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

Prices are currently low for flights on this route. Typical prices usually range from $77 to $105. The lowest price recently found on this route was $72.

Question 1

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

Accepted Answer

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $278.

Question 2

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

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from $77 to $105.
The lowest price recently found on this route was $72.

Question 3

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

Accepted Answer

Flying to Chicago Midway Airport from Orlando at noon is the least expensive time of day to depart. momondo users have found prices as low as $170 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $233. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 4

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

Accepted Answer

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

Question 5

What is the cheapest Orlando to Chicago Midway flight route?

Accepted Answer

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

Question 6

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

Accepted Answer

As of January 2026, 6 flights take off from Orlando and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00AM, with 42% of daily flights taking off in the evening.

Question 7

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

Accepted Answer

As of January 2026, prices for Orlando to Chicago Midway Airport flights are approximately 134% more expensive when compared to flights at the same time last year.

Question 8

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

Accepted Answer

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $201 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 for as low as $158 on momondo.

Question 9

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

Accepted Answer

Frontier is the most popular carrier operating from Orlando to Chicago Midway

Question 10

What is the cheapest month to fly to Chicago Midway Airport?

Accepted Answer

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $92. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Orlando during the month October is also very affordable. Most momondo users find prices during this month for around $134.

Question 11

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

Accepted Answer

As of January 2026, 45 flights take off from Orlando and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

Question 12

What airlines fly to Chicago Midway Airport?

Accepted Answer

Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Orlando according to our data. Frontier is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Question 13

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

Accepted Answer

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.

Question 14

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

Accepted Answer

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.

Question 15

How often are flights from Orlando to Chicago delayed?

Accepted Answer

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 135 minutes.

Question 16

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

Accepted Answer

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.

Question 17

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

Accepted Answer

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

Question 18

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

Accepted Answer

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

Question 19

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

Accepted Answer

As of January 2026, there are 3 operators available to choose from for flights from Orlando to Chicago Midway Airport.

Question 20

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

Accepted Answer

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 Midway Airport.

Question 21

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

Accepted Answer

The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best Price Found	$149
Fastest flight time	2h 45m
Direct flights	Every day

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $69	Free Cancellation	Rating 5.7 3,061 reviews	Search Frontier flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,029 reviews	Search Delta flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights

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 3/5. 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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How to get the cheapest flight ticket from Orlando to Chicago Midway Airport

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

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.

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

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

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

As of January 2026, prices for Orlando to Chicago Midway Airport flights are approximately 134% 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 is the most popular carrier 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 135 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. 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, 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 to Chicago Midway Airport on average per day?

As of January 2026, 6 flights take off from Orlando and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00AM, with 42% of daily flights taking off in the evening.

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

As of January 2026, 45 flights take off from Orlando and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

When to book flights from Orlando to Chicago Midway Airport

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

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

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

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

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