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Cheap flights from Orlando Airport to Chicago from £37

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 5/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Cheap return flights

Spirit Airlines Logo
19:50 - 21:58MCO-ORD
3h 08mdirect
Spirit Airlines Logo
06:30 - 10:13ORD-MCO
2h 43mdirect
£80Spirit Airlines
Find Deal
Wed, 24 Sep - Thu, 25 Sep
Spirit Airlines Logo
14:07 - 16:12MCO-ORD
3h 05mdirect
Spirit Airlines Logo
10:18 - 19:55ORD-MCO
8h 37m1 stop
£112Spirit Airlines
Find Deal
Wed, 24 Sep - Thu, 25 Sep
Southwest Logo
15:50 - 17:55MCO-ORD
3h 05mdirect
Southwest Logo
11:25 - 15:10ORD-MCO
2h 45mdirect
£115Southwest
Find Deal
Wed, 24 Sep - Tue, 30 Sep
Southwest Logo
15:50 - 17:55MCO-ORD
3h 05mdirect
Southwest Logo
06:00 - 09:45ORD-MCO
2h 45mdirect
£116Southwest
Find Deal
Thu, 7 Aug - Mon, 11 Aug
Delta Logo
06:15 - 12:50MCO-ORD
7h 35m1 stop
Delta Logo
14:00 - 22:43ORD-MCO
7h 43m1 stop
£144Delta
Find Deal
Fri, 1 Aug - Tue, 5 Aug
Delta Logo
17:45 - 21:30MCO-ORD
4h 45m1 stop
Delta Logo
11:01 - 16:46ORD-MCO
4h 45m1 stop
£145Delta
Find Deal
Tue, 29 Jul - Wed, 6 Aug
JetBlue Logo
09:00 - 15:32MCO-ORD
7h 32m1 stop
JetBlue Logo
09:42 - 18:02ORD-MCO
7h 20m1 stop
£159JetBlue
Find Deal
Tue, 2 Sep - Sat, 6 Sep
United Airlines Logo
11:00 - 13:06MCO-ORD
3h 06mdirect
United Airlines Logo
10:35 - 14:27ORD-MCO
2h 52mdirect
£166United Airlines
Find Deal
Tue, 2 Sep - Wed, 10 Sep
United Airlines Logo
07:15 - 09:22MCO-ORD
3h 07mdirect
United Airlines Logo
17:51 - 21:47ORD-MCO
2h 56mdirect
£167United Airlines
Find Deal
Fri, 1 Aug - Tue, 5 Aug
JetBlue Logo
13:25 - 20:50MCO-ORD
8h 25m1 stop
JetBlue Logo
09:42 - 18:02ORD-MCO
7h 20m1 stop
£181JetBlue
Find Deal
Mon, 8 Sep - Sat, 13 Sep

Southwest flights from Orlando Airport to Chicago

Our best Southwest deals on Orlando Airport to Chicago flight tickets
Southwest
24 Sept
MCO15:50Orlando
3h 05m
ORD17:55Chicago O'Hare Intl
30 Sept
ORD11:25Chicago O'Hare Intl
2h 45m
MCO15:10Orlando
Southwest
7 Aug
MCO15:50Orlando
3h 05m
ORD17:55Chicago O'Hare Intl
11 Aug
ORD06:00Chicago O'Hare Intl
2h 45m
MCO09:45Orlando
Southwest
1 Aug
MCO15:45Orlando
3h 10m
ORD17:55Chicago O'Hare Intl
8 Aug
ORD11:25Chicago O'Hare Intl
2h 45m
MCO15:10Orlando

JetBlue flights from Orlando Airport to Chicago

Our best JetBlue deals on Orlando Airport to Chicago flight tickets
JetBlue
2 Sept
MCO09:00Orlando
7h 32m
1 stop
ORD15:32Chicago O'Hare Intl
6 Sept
ORD09:42Chicago O'Hare Intl
7h 20m
1 stop
MCO18:02Orlando
JetBlue
8 Sept
MCO13:25Orlando
8h 25m
1 stop
ORD20:50Chicago O'Hare Intl
13 Sept
ORD09:42Chicago O'Hare Intl
7h 20m
1 stop
MCO18:02Orlando
JetBlue
8 Sept
MCO13:25Orlando
8h 25m
1 stop
ORD20:50Chicago O'Hare Intl
14 Sept
ORD06:45Chicago O'Hare Intl
7h 10m
1 stop
MCO14:55Orlando

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 £102, 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 £111.

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 £148. 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 £456.

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

Flying to Chicago from Orlando Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as £257 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £491.

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 £162 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 £133 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 33% 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

£37

Fastest flight time

3h 03m

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 £37. The best return flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is £80.
The fastest flight from Orlando Airport to Chicago takes 3h 03m
Direct flights go from Orlando Airport to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • 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?

  • What is the most popular airline 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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1 adult
Tue 8/7
Tue 15/7

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