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

5 flights are operational daily from Orlando Airport to Chicago Midway Airport as of November 2025. The most popular departure time for this route is 12:00PM, with 52% of flights per day taking off in the afternoon.

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

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

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

Frontier, Southwest, and Delta are the most popular carriers operating from Orlando to Chicago Midway

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 140 minutes.

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

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

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. Saturday has historically seen more delays on average compared to the rest of the week.

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

38 flights are operational weekly from Orlando Airport to Chicago Midway Airport as of November 2025. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.

What airlines fly to Chicago Midway Airport?

Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Orlando Airport according to our data. Frontier is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Orlando Airport to Chicago Midway Airport were last updated today.

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

There are 4 operators available for flights from Orlando Airport to Chicago Midway Airport as of November 2025.

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

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 Midway Airport.

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

The travel and health documents you'll need for your trip to Chicago Midway Airport 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 Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$53 Cheap Flights from Orlando Airport to Chicago Midway Airport in 2025/26

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9:33 pm - 11:29 pmMCO-MDW

2h 56mnonstop

5:47 pm - 9:35 pmMDW-MCO

2h 48mnonstop

$81Frontier

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Fri, Nov 21 - Mon, Nov 24

2:34 pm - 4:30 pmMCO-MDW

2h 56mnonstop

4:46 pm - 8:34 pmMDW-MCO

2h 48mnonstop

$82Frontier

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Thu, Nov 20 - Fri, Nov 28

2:34 pm - 4:30 pmMCO-MDW

2h 56mnonstop

6:02 pm - 9:49 pmMDW-MCO

2h 47mnonstop

$83Frontier

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Thu, Nov 27 - Sat, Nov 29

8:40 pm - 10:39 pmMCO-MDW

2h 59mnonstop

12:35 pm - 12:59 amMDW-MCO

11h 24m1 stop

$84Frontier

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Fri, Dec 12 - Mon, Dec 15

2:34 pm - 4:30 pmMCO-MDW

2h 56mnonstop

5:30 pm - 9:18 pmMDW-MCO

2h 48mnonstop

$85Frontier

Find Deal

Thu, Nov 20 - Sun, Nov 23

3:10 pm - 5:07 pmMCO-MDW

2h 57mnonstop

5:47 pm - 9:35 pmMDW-MCO

2h 48mnonstop

$87Frontier

Find Deal

Sat, Nov 22 - Mon, Nov 24

2:34 pm - 4:30 pmMCO-MDW

2h 56mnonstop

6:02 pm - 9:49 pmMDW-MCO

2h 47mnonstop

$88Frontier

Find Deal

Sun, Nov 23 - Sat, Nov 29

6:35 am - 8:32 amMCO-MDW

2h 57mnonstop

4:46 pm - 8:34 pmMDW-MCO

2h 48mnonstop

$89Frontier

Find Deal

Mon, Nov 17 - Fri, Nov 28

5:53 pm - 7:50 pmMCO-MDW

2h 57mnonstop

6:00 am - 3:11 pmMDW-MCO

8h 11m1 stop

$113Multiple Airlines

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Fri, Jan 23 - Sun, Jan 25

8:40 pm - 10:39 pmMCO-MDW

2h 59mnonstop

7:44 am - 4:57 pmMDW-MCO

8h 13m1 stop

$117Multiple Airlines

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Fri, Dec 12 - Tue, Dec 16

Frontier flights from Orlando Airport to Chicago Midway Airport

Our best Frontier deals on Orlando Airport to Chicago Midway Airport flight tickets

Frontier

Nov 21

MCO9:33 pmOrlando

2h 56m

MDW11:29 pmChicago Midway

Nov 24

MDW5:47 pmChicago Midway

2h 48m

MCO9:35 pmOrlando

$81

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Frontier

Nov 20

MCO2:34 pmOrlando

2h 56m

MDW4:30 pmChicago Midway

Nov 28

MDW4:46 pmChicago Midway

2h 48m

MCO8:34 pmOrlando

$82

Find similar

Frontier

Nov 27

MCO2:34 pmOrlando

2h 56m

MDW4:30 pmChicago Midway

Nov 29

MDW6:02 pmChicago Midway

2h 47m

MCO9:49 pmOrlando

$83

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OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 11/21

9:33 pm-11:29 pm

Nonstop2h 56m

Chicago Midway

Mon 11/24

5:47 pm-9:35 pm

Nonstop2h 48m

$81

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/20

2:34 pm-4:30 pm

Nonstop2h 56m

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$82

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/27

2:34 pm-4:30 pm

Nonstop2h 56m

Chicago Midway

Sat 11/29

6:02 pm-9:49 pm

Nonstop2h 47m

$83

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/12

8:40 pm-10:39 pm

Nonstop2h 59m

Chicago Midway

Mon 12/15

12:35 pm-12:59 am

1 stop11h 24m

$84

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/20

2:34 pm-4:30 pm

Nonstop2h 56m

Chicago Midway

Sun 11/23

5:30 pm-9:18 pm

Nonstop2h 48m

$85

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 11/22

3:10 pm-5:07 pm

Nonstop2h 57m

Chicago Midway

Mon 11/24

5:47 pm-9:35 pm

Nonstop2h 48m

$87

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 11/23

2:34 pm-4:30 pm

Nonstop2h 56m

Chicago Midway

Sat 11/29

6:02 pm-9:49 pm

Nonstop2h 47m

$88

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 11/17

6:35 am-8:32 am

Nonstop2h 57m

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$89

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/23

5:53 pm-7:50 pm

Nonstop2h 57m

Chicago Midway

Sun 1/25

6:00 am-3:11 pm

1 stop8h 11m

$113

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/12

8:40 pm-10:39 pm

Nonstop2h 59m

Chicago Midway

Tue 12/16

7:44 am-4:57 pm

1 stop8h 13m

$117

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

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 Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $89. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month September is also very affordable. Most momondo users find prices during this month for around $161.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando Airport. The lowest ticket price found for a Friday departure recently was $175. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Orlando Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $290.

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

Flying to Chicago Midway Airport from Orlando Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $174 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $268. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Orlando to Chicago Midway flight route?

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

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

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $204 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando Airport for as low as $167 on momondo.

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

There is only 1 cabin class available to choose from on Orlando to Chicago Midway 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 Midway Airport flight prices changed over time?

As of November 2025, prices for Orlando Airport to Chicago Midway Airport flights are approximately 103% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago Midway Airport

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

Estimated round-trip price

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

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

Best Price Found	$95
Fastest flight time	2h 50m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Orlando Airport in the past 72 hours is $95. The best round-trip flight deal from Orlando Airport to Chicago Midway Airport found on momondo in the last 72 hours is $98.

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

Direct flights go from Orlando Airport to Chicago Midway Airport every day.

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How far is Orlando to Chicago Midway by plane?
The distance between Orlando and Chicago Midway is about 990.5 mi. 2h 56m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando Airport to Chicago Midway Airport?
Prices for flights from Orlando Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Orlando Airport to Chicago Midway Airport?
There are 4 operators available for flights from Orlando Airport to Chicago Midway Airport as of November 2025.
How old do you have to be to fly from Orlando Airport to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport 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 Midway Airport. 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 Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Orlando Airport and Chicago Midway Airport, the leading plane model is Airbus A320neo, making up 15.48% of the total bookings. Other popular models include Airbus A321neo with 15.09%, Boeing 737 MAX 8 with 14.33%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 11.25%.
What is the most popular airline from Orlando Airport to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Orlando Airport to Chicago Midway Airport is Frontier, representing 55% of all bookings. The subsequent popular airlines are Southwest at 40%, Delta at 3%, and Spirit Airlines at 2%.

Best airlines flying from Orlando Airport to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $68	Free Cancellation	Rating 5.8 3,117 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $88	Free Cancellation	Rating 6.3 8,114 reviews	Search Spirit Airlines flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights

Southwest Flights From Orlando Airport to Chicago Midway Airport
The lowest priced Southwest flight from Orlando Airport to Chicago Midway Airport from the last 72 hours was $159. Generally, Southwest has 37 flights on this route every week with an average price of $321. Southwest is rated 8.0/10 by our users.
Frontier Flights From Orlando Airport to Chicago Midway Airport
Frontier (5.8/10 from 3,117 reviews) operates around 1 flight from Orlando Airport to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $165, with deals from around $68 rare but found on momondo. Referenced prices are for round-trip Orlando Airport to Chicago Midway Airport flight searches in the last 72 hours.

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?

It is quick and easy to find Orlando to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Orlando on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Orlando to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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 Midway Airport trip

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Cheap flights from Orlando Airport to Chicago from $53

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 12/15. 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 Midway Airport

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

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 Midway Airport?

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

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

What is the cheapest Orlando to Chicago Midway flight route?

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

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

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

There is only 1 cabin class available to choose from on Orlando to Chicago Midway 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 Midway Airport flight prices changed over time?

As of November 2025, prices for Orlando Airport to Chicago Midway Airport flights are approximately 103% more expensive when compared to flights at the same time last year.

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

Frontier, Southwest, and Delta are the most popular carriers operating from Orlando to Chicago Midway

What airlines fly to Chicago Midway Airport?

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 140 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 at night 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. Saturday 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, Frontier have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

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

5 flights are operational daily from Orlando Airport to Chicago Midway Airport as of November 2025. The most popular departure time for this route is 12:00PM, with 52% of flights per day taking off in the afternoon.

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

38 flights are operational weekly from Orlando Airport to Chicago Midway Airport as of November 2025. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.

When to book flights from Orlando Airport to Chicago Midway Airport

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

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

Best Price Found

Fastest flight time

Direct flights

How far is Orlando to Chicago Midway by plane?

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

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

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

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

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

What is the most popular airline from Orlando Airport to Chicago Midway Airport?

Best airlines flying from Orlando Airport to Chicago Midway Airport

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

Southwest Flights From Orlando Airport to Chicago Midway Airport

Frontier Flights From Orlando Airport to Chicago Midway Airport

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 Midway Airport 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 Chicago

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Popular flights according to clicks in the last 7 days on momondo