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Cheap flights from Orlando Airport to Chicago from £40

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 18/11. 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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0 bags
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Cheap return flights

Spirit Airlines Logo
14:07 - 16:12MCO-ORD
3h 05mdirect
Spirit Airlines Logo
17:17 - 21:06ORD-MCO
2h 49mdirect
£87Spirit Airlines
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Wed, 24 Sep - Thu, 25 Sep
Spirit Airlines Logo
08:00 - 10:06MCO-ORD
3h 06mdirect
Spirit Airlines Logo
16:36 - 20:23ORD-MCO
2h 47mdirect
£94Spirit Airlines
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Thu, 7 Aug - Fri, 8 Aug
Spirit Airlines Logo
10:16 - 19:42MCO-ORD
10h 26m1 stop
Spirit Airlines Logo
17:17 - 21:06ORD-MCO
2h 49mdirect
£107Spirit Airlines
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Sun, 31 Aug - Sun, 7 Sep
Southwest Logo
09:50 - 11:50MCO-ORD
3h 00mdirect
Southwest Logo
06:00 - 09:45ORD-MCO
2h 45mdirect
£117Southwest
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Thu, 28 Aug - Mon, 1 Sep
Southwest Logo
15:50 - 17:55MCO-ORD
3h 05mdirect
Southwest Logo
06:00 - 09:35ORD-MCO
2h 35mdirect
£118Southwest
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Fri, 10 Oct - Sat, 11 Oct
Delta Logo
06:15 - 10:16MCO-ORD
5h 01m1 stop
Delta Logo
09:47 - 17:36ORD-MCO
6h 49m1 stop
£147Delta
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Thu, 7 Aug - Wed, 13 Aug
United Airlines Logo
11:15 - 13:15MCO-ORD
3h 00mdirect
United Airlines Logo
08:55 - 14:59ORD-MCO
5h 04m1 stop
£151United Airlines
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Tue, 23 Dec - Tue, 6 Jan
United Airlines Logo
07:30 - 09:33MCO-ORD
3h 03mdirect
United Airlines Logo
14:10 - 18:01ORD-MCO
2h 51mdirect
£155United Airlines
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Thu, 27 Nov - Tue, 2 Dec
JetBlue Logo
11:05 - 18:34MCO-ORD
8h 29m1 stop
JetBlue Logo
10:10 - 18:25ORD-MCO
7h 15m1 stop
£162JetBlue
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Sun, 21 Dec - Tue, 30 Dec
Delta Logo
12:10 - 18:49MCO-ORD
7h 39m1 stop
Delta Logo
19:59 - 01:28ORD-MCO
4h 29m1 stop
£166Delta
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Tue, 5 Aug - Thu, 7 Aug

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
24 Sept
MCO14:07Orlando
3h 05m
ORD16:12Chicago O'Hare Intl
25 Sept
ORD17:17Chicago O'Hare Intl
2h 49m
MCO21:06Orlando
£87
Find similar
Spirit Airlines
7 Aug
MCO08:00Orlando
3h 06m
ORD10:06Chicago O'Hare Intl
8 Aug
ORD16:36Chicago O'Hare Intl
2h 47m
MCO20:23Orlando
£94
Find similar
Spirit Airlines
31 Aug
MCO10:16Orlando
10h 26m
1 stop
ORD19:42Chicago O'Hare Intl
7 Sept
ORD17:17Chicago O'Hare Intl
2h 49m
MCO21:06Orlando
£107
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Southwest flights from Orlando Airport to Chicago

Our best Southwest deals on Orlando Airport to Chicago flight tickets
Southwest
28 Aug
MCO09:50Orlando
3h 00m
ORD11:50Chicago O'Hare Intl
1 Sept
ORD06:00Chicago O'Hare Intl
2h 45m
MCO09:45Orlando
£117
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Southwest
10 Oct
MCO15:50Orlando
3h 05m
ORD17:55Chicago O'Hare Intl
11 Oct
ORD06:00Chicago O'Hare Intl
2h 35m
MCO09:35Orlando
£118
Find similar
Southwest
29 Aug
MCO09:50Orlando
3h 00m
ORD11:50Chicago O'Hare Intl
1 Sept
ORD06:00Chicago O'Hare Intl
2h 45m
MCO09:45Orlando
£119
Find similar

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 September. Flight prices, which tend to average around £101, 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 Airport during February instead. Flights to Chicago in February, while not as cheap as those in September, still average around £113.

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 £151. 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 £494.

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 £243 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £501.

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 £164 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 £136 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 July 2025, prices for Orlando Airport to Chicago flights are approximately 64% 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

Best price found

£40

Fastest flight time

2h 59m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Orlando Airport in the past 72 hours is £40. The best return flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is £87.
The fastest flight from Orlando Airport to Chicago takes 2h 59m
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