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

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

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

As of July 2025, 397 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Sun, with 16% of weekly flights taking off on this day.

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

The number of flights available between Orlando and Chicago is 56 per day as of July 2025. The most frequent departure time is 14:00, with 49% of daily flights leaving in the afternoon.

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.

£39 Cheap Flights from Orlando to Chicago in 2025

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

Prices are currently low for flights on this route. Typical prices usually range from £101 to £186. The lowest price recently found on this route was £86.

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Find the cheapest flights from Orlando to Chicago

Round-trip

One-way

Last minute

Direct

Cheap return flights

19:50 - 21:58MCO-ORD

3h 08mdirect

17:17 - 21:06ORD-MCO

2h 49mdirect

£86Spirit Airlines

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Wed, 24 Sep - Thu, 25 Sep

09:50 - 11:50MCO-ORD

3h 00mdirect

06:00 - 09:45ORD-MCO

2h 45mdirect

£97Southwest

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Thu, 14 Aug - Tue, 19 Aug

07:25 - 11:50MCO-ORD

5h 25m1 stop

06:00 - 09:45ORD-MCO

2h 45mdirect

£105Southwest

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Wed, 20 Aug - Sat, 23 Aug

09:50 - 11:50MCO-ORD

3h 00mdirect

07:30 - 18:35ORD-MCO

10h 05m2 stops

£108Southwest

Find Deal

Thu, 14 Aug - Tue, 19 Aug

09:50 - 11:50MCO-ORD

3h 00mdirect

07:30 - 18:35ORD-MCO

10h 05m2 stops

£109Southwest

Find Deal

Fri, 22 Aug - Tue, 26 Aug

07:10 - 12:45MCO-ORD

6h 35m1 stop

15:10 - 21:50ORD-MCO

5h 40m1 stop

£112Southwest

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Sat, 23 Aug - Tue, 26 Aug

08:50 - 21:30MCO-ORD

13h 40m2 stops

06:00 - 09:45ORD-MCO

2h 45mdirect

£113Southwest

Find Deal

Wed, 3 Sep - Mon, 8 Sep

19:45 - 23:58MCO-ORD

5h 13m1 stop

05:40 - 11:49ORD-MCO

5h 09m1 stop

£146Delta

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Tue, 23 Dec - Wed, 31 Dec

18:59 - 00:09MCO-ORD

6h 10m1 stop

19:59 - 01:28ORD-MCO

4h 29m1 stop

£147Delta

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Fri, 1 Aug - Mon, 4 Aug

09:32 - 11:39MCO-ORD

3h 07mdirect

17:51 - 21:47ORD-MCO

2h 56mdirect

£170United Airlines

Find Deal

Thu, 7 Aug - Sun, 10 Aug

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets

Spirit Airlines

24 Sept

MCO19:50Orlando

3h 08m

ORD21:58Chicago O'Hare Intl

25 Sept

ORD17:17Chicago O'Hare Intl

2h 49m

MCO21:06Orlando

£86

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Spirit Airlines

24 Sept

MCO14:07Orlando

3h 05m

ORD16:12Chicago O'Hare Intl

25 Sept

ORD20:56Chicago O'Hare Intl

10h 50m

1 stop

MCO08:46Orlando

£116

Find similar

Spirit Airlines

15 Jul

MCO21:59Orlando

10h 05m

1 stop

ORD07:04Chicago O'Hare Intl

18 Jul

ORD16:37Chicago O'Hare Intl

5h 23m

1 stop

MCO23:00Orlando

£256

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Southwest flights from Orlando to Chicago

Our best Southwest deals on Orlando to Chicago flight tickets

Southwest

14 Aug

MCO09:50Orlando

3h 00m

ORD11:50Chicago O'Hare Intl

19 Aug

ORD06:00Chicago O'Hare Intl

2h 45m

MCO09:45Orlando

£97

Find similar

Southwest

20 Aug

MCO07:25Orlando

5h 25m

1 stop

ORD11:50Chicago O'Hare Intl

23 Aug

ORD06:00Chicago O'Hare Intl

2h 45m

MCO09:45Orlando

£104

Find similar

Southwest

14 Aug

MCO09:50Orlando

3h 00m

ORD11:50Chicago O'Hare Intl

19 Aug

ORD07:30Chicago O'Hare Intl

10h 05m

2 stops

MCO18:35Orlando

£108

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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

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 £99, 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 August instead. Flights to Chicago in August, while not as cheap as those in September, still average around £117.

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 £150. 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 £462.

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 £260 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £497.

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 £165 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 £135 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 July 2025, prices for Orlando to Chicago flights are approximately 15% 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

Best price found	£39
Fastest flight time	3h 00m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Orlando in the past 72 hours is £39. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £86.

The fastest flight from Orlando to Chicago takes 3h 00m

Direct flights go from Orlando to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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How far is Orlando to Chicago by plane?
The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 00m 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 (19.50% of total bookings). The next most popular plane models are Airbus A321-100/200 (12.32%), Airbus A320neo (11.35%), and Boeing 737 MAX 8 (10.62%).

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.