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Cheap flights from Orlando Airport to Chicago Midway Airport from $40

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 2/7. 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 from Orlando Airport to Chicago

The cheapest plane tickets from Orlando Airport to Chicago found on KAYAK recently.
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$80Frontier
Find Deal
Fri, Feb 7 - Sun, Feb 9
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$87Frontier
Find Deal
Fri, Feb 7 - Sun, Feb 9
10:39 am - 6:26 pmMCO-MDW
8h 47m1 stop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$95Frontier
Find Deal
Thu, Feb 6 - Sun, Feb 9
10:39 am - 6:26 pmMCO-MDW
8h 47m1 stop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$99Frontier
Find Deal
Thu, Feb 6 - Sun, Feb 9
6:31 pm - 12:54 amMCO-MDW
7h 23m1 stop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$103Frontier
Find Deal
Fri, Feb 7 - Sun, Feb 9
1:48 pm - 6:23 pmMCO-MDW
5h 35m1 stop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$107Frontier
Find Deal
Wed, Feb 26 - Sat, Mar 1
8:24 pm - 5:31 amMCO-MDW
10h 07m1 stop
8:30 am - 12:18 pmMDW-MCO
2h 48mnonstop
$108Frontier
Find Deal
Sat, Feb 15 - Tue, Feb 18
8:12 am - 3:06 pmMCO-MDW
7h 54m1 stop
10:26 am - 6:45 pmMDW-MCO
7h 19m1 stop
$109Frontier
Find Deal
Wed, Feb 26 - Sat, Mar 1
6:15 am - 10:12 amMCO-MDW
4h 57m1 stop
5:05 pm - 10:38 pmMDW-MCO
4h 33m1 stop
$227Delta
Find Deal
Thu, Feb 27 - Mon, Mar 3
8:45 am - 1:05 pmMCO-MDW
5h 20m1 stop
12:44 pm - 6:39 pmMDW-MCO
4h 55m1 stop
$234Delta
Find Deal
Fri, Feb 14 - Tue, Feb 18
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$40Frontier
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Fri, Feb 7
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$42Frontier
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Fri, Jan 31
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$44Frontier
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Fri, Feb 7
7:35 pm - 9:30 pmMCO-MDW
2h 55mnonstop
$99Southwest
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Tue, Mar 11
4:10 pm - 10:23 pmMCO-MDW
7h 13m1 stop
$109Delta
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Tue, Mar 18
7:00 am - 6:41 pmMCO-MDW
12h 41m1 stop
Thu, May 29
10:20 pm - 12:10 amMCO-MDW
2h 50mnonstop
$118Southwest
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Fri, Feb 21
11:35 am - 6:41 pmMCO-MDW
8h 06m1 stop
$127Avelo Airlines
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Sun, May 25
7:50 pm - 8:51 amMCO-MDW
14h 01m2 stops
$163Delta
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Tue, Feb 25
6:44 pm - 5:36 pmMCO-MDW
23h 52m3 stops
Wed, Mar 5
8:26 am - 10:28 amMCO-MDW
3h 02mnonstop
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$194Frontier
Find Deal
Mon, Jan 27 - Mon, Feb 3
1:39 pm - 12:17 amMCO-MDW
11h 38m1 stop
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$195Frontier
Find Deal
Tue, Jan 28 - Mon, Feb 3
8:00 am - 10:02 amMCO-MDW
3h 02mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$196Frontier
Find Deal
Sun, Jan 26 - Sun, Feb 2
1:39 pm - 12:17 amMCO-MDW
11h 38m1 stop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$197Frontier
Find Deal
Tue, Jan 28 - Sun, Feb 2
8:00 am - 10:02 amMCO-MDW
3h 02mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$198Frontier
Find Deal
Sun, Jan 26 - Sun, Feb 2
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
12:25 pm - 6:50 pmMDW-MCO
5h 25m1 stop
$332Southwest
Find Deal
Tue, Jan 28 - Thu, Jan 30
1:05 pm - 3:00 pmMCO-MDW
2h 55mnonstop
1:20 pm - 4:55 pmMDW-MCO
2h 35mnonstop
$362Southwest
Find Deal
Tue, Jan 28 - Thu, Jan 30
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
$587Southwest
Find Deal
Mon, Jan 27 - Mon, Feb 3
6:15 am - 11:59 amMCO-MDW
6h 44m1 stop
5:07 pm - 10:38 pmMDW-MCO
4h 31m1 stop
$857Delta
Find Deal
Fri, Jan 24 - Fri, Jan 24
6:15 am - 10:12 amMCO-MDW
4h 57m1 stop
9:34 am - 6:02 pmMDW-MCO
7h 28m2 stops
$1,403Delta
Find Deal
Sat, Jan 25 - Wed, Jan 29
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$80Frontier
Find Deal
Fri, Feb 7 - Sun, Feb 9
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$87Frontier
Find Deal
Fri, Feb 7 - Sun, Feb 9
1:13 pm - 3:12 pmMCO-MDW
2h 59mnonstop
8:30 am - 12:18 pmMDW-MCO
2h 48mnonstop
$113Frontier
Find Deal
Tue, Feb 25 - Tue, Mar 4
1:13 pm - 3:12 pmMCO-MDW
2h 59mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$114Frontier
Find Deal
Tue, Feb 25 - Sat, Mar 1
5:26 pm - 7:29 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$117Frontier
Find Deal
Thu, Feb 27 - Sun, Mar 2
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$118Frontier
Find Deal
Fri, Feb 28 - Sun, Mar 2
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$119Frontier
Find Deal
Fri, Feb 21 - Mon, Feb 24
5:26 pm - 7:29 pmMCO-MDW
3h 03mnonstop
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
$120Frontier
Find Deal
Thu, Feb 20 - Sun, Feb 23
3:35 pm - 5:30 pmMCO-MDW
2h 55mnonstop
3:10 pm - 6:50 pmMDW-MCO
2h 40mnonstop
$284Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:15 pm - 10:10 pmMCO-MDW
2h 55mnonstop
3:50 pm - 7:30 pmMDW-MCO
2h 40mnonstop
$296Southwest
Find Deal
Thu, Feb 6 - Mon, Feb 10

Frontier flights from Orlando Airport to Chicago Midway Airport

Our best Frontier deals on Orlando Airport to Chicago Midway Airport flight tickets
Frontier
Feb 7
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Feb 9
MDW10:58 amChicago Midway
2h 47m
MCO2:45 pmOrlando
Frontier
Feb 7
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Feb 9
MDW10:58 amChicago Midway
2h 47m
MCO2:45 pmOrlando
Frontier
Jan 31
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Feb 2
MDW10:58 amChicago Midway
2h 47m
MCO2:45 pmOrlando

Delta flights from Orlando Airport to Chicago Midway Airport

Our best Delta deals on Orlando Airport to Chicago Midway Airport flight tickets
Delta
Feb 27
MCO6:15 amOrlando
4h 57m
1 stop
MDW10:12 amChicago Midway
Mar 3
MDW5:05 pmChicago Midway
4h 33m
1 stop
MCO10:38 pmOrlando
Delta
Feb 14
MCO8:45 amOrlando
5h 20m
1 stop
MDW1:05 pmChicago Midway
Feb 18
MDW12:44 pmChicago Midway
4h 55m
1 stop
MCO6:39 pmOrlando
Delta
Feb 15
MCO6:15 amOrlando
4h 57m
1 stop
MDW10:12 amChicago Midway
Feb 17
MDW2:08 pmChicago Midway
6h 05m
1 stop
MCO9:13 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 typical price of a round-trip flight between Orlando Airport and Chicago Midway Airport?

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 $157. 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 $155. 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, Tuesday 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 $235.

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

Flying to Chicago Midway Airport from Orlando Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $167 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $175. 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?

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando Airport when booking 19 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $183 when searching 19 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando Airport for as low as $115 on momondo.

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.

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

As of January 2025, prices for Orlando Airport to Chicago Midway Airport flights are approximately 123% 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

$40

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 $40. The best round-trip flight deal from Orlando Airport to Chicago Midway Airport found on momondo in the last 72 hours is $80.
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 54m 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
6.0
3,440 reviews
Search Frontier flights
SouthwestPriceFrom $178Free CancellationRating
8.1
4,647 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,508 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 $178. Generally, Southwest has 49 flights on this route every week with an average price of $381. Southwest is rated 8.1/10 by our users.

  • Frontier Flights From Orlando Airport to Chicago Midway Airport

    Frontier (6.0/10 from 3,440 reviews) operates around 1 flight from Orlando Airport to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $165, 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.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

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.


An easier way to manage your Chicago Midway Airport trip

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