Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Orlando Airport to Chicago from £39

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 17/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
Voted winner of Europe's Best Travel App 2023

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Orlando Airport to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
19:15 - 21:19MCO-ORD
3h 04mdirect
Spirit Airlines Logo
07:15 - 11:07ORD-MCO
2h 52mdirect
£63Spirit Airlines
Find Deal
Thu, 4 Dec - Mon, 8 Dec
Spirit Airlines Logo
13:56 - 16:03MCO-ORD
3h 07mdirect
Spirit Airlines Logo
16:58 - 20:42ORD-MCO
2h 44mdirect
£78Spirit Airlines
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Southwest Logo
19:45 - 21:50MCO-ORD
3h 05mdirect
Southwest Logo
06:05 - 09:45ORD-MCO
2h 40mdirect
£80Southwest
Find Deal
Wed, 24 Dec - Wed, 31 Dec
Spirit Airlines Logo
07:00 - 19:16MCO-ORD
13h 16m1 stop
Spirit Airlines Logo
06:05 - 09:48ORD-MCO
2h 43mdirect
£82Spirit Airlines
Find Deal
Thu, 22 Jan - Sun, 25 Jan
United Airlines Logo
09:25 - 11:29MCO-ORD
3h 04mdirect
United Airlines Logo
06:00 - 09:48ORD-MCO
2h 48mdirect
£93United Airlines
Find Deal
Sat, 13 Dec - Mon, 22 Dec
United Airlines Logo
07:18 - 09:35MCO-ORD
3h 17mdirect
United Airlines Logo
19:50 - 23:43ORD-MCO
2h 53mdirect
£98United Airlines
Find Deal
Thu, 12 Feb - Sun, 15 Feb
Southwest Logo
13:15 - 15:25MCO-ORD
3h 10mdirect
Southwest Logo
15:45 - 19:30ORD-MCO
2h 45mdirect
£99Southwest
Find Deal
Fri, 13 Feb - Sun, 15 Feb
Delta Logo
18:35 - 00:01MCO-ORD
6h 26m1 stop
Delta Logo
08:55 - 17:00ORD-MCO
7h 05m1 stop
£147Delta
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Delta Logo
11:20 - 16:46MCO-ORD
6h 26m1 stop
Delta Logo
18:08 - 23:48ORD-MCO
4h 40m1 stop
£148Delta
Find Deal
Fri, 14 Nov - Mon, 24 Nov
JetBlue Logo
10:00 - 17:31MCO-ORD
8h 31m1 stop
JetBlue Logo
11:30 - 23:07ORD-MCO
10h 37m1 stop
£170JetBlue
Find Deal
Wed, 8 Apr - Mon, 13 Apr

United Airlines flights from Orlando Airport to Chicago

Our best United Airlines deals on Orlando Airport to Chicago flight tickets
United Airlines
13 Dec
MCO09:25Orlando
3h 04m
ORD11:29Chicago O'Hare Intl
22 Dec
ORD06:00Chicago O'Hare Intl
2h 48m
MCO09:48Orlando
£93
Find similar
United Airlines
12 Feb
MCO07:18Orlando
3h 17m
ORD09:35Chicago O'Hare Intl
15 Feb
ORD19:50Chicago O'Hare Intl
2h 53m
MCO23:43Orlando
£98
Find similar
United Airlines
16 Jan
MCO18:15Orlando
3h 09m
ORD20:24Chicago O'Hare Intl
19 Jan
ORD14:30Chicago O'Hare Intl
2h 51m
MCO18:21Orlando
£102
Find similar

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
4 Dec
MCO19:15Orlando
3h 04m
ORD21:19Chicago O'Hare Intl
8 Dec
ORD07:15Chicago O'Hare Intl
2h 52m
MCO11:07Orlando
£63
Find similar
Spirit Airlines
21 Nov
MCO13:56Orlando
3h 07m
ORD16:03Chicago O'Hare Intl
24 Nov
ORD16:58Chicago O'Hare Intl
2h 44m
MCO20:42Orlando
£78
Find similar
Spirit Airlines
22 Jan
MCO07:00Orlando
13h 16m
1 stop
ORD19:16Chicago O'Hare Intl
25 Jan
ORD06:05Chicago O'Hare Intl
2h 43m
MCO09:48Orlando
£82
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Orlando Airport to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 279,928 searches. Data last updated 22 October 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 4/12

19:15-21:19

Nonstop3h 04m

Chicago O'Hare Intl

Mon 8/12

07:15-11:07

Nonstop2h 52m

£63

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 21/11

13:56-16:03

Nonstop3h 07m

Chicago O'Hare Intl

Mon 24/11

16:58-20:42

Nonstop2h 44m

£78

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 24/12

19:45-21:50

Nonstop3h 05m

Chicago O'Hare Intl

Wed 31/12

06:05-09:45

Nonstop2h 40m

£80

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 22/1

07:00-19:16

1 stop13h 16m

Chicago O'Hare Intl

Sun 25/1

06:05-09:48

Nonstop2h 43m

£82

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 13/12

09:25-11:29

Nonstop3h 04m

Chicago O'Hare Intl

Mon 22/12

06:00-09:48

Nonstop2h 48m

£93

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 12/2

07:18-09:35

Nonstop3h 17m

Chicago O'Hare Intl

Sun 15/2

19:50-23:43

Nonstop2h 53m

£98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 13/2

13:15-15:25

Nonstop3h 10m

Chicago O'Hare Intl

Sun 15/2

15:45-19:30

Nonstop2h 45m

£99

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 5/12

18:35-00:01

1 stop6h 26m

Chicago O'Hare Intl

Mon 8/12

08:55-17:00

1 stop7h 05m

£147

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 14/11

11:20-16:46

1 stop6h 26m

Chicago O'Hare Intl

Mon 24/11

18:08-23:48

1 stop4h 40m

£148

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/4

10:00-17:31

1 stop8h 31m

Chicago O'Hare Intl

Mon 13/4

11:30-23:07

1 stop10h 37m

£170

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando Airport 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

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Orlando Airport is in February. Flight prices, which tend to average around £114, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Chicago from Orlando Airport during September instead. Flights to Chicago in September, while not as cheap as those in February, still average around £116.

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 £113. 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 £466.

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

Flying to Chicago from Orlando Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as £244 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £501.

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 Airport 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 Airport for as low as £138 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 Airport to Chicago flight prices changed over time?

As of October 2025, prices for Orlando Airport to Chicago flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago

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

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

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

Fastest flight time

3h 00m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Orlando Airport to Chicago takes 3h 00m
Direct flights go from Orlando Airport to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Orlando to Chicago by plane?

    Chicago is 993.7 mi away from Orlando. In terms of flight time, this usually takes a little over 3h 03m.

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

    Prices for flights from Orlando Airport to Chicago refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Orlando Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Orlando to Chicago for you.

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?

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 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 21/11
Fri 28/11
By creating a price alert you accept our terms of use and privacy policy.

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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport