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

As of October 2025, 430 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

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

As of October 2025, there are 61 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 2:00PM, with 43% of flights taking off in the afternoon.

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

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

What airlines fly to Chicago?

Frontier, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Orlando according to our data. Frontier is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Orlando to Chicago refresh daily.

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

The number of operators available for flights from Orlando to Chicago is 7 as of October 2025.

How old do you have to be to fly from Orlando 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 to Chicago.

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

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$48 Cheap Flights from Orlando to Chicago in 2025/26

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 to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:35 am - 8:32 amMCO-MDW

2h 57mnonstop

10:12 am - 1:50 pmMDW-MCO

2h 38mnonstop

$81Frontier

Find Deal

Fri, Oct 31 - Sun, Nov 2

10:17 am - 12:26 pmMCO-ORD

3h 09mnonstop

5:25 am - 9:07 amORD-MCO

2h 42mnonstop

$82Frontier

Find Deal

Fri, Oct 31 - Sun, Nov 2

10:17 am - 12:26 pmMCO-ORD

3h 09mnonstop

6:48 am - 10:30 amORD-MCO

2h 42mnonstop

$83Multiple Airlines

Find Deal

Fri, Nov 14 - Wed, Nov 19

11:00 am - 1:16 pmMCO-ORD

3h 16mnonstop

12:09 pm - 4:01 pmORD-MCO

2h 52mnonstop

$84Multiple Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

2:26 pm - 4:23 pmMCO-ORD

2h 57mnonstop

6:48 am - 10:30 amORD-MCO

2h 42mnonstop

$85Spirit Airlines

Find Deal

Sat, Nov 1 - Tue, Nov 4

7:30 pm - 9:33 pmMCO-ORD

3h 03mnonstop

6:48 am - 10:30 amORD-MCO

2h 42mnonstop

$87Spirit Airlines

Find Deal

Fri, Oct 31 - Mon, Nov 3

2:44 pm - 4:28 pmSFB-RFD

2h 44mnonstop

5:18 pm - 8:47 pmRFD-SFB

2h 29mnonstop

$114Allegiant Air

Find Deal

Fri, Nov 7 - Mon, Nov 10

8:00 am - 9:48 amSFB-RFD

2h 48mnonstop

10:38 am - 2:15 pmRFD-SFB

2h 37mnonstop

$129Allegiant Air

Find Deal

Fri, Dec 12 - Wed, Dec 17

7:05 pm - 9:00 pmMCO-MDW

2h 55mnonstop

5:30 pm - 9:05 pmMDW-MCO

2h 35mnonstop

$137Southwest

Find Deal

Thu, Feb 5 - Sun, Feb 8

7:05 pm - 9:00 pmMCO-MDW

2h 55mnonstop

1:50 pm - 8:00 pmMDW-MCO

5h 10m1 stop

$143Southwest

Find Deal

Thu, Feb 5 - Sun, Feb 8

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets

Spirit Airlines

Nov 1

MCO2:26 pmOrlando

2h 57m

ORD4:23 pmChicago O'Hare Intl

Nov 4

ORD6:48 amChicago O'Hare Intl

2h 42m

MCO10:30 amOrlando

$85

Find similar

Spirit Airlines

Oct 31

MCO7:30 pmOrlando

3h 03m

ORD9:33 pmChicago O'Hare Intl

Nov 3

ORD6:48 amChicago O'Hare Intl

2h 42m

MCO10:30 amOrlando

$87

Find similar

Spirit Airlines

Oct 29

MCO6:26 amOrlando

9h 19m

1 stop

ORD2:45 pmChicago O'Hare Intl

Oct 31

ORD7:51 pmChicago O'Hare Intl

2h 52m

MCO11:43 pmOrlando

$91

Find similar

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets

Frontier

Oct 31

MCO6:35 amOrlando

2h 57m

MDW8:32 amChicago Midway

Nov 2

MDW10:12 amChicago Midway

2h 38m

MCO1:50 pmOrlando

$81

Find similar

Frontier

Oct 31

MCO10:17 amOrlando

3h 09m

ORD12:26 pmChicago O'Hare Intl

Nov 2

ORD5:25 amChicago O'Hare Intl

2h 42m

MCO9:07 amOrlando

$82

Find similar

Frontier

Oct 22

MCO12:58 pmOrlando

3h 10m

ORD3:08 pmChicago O'Hare Intl

Oct 25

ORD8:30 amChicago O'Hare Intl

2h 48m

MCO12:18 pmOrlando

$83

Find similar

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/31

6:35 am-8:32 am

Nonstop2h 57m

Chicago Midway

Sun 11/2

10:12 am-1:50 pm

Nonstop2h 38m

$81

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 10/31

10:17 am-12:26 pm

Nonstop3h 09m

Chicago O'Hare Intl

Sun 11/2

5:25 am-9:07 am

Nonstop2h 42m

$82

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 11/14

10:17 am-12:26 pm

Nonstop3h 09m

Chicago O'Hare Intl

Wed 11/19

6:48 am-10:30 am

Nonstop2h 42m

$83

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 12/5

11:00 am-1:16 pm

Nonstop3h 16m

Chicago O'Hare Intl

Sun 12/7

12:09 pm-4:01 pm

Nonstop2h 52m

$84

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 11/1

2:26 pm-4:23 pm

Nonstop2h 57m

Chicago O'Hare Intl

Tue 11/4

6:48 am-10:30 am

Nonstop2h 42m

$85

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 10/31

7:30 pm-9:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Mon 11/3

6:48 am-10:30 am

Nonstop2h 42m

$87

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 11/7

2:44 pm-4:28 pm

Nonstop2h 44m

Chicago Greater Rockford

Mon 11/10

5:18 pm-8:47 pm

Nonstop2h 29m

$114

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 12/12

8:00 am-9:48 am

Nonstop2h 48m

Chicago Greater Rockford

Wed 12/17

10:38 am-2:15 pm

Nonstop2h 37m

$129

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/5

7:05 pm-9:00 pm

Nonstop2h 55m

Chicago Midway

Sun 2/8

5:30 pm-9:05 pm

Nonstop2h 35m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/5

7:05 pm-9:00 pm

Nonstop2h 55m

Chicago Midway

Sun 2/8

1:50 pm-8:00 pm

1 stop5h 10m

$143

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 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

Other information

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $117. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Orlando to Chicago during August average around $159.

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 $234. 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 to Chicago for around $446.

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 to Chicago during this time can be as low as $241. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $535.

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 to Chicago?

You are more likely to see cheaper flights to Chicago from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $222 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $185 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 to Chicago flights?

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

How have Orlando to Chicago flight prices changed over time?

As of October 2025, prices for Orlando to Chicago flights are approximately 77% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago

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

Estimated round-trip price

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

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

Best Price Found	$82
Fastest flight time	2h 44m
Direct flights	Mon, Tue, Wed, Thu, Sat and Sun
Airports in Chicago	2 airports

The best one-way flight to Chicago from Orlando in the past 72 hours is $82. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $82.

The fastest flight from Orlando to Chicago takes 2h 44m

Direct flights go from Orlando to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. The only airline offering direct flights is Spirit Airlines.

There are 2 airports near Chicago: Chicago Greater Rockford (RFD), Chicago Midway (MDW)

Search flight deals

How far is Orlando to Chicago by plane?
Chicago is 985.3 mi away from Orlando. 2h 44m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How many operators does momondo search for flights from Orlando to Chicago?
The number of operators available for flights from Orlando to Chicago is 7 as of October 2025.
How old do you have to be to fly from Orlando 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 to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Orlando to Chicago?
Based on momondo bookings for flights between Orlando and Chicago, the leading plane model is Airbus A321neo, making up 15.62% of the total bookings. Other popular models include Airbus A321-100/200 with 11.95%, Airbus A321 (sharklets) with 11.58%, and Airbus A320neo with 10.38%.
What is the most popular airline from Orlando to Chicago?
momondo data reveals that the most frequently booked airline on the route from Orlando to Chicago is Frontier, representing 50% of all bookings. The subsequent popular airlines are Spirit Airlines at 18%, American Airlines at 15%, and Southwest at 11%.

Best airlines flying from Orlando to Chicago

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $70	Free Cancellation	Rating 5.8 3,137 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $74	Free Cancellation	Rating 6.3 8,099 reviews	Search Spirit Airlines flights
Allegiant Air	PriceFrom $82	Free Cancellation	Rating 7.2 694 reviews	Search Allegiant Air flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 7,980 reviews	Search Delta flights
United Airlines	PriceFrom $159	Free Cancellation	Rating 7.4 8,982 reviews	Search United Airlines flights
American Airlines	PriceFrom $159	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights

Southwest Flights From Orlando to Chicago
Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 73 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $159 round-trip, up to an average price of $295. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Orlando to Chicago
$159 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $319, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,982 user reviews) flies into Chicago from Orlando 45 times in an average week so prices can vary.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.

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

Sat 11/15

Sat 11/22

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

Cheap flights from Orlando to Chicago from $48

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 to Chicago departing on 10/31. 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 to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando 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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $117. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Orlando to Chicago during August average around $159.

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 to Chicago during this time can be as low as $241. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $535.

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 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 to Chicago flights?

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

How have Orlando to Chicago flight prices changed over time?

As of October 2025, prices for Orlando to Chicago flights are approximately 77% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

As of October 2025, there are 61 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 2:00PM, with 43% of flights taking off in the afternoon.

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

As of October 2025, 430 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

When to book flights from Orlando to Chicago

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

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

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

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

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

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

What is the most popular airline from Orlando to Chicago?

Best airlines flying from Orlando to Chicago

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

Southwest Flights From Orlando to Chicago

United Airlines Flights From Orlando 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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago