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Cheap flights from Orlando Airport to Chicago from £43

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 14/1. 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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0 bags
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Find the cheapest flights from Orlando Airport to Chicago

Cheap return flights

Logo
06:31 - 10:52MCO-ORD
5h 21m1 stop
Logo
20:49 - 00:35ORD-MCO
2h 46mdirect
£72
Find Deal
Tue, 16 Sep - Sun, 21 Sep
Logo
13:02 - 15:17MCO-ORD
3h 15mdirect
Logo
06:30 - 10:13ORD-MCO
2h 43mdirect
£77
Find Deal
Sat, 20 Sep - Wed, 24 Sep
Spirit Airlines Logo
19:50 - 21:58MCO-ORD
3h 08mdirect
Spirit Airlines Logo
17:17 - 21:06ORD-MCO
2h 49mdirect
£82Spirit Airlines
Find Deal
Tue, 16 Sep - Tue, 23 Sep
Spirit Airlines Logo
19:50 - 21:58MCO-ORD
3h 08mdirect
Spirit Airlines Logo
17:17 - 21:06ORD-MCO
2h 49mdirect
£86Spirit Airlines
Find Deal
Fri, 19 Sep - Tue, 23 Sep
Frontier Logo
13:02 - 15:17MCO-ORD
3h 15mdirect
Frontier Logo
11:36 - 22:22ORD-MCO
9h 46m1 stop
£86Frontier
Find Deal
Sat, 20 Sep - Mon, 22 Sep
Frontier Logo
17:24 - 19:44MCO-ORD
3h 20mdirect
Frontier Logo
11:36 - 22:22ORD-MCO
9h 46m1 stop
£87Frontier
Find Deal
Thu, 18 Sep - Mon, 22 Sep
United Airlines Logo
10:30 - 12:34MCO-ORD
3h 04mdirect
United Airlines Logo
14:10 - 18:01ORD-MCO
2h 51mdirect
£112United Airlines
Find Deal
Wed, 12 Nov - Wed, 12 Nov
Southwest Logo
13:20 - 15:20MCO-ORD
3h 00mdirect
Southwest Logo
06:00 - 09:45ORD-MCO
2h 45mdirect
£117Southwest
Find Deal
Sat, 20 Sep - Sun, 21 Sep
Southwest Logo
06:50 - 12:15MCO-ORD
6h 25m1 stop
Southwest Logo
15:45 - 19:25ORD-MCO
2h 40mdirect
£135Southwest
Find Deal
Wed, 19 Nov - Wed, 19 Nov
United Airlines Logo
07:30 - 09:36MCO-ORD
3h 06mdirect
United Airlines Logo
17:55 - 21:46ORD-MCO
2h 51mdirect
£168United Airlines
Find Deal
Sat, 20 Sep - Sat, 20 Sep

Southwest flights from Orlando Airport to Chicago

Our best Southwest deals on Orlando Airport to Chicago flight tickets
Southwest
20 Sept
MCO13:20Orlando
3h 00m
ORD15:20Chicago O'Hare Intl
21 Sept
ORD06:00Chicago O'Hare Intl
2h 45m
MCO09:45Orlando
£117
Find similar
Southwest
19 Nov
MCO06:50Orlando
6h 25m
1 stop
ORD12:15Chicago O'Hare Intl
19 Nov
ORD15:45Chicago O'Hare Intl
2h 40m
MCO19:25Orlando
£135
Find similar
Southwest
12 Sept
MCO09:50Orlando
3h 00m
ORD11:50Chicago O'Hare Intl
19 Sept
ORD11:25Chicago O'Hare Intl
2h 45m
MCO15:10Orlando
£143
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Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
16 Sept
MCO19:50Orlando
3h 08m
ORD21:58Chicago O'Hare Intl
23 Sept
ORD17:17Chicago O'Hare Intl
2h 49m
MCO21:06Orlando
£82
Find similar
Spirit Airlines
19 Sept
MCO19:50Orlando
3h 08m
ORD21:58Chicago O'Hare Intl
23 Sept
ORD17:17Chicago O'Hare Intl
2h 49m
MCO21:06Orlando
£86
Find similar
Spirit Airlines
24 Sept
MCO19:50Orlando
3h 08m
ORD21:58Chicago O'Hare Intl
25 Sept
ORD06:30Chicago O'Hare Intl
2h 43m
MCO10:13Orlando
£93
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Orlando Airport 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 19 August 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 16/9

06:31-10:52

1 stop5h 21m

Chicago O'Hare Intl

Sun 21/9

20:49-00:35

Nonstop2h 46m

£72

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 20/9

13:02-15:17

Nonstop3h 15m

Chicago O'Hare Intl

Wed 24/9

06:30-10:13

Nonstop2h 43m

£77

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 16/9

19:50-21:58

Nonstop3h 08m

Chicago O'Hare Intl

Tue 23/9

17:17-21:06

Nonstop2h 49m

£82

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 19/9

19:50-21:58

Nonstop3h 08m

Chicago O'Hare Intl

Tue 23/9

17:17-21:06

Nonstop2h 49m

£86

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 20/9

13:02-15:17

Nonstop3h 15m

Chicago O'Hare Intl

Mon 22/9

11:36-22:22

1 stop9h 46m

£86

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 18/9

17:24-19:44

Nonstop3h 20m

Chicago O'Hare Intl

Mon 22/9

11:36-22:22

1 stop9h 46m

£87

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 12/11

10:30-12:34

Nonstop3h 04m

Chicago O'Hare Intl

Wed 12/11

14:10-18:01

Nonstop2h 51m

£112

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 20/9

13:20-15:20

Nonstop3h 00m

Chicago O'Hare Intl

Sun 21/9

06:00-09:45

Nonstop2h 45m

£117

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 19/11

06:50-12:15

1 stop6h 25m

Chicago O'Hare Intl

Wed 19/11

15:45-19:25

Nonstop2h 40m

£135

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 20/9

07:30-09:36

Nonstop3h 06m

Chicago O'Hare Intl

Sat 20/9

17:55-21:46

Nonstop2h 51m

£168

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 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 £100, 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 £112.

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 £121. 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 £489.

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 £241 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £496.

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 £160 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 £123 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 August 2025, prices for Orlando Airport to Chicago flights are approximately 7% 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

£43

Fastest flight time

3h 00m

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 £43. The best return flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is £72.
The fastest flight from Orlando Airport to Chicago takes 3h 00m
Direct flights go from Orlando Airport to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • 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