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Cheap flights from Orlando Airport to Chicago from £37

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 24/1. 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
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Cheap return flights

Spirit Airlines Logo
15:53 - 17:53MCO-ORD
3h 00mdirect
Spirit Airlines Logo
06:00 - 09:44ORD-MCO
2h 44mdirect
£73Spirit Airlines
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Tue, 14 Oct - Tue, 21 Oct
United Airlines Logo
07:15 - 09:21MCO-ORD
3h 06mdirect
United Airlines Logo
07:13 - 11:07ORD-MCO
2h 54mdirect
£117United Airlines
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Thu, 16 Oct - Sun, 19 Oct
Southwest Logo
15:50 - 17:55MCO-ORD
3h 05mdirect
Southwest Logo
15:10 - 18:50ORD-MCO
2h 40mdirect
£131Southwest
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Thu, 9 Oct - Sat, 11 Oct
Delta Logo
09:00 - 12:16MCO-ORD
4h 16m1 stop
Delta Logo
10:30 - 18:40ORD-MCO
7h 10m1 stop
£144Delta
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Wed, 22 Oct - Mon, 27 Oct
Southwest Logo
06:30 - 11:50MCO-ORD
6h 20m1 stop
Southwest Logo
15:10 - 18:50ORD-MCO
2h 40mdirect
£145Southwest
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Wed, 8 Oct - Sat, 11 Oct
Delta Logo
11:00 - 14:33MCO-ORD
4h 33m1 stop
Delta Logo
16:56 - 22:35ORD-MCO
4h 39m1 stop
£164Delta
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Tue, 30 Sep - Sat, 11 Oct
American Airlines Logo
06:47 - 08:56MCO-ORD
3h 09mdirect
American Airlines Logo
19:34 - 23:24ORD-MCO
2h 50mdirect
£196American Airlines
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Mon, 10 Nov - Thu, 13 Nov
Sun Country Air Logo
13:54 - 08:20MCO-ORD
19h 26m1 stop
Sun Country Air Logo
20:22 - 15:54ORD-MCO
18h 32m1 stop
£212Sun Country Air
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Wed, 26 Nov - Mon, 1 Dec
Sun Country Air Logo
20:11 - 16:50MCO-ORD
21h 39m1 stop
Sun Country Air Logo
10:51 - 21:00ORD-MCO
9h 09m1 stop
£224Sun Country Air
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Fri, 19 Dec - Mon, 22 Dec
American Airlines Logo
06:00 - 11:06MCO-ORD
6h 06m1 stop
American Airlines Logo
11:40 - 18:45ORD-MCO
6h 05m1 stop
£228American Airlines
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Mon, 10 Nov - Thu, 13 Nov

United Airlines flights from Orlando Airport to Chicago

Our best United Airlines deals on Orlando Airport to Chicago flight tickets
United Airlines
16 Oct
MCO07:15Orlando
3h 06m
ORD09:21Chicago O'Hare Intl
19 Oct
ORD07:13Chicago O'Hare Intl
2h 54m
MCO11:07Orlando
£117
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United Airlines
11 Oct
MCO16:35Orlando
3h 06m
ORD18:41Chicago O'Hare Intl
15 Oct
ORD07:13Chicago O'Hare Intl
2h 54m
MCO11:07Orlando
£151
Find similar
United Airlines
3 Oct
MCO14:30Orlando
3h 06m
ORD16:36Chicago O'Hare Intl
5 Oct
ORD06:00Chicago O'Hare Intl
2h 48m
MCO09:48Orlando
£168
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Sun Country Air flights from Orlando Airport to Chicago

Our best Sun Country Air deals on Orlando Airport to Chicago flight tickets
Sun Country Air
26 Nov
MCO13:54Orlando
19h 26m
1 stop
ORD08:20Chicago O'Hare Intl
1 Dec
ORD20:22Chicago O'Hare Intl
18h 32m
1 stop
MCO15:54Orlando
£212
Find similar
Sun Country Air
19 Dec
MCO20:11Orlando
21h 39m
1 stop
ORD16:50Chicago O'Hare Intl
22 Dec
ORD10:51Chicago O'Hare Intl
9h 09m
1 stop
MCO21:00Orlando
£224
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Sun Country Air
20 Dec
MCO07:20Orlando
10h 30m
1 stop
ORD16:50Chicago O'Hare Intl
31 Dec
ORD11:45Chicago O'Hare Intl
6h 21m
1 stop
MCO19:06Orlando
£229
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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 17 September 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

Tue 14/10

15:53-17:53

Nonstop3h 00m

Chicago O'Hare Intl

Tue 21/10

06:00-09:44

Nonstop2h 44m

£73

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 16/10

07:15-09:21

Nonstop3h 06m

Chicago O'Hare Intl

Sun 19/10

07:13-11:07

Nonstop2h 54m

£117

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 9/10

15:50-17:55

Nonstop3h 05m

Chicago O'Hare Intl

Sat 11/10

15:10-18:50

Nonstop2h 40m

£131

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 22/10

09:00-12:16

1 stop4h 16m

Chicago O'Hare Intl

Mon 27/10

10:30-18:40

1 stop7h 10m

£144

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/10

06:30-11:50

1 stop6h 20m

Chicago O'Hare Intl

Sat 11/10

15:10-18:50

Nonstop2h 40m

£145

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 30/9

11:00-14:33

1 stop4h 33m

Chicago O'Hare Intl

Sat 11/10

16:56-22:35

1 stop4h 39m

£164

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 10/11

06:47-08:56

Nonstop3h 09m

Chicago O'Hare Intl

Thu 13/11

19:34-23:24

Nonstop2h 50m

£196

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 26/11

13:54-08:20

1 stop19h 26m

Chicago O'Hare Intl

Mon 1/12

20:22-15:54

1 stop18h 32m

£212

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 19/12

20:11-16:50

1 stop21h 39m

Chicago O'Hare Intl

Mon 22/12

10:51-21:00

1 stop9h 09m

£224

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 10/11

06:00-11:06

1 stop6h 06m

Chicago O'Hare Intl

Thu 13/11

11:40-18:45

1 stop6h 05m

£228

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 £111, 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 April instead. Flights to Chicago in April, 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 £111. 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 £485.

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

Flying to Chicago from Orlando Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as £279 when looking at flights departing in the evening. Flights at midday are often more expensive, with an average ticket price of £492.

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 £161 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 £129 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 September 2025, prices for Orlando Airport to Chicago flights are approximately 3% 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)
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  • 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 00m.

  • 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.

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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