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Cheap flights from Chicago Midway Airport to Orlando from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Orlando departing on 1/13. 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 Chicago Midway Airport to Orlando

Cheap round-trip flights

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

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Orlando? 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 Orlando, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Orlando

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

All round-trip flight deals to Orlando

The cheapest plane tickets to Orlando found on KAYAK recently.
7:30 am - 4:01 pmMDW-MCO
7h 31m1 stop
8:00 am - 10:02 amMCO-MDW
3h 02mnonstop
$98Frontier
Find Deal
Sat, Feb 8 - Sun, Feb 9
7:30 am - 4:01 pmMDW-MCO
7h 31m1 stop
5:12 pm - 7:15 pmMCO-MDW
3h 03mnonstop
$108Frontier
Find Deal
Sat, Feb 8 - Sat, Feb 15
12:36 pm - 1:43 amMDW-MCO
12h 07m1 stop
11:06 am - 11:20 pmMCO-MDW
13h 14m1 stop
$109Frontier
Find Deal
Thu, Dec 12 - Wed, Dec 18
8:25 am - 2:55 pmMDW-MCO
5h 30m1 stop
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
$110Frontier
Find Deal
Mon, Jan 6 - Fri, Jan 10
12:36 pm - 1:43 amMDW-MCO
12h 07m1 stop
8:26 am - 10:21 amMCO-MDW
2h 55mnonstop
$112Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
5:50 pm - 12:05 amMDW-MCO
5h 15m1 stop
6:15 am - 9:50 amMCO-MDW
4h 35m1 stop
$196Delta
Find Deal
Sat, Dec 14 - Tue, Dec 17
12:25 pm - 6:50 pmMDW-MCO
5h 25m1 stop
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
$253Southwest
Find Deal
Wed, Feb 19 - Tue, Feb 25
5:00 pm - 8:35 pmMDW-MCO
2h 35mnonstop
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
$263Southwest
Find Deal
Sat, Feb 1 - Tue, Feb 4
2:22 pm - 7:56 amMDW-SFB
16h 34m2 stops
9:10 am - 7:50 amSFB-MDW
23h 40m2 stops
$518Allegiant Air
Find Deal
Sun, Mar 9 - Sun, Mar 16
7:14 pm - 10:56 pmMDW-SFB
26h 42m2 stops
6:43 pm - 4:48 pmSFB-MDW
23h 05m2 stops
$799Allegiant Air
Find Deal
Sun, Dec 22 - Sat, Dec 28
4:35 pm - 12:40 amMDW-MCO
7h 05m1 stop
$53Frontier
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Mon, Jan 13
2:56 pm - 12:22 amMDW-MCO
8h 26m1 stop
$54Frontier
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Thu, Jan 23
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
$79Southwest
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Tue, Jan 7
10:57 am - 4:09 pmMDW-MCO
4h 12m1 stop
$98Delta
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Tue, Jan 21
4:27 pm - 12:36 pmMDW-MCO
19h 09m2 stops
Fri, Dec 6
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
$114Southwest
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Tue, Jan 21
9:30 am - 5:01 pmMDW-MCO
6h 31m1 stop
$128Delta
Find Deal
Tue, Dec 10
7:14 pm - 10:56 pmMDW-SFB
26h 42m2 stops
$164Allegiant Air
Find Deal
Sun, Jan 5
9:21 am - 10:45 pmMDW-MCO
12h 24m2 stops
Sun, Feb 9
6:16 pm - 9:36 amMDW-SFB
14h 20m1 stop
$175Allegiant Air
Find Deal
Wed, Nov 27
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
$181Frontier
Find Deal
Tue, Nov 26 - Fri, Dec 6
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
$182Frontier
Find Deal
Tue, Nov 26 - Wed, Dec 25
7:32 pm - 11:32 pmMDW-MCO
3h 00mnonstop
4:11 pm - 9:17 pmMCO-MDW
6h 06m1 stop
$183Frontier
Find Deal
Tue, Nov 26 - Wed, Dec 25
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
4:42 pm - 6:37 pmMCO-MDW
2h 55mnonstop
$200Frontier
Find Deal
Tue, Nov 26 - Tue, Nov 26
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
4:42 pm - 6:37 pmMCO-MDW
2h 55mnonstop
$216Frontier
Find Deal
Tue, Nov 26 - Tue, Nov 26
5:10 am - 11:13 pmMDW-MCO
41h 03m2 stops
6:00 am - 7:55 amMCO-MDW
2h 55mnonstop
Sat, Nov 23 - Fri, Nov 29
5:10 am - 11:13 pmMDW-MCO
41h 03m2 stops
6:10 am - 8:05 amMCO-MDW
2h 55mnonstop
Sat, Nov 23 - Sat, Nov 30
2:13 pm - 8:00 pmMDW-SFB
4h 47m1 stop
8:56 am - 5:26 pmSFB-MDW
9h 30m1 stop
$354Allegiant Air
Find Deal
Mon, Nov 25 - Wed, Nov 27
3:14 pm - 10:46 pmMDW-SFB
6h 32m1 stop
9:50 pm - 11:55 amSFB-MDW
15h 05m1 stop
$365Allegiant Air
Find Deal
Fri, Nov 22 - Tue, Nov 26
7:45 am - 11:25 amMDW-MCO
2h 40mnonstop
10:25 am - 12:15 pmMCO-MDW
2h 50mnonstop
$563Southwest
Find Deal
Fri, Nov 22 - Wed, Dec 4
12:29 pm - 4:17 pmMDW-MCO
2h 48mnonstop
5:12 pm - 7:15 pmMCO-MDW
3h 03mnonstop
$110Frontier
Find Deal
Tue, Feb 25 - Tue, Mar 4
12:29 pm - 4:17 pmMDW-MCO
2h 48mnonstop
5:12 pm - 7:15 pmMCO-MDW
3h 03mnonstop
$112Frontier
Find Deal
Tue, Feb 18 - Thu, Feb 27
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$113Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
5:47 pm - 7:42 pmMCO-MDW
2h 55mnonstop
$114Frontier
Find Deal
Sun, Dec 15 - Thu, Dec 19
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$115Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
12:29 pm - 4:17 pmMDW-MCO
2h 48mnonstop
5:12 pm - 7:15 pmMCO-MDW
3h 03mnonstop
$116Frontier
Find Deal
Mon, Feb 17 - Thu, Feb 27
11:33 am - 3:25 pmMDW-MCO
2h 52mnonstop
8:00 am - 9:55 amMCO-MDW
2h 55mnonstop
$117Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
6:49 pm - 10:43 pmMDW-MCO
2h 54mnonstop
5:47 pm - 7:42 pmMCO-MDW
2h 55mnonstop
$118Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 19
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$158Southwest
Find Deal
Tue, Jan 14 - Wed, Jan 15
3:55 pm - 7:35 pmMDW-MCO
2h 40mnonstop
6:30 am - 8:25 amMCO-MDW
2h 55mnonstop
$193Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15

Frontier flights from Chicago Midway Airport to Orlando

Our best Frontier deals on Chicago Midway Airport to Orlando flight tickets
Frontier
Feb 8
MDW7:30 amChicago Midway
7h 31m
1 stop
MCO4:01 pmOrlando
Feb 9
MCO8:00 amOrlando
3h 02m
MDW10:02 amChicago Midway
Frontier
Feb 8
MDW7:30 amChicago Midway
7h 31m
1 stop
MCO4:01 pmOrlando
Feb 15
MCO5:12 pmOrlando
3h 03m
MDW7:15 pmChicago Midway
Frontier
Dec 12
MDW12:36 pmChicago Midway
12h 07m
1 stop
MCO1:43 amOrlando
Dec 18
MCO11:06 amOrlando
13h 14m
1 stop
MDW11:20 pmChicago Midway

Southwest flights from Chicago Midway Airport to Orlando

Our best Southwest deals on Chicago Midway Airport to Orlando flight tickets
Southwest
Feb 19
MDW12:25 pmChicago Midway
5h 25m
1 stop
MCO6:50 pmOrlando
Feb 25
MCO7:50 pmOrlando
2h 55m
MDW9:45 pmChicago Midway
Southwest
Feb 1
MDW5:00 pmChicago Midway
2h 35m
MCO8:35 pmOrlando
Feb 4
MCO7:50 pmOrlando
2h 55m
MDW9:45 pmChicago Midway
Southwest
Dec 3
MDW11:55 amChicago Midway
5h 10m
1 stop
MCO6:05 pmOrlando
Dec 4
MCO5:00 pmOrlando
2h 50m
MDW6:50 pmChicago Midway

See travel insights to Orlando from

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

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 Orlando?

The month of May is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $176. If you’re not able to fly to Orlando in May, then April is your next best option. Flight prices from Chicago Midway Airport to Orlando during April average around $186.

What is the cheapest day to depart on your flight to Orlando?

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $233. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $301.

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

The cheapest time of day to fly to Orlando is in the evening when flights can be purchased for as low as $197. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $288.

What is the cheapest Chicago Midway to Orlando flight route?

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

How far in advance should I book a flight to Orlando?

In general, most travelers find the cheapest time to book a flight to Orlando is about 30 days prior to their departure date when tickets on average are $258. Keep in mind that you might be able to find cheaper flights to Orlando at any time. In fact, our users found flights for as low as $142 in the past 72 hours.

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

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

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

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

As of November 2024, prices for Chicago Midway Airport to Orlando flights are approximately 7% more expensive when compared to flights at the same time last year.

Cheap Chicago Midway Airport to Orlando flight deals and tips

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

Best Price Found

$53

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Orlando

1 airport
The best one-way flight to Orlando from Chicago Midway Airport in the past 72 hours is $53. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $98.
The fastest flight from Chicago Midway Airport to Orlando takes 2h 35m
Direct flights go from Chicago Midway Airport to Orlando every day.
There is 1 airport near Orlando: Orlando (MCO)

  • How far is Chicago Midway to Orlando by plane?

    Orlando is 982.0 mi away from Chicago Midway. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago Midway Airport to Orlando are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Orlando.

  • What documentation or ID do you need to fly to Orlando?

    The necessary travel and health documents for your Orlando trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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


Best airlines flying from Chicago Midway Airport to Orlando

Compare and see reviews for airlines that fly from Chicago Midway Airport to Orlando with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $23Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
FrontierPriceFrom $80Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
United AirlinesPriceFrom $154Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $254Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
  • Southwest Flights From Chicago Midway Airport to Orlando

    Across 45 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $417, with the best Southwest deals starting from $254 round-trip. 5,005 users have rated Southwest on momondo, with an average score of 8.1/10.

  • Frontier Flights From Chicago Midway Airport to Orlando

    Frontier (6.1/10 from 3,536 reviews) operates around 2 flights from Chicago Midway Airport to Orlando in any given week. The average Frontier airfare for this route is around $217, with deals from around $80 rare but found on momondo. Referenced prices are for round-trip Chicago Midway Airport to Orlando flight searches in the last 72 hours.


Why use momondo?

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

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 Chicago to Orlando for you.

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

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

How can momondo help me find flights from Chicago to Orlando?

momondo provides multiple filters to help you find the best flight to Orlando from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Orlando right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Orlando, momondo offers a useful price alert feature which will track prices for flights to Orlando from Chicago and alert you when they change.


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Fly into one of these airports located in Orlando

Airports listed have a maximum distance of 18.3 mi from Orlando