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

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

What is the most popular plane model from Orlando Airport to Chicago?

What is the most popular airline 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

Southwest Flights From Orlando Airport to Chicago

United Airlines Flights From Orlando Airport to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

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