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

As of February 2026, 321 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.

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

Tuesday is statistically the day of the week that experiences the fewest 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.

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

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

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

The number of flights available between Orlando and Chicago is 45 per day as of February 2026. The most frequent departure time is 14:00, with 54% of daily flights leaving in the afternoon.

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

United Airlines is the most popular carrier operating from Orlando to Chicago

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

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 10% of their flights experiencing any sort of delay.

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

Prices for flights from Orlando to Chicago refresh daily.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

£48 Cheap Flights from Orlando to Chicago in 2026

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Find the cheapest flights from Orlando to Chicago

Round-trip

One-way

Last minute

Direct

Cheap return flights

Enter your travel dates to find the best prices.

07:00 - 09:18

MCO

ORD

3h 18mdirect

17:50 - 21:40

ORD

MCO

2h 50mdirect

£138United Airlines

Thu, 26 Feb - Mon, 2 Mar

07:30 - 09:45

MCO

ORD

3h 15mdirect

05:55 - 09:35

ORD

MCO

2h 40mdirect

£144Southwest

Wed, 1 Apr - Tue, 7 Apr

20:43 - 23:00

MCO

ORD

3h 17mdirect

17:50 - 21:40

ORD

MCO

2h 50mdirect

£145United Airlines

Thu, 26 Feb - Mon, 2 Mar

20:43 - 23:00

MCO

ORD

3h 17mdirect

15:41 - 19:30

ORD

MCO

2h 49mdirect

£145United Airlines

Fri, 27 Feb - Sun, 1 Mar

09:05 - 11:10

MCO

ORD

3h 05mdirect

16:25 - 20:10

ORD

MCO

2h 45mdirect

£170Southwest

Sat, 14 Feb - Sat, 21 Feb

11:30 - 16:49

MCO

ORD

6h 19m

1 stop

07:10 - 12:51

ORD

MCO

4h 41m

1 stop

£173Delta

Tue, 17 Mar - Sun, 22 Mar

09:05 - 11:10

MCO

ORD

3h 05mdirect

15:45 - 19:30

ORD

MCO

2h 45mdirect

£181Southwest

Mon, 23 Feb - Mon, 23 Feb

22:30 - 13:55

MCO

ORD

16h 25m

2 stops

14:40 - 08:35

ORD

MCO

16h 55m

2 stops

£193Southwest

Fri, 6 Mar - Mon, 9 Mar

06:15 - 10:08

MCO

ORD

4h 53m

1 stop

06:45 - 15:13

ORD

MCO

7h 28m

1 stop

£196Delta

Sun, 15 Feb - Sun, 22 Feb

12:12 - 14:29

MCO

ORD

3h 17mdirect

19:50 - 23:43

ORD

MCO

2h 53mdirect

£196United Airlines

Fri, 13 Feb - Sun, 15 Feb

Southwest flights from Orlando to Chicago

Our best Southwest deals on Orlando to Chicago flight tickets

Southwest

1 Apr

MCO07:30Orlando

3h 15m

ORD09:45Chicago O'Hare Intl

7 Apr

ORD05:55Chicago O'Hare Intl

2h 40m

MCO09:35Orlando

£144

Southwest

27 Feb

MCO09:05Orlando

3h 05m

ORD11:10Chicago O'Hare Intl

1 Mar

ORD16:25Chicago O'Hare Intl

2h 45m

MCO20:10Orlando

£145

Southwest

14 Feb

MCO09:05Orlando

3h 05m

ORD11:10Chicago O'Hare Intl

21 Feb

ORD16:25Chicago O'Hare Intl

2h 45m

MCO20:10Orlando

£170

Delta flights from Orlando to Chicago

Our best Delta deals on Orlando to Chicago flight tickets

Delta

17 Mar

MCO11:30Orlando

6h 19m

1 stop

ORD16:49Chicago O'Hare Intl

22 Mar

ORD07:10Chicago O'Hare Intl

4h 41m

1 stop

MCO12:51Orlando

£173

Delta

22 Mar

MCO18:34Orlando

6h 20m

1 stop

ORD23:54Chicago O'Hare Intl

23 Mar

ORD09:50Chicago O'Hare Intl

6h 02m

1 stop

MCO16:52Orlando

£188

Delta

15 Feb

MCO06:15Orlando

4h 53m

1 stop

ORD10:08Chicago O'Hare Intl

22 Feb

ORD06:45Chicago O'Hare Intl

7h 28m

1 stop

MCO15:13Orlando

£196

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 26/2

07:00-09:18

Nonstop3h 18m

Chicago O'Hare Intl

Mon 2/3

17:50-21:40

Nonstop2h 50m

£138

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/4

07:30-09:45

Nonstop3h 15m

Chicago O'Hare Intl

Tue 7/4

05:55-09:35

Nonstop2h 40m

£144

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 26/2

20:43-23:00

Nonstop3h 17m

Chicago O'Hare Intl

Mon 2/3

17:50-21:40

Nonstop2h 50m

£145

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 27/2

20:43-23:00

Nonstop3h 17m

Chicago O'Hare Intl

Sun 1/3

15:41-19:30

Nonstop2h 49m

£145

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 14/2

09:05-11:10

Nonstop3h 05m

Chicago O'Hare Intl

Sat 21/2

16:25-20:10

Nonstop2h 45m

£170

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 17/3

11:30-16:49

1 stop6h 19m

Chicago O'Hare Intl

Sun 22/3

07:10-12:51

1 stop4h 41m

£173

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 23/2

09:05-11:10

Nonstop3h 05m

Chicago O'Hare Intl

Mon 23/2

15:45-19:30

Nonstop2h 45m

£181

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 6/3

22:30-13:55

2 stops16h 25m

Chicago O'Hare Intl

Mon 9/3

14:40-08:35

2 stops16h 55m

£193

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 15/2

06:15-10:08

1 stop4h 53m

Chicago O'Hare Intl

Sun 22/2

06:45-15:13

1 stop7h 28m

£196

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 13/2

12:12-14:29

Nonstop3h 17m

Chicago O'Hare Intl

Sun 15/2

19:50-23:43

Nonstop2h 53m

£196

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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

Delays

Other information

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

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Orlando is in September. Flight prices, which tend to average around £84, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Orlando during February instead. Flights to Chicago in February, while not as cheap as those in September, still average around £110.

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 Wednesday when prices can be found for as low as £110. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £456.

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

Flying to Chicago from Orlando in the morning is the least expensive time of day to depart. momondo users have found prices as low as £186 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £456.

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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £155 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as £120 on momondo.

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

There are 3 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.

How have Orlando to Chicago flight prices changed over time?

As of February 2026, prices for Orlando to Chicago flights are approximately 4% cheaper 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 return 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

Fastest flight time	3h 26m
Direct flights	Every day
Airports in Chicago	3 airports

The fastest flight from Orlando to Chicago takes 3h 26m

Direct flights go from Orlando to Chicago every day.

There are 3 airports in Chicago. From Orlando there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Orlando to Chicago by plane?
The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 26m by plane in normal conditions.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How old do you have to be to fly from Orlando to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek 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 this flight route, the most popular plane model on flight routes from Orlando to Chicago is Airbus A321neo (18.17% of total bookings). The next most popular plane models are Airbus A320 (sharklets) (11.76%), Airbus A320neo (10.90%), and Airbus A321 (sharklets) (10.84%).

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?

Yes. momondo enables you to select and highlight flights to Chicago from Orlando with this policy.

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?

If you are not ready to book a flight from Orlando to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

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

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Find better results for your trip to the United States

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Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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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 16/5. 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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See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando to Chicago

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

Flying to Chicago from Orlando in the morning is the least expensive time of day to depart. momondo users have found prices as low as £186 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £456.

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 3 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.

How have Orlando to Chicago flight prices changed over time?

As of February 2026, prices for Orlando to Chicago flights are approximately 4% cheaper when compared to flights at the same time last year.

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

United Airlines is the most popular carrier operating from Orlando 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 departing 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 that experiences the fewest 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 fewest 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 to Chicago on average per day?

The number of flights available between Orlando and Chicago is 45 per day as of February 2026. The most frequent departure time is 14:00, with 54% of daily flights leaving in the afternoon.

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

As of February 2026, 321 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% 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

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 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?

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, organise 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