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Cheap flights from Orlando Airport to Chicago from $49

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 1/15. 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.
12:40 pm - 10:27 pmMCO-ORD
10h 47m1 stop
10:59 am - 2:51 pmORD-MCO
2h 52mnonstop
$102Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
6:06 pm - 9:58 pmORD-MCO
2h 52mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
6:00 am - 4:31 pmMCO-ORD
11h 31m1 stop
8:44 pm - 12:51 amORD-MCO
3h 07mnonstop
$106Frontier
Find Deal
Wed, Feb 26 - Sat, Mar 1
3:34 pm - 10:27 pmMCO-ORD
7h 53m1 stop
10:09 am - 12:41 amORD-MCO
13h 32m1 stop
$107Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
8:00 am - 11:50 amORD-MCO
2h 50mnonstop
$115Spirit Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
1:20 pm - 4:55 pmMDW-MCO
2h 35mnonstop
$164Southwest
Find Deal
Thu, Jan 23 - Tue, Jan 28
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$190Southwest
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Wed, Jan 8 - Sun, Jan 12
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$214American Airlines
Find Deal
Fri, Jan 10 - Sun, Jan 12
11:00 am - 1:06 pmMCO-ORD
3h 06mnonstop
6:30 am - 3:26 pmORD-MCO
7h 56m1 stop
$243United Airlines
Find Deal
Sat, Jan 18 - Mon, Jan 20
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$253American Airlines
Find Deal
Tue, Jan 21 - Sat, Jan 25
5:07 am - 12:39 pmMCO-ORD
8h 32m1 stop
$49Spirit Airlines
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Wed, Jan 15
5:07 am - 12:39 pmMCO-ORD
8h 32m1 stop
$51Spirit Airlines
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Wed, Jan 15
3:34 pm - 10:27 pmMCO-ORD
7h 53m1 stop
$53Frontier
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Thu, Jan 23
3:34 pm - 10:42 pmMCO-ORD
8h 08m1 stop
$54Frontier
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Thu, Jan 9
4:56 pm - 11:29 pmMCO-MDW
7h 33m1 stop
$54Frontier
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Sat, Jan 18
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
$79Southwest
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Wed, Jan 22
7:34 pm - 9:44 pmMCO-ORD
3h 10mnonstop
$85United Airlines
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Fri, Feb 28
7:15 am - 9:10 amMCO-MDW
2h 55mnonstop
$85Southwest
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Thu, Jan 16
6:57 pm - 12:15 amMCO-ORD
6h 18m1 stop
$90United Airlines
Find Deal
Fri, Feb 28
6:00 am - 8:16 amMCO-ORD
3h 16mnonstop
$232American Airlines
Find Deal
Mon, Jan 6
4:20 pm - 9:04 pmMCO-MDW
5h 44m1 stop
7:17 am - 12:09 amMDW-MCO
15h 52m1 stop
$198Frontier
Find Deal
Mon, Dec 23 - Thu, Jan 2
11:44 am - 9:15 pmMCO-ORD
10h 31m1 stop
6:10 am - 8:14 pmORD-MCO
13h 04m1 stop
$216Frontier
Find Deal
Sun, Dec 22 - Sat, Jan 4
7:30 am - 9:54 amMCO-ORD
3h 24mnonstop
3:31 pm - 7:32 pmORD-MCO
3h 01mnonstop
Mon, Dec 23 - Tue, Dec 31
7:35 pm - 9:03 amMCO-ORD
14h 28m1 stop
10:15 pm - 7:46 amORD-MCO
8h 31m1 stop
Mon, Dec 23 - Thu, Jan 2
7:35 pm - 9:03 amMCO-ORD
14h 28m1 stop
6:35 pm - 2:46 pmORD-MCO
19h 11m1 stop
$305Sun Country Air
Find Deal
Mon, Dec 23 - Tue, Dec 31
7:35 pm - 9:03 amMCO-ORD
14h 28m1 stop
7:30 pm - 3:26 pmORD-MCO
18h 56m1 stop
$345Sun Country Air
Find Deal
Mon, Dec 23 - Mon, Dec 30
6:25 am - 11:04 amMCO-ORD
5h 39m1 stop
8:14 pm - 12:21 amORD-MCO
3h 07mnonstop
$362Spirit Airlines
Find Deal
Fri, Dec 20 - Fri, Jan 3
7:50 pm - 9:53 pmMCO-ORD
3h 03mnonstop
8:14 pm - 12:21 amORD-MCO
3h 07mnonstop
$385Spirit Airlines
Find Deal
Thu, Dec 19 - Fri, Jan 3
1:15 pm - 3:05 pmMCO-MDW
2h 50mnonstop
6:50 pm - 10:25 pmMDW-MCO
2h 35mnonstop
$823Southwest
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Sat, Dec 21 - Sat, Dec 21
7:50 am - 12:05 pmMCO-MDW
5h 15m1 stop
2:25 pm - 7:50 pmMDW-MCO
4h 25m1 stop
$836Southwest
Find Deal
Sat, Dec 21 - Sat, Dec 21
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
6:06 pm - 9:58 pmORD-MCO
2h 52mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
5:18 pm - 7:39 pmMCO-ORD
3h 21mnonstop
3:14 pm - 7:15 pmORD-MCO
3h 01mnonstop
$110Frontier
Find Deal
Sat, Feb 15 - Tue, Feb 18
6:34 pm - 8:56 pmMCO-ORD
3h 22mnonstop
4:11 pm - 8:07 pmORD-MCO
2h 56mnonstop
$113Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
8:00 am - 11:50 amORD-MCO
2h 50mnonstop
$115Spirit Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
7:15 am - 9:21 amMCO-ORD
3h 06mnonstop
12:05 pm - 3:57 pmORD-MCO
2h 52mnonstop
$157United Airlines
Find Deal
Wed, Jan 22 - Sat, Jan 25
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
1:20 pm - 4:55 pmMDW-MCO
2h 35mnonstop
$164Southwest
Find Deal
Thu, Jan 23 - Tue, Jan 28
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$177American Airlines
Find Deal
Wed, Jan 22 - Sat, Jan 25
3:40 pm - 5:35 pmMCO-MDW
2h 55mnonstop
8:30 pm - 12:10 amMDW-MCO
2h 40mnonstop
$178Southwest
Find Deal
Wed, Feb 19 - Sun, Feb 23
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$214American Airlines
Find Deal
Fri, Jan 10 - Sun, Jan 12
11:00 am - 1:06 pmMCO-ORD
3h 06mnonstop
1:10 pm - 5:02 pmORD-MCO
2h 52mnonstop
$259United Airlines
Find Deal
Thu, Jan 9 - Tue, Jan 14

American Airlines flights from Orlando Airport to Chicago

Our best American Airlines deals on Orlando Airport to Chicago flight tickets
American Airlines
Jan 10
MCO7:00 amOrlando
3h 05m
ORD9:05 amChicago O'Hare Intl
Jan 12
ORD6:45 pmChicago O'Hare Intl
2h 50m
MCO10:35 pmOrlando
American Airlines
Jan 21
MCO7:00 amOrlando
3h 05m
ORD9:05 amChicago O'Hare Intl
Jan 25
ORD6:45 pmChicago O'Hare Intl
2h 50m
MCO10:35 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
MCO1:59 pmOrlando
3h 11m
ORD4:10 pmChicago O'Hare Intl
Jan 19
ORD6:06 pmChicago O'Hare Intl
2h 52m
MCO9:58 pmOrlando
Spirit Airlines
Jan 15
MCO1:59 pmOrlando
3h 11m
ORD4:10 pmChicago O'Hare Intl
Jan 22
ORD8:00 amChicago O'Hare Intl
2h 50m
MCO11:50 amOrlando
Spirit Airlines
Jan 14
MCO1:59 pmOrlando
3h 11m
ORD4:10 pmChicago O'Hare Intl
Jan 22
ORD8:00 amChicago O'Hare Intl
2h 50m
MCO11:50 amOrlando

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 month of February is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $118. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Orlando Airport to Chicago during April average around $124.

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 Friday when prices can be found for as low as $183. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $256.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $125. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $228.

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 best time to book a flight to Chicago from Orlando Airport is 54 days out, which is when prices tend to be around $198. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $123.

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

There are 4 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 Airport to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a Orlando Airport to Chicago flight.

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

As of December 2024, prices for Orlando Airport to Chicago flights are approximately 41% 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

$49

Fastest flight time

2h 45m

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 $49. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $102.
The fastest flight from Orlando Airport to Chicago takes 2h 45m
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 54m.

  • 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
FrontierPriceFrom $57Free CancellationRating
6.1
3,479 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $58Free CancellationRating
6.3
8,119 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $151Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $170Free CancellationRating
8.1
4,848 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,604 reviews
Search Delta flights
  • Southwest Flights From Orlando Airport to Chicago

    Across 27 Southwest flights from Orlando Airport to Chicago this week, the average price was $376, with the best Southwest deals starting from $170 round-trip. 4,848 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, 9,055 ratings). United Airlines flies from Orlando Airport to Chicago around 12 times per week, with deals starting from $151 round-trip and rising to an average price of around $320.


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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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