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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 11/23. 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 Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Orlando Airport 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 Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Orlando Airport 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 layovers.

Cheap bus & train deals from Orlando Airport to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:05 pm - 8:15 pmMCO-ORD
3h 10mnonstop
8:21 pm - 12:24 amORD-MCO
3h 03mnonstop
Sat, Nov 23 - Mon, Nov 25
6:05 pm - 8:15 pmMCO-ORD
3h 10mnonstop
8:21 pm - 12:24 amORD-MCO
3h 03mnonstop
Sat, Nov 23 - Mon, Nov 25
4:39 pm - 6:55 pmMCO-ORD
3h 16mnonstop
8:21 pm - 12:24 amORD-MCO
3h 03mnonstop
$98Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
6:10 am - 8:05 amMCO-MDW
2h 55mnonstop
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
$98Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
4:39 pm - 6:55 pmMCO-ORD
3h 16mnonstop
11:51 am - 3:38 pmORD-MCO
2h 47mnonstop
Sat, Nov 23 - Sun, Nov 24
3:34 pm - 10:27 pmMCO-ORD
7h 53m1 stop
4:18 pm - 8:15 pmORD-MCO
2h 57mnonstop
$103Frontier
Find Deal
Thu, Jan 16 - Sun, Jan 19
1:57 pm - 4:08 pmMCO-ORD
3h 11mnonstop
12:17 pm - 4:04 pmORD-MCO
2h 47mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:05 am - 9:27 amMCO-ORD
3h 22mnonstop
10:59 am - 2:51 pmORD-MCO
2h 52mnonstop
$105Frontier
Find Deal
Thu, Jan 16 - Sun, Jan 19
6:11 pm - 8:15 pmMCO-ORD
3h 04mnonstop
1:13 pm - 5:16 pmORD-MCO
3h 03mnonstop
$115Spirit Airlines
Find Deal
Wed, Dec 4 - Sun, Dec 8
6:00 am - 12:50 pmMCO-ORD
7h 50m1 stop
1:45 pm - 9:52 pmORD-MCO
7h 07m1 stop
$206Delta
Find Deal
Wed, Dec 4 - Sat, Dec 7
6:05 pm - 8:15 pmMCO-ORD
3h 10mnonstop
$37Spirit Airlines
Find Deal
Sat, Nov 23
6:05 pm - 8:15 pmMCO-ORD
3h 10mnonstop
$38Spirit Airlines
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Wed, Nov 20
6:00 am - 7:55 amMCO-MDW
2h 55mnonstop
$38Frontier
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Thu, Nov 21
9:56 am - 12:05 pmMCO-ORD
3h 09mnonstop
$39Frontier
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Wed, Nov 20
6:15 am - 8:10 amMCO-MDW
2h 55mnonstop
$39Frontier
Find Deal
Fri, Nov 22
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
$79Southwest
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Tue, Jan 14
7:34 pm - 9:44 pmMCO-ORD
3h 10mnonstop
$84United Airlines
Find Deal
Sat, Feb 15
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
$99Southwest
Find Deal
Thu, Jan 9
7:10 am - 9:26 amMCO-ORD
3h 16mnonstop
$104United Airlines
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Fri, Feb 28
3:35 pm - 5:39 pmMCO-ORD
3h 04mnonstop
$189American Airlines
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Thu, Nov 21
5:00 am - 10:05 amMCO-ORD
6h 05m1 stop
7:50 pm - 11:48 pmORD-MCO
2h 58mnonstop
Tue, Nov 19 - Sat, Nov 23
2:57 pm - 6:25 amMCO-ORD
16h 28m2 stops
8:04 pm - 11:55 pmORD-MCO
2h 51mnonstop
$149Spirit Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
2:57 pm - 6:25 amMCO-ORD
16h 28m2 stops
1:09 pm - 4:57 pmORD-MCO
2h 48mnonstop
$166Spirit Airlines
Find Deal
Sat, Nov 16 - Tue, Nov 19
10:26 am - 4:56 pmMCO-ORD
7h 30m1 stop
7:50 pm - 11:48 pmORD-MCO
2h 58mnonstop
$190Frontier
Find Deal
Tue, Nov 19 - Sat, Nov 23
5:16 pm - 7:31 pmMCO-ORD
3h 15mnonstop
1:11 pm - 5:12 pmORD-MCO
3h 01mnonstop
$206Frontier
Find Deal
Mon, Nov 18 - Wed, Nov 20
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
4:40 pm - 10:40 pmMDW-MCO
5h 00m1 stop
$337Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 19
10:40 am - 2:40 pmMCO-MDW
5h 00m1 stop
4:40 pm - 10:40 pmMDW-MCO
5h 00m1 stop
$361Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 19
11:00 am - 4:10 pmMCO-MDW
6h 10m1 stop
6:00 am - 11:40 amMDW-MCO
4h 40m1 stop
$621Delta
Find Deal
Sat, Nov 16 - Wed, Nov 20
10:00 am - 2:34 pmMCO-MDW
5h 34m1 stop
5:42 pm - 11:58 pmMDW-MCO
5h 16m1 stop
$636Delta
Find Deal
Tue, Nov 19 - Fri, Nov 22
5:05 pm - 8:45 amMCO-MDW
16h 40m2 stops
7:55 pm - 12:52 pmMDW-MCO
15h 57m1 stop
$1,213Volaris
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Fri, Nov 15 - Sun, Nov 17
6:11 pm - 8:15 pmMCO-ORD
3h 04mnonstop
1:13 pm - 5:16 pmORD-MCO
3h 03mnonstop
$95Spirit Airlines
Find Deal
Wed, Dec 4 - Tue, Dec 10
4:46 pm - 6:50 pmMCO-ORD
3h 04mnonstop
1:13 pm - 5:16 pmORD-MCO
3h 03mnonstop
$96Spirit Airlines
Find Deal
Thu, Dec 5 - Tue, Dec 10
6:10 am - 8:05 amMCO-MDW
2h 55mnonstop
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
$98Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
1:57 pm - 4:08 pmMCO-ORD
3h 11mnonstop
12:17 pm - 4:04 pmORD-MCO
2h 47mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:05 am - 9:27 amMCO-ORD
3h 22mnonstop
10:59 am - 2:51 pmORD-MCO
2h 52mnonstop
$105Frontier
Find Deal
Thu, Jan 16 - Sun, Jan 19
4:46 pm - 6:50 pmMCO-ORD
3h 04mnonstop
1:13 pm - 5:16 pmORD-MCO
3h 03mnonstop
$106Spirit Airlines
Find Deal
Mon, Dec 9 - Tue, Dec 10
6:54 pm - 8:58 pmMCO-ORD
3h 04mnonstop
10:59 am - 2:54 pmORD-MCO
2h 55mnonstop
Fri, Dec 13 - Mon, Dec 16
6:11 pm - 8:15 pmMCO-ORD
3h 04mnonstop
10:59 am - 2:54 pmORD-MCO
2h 55mnonstop
Wed, Dec 11 - Mon, Dec 16
8:20 pm - 10:15 pmMCO-MDW
2h 55mnonstop
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
$193Southwest
Find Deal
Sat, Jan 11 - Tue, Jan 14
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
7:15 pm - 10:55 pmMDW-MCO
2h 40mnonstop
$194Southwest
Find Deal
Wed, Dec 11 - Mon, Dec 16

Frontier flights from Orlando Airport to Chicago

Our best Frontier deals on Orlando Airport to Chicago flight tickets
Frontier
Nov 22
MCO6:15 amOrlando
2h 55m
MDW8:10 amChicago Midway
Nov 25
MDW8:50 amChicago Midway
2h 49m
MCO12:39 pmOrlando
Frontier
Nov 23
MCO4:39 pmOrlando
3h 16m
ORD6:55 pmChicago O'Hare Intl
Nov 25
ORD8:21 pmChicago O'Hare Intl
3h 03m
MCO12:24 amOrlando
Frontier
Jan 16
MCO3:34 pmOrlando
7h 53m
1 stop
ORD10:27 pmChicago O'Hare Intl
Jan 19
ORD4:18 pmChicago O'Hare Intl
2h 57m
MCO8:15 pmOrlando

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
Jan 16
MCO1:57 pmOrlando
3h 11m
ORD4:08 pmChicago O'Hare Intl
Jan 19
ORD12:17 pmChicago O'Hare Intl
2h 47m
MCO4:04 pmOrlando
Spirit Airlines
Nov 21
MCO8:50 amOrlando
3h 06m
ORD10:56 amChicago O'Hare Intl
Nov 23
ORD11:51 amChicago O'Hare Intl
2h 47m
MCO3:38 pmOrlando
Spirit Airlines
Dec 4
MCO6:11 pmOrlando
3h 04m
ORD8:15 pmChicago O'Hare Intl
Dec 8
ORD1:13 pmChicago O'Hare Intl
3h 03m
MCO5:16 pmOrlando

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 from Orlando Airport to Chicago?

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

What is the cheapest day to depart Orlando Airport for Chicago?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Monday

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

In the evening. Orlando Airport to Chicago flights are approximately 41% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago from Orlando Airport?

Spirit Airlines. Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Orlando Airport to Chicago

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

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

How many flights depart from Orlando Airport to Chicago on average per day?

43 flights are operational weekly from Orlando Airport to Chicago as of November 2024. The most popular departure time for this route is 12:00PM, with 48% of flights per day taking off in the afternoon.

How many flights depart from Orlando Airport to Chicago on average per week?

305 flights are operational weekly from Orlando Airport to Chicago as of November 2024. The most popular departure day for this route is Thursday, with 18% of flights per week taking off on this day.

What cabin class options are available on Orlando Airport to Chicago flights?

There are 4 cabin classes available to choose from on Orlando Airport 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 Airport to Chicago flights?

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

How have Orlando Airport to Chicago flight prices changed over time?

As of November 2024, prices for Orlando Airport to Chicago flights are approximately 5% 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 round-trip 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

2h 48m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Orlando Airport in the past 72 hours is $37. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $95.
The fastest flight from Orlando Airport to Chicago takes 2h 48m
Direct flights go from Orlando Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Orlando to Chicago by plane?

    There are 993.7 mi between Orlando and Chicago. A reasonable flight in good conditions will take 2h 48m.

  • When did momondo last update prices for flights from Orlando Airport to Chicago?

    Prices for flights from Orlando Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Orlando Airport to Chicago?

  • How old do you have to be to fly from Orlando Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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?


Best airlines flying from Orlando Airport to Chicago

Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $56Free CancellationRating
6.3
8,166 reviews
Search Spirit Airlines flights
FrontierPriceFrom $56Free CancellationRating
6.1
3,550 reviews
Search Frontier flights
United AirlinesPriceFrom $153Free CancellationRating
7.4
9,186 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $170Free CancellationRating
8.1
5,046 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,787 reviews
Search Delta flights
  • Southwest Flights From Orlando Airport to Chicago

    Across 53 Southwest flights from Orlando Airport to Chicago this week, the average price was $288, with the best Southwest deals starting from $170 round-trip. 5,046 users have rated Southwest on momondo, with an average score of 8.1/10.

  • United Airlines Flights From Orlando Airport to Chicago

    Another popular option for Orlando Airport to Chicago flights is United Airlines (7.4/10, 9,186 ratings). United Airlines flies from Orlando Airport to Chicago around 25 times per week, with deals starting from $153 round-trip and rising to an average price of around $318.


Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

Finding the right flight to Chicago from Orlando is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

All flight searches from Orlando to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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?

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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago