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Cheap flights from Orlando to Chicago from £63

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 22/1. 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.
06:00 - 12:55MCO-ORD
7h 55m1 stop
14:15 - 21:13ORD-MCO
5h 58m1 stop
£156Delta
Find Deal
Wed, 22 Jan - Sat, 25 Jan
05:30 - 09:55MCO-ORD
5h 25m1 stop
08:00 - 13:52ORD-MCO
4h 52m1 stop
£164Delta
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Sat, 11 Jan - Tue, 28 Jan
07:15 - 09:21MCO-ORD
3h 06mdirect
10:40 - 14:30ORD-MCO
2h 50mdirect
£185United Airlines
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Thu, 6 Feb - Tue, 11 Feb
19:08 - 23:22MCO-ORD
5h 14m1 stop
13:10 - 17:02ORD-MCO
2h 52mdirect
£204United Airlines
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Sat, 11 Jan - Wed, 29 Jan
06:00 - 12:22MCO-ORD
7h 22m1 stop
11:44 - 21:33ORD-MCO
8h 49m1 stop
£207JetBlue
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Mon, 10 Mar - Wed, 12 Mar
16:45 - 22:20MCO-ORD
6h 35m1 stop
07:00 - 22:15ORD-MCO
14h 15m2 stops
£222Southwest
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Wed, 19 Feb - Sat, 22 Feb
10:55 - 16:45MCO-ORD
6h 50m1 stop
11:25 - 21:00ORD-MCO
8h 35m2 stops
£225Southwest
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Thu, 30 Jan - Mon, 3 Feb
13:50 - 10:46MCO-ORD
21h 56m1 stop
19:05 - 18:30ORD-MCO
22h 25m1 stop
£243Sun Country Air
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Thu, 17 Apr - Sun, 20 Apr
07:00 - 15:29MCO-ORD
9h 29m1 stop
17:45 - 01:17ORD-MCO
6h 32m1 stop
£249JetBlue
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Sun, 23 Mar - Wed, 26 Mar
19:15 - 19:11MCO-ORD
24h 56m1 stop
20:10 - 18:17ORD-MCO
21h 07m1 stop
£290Sun Country Air
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Thu, 12 Jun - Sun, 15 Jun
07:15 - 09:21MCO-ORD
3h 06mdirect
£63United Airlines
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Wed, 22 Jan
12:30 - 14:37MCO-ORD
3h 07mdirect
£76United Airlines
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Tue, 14 Jan
05:30 - 09:55MCO-ORD
5h 25m1 stop
£78Delta
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Sat, 25 Jan
06:25 - 15:44MCO-ORD
10h 19m1 stop
£83JetBlue
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Sun, 2 Feb
06:05 - 12:40MCO-ORD
7h 35m1 stop
£92Delta
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Wed, 19 Mar
06:00 - 12:22MCO-ORD
7h 22m1 stop
£103JetBlue
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Thu, 13 Mar
19:30 - 19:09MCO-ORD
24h 39m1 stop
£110Sun Country Air
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Thu, 29 May
12:30 - 19:11MCO-ORD
7h 41m1 stop
£114Sun Country Air
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Thu, 19 Jun
13:20 - 22:20MCO-ORD
10h 00m2 stops
£124Southwest
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Wed, 19 Feb
08:55 - 22:20MCO-ORD
14h 25m2 stops
£126Southwest
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Mon, 13 Jan
13:45 - 09:03MCO-ORD
20h 18m1 stop
19:33 - 21:36ORD-MCO
25h 03m1 stop
£388Sun Country Air
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Tue, 24 Dec - Fri, 27 Dec
19:35 - 18:52MCO-ORD
24h 17m1 stop
18:35 - 12:21ORD-MCO
16h 46m1 stop
£394Sun Country Air
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Wed, 25 Dec - Tue, 31 Dec
07:30 - 14:25MCO-ORD
7h 55m1 stop
05:45 - 14:15ORD-MCO
7h 30m2 stops
£482Southwest
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Wed, 25 Dec - Tue, 31 Dec
12:00 - 16:15MCO-ORD
5h 15m1 stop
17:30 - 00:10ORD-MCO
5h 40m1 stop
£608Delta
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Tue, 24 Dec - Thu, 2 Jan
16:15 - 18:17MCO-ORD
3h 02mdirect
11:05 - 14:55ORD-MCO
2h 50mdirect
£637United Airlines
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Mon, 23 Dec - Wed, 1 Jan
12:40 - 18:52MCO-ORD
7h 12m1 stop
17:30 - 00:10ORD-MCO
5h 40m1 stop
£646Delta
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Tue, 24 Dec - Sat, 28 Dec
07:50 - 16:45MCO-ORD
9h 55m2 stops
14:45 - 23:45ORD-MCO
8h 00m1 stop
£655Southwest
Find Deal
Wed, 25 Dec - Sat, 28 Dec
09:27 - 11:34MCO-ORD
3h 07mdirect
05:00 - 08:51ORD-MCO
2h 51mdirect
£739United Airlines
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Tue, 24 Dec - Sat, 28 Dec
19:53 - 16:50MCO-ORD
21h 57m2 stops
14:01 - 07:30ORD-MCO
16h 29m1 stop
£977Alaska Airlines
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Wed, 25 Dec - Thu, 2 Jan
07:00 - 23:59MCO-ORD
17h 59m1 stop
07:00 - 23:59ORD-MCO
15h 59m2 stops
£997Alaska Airlines
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Fri, 27 Dec - Fri, 3 Jan
07:15 - 09:21MCO-ORD
3h 06mdirect
10:40 - 14:30ORD-MCO
2h 50mdirect
£185United Airlines
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Thu, 6 Feb - Tue, 11 Feb
12:30 - 14:37MCO-ORD
3h 07mdirect
07:20 - 11:17ORD-MCO
2h 57mdirect
£236United Airlines
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Fri, 10 Jan - Sun, 12 Jan
09:28 - 11:38MCO-ORD
3h 10mdirect
13:10 - 17:01ORD-MCO
2h 51mdirect
£243United Airlines
Find Deal
Fri, 25 Apr - Wed, 30 Apr
09:45 - 11:52MCO-ORD
3h 07mdirect
13:10 - 17:02ORD-MCO
2h 52mdirect
£591United Airlines
Find Deal
Fri, 7 Feb - Mon, 10 Feb
07:10 - 09:26MCO-ORD
3h 16mdirect
14:33 - 18:24ORD-MCO
2h 51mdirect
£674United Airlines
Find Deal
Thu, 13 Feb - Fri, 14 Feb
06:00 - 08:05MCO-ORD
3h 05mdirect
11:05 - 14:55ORD-MCO
2h 50mdirect
£693United Airlines
Find Deal
Sun, 5 Jan - Sun, 5 Jan

JetBlue flights from Orlando to Chicago

Our best JetBlue deals on Orlando to Chicago flight tickets
JetBlue
10 Mar
MCO06:00Orlando
7h 22m
1 stop
ORD12:22Chicago O'Hare Intl
12 Mar
ORD11:44Chicago O'Hare Intl
8h 49m
1 stop
MCO21:33Orlando
JetBlue
23 Mar
MCO07:00Orlando
9h 29m
1 stop
ORD15:29Chicago O'Hare Intl
26 Mar
ORD17:45Chicago O'Hare Intl
6h 32m
1 stop
MCO01:17Orlando
JetBlue
4 Apr
MCO11:11Orlando
7h 56m
1 stop
ORD18:07Chicago O'Hare Intl
7 Apr
ORD09:43Chicago O'Hare Intl
7h 01m
1 stop
MCO17:44Orlando

United Airlines flights from Orlando to Chicago

Our best United Airlines deals on Orlando to Chicago flight tickets
United Airlines
6 Feb
MCO07:15Orlando
3h 06m
ORD09:21Chicago O'Hare Intl
11 Feb
ORD10:40Chicago O'Hare Intl
2h 50m
MCO14:30Orlando
United Airlines
11 Jan
MCO19:08Orlando
5h 14m
1 stop
ORD23:22Chicago O'Hare Intl
29 Jan
ORD13:10Chicago O'Hare Intl
2h 52m
MCO17:02Orlando
United Airlines
10 Jan
MCO12:30Orlando
3h 07m
ORD14:37Chicago O'Hare Intl
12 Jan
ORD07:20Chicago O'Hare Intl
2h 57m
MCO11:17Orlando

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 February. Flight prices, which tend to average around £94, 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 during April instead. Flights to Chicago in April, while not as cheap as those in February, still average around £103.

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 Monday when prices can be found for as low as £0. 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 Tuesday, with ticket prices averaging around £297.

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

Flying to Chicago from Orlando at midday is the least expensive time of day to depart. momondo users have found prices as low as £0 when looking at flights departing at midday. Flights in the morning are often more expensive, with an average ticket price of £141.

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?

The ideal time to book your flight to Chicago is 54 days in advance, when prices tend to average £157. However, in the past 72 hours, people saw flights from Orlando for as low as £78.

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.

Can stopping save me money on Orlando to Chicago flights?

You could potentially save up to 24% on your flight if you consider stops on a Orlando to Chicago flight.

How have Orlando to Chicago flight prices changed over time?

As of December 2024, prices for Orlando to Chicago flights are approximately 3% more expensive 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

£63

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 £63. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £156.
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 06m 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