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Cheap flights from Orlando to Chicago from £62

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 21/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Orlando to Chicago

Cheap return flights

These are some of the best return flight deals from Orlando to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Orlando to Chicago.

Cheap last-minute flights

Planning a quick getaway from Orlando to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Orlando to Chicago

Find recent round-trip train or bus tickets from Orlando to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
19:34 - 21:44MCO-ORD
3h 10mdirect
09:03 - 17:28ORD-MCO
7h 25m1 stop
£144United Airlines
Find Deal
Fri, 28 Feb - Tue, 4 Mar
06:00 - 12:55MCO-ORD
7h 55m1 stop
08:00 - 15:02ORD-MCO
6h 02m1 stop
£155Delta
Find Deal
Sat, 1 Feb - Sat, 8 Feb
10:10 - 17:18MCO-ORD
8h 08m1 stop
09:05 - 16:17ORD-MCO
6h 12m1 stop
£179JetBlue
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Tue, 4 Feb - Sun, 9 Feb
05:45 - 15:40MCO-ORD
10h 55m1 stop
16:25 - 01:28ORD-MCO
8h 03m1 stop
£204JetBlue
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Thu, 6 Mar - Mon, 10 Mar
11:18 - 18:39MCO-ORD
8h 21m1 stop
18:35 - 15:15ORD-MCO
19h 40m1 stop
£233Sun Country Air
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Fri, 25 Apr - Mon, 28 Apr
13:00 - 21:30MCO-ORD
9h 30m2 stops
16:35 - 22:55ORD-MCO
5h 20m1 stop
£253Southwest
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Wed, 5 Feb - Sun, 9 Feb
07:10 - 19:05MCO-ORD
12h 55m1 stop
10:00 - 18:56ORD-MCO
7h 56m1 stop
£257Sun Country Air
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Sat, 21 Dec - Tue, 24 Dec
13:10 - 22:35MCO-ORD
10h 25m2 stops
07:30 - 21:40ORD-MCO
13h 10m2 stops
£257Southwest
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Thu, 16 Jan - Sun, 19 Jan
08:40 - 23:59MCO-ORD
16h 19m2 stops
18:55 - 15:17ORD-MCO
19h 22m1 stop
£369Alaska Airlines
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Thu, 16 Jan - Sun, 19 Jan
18:22 - 13:07MCO-ORD
19h 45m2 stops
18:55 - 05:40ORD-MCO
33h 45m1 stop
£377Alaska Airlines
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Tue, 21 Jan - Sat, 25 Jan
18:18 - 20:25MCO-ORD
3h 07mdirect
£62United Airlines
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Tue, 21 Jan
06:00 - 12:55MCO-ORD
7h 55m1 stop
£77Delta
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Sat, 11 Jan
19:34 - 21:44MCO-ORD
3h 10mdirect
£78United Airlines
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Fri, 28 Feb
06:25 - 15:44MCO-ORD
10h 19m1 stop
£82JetBlue
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Sun, 19 Jan
12:31 - 08:10MCO-ORD
20h 39m1 stop
£84Spirit Airlines
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Tue, 17 Dec
08:40 - 10:45MCO-ORD
3h 05mdirect
£100Southwest
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Sat, 14 Dec
11:15 - 17:56MCO-ORD
7h 41m1 stop
£102JetBlue
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Wed, 9 Apr
21:50 - 15:52MCO-ORD
19h 02m1 stop
£109Sun Country Air
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Sat, 21 Dec
08:05 - 13:00MCO-ORD
5h 55m1 stop
£113Southwest
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Mon, 3 Mar
19:00 - 18:06MCO-ORD
24h 06m1 stop
£133Sun Country Air
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Thu, 10 Apr
06:00 - 15:53MCO-ORD
10h 53m1 stop
08:51 - 19:53ORD-MCO
10h 02m1 stop
£328JetBlue
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Mon, 25 Nov - Sat, 14 Dec
15:05 - 22:46MCO-ORD
8h 41m1 stop
12:15 - 21:57ORD-MCO
8h 42m1 stop
£421JetBlue
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Sat, 23 Nov - Wed, 27 Nov
13:20 - 21:06MCO-ORD
8h 46m1 stop
07:15 - 18:25ORD-MCO
10h 10m1 stop
£467JetBlue
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Thu, 21 Nov - Thu, 28 Nov
14:00 - 21:30MCO-ORD
8h 30m1 stop
07:00 - 18:50ORD-MCO
10h 50m2 stops
£478Southwest
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Sat, 23 Nov - Thu, 28 Nov
09:45 - 21:30MCO-ORD
12h 45m2 stops
07:30 - 19:30ORD-MCO
11h 00m2 stops
£482Southwest
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Sat, 23 Nov - Fri, 29 Nov
07:00 - 10:50MCO-ORD
4h 50m1 stop
09:25 - 15:54ORD-MCO
5h 29m1 stop
£486Delta
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Fri, 22 Nov - Wed, 27 Nov
12:20 - 17:28MCO-ORD
6h 08m1 stop
18:50 - 23:59ORD-MCO
28h 09m1 stop
£488Sun Country Air
Find Deal
Sun, 24 Nov - Tue, 26 Nov
15:12 - 18:46MCO-ORD
4h 34m1 stop
10:15 - 16:47ORD-MCO
5h 32m1 stop
£502Delta
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Fri, 22 Nov - Thu, 28 Nov
07:30 - 09:33MCO-ORD
3h 03mdirect
14:18 - 18:06ORD-MCO
2h 48mdirect
£632United Airlines
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Fri, 22 Nov - Thu, 28 Nov
18:10 - 20:13MCO-ORD
3h 03mdirect
14:20 - 18:08ORD-MCO
2h 48mdirect
£653United Airlines
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Sun, 24 Nov - Tue, 26 Nov
16:13 - 18:15MCO-ORD
3h 02mdirect
17:55 - 21:44ORD-MCO
2h 49mdirect
£171United Airlines
Find Deal
Tue, 10 Dec - Sat, 14 Dec
11:00 - 13:03MCO-ORD
3h 03mdirect
17:55 - 21:44ORD-MCO
2h 49mdirect
£256United Airlines
Find Deal
Thu, 5 Dec - Mon, 9 Dec
06:00 - 08:05MCO-ORD
3h 05mdirect
13:18 - 17:10ORD-MCO
2h 52mdirect
£321United Airlines
Find Deal
Tue, 24 Dec - Tue, 24 Dec
11:00 - 13:05MCO-ORD
3h 05mdirect
06:00 - 09:40ORD-MCO
2h 40mdirect
£322Southwest
Find Deal
Fri, 18 Apr - Sun, 20 Apr
16:13 - 18:15MCO-ORD
3h 02mdirect
17:50 - 21:42ORD-MCO
2h 52mdirect
£482United Airlines
Find Deal
Tue, 17 Dec - Sat, 28 Dec
10:15 - 12:21MCO-ORD
3h 06mdirect
14:15 - 18:06ORD-MCO
2h 51mdirect
£490United Airlines
Find Deal
Sat, 21 Dec - Tue, 24 Dec
07:15 - 09:21MCO-ORD
3h 06mdirect
14:17 - 18:07ORD-MCO
2h 50mdirect
£514United Airlines
Find Deal
Sat, 21 Dec - Sun, 22 Dec
16:15 - 18:17MCO-ORD
3h 02mdirect
17:50 - 21:42ORD-MCO
2h 52mdirect
£538United Airlines
Find Deal
Tue, 24 Dec - Sat, 28 Dec
16:15 - 18:17MCO-ORD
3h 02mdirect
17:50 - 21:42ORD-MCO
2h 52mdirect
£561United Airlines
Find Deal
Fri, 20 Dec - Sat, 28 Dec
16:13 - 18:15MCO-ORD
3h 02mdirect
15:45 - 19:36ORD-MCO
2h 51mdirect
£565United Airlines
Find Deal
Tue, 17 Dec - Fri, 27 Dec

United Airlines flights from Orlando to Chicago

Our best United Airlines deals on Orlando to Chicago flight tickets
United Airlines
28 Feb
MCO19:34Orlando
3h 10m
ORD21:44Chicago O'Hare Intl
4 Mar
ORD09:03Chicago O'Hare Intl
7h 25m
1 stop
MCO17:28Orlando
United Airlines
28 Feb
MCO18:57Orlando
6h 18m
1 stop
ORD00:15Chicago O'Hare Intl
3 Mar
ORD06:10Chicago O'Hare Intl
2h 45m
MCO09:55Orlando
United Airlines
10 Dec
MCO16:13Orlando
3h 02m
ORD18:15Chicago O'Hare Intl
14 Dec
ORD17:55Chicago O'Hare Intl
2h 49m
MCO21:44Orlando

Alaska Airlines flights from Orlando to Chicago

Our best Alaska Airlines deals on Orlando to Chicago flight tickets
Alaska Airlines
16 Jan
MCO08:40Orlando
16h 19m
2 stops
ORD23:59Chicago O'Hare Intl
19 Jan
ORD18:55Chicago O'Hare Intl
19h 22m
1 stop
MCO15:17Orlando
Alaska Airlines
21 Jan
MCO18:22Orlando
19h 45m
2 stops
ORD13:07Chicago O'Hare Intl
25 Jan
ORD18:55Chicago O'Hare Intl
33h 45m
1 stop
MCO05:40Orlando
Alaska Airlines
26 Feb
MCO07:08Orlando
11h 52m
1 stop
ORD18:00Chicago O'Hare Intl
1 Mar
ORD16:05Chicago O'Hare Intl
12h 43m
2 stops
MCO05:48Orlando

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 cheapest month to fly from Orlando to Chicago?

February. The cheapest time of year to fly to Chicago from Orlando is February. The most expensive is June.

What is the cheapest day to depart Orlando for Chicago?

Friday. The cheapest day of the week is usually Friday. The most expensive is usually Tuesday.

When is the cheapest time to fly from Orlando to Chicago?

In the afternoon. Orlando to Chicago flights are approximately 57% more expensive in the evening than in the afternoon

What is the cheapest Orlando to Chicago flight route?

Orlando - Chicago O'Hare Intl. Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices

How far in advance should you book Orlando to Chicago flights?

29 days before. The cheapest time to buy a flight from Orlando to Chicago is approximately 29 days to departure

Can stopping save me money on Orlando to Chicago flights?

No. A direct flight is the cheapest option for a flight between Orlando to Chicago.

How have Orlando to Chicago flight prices changed over time?

As of November 2024, prices for Orlando to Chicago flights are approximately 12% cheaper when compared to flights at the same time last year.

Cheap Orlando to Chicago flight deals and tips

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

Best price found

£62

Fastest flight time

3h 02m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Orlando in the past 72 hours is £62. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £144.
The fastest flight from Orlando to Chicago takes 3h 02m
Direct flights go from Orlando to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Orlando to Chicago by plane?

    The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 02m 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