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Cheap flights from Chicago Midway Airport to Orlando from $38

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 1/27. 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.
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$90Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$91Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$92Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:40 pm - 6:26 pmMCO-MDW
6h 46m1 stop
$93Frontier
Find Deal
Sun, Feb 2 - Thu, Feb 6
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
10:39 am - 6:26 pmMCO-MDW
8h 47m1 stop
$94Frontier
Find Deal
Sun, Feb 2 - Thu, Feb 6
10:57 am - 5:15 pmMDW-MCO
5h 18m1 stop
5:30 am - 10:12 amMCO-MDW
5h 42m1 stop
$203Delta
Find Deal
Tue, Feb 11 - Wed, Feb 19
2:55 pm - 9:07 pmMDW-MCO
5h 12m1 stop
5:30 am - 9:09 amMCO-MDW
4h 39m1 stop
$221Delta
Find Deal
Tue, Mar 25 - Wed, Mar 26
2:53 pm - 11:38 pmMDW-SFB
7h 45m1 stop
7:00 am - 7:46 pmSFB-MDW
13h 46m1 stop
$342Allegiant Air
Find Deal
Fri, Jun 6 - Fri, Jun 13
2:53 pm - 11:38 pmMDW-SFB
7h 45m1 stop
6:15 am - 7:15 amSFB-MDW
26h 00m2 stops
$430Allegiant Air
Find Deal
Mon, Jun 23 - Thu, Jun 26
9:13 pm - 5:10 pmMDW-SFB
18h 57m2 stops
4:43 pm - 10:47 amSFB-MDW
19h 04m2 stops
$484Allegiant Air
Find Deal
Wed, Jul 2 - Wed, Jul 9
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$38Frontier
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Mon, Jan 27
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$39Frontier
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Sun, Feb 2
5:35 am - 9:10 amMDW-MCO
2h 35mnonstop
$96Southwest
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Tue, Mar 18
7:55 pm - 11:30 pmMDW-MCO
2h 35mnonstop
$99Southwest
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Tue, Apr 22
5:05 pm - 10:38 pmMDW-MCO
4h 33m1 stop
$104Delta
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Tue, Feb 18
2:55 pm - 9:07 pmMDW-MCO
5h 12m1 stop
$111Delta
Find Deal
Tue, Mar 25
2:53 pm - 11:38 pmMDW-SFB
7h 45m1 stop
$152Allegiant Air
Find Deal
Mon, Jun 16
5:10 am - 5:19 amMDW-MCO
47h 09m3 stops
Thu, Feb 13
8:04 pm - 9:17 amMDW-MCO
12h 13m1 stop
$181Allegiant Air
Find Deal
Fri, May 23
6:20 pm - 4:36 pmMDW-MCO
21h 16m3 stops
Sun, Mar 2
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$202Frontier
Find Deal
Sun, Jan 19 - Fri, Jan 24
4:27 pm - 12:41 amMDW-MCO
7h 14m1 stop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$203Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$208Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
4:27 pm - 12:41 amMDW-MCO
7h 14m1 stop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$209Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
4:27 pm - 12:41 amMDW-MCO
7h 14m1 stop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$213Frontier
Find Deal
Sun, Jan 19 - Fri, Jan 24
4:27 pm - 12:41 amMDW-MCO
7h 14m1 stop
8:26 am - 10:28 amMCO-MDW
3h 02mnonstop
$266Frontier
Find Deal
Mon, Jan 20 - Mon, Jan 27
2:35 pm - 6:10 pmMDW-MCO
2h 35mnonstop
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$567Southwest
Find Deal
Sat, Jan 18 - Wed, Jan 22
11:25 am - 5:40 pmMDW-MCO
5h 15m1 stop
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$572Southwest
Find Deal
Sat, Jan 18 - Wed, Jan 22
9:15 am - 3:35 pmMDW-MCO
5h 20m1 stop
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$577Southwest
Find Deal
Thu, Jan 16 - Wed, Jan 22
9:34 am - 7:00 pmMDW-MCO
8h 26m2 stops
5:30 am - 10:12 amMCO-MDW
5h 42m1 stop
$1,649Delta
Find Deal
Sat, Jan 18 - Sun, Jan 19
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$90Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$91Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$92Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$93Frontier
Find Deal
Sun, Feb 2 - Fri, Feb 7
12:58 pm - 4:51 pmMDW-MCO
2h 53mnonstop
9:25 pm - 11:24 pmMCO-MDW
2h 59mnonstop
$98Frontier
Find Deal
Sat, Apr 12 - Tue, Apr 15
4:40 pm - 8:30 pmMDW-MCO
2h 50mnonstop
5:46 pm - 7:47 pmMCO-MDW
3h 01mnonstop
$100Frontier
Find Deal
Tue, Apr 8 - Sat, Apr 19
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
$101Frontier
Find Deal
Mon, Feb 17 - Fri, Feb 21
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
5:32 pm - 7:35 pmMCO-MDW
3h 03mnonstop
$102Frontier
Find Deal
Sat, Mar 1 - Thu, Mar 6
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
5:16 pm - 7:19 pmMCO-MDW
3h 03mnonstop
$103Frontier
Find Deal
Sun, Feb 9 - Fri, Feb 14
12:43 pm - 4:31 pmMDW-MCO
2h 48mnonstop
6:50 am - 8:53 amMCO-MDW
3h 03mnonstop
$104Frontier
Find Deal
Sat, Mar 1 - Sat, Mar 8

Frontier flights from Chicago Midway Airport to Orlando

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

Delta flights from Chicago Midway Airport to Orlando

Our best Delta deals on Chicago Midway Airport to Orlando flight tickets
Delta
Feb 11
MDW10:57 amChicago Midway
5h 18m
1 stop
MCO5:15 pmOrlando
Feb 19
MCO5:30 amOrlando
5h 42m
1 stop
MDW10:12 amChicago Midway
Delta
Mar 25
MDW2:55 pmChicago Midway
5h 12m
1 stop
MCO9:07 pmOrlando
Mar 26
MCO5:30 amOrlando
4h 39m
1 stop
MDW9:09 amChicago Midway
Delta
Jan 24
MDW12:44 pmChicago Midway
5h 58m
1 stop
MCO7:42 pmOrlando
Jan 28
MCO7:00 amOrlando
5h 59m
1 stop
MDW11:59 amChicago 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 typical price of a round-trip flight between Chicago Midway Airport and Orlando?

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 $164. 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 $191.

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 $236. 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 $315.

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 afternoon when flights can be purchased for as low as $202. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $289.

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?

You are more likely to see cheaper flights to Orlando from Chicago Midway Airport when booking 3 weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $296 when searching 3 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago Midway Airport for as low as $186 on momondo.

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.

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

As of January 2025, prices for Chicago Midway Airport to Orlando flights are approximately 63% 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

$38

Fastest flight time

2h 30m

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 $38. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $90.
The fastest flight from Chicago Midway Airport to Orlando takes 2h 30m
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 41m, 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 $65Free CancellationRating
6.3
8,095 reviews
Search Spirit Airlines flights
FrontierPriceFrom $93Free CancellationRating
6.0
3,433 reviews
Search Frontier flights
United AirlinesPriceFrom $154Free CancellationRating
7.4
8,963 reviews
Search United Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,511 reviews
Search Delta flights
SouthwestPriceFrom $246Free CancellationRating
8.1
4,659 reviews
Search Southwest flights
  • Southwest Flights From Chicago Midway Airport to Orlando

    Across 30 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $411, with the best Southwest deals starting from $246 round-trip. 4,659 users have rated Southwest on momondo, with an average score of 8.1/10.


Traveling to a place near Orlando?

Book flights to Orlando if you plan to visit one of these locations
Bay Lake

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