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

The number of flights available between Orlando and Chicago is 46 per day as of July 2025. The most frequent departure time is 14:00, with 49% of daily flights leaving in the afternoon.

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

As of July 2025, 326 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.

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

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from Orlando to Chicago

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.

£35 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 £91 to £185. The lowest price recently found on this route was £75.

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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

£75Spirit Airlines

Find Deal

Fri, 12 Sep - Sun, 14 Sep

14:07 - 16:12MCO-ORD

3h 05mdirect

06:30 - 10:13ORD-MCO

2h 43mdirect

£83Spirit Airlines

Find Deal

Wed, 24 Sep - Thu, 25 Sep

06:31 - 17:39MCO-ORD

12h 08m1 stop

17:17 - 21:06ORD-MCO

2h 49mdirect

£104Spirit Airlines

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Fri, 12 Sep - Sun, 14 Sep

08:45 - 10:45MCO-ORD

3h 00mdirect

06:00 - 09:45ORD-MCO

2h 45mdirect

£119Southwest

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Sat, 6 Sep - Mon, 8 Sep

11:00 - 13:06MCO-ORD

3h 06mdirect

07:10 - 11:04ORD-MCO

2h 54mdirect

£119United Airlines

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Fri, 29 Aug - Mon, 1 Sep

11:00 - 13:05MCO-ORD

3h 05mdirect

06:00 - 09:45ORD-MCO

2h 45mdirect

£131Southwest

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Wed, 27 Aug - Mon, 1 Sep

16:50 - 21:36MCO-ORD

5h 46m1 stop

09:47 - 15:31ORD-MCO

4h 44m1 stop

£157Delta

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Tue, 19 Aug - Wed, 27 Aug

09:35 - 11:41MCO-ORD

3h 06mdirect

17:55 - 21:46ORD-MCO

2h 51mdirect

£170United Airlines

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Wed, 3 Sep - Sat, 6 Sep

15:10 - 21:48MCO-ORD

7h 38m1 stop

14:20 - 22:24ORD-MCO

7h 04m1 stop

£178JetBlue

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Thu, 11 Dec - Mon, 12 Jan

06:00 - 12:16MCO-ORD

7h 16m1 stop

05:45 - 10:48ORD-MCO

4h 03m1 stop

£191Delta

Find Deal

Wed, 20 Aug - Sun, 24 Aug

Alaska Airlines flights from Orlando to Chicago

Our best Alaska Airlines deals on Orlando to Chicago flight tickets

Alaska Airlines

13 Aug

MCO07:20Orlando

16h 10m

1 stop

ORD22:30Chicago O'Hare Intl

18 Aug

ORD07:00Chicago O'Hare Intl

16h 33m

2 stops

MCO00:33Orlando

£611

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Alaska Airlines

13 Aug

MCO07:20Orlando

17h 19m

2 stops

ORD23:39Chicago O'Hare Intl

18 Aug

ORD07:00Chicago O'Hare Intl

16h 33m

2 stops

MCO00:33Orlando

£624

Find similar

Alaska Airlines

13 Aug

MCO10:00Orlando

13h 30m

1 stop

ORD22:30Chicago O'Hare Intl

17 Aug

ORD07:00Chicago O'Hare Intl

16h 33m

2 stops

MCO00:33Orlando

£656

Find similar

Southwest flights from Orlando to Chicago

Our best Southwest deals on Orlando to Chicago flight tickets

Southwest

6 Sept

MCO08:45Orlando

3h 00m

ORD10:45Chicago O'Hare Intl

8 Sept

ORD06:00Chicago O'Hare Intl

2h 45m

MCO09:45Orlando

£119

Find similar

Southwest

27 Aug

MCO11:00Orlando

3h 05m

ORD13:05Chicago O'Hare Intl

1 Sept

ORD06:00Chicago O'Hare Intl

2h 45m

MCO09:45Orlando

£131

Find similar

Southwest

31 Aug

MCO20:15Orlando

3h 05m

ORD22:20Chicago O'Hare Intl

1 Sept

ORD06:00Chicago O'Hare Intl

2h 45m

MCO09:45Orlando

£134

Find similar

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 12/9

19:50-21:58

Nonstop3h 08m

Chicago O'Hare Intl

Sun 14/9

17:17-21:06

Nonstop2h 49m

£75

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 24/9

14:07-16:12

Nonstop3h 05m

Chicago O'Hare Intl

Thu 25/9

06:30-10:13

Nonstop2h 43m

£83

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 12/9

06:31-17:39

1 stop12h 08m

Chicago O'Hare Intl

Sun 14/9

17:17-21:06

Nonstop2h 49m

£104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 6/9

08:45-10:45

Nonstop3h 00m

Chicago O'Hare Intl

Mon 8/9

06:00-09:45

Nonstop2h 45m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 29/8

11:00-13:06

Nonstop3h 06m

Chicago O'Hare Intl

Mon 1/9

07:10-11:04

Nonstop2h 54m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 27/8

11:00-13:05

Nonstop3h 05m

Chicago O'Hare Intl

Mon 1/9

06:00-09:45

Nonstop2h 45m

£131

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 19/8

16:50-21:36

1 stop5h 46m

Chicago O'Hare Intl

Wed 27/8

09:47-15:31

1 stop4h 44m

£157

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 3/9

09:35-11:41

Nonstop3h 06m

Chicago O'Hare Intl

Sat 6/9

17:55-21:46

Nonstop2h 51m

£170

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 11/12

15:10-21:48

1 stop7h 38m

Chicago O'Hare Intl

Mon 12/1

14:20-22:24

1 stop7h 04m

£178

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 20/8

06:00-12:16

1 stop7h 16m

Chicago O'Hare Intl

Sun 24/8

05:45-10:48

1 stop4h 03m

£191

Flights are sorted by cheapest return 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 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 £100, 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 £119.

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 £123. 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 Friday, with ticket prices averaging around £497.

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

Flying to Chicago from Orlando in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as £245 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £504.

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 £164 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 13% 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	£35
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 £35. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £75.

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 (17.03% of total bookings). The next most popular plane models are Airbus A321-100/200 (14.82%), Boeing 737 MAX 8 (10.68%), and Airbus A320neo (10.40%).

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.