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Cheap flights from Orlando Airport to Chicago from £49

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 5/2. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
13:56 - 16:03MCO-ORD
3h 07mdirect
Spirit Airlines Logo
06:48 - 10:30ORD-MCO
2h 42mdirect
£87Spirit Airlines
Find Deal
Tue, 25 Nov - Sat, 29 Nov
United Airlines Logo
16:40 - 18:45MCO-ORD
3h 05mdirect
United Airlines Logo
07:20 - 11:15ORD-MCO
2h 55mdirect
£104United Airlines
Find Deal
Fri, 16 Jan - Sun, 18 Jan
Multiple Airlines Logo
19:50 - 18:46MCO-ORD
47h 56m2 stops
Multiple Airlines Logo
14:36 - 18:41ORD-MCO
3h 05mdirect
£119Multiple Airlines
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Sun, 30 Nov - Sun, 7 Dec
Southwest Logo
06:40 - 12:15MCO-ORD
6h 35m1 stop
Southwest Logo
13:45 - 20:50ORD-MCO
6h 05m1 stop
£119Southwest
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Fri, 16 Jan - Mon, 19 Jan
Delta Logo
05:30 - 10:14MCO-ORD
5h 44m1 stop
Delta Logo
16:20 - 22:50ORD-MCO
5h 30m1 stop
£150Delta
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Tue, 2 Dec - Tue, 9 Dec
Southwest Logo
09:05 - 11:10MCO-ORD
3h 05mdirect
Southwest Logo
06:05 - 09:45ORD-MCO
2h 40mdirect
£170Southwest
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Sat, 6 Dec - Sun, 7 Dec
JetBlue Logo
11:00 - 17:31MCO-ORD
7h 31m1 stop
JetBlue Logo
11:30 - 23:07ORD-MCO
10h 37m1 stop
£173JetBlue
Find Deal
Wed, 8 Apr - Mon, 13 Apr
Delta Logo
06:15 - 10:14MCO-ORD
4h 59m1 stop
Delta Logo
10:45 - 18:43ORD-MCO
6h 58m1 stop
£204Delta
Find Deal
Fri, 5 Dec - Sun, 7 Dec
JetBlue Logo
07:55 - 17:31MCO-ORD
10h 36m1 stop
JetBlue Logo
13:45 - 22:00ORD-MCO
7h 15m1 stop
£205JetBlue
Find Deal
Mon, 30 Mar - Fri, 10 Apr
Multiple Airlines Logo
18:02 - 13:22MCO-ORD
20h 20m1 stop
Multiple Airlines Logo
14:36 - 18:41ORD-MCO
3h 05mdirect
£211Multiple Airlines
Find Deal
Sun, 30 Nov - Sun, 7 Dec

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
25 Nov
MCO13:56Orlando
3h 07m
ORD16:03Chicago O'Hare Intl
29 Nov
ORD06:48Chicago O'Hare Intl
2h 42m
MCO10:30Orlando
£87
Find similar
Spirit Airlines
25 Nov
MCO06:30Orlando
9h 01m
1 stop
ORD14:31Chicago O'Hare Intl
29 Nov
ORD06:48Chicago O'Hare Intl
2h 42m
MCO10:30Orlando
£144
Find similar
Spirit Airlines
30 Nov
MCO19:50Orlando
18h 33m
2 stops
ORD13:23Chicago O'Hare Intl
7 Dec
ORD13:52Chicago O'Hare Intl
8h 57m
1 stop
MCO23:49Orlando
£205
Find similar

United Airlines flights from Orlando Airport to Chicago

Our best United Airlines deals on Orlando Airport to Chicago flight tickets
United Airlines
16 Jan
MCO16:40Orlando
3h 05m
ORD18:45Chicago O'Hare Intl
18 Jan
ORD07:20Chicago O'Hare Intl
2h 55m
MCO11:15Orlando
£104
Find similar
United Airlines
4 Dec
MCO10:30Orlando
3h 03m
ORD12:33Chicago O'Hare Intl
7 Dec
ORD18:12Chicago O'Hare Intl
2h 56m
MCO22:08Orlando
£121
Find similar
United Airlines
24 Dec
MCO09:26Orlando
3h 09m
ORD11:35Chicago O'Hare Intl
31 Dec
ORD07:13Chicago O'Hare Intl
2h 52m
MCO11:05Orlando
£157
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 3 November 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 25/11

13:56-16:03

Nonstop3h 07m

Chicago O'Hare Intl

Sat 29/11

06:48-10:30

Nonstop2h 42m

£87

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 16/1

16:40-18:45

Nonstop3h 05m

Chicago O'Hare Intl

Sun 18/1

07:20-11:15

Nonstop2h 55m

£104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 30/11

19:50-18:46

2 stops47h 56m

Chicago O'Hare Intl

Sun 7/12

14:36-18:41

Nonstop3h 05m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 16/1

06:40-12:15

1 stop6h 35m

Chicago O'Hare Intl

Mon 19/1

13:45-20:50

1 stop6h 05m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 2/12

05:30-10:14

1 stop5h 44m

Chicago O'Hare Intl

Tue 9/12

16:20-22:50

1 stop5h 30m

£150

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 6/12

09:05-11:10

Nonstop3h 05m

Chicago O'Hare Intl

Sun 7/12

06:05-09:45

Nonstop2h 40m

£170

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/4

11:00-17:31

1 stop7h 31m

Chicago O'Hare Intl

Mon 13/4

11:30-23:07

1 stop10h 37m

£173

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 5/12

06:15-10:14

1 stop4h 59m

Chicago O'Hare Intl

Sun 7/12

10:45-18:43

1 stop6h 58m

£204

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 30/3

07:55-17:31

1 stop10h 36m

Chicago O'Hare Intl

Fri 10/4

13:45-22:00

1 stop7h 15m

£205

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 30/11

18:02-13:22

1 stop20h 20m

Chicago O'Hare Intl

Sun 7/12

14:36-18:41

Nonstop3h 05m

£211

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 £116, 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 £118.

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 £115. 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 £474.

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 £248 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £511.

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 Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £166 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 £141 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 November 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 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.

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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