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Cheap flights from Orlando 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 to Chicago departing on 4/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines Logo
21:00 - 23:06MCO-ORD
3h 06mdirect
Spirit Airlines Logo
06:48 - 10:30ORD-MCO
2h 42mdirect
£104Spirit Airlines
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Thu, 20 Nov - Fri, 21 Nov
Spirit Airlines Logo
21:00 - 23:06MCO-ORD
3h 06mdirect
Spirit Airlines Logo
21:22 - 10:14ORD-MCO
11h 52m1 stop
£110Spirit Airlines
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Thu, 27 Nov - Sun, 30 Nov
Southwest Logo
09:05 - 11:10MCO-ORD
3h 05mdirect
Southwest Logo
13:45 - 21:25ORD-MCO
6h 40m1 stop
£112Southwest
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Fri, 23 Jan - Mon, 26 Jan
United Airlines Logo
10:30 - 12:33MCO-ORD
3h 03mdirect
United Airlines Logo
14:10 - 18:01ORD-MCO
2h 51mdirect
£115United Airlines
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Tue, 9 Dec - Tue, 9 Dec
Southwest Logo
07:30 - 12:15MCO-ORD
5h 45m1 stop
Southwest Logo
14:15 - 22:00ORD-MCO
6h 45m1 stop
£119Southwest
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Tue, 6 Jan - Thu, 8 Jan
United Airlines Logo
09:25 - 11:29MCO-ORD
3h 04mdirect
United Airlines Logo
16:05 - 19:56ORD-MCO
2h 51mdirect
£121United Airlines
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Thu, 4 Dec - Sun, 7 Dec
JetBlue Logo
11:00 - 17:31MCO-ORD
7h 31m1 stop
JetBlue Logo
11:30 - 23:07ORD-MCO
10h 37m1 stop
£172JetBlue
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Wed, 8 Apr - Mon, 13 Apr
Delta Logo
18:52 - 00:01MCO-ORD
6h 09m1 stop
Delta Logo
10:46 - 18:45ORD-MCO
6h 59m1 stop
£178Delta
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Fri, 14 Nov - Wed, 19 Nov
Delta Logo
05:30 - 10:19MCO-ORD
5h 49m1 stop
Delta Logo
16:26 - 21:48ORD-MCO
4h 22m1 stop
£222Delta
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Sun, 9 Nov - Wed, 19 Nov
JetBlue Logo
10:00 - 17:31MCO-ORD
8h 31m1 stop
JetBlue Logo
08:00 - 18:59ORD-MCO
9h 59m1 stop
£232JetBlue
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Wed, 8 Apr - Wed, 15 Apr

Delta flights from Orlando to Chicago

Our best Delta deals on Orlando to Chicago flight tickets
Delta
14 Nov
MCO18:52Orlando
6h 09m
1 stop
ORD00:01Chicago O'Hare Intl
19 Nov
ORD10:46Chicago O'Hare Intl
6h 59m
1 stop
MCO18:45Orlando
£178
Find similar
Delta
9 Nov
MCO05:30Orlando
5h 49m
1 stop
ORD10:19Chicago O'Hare Intl
19 Nov
ORD16:26Chicago O'Hare Intl
4h 22m
1 stop
MCO21:48Orlando
£222
Find similar
Delta
19 Nov
MCO13:15Orlando
7h 08m
1 stop
ORD19:23Chicago O'Hare Intl
29 Nov
ORD18:15Chicago O'Hare Intl
5h 41m
1 stop
MCO00:56Orlando
£241
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Sun Country Air flights from Orlando to Chicago

Our best Sun Country Air deals on Orlando to Chicago flight tickets
Sun Country Air
23 Nov
MCO19:35Orlando
16h 04m
1 stop
ORD10:39Chicago O'Hare Intl
27 Nov
ORD09:20Chicago O'Hare Intl
24h 27m
1 stop
MCO10:47Orlando
£216
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Sun Country Air
22 Nov
MCO20:23Orlando
15h 16m
1 stop
ORD10:39Chicago O'Hare Intl
28 Nov
ORD11:00Chicago O'Hare Intl
7h 47m
1 stop
MCO19:47Orlando
£227
Find similar
Sun Country Air
23 Nov
MCO19:35Orlando
16h 04m
1 stop
ORD10:39Chicago O'Hare Intl
28 Nov
ORD11:00Chicago O'Hare Intl
7h 47m
1 stop
MCO19:47Orlando
£231
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momondo Fare Finder

 
Customise your flight search to find flights from Orlando 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 31 October 2025.
Use the filters below to find and compare flights from Orlando to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 20/11

21:00-23:06

Nonstop3h 06m

Chicago O'Hare Intl

Fri 21/11

06:48-10:30

Nonstop2h 42m

£104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 27/11

21:00-23:06

Nonstop3h 06m

Chicago O'Hare Intl

Sun 30/11

21:22-10:14

1 stop11h 52m

£110

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 23/1

09:05-11:10

Nonstop3h 05m

Chicago O'Hare Intl

Mon 26/1

13:45-21:25

1 stop6h 40m

£112

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/12

10:30-12:33

Nonstop3h 03m

Chicago O'Hare Intl

Tue 9/12

14:10-18:01

Nonstop2h 51m

£115

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 6/1

07:30-12:15

1 stop5h 45m

Chicago O'Hare Intl

Thu 8/1

14:15-22:00

1 stop6h 45m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 4/12

09:25-11:29

Nonstop3h 04m

Chicago O'Hare Intl

Sun 7/12

16:05-19:56

Nonstop2h 51m

£121

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

£172

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 14/11

18:52-00:01

1 stop6h 09m

Chicago O'Hare Intl

Wed 19/11

10:46-18:45

1 stop6h 59m

£178

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 9/11

05:30-10:19

1 stop5h 49m

Chicago O'Hare Intl

Wed 19/11

16:26-21:48

1 stop4h 22m

£222

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/4

10:00-17:31

1 stop8h 31m

Chicago O'Hare Intl

Wed 15/4

08:00-18:59

1 stop9h 59m

£232

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 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 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 £89, 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 January instead. Flights to Chicago in January, 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 £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 £473.

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 £248 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £510.

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 £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 for as low as £140 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 October 2025, prices for Orlando to Chicago flights are approximately 74% more expensive 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

Fastest flight time

3h 00m

Direct flights

Every day

Airports in Chicago

1 airport
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 03m 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?

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.

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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