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Cheap flights from Orlando Airport to Chicago Midway Airport from $54

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 Midway Airport departing on 3/3. 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.
4:56 pm - 11:29 pmMCO-MDW
7h 33m1 stop
7:30 am - 4:01 pmMDW-MCO
7h 31m1 stop
$108Frontier
Find Deal
Sat, Jan 18 - Sat, Jan 25
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
4:35 pm - 12:40 amMDW-MCO
7h 05m1 stop
$110Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
10:39 am - 6:37 pmMCO-MDW
8h 58m1 stop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$112Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$113Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$114Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$163Southwest
Find Deal
Wed, Feb 5 - Mon, Feb 10
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
$173Southwest
Find Deal
Wed, Jan 15 - Wed, Jan 22
5:01 pm - 10:04 pmMCO-MDW
6h 03m1 stop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
Sat, Feb 15 - Sun, Feb 16
6:30 pm - 10:20 pmMCO-MDW
4h 50m1 stop
5:05 pm - 12:35 amMDW-MCO
6h 30m1 stop
$196Delta
Find Deal
Thu, Jan 30 - Tue, Feb 4
6:20 am - 12:30 pmMCO-MDW
7h 10m1 stop
1:05 pm - 8:37 pmMDW-MCO
6h 32m1 stop
$324Delta
Find Deal
Fri, Apr 25 - Wed, Apr 30
7:51 pm - 11:58 pmMCO-MDW
5h 07m1 stop
$54Frontier
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Mon, Mar 3
12:40 pm - 6:26 pmMCO-MDW
6h 46m1 stop
$56Frontier
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Thu, Jan 30
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
$58Frontier
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Fri, Jan 10
4:56 pm - 11:29 pmMCO-MDW
7h 33m1 stop
$59Frontier
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Sat, Jan 25
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$79Southwest
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Wed, Feb 5
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$85Southwest
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Thu, Jan 23
6:00 am - 1:05 pmMCO-MDW
8h 05m1 stop
$98Delta
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Thu, Feb 20
6:05 am - 12:36 pmMCO-MDW
7h 31m1 stop
$116Delta
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Tue, Mar 11
8:00 am - 8:31 amMCO-MDW
25h 31m2 stops
Wed, Jan 8
8:00 am - 8:31 amMCO-MDW
25h 31m2 stops
Sat, Feb 8
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
9:59 pm - 10:22 amMDW-MCO
11h 23m1 stop
$188Frontier
Find Deal
Wed, Dec 25 - Mon, Jan 6
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
10:26 am - 2:15 pmMDW-MCO
2h 49mnonstop
$190Frontier
Find Deal
Wed, Dec 25 - Mon, Jan 6
10:52 pm - 6:39 amMCO-MDW
8h 47m1 stop
2:20 pm - 9:17 pmMDW-MCO
5h 57m1 stop
$208Frontier
Find Deal
Wed, Dec 25 - Mon, Jan 6
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
12:58 pm - 4:52 pmMDW-MCO
2h 54mnonstop
$241Frontier
Find Deal
Wed, Dec 25 - Sun, Jan 5
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
6:49 pm - 10:43 pmMDW-MCO
2h 54mnonstop
$246Frontier
Find Deal
Wed, Dec 25 - Fri, Jan 3
1:55 pm - 6:10 pmMCO-MDW
5h 15m1 stop
2:50 pm - 8:05 pmMDW-MCO
4h 15m1 stop
$596Southwest
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Sat, Dec 28 - Tue, Dec 31
1:10 pm - 4:17 pmMCO-MDW
4h 07m1 stop
10:08 am - 3:09 pmMDW-MCO
4h 01m1 stop
$712Delta
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Thu, Dec 26 - Tue, Dec 31
12:40 pm - 4:10 pmMCO-MDW
4h 30m1 stop
6:25 pm - 12:10 amMDW-MCO
4h 45m1 stop
$764Delta
Find Deal
Tue, Dec 24 - Thu, Jan 2
6:00 am - 9:23 amMCO-MDW
4h 23m1 stop
9:30 am - 4:59 pmMDW-MCO
6h 29m1 stop
$796Delta
Find Deal
Tue, Dec 24 - Wed, Jan 1
10:20 am - 12:10 pmMCO-MDW
2h 50mnonstop
3:55 pm - 7:30 pmMDW-MCO
2h 35mnonstop
$827Southwest
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Thu, Dec 26 - Sat, Dec 28
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$110Frontier
Find Deal
Fri, Feb 14 - Sat, Feb 15
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
8:30 am - 12:18 pmMDW-MCO
2h 48mnonstop
$112Frontier
Find Deal
Fri, Feb 14 - Tue, Feb 18
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$113Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$114Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$122Frontier
Find Deal
Fri, Feb 21 - Mon, Feb 24
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$123Frontier
Find Deal
Fri, Feb 21 - Mon, Feb 24
8:26 am - 10:21 amMCO-MDW
2h 55mnonstop
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$129Frontier
Find Deal
Mon, Jan 13 - Mon, Jan 20
8:00 am - 10:02 amMCO-MDW
3h 02mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$130Frontier
Find Deal
Sun, Jan 19 - Sun, Jan 26
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$163Southwest
Find Deal
Wed, Feb 5 - Mon, Feb 10
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
$173Southwest
Find Deal
Wed, Jan 15 - Wed, Jan 22

Frontier flights from Orlando Airport to Chicago Midway Airport

Our best Frontier deals on Orlando Airport to Chicago Midway Airport flight tickets
Frontier
Jan 18
MCO4:56 pmOrlando
7h 33m
1 stop
MDW11:29 pmChicago Midway
Jan 25
MDW7:30 amChicago Midway
7h 31m
1 stop
MCO4:01 pmOrlando
Frontier
Jan 10
MCO12:38 pmOrlando
2h 55m
MDW2:33 pmChicago Midway
Jan 13
MDW4:35 pmChicago Midway
7h 05m
1 stop
MCO12:40 amOrlando
Frontier
Jan 9
MCO10:39 amOrlando
8h 58m
1 stop
MDW6:37 pmChicago Midway
Jan 12
MDW10:58 amChicago Midway
2h 49m
MCO2:47 pmOrlando

Southwest flights from Orlando Airport to Chicago Midway Airport

Our best Southwest deals on Orlando Airport to Chicago Midway Airport flight tickets
Southwest
Feb 5
MCO7:10 amOrlando
2h 55m
MDW9:05 amChicago Midway
Feb 10
MDW7:05 pmChicago Midway
2h 40m
MCO10:45 pmOrlando
Southwest
Jan 15
MCO10:25 amOrlando
2h 55m
MDW12:20 pmChicago Midway
Jan 22
MDW3:25 pmChicago Midway
2h 40m
MCO7:05 pmOrlando
Southwest
Jan 30
MCO7:10 amOrlando
2h 55m
MDW9:05 amChicago Midway
Feb 4
MDW1:45 pmChicago Midway
4h 25m
1 stop
MCO7:10 pmOrlando

See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando Airport to Chicago Midway Airport

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 Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $144. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month April is also very affordable. Most momondo users find prices during this month for around $158.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando Airport. The lowest ticket price found for a Friday departure recently was $148. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Orlando Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $239.

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

Flying to Chicago Midway Airport from Orlando Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $163 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $190. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Orlando to Chicago Midway flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Orlando Airport to Chicago Midway Airport 57 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $181. In the past 72 hours, momondo users found flights from Orlando Airport to Chicago Midway Airport for as low as $76.

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

There are 1 cabin classes available to choose from on Orlando to Chicago Midway 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 Midway Airport flights?

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

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

As of December 2024, prices for Orlando Airport to Chicago Midway Airport flights are approximately 70% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Orlando Airport to Chicago Midway Airport (MCO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando Airport to Chicago Midway Airport

Best Price Found

$54

Fastest flight time

2h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Orlando Airport in the past 72 hours is $54. The best round-trip flight deal from Orlando Airport to Chicago Midway Airport found on momondo in the last 72 hours is $108.
The fastest flight from Orlando Airport to Chicago Midway Airport takes 2h 50m
Direct flights go from Orlando Airport to Chicago Midway Airport every day.

  • How far is Orlando to Chicago Midway by plane?

    The distance between Orlando and Chicago Midway is about 990.5 mi. 2h 50m is a normal flight duration for this route.

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

    Prices for flights from Orlando Airport to Chicago Midway Airport were last updated today.

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

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

    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 Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Orlando Airport to Chicago Midway Airport?

  • What is the most popular airline from Orlando Airport to Chicago Midway Airport?


Best airlines flying from Orlando Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Orlando Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $76Free CancellationRating
6.1
3,469 reviews
Search Frontier flights
SouthwestPriceFrom $170Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,594 reviews
Search Delta flights
  • Southwest Flights From Orlando Airport to Chicago Midway Airport

    The lowest priced Southwest flight from Orlando Airport to Chicago Midway Airport from the last 72 hours was $170. Generally, Southwest has 46 flights on this route every week with an average price of $343. Southwest is rated 8.1/10 by our users.

  • Frontier Flights From Orlando Airport to Chicago Midway Airport

    Frontier (6.1/10 from 3,469 reviews) operates around 8 flights from Orlando Airport to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $166, with deals from around $76 rare but found on momondo. Referenced prices are for round-trip Orlando Airport to Chicago Midway Airport flight searches in the last 72 hours.


Why use momondo?

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

It is quick and easy to find Orlando to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Orlando on momondo can be compared and filtered by various policies on offer, including flexible booking.

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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