Cheap flights from Chicago Midway Airport to Orlando from $44

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 10/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Frontier Logo
8:35 am - 12:20 pmMDW-MCO
2h 45mnonstop
Frontier Logo
6:23 pm - 8:22 pmMCO-MDW
2h 59mnonstop
$103Frontier
Find Deal
Mon, Jul 28 - Thu, Jul 31
Frontier Logo
8:35 am - 12:20 pmMDW-MCO
2h 45mnonstop
Frontier Logo
6:23 pm - 8:22 pmMCO-MDW
2h 59mnonstop
$106Frontier
Find Deal
Mon, Aug 11 - Sat, Aug 16
Frontier Logo
9:17 am - 1:03 pmMDW-MCO
2h 46mnonstop
Frontier Logo
1:33 pm - 3:29 pmMCO-MDW
2h 56mnonstop
$107Frontier
Find Deal
Fri, Aug 22 - Mon, Aug 25
Southwest Logo
6:45 pm - 10:20 pmMDW-MCO
2h 35mnonstop
Southwest Logo
7:10 am - 8:55 amMCO-MDW
2h 45mnonstop
$131Southwest
Find Deal
Thu, Aug 14 - Tue, Aug 19
Southwest Logo
11:40 am - 7:20 pmMDW-MCO
6h 40m1 stop
Southwest Logo
5:40 pm - 7:25 pmMCO-MDW
2h 45mnonstop
$141Southwest
Find Deal
Sat, Aug 30 - Thu, Sep 4
Southwest Logo
5:50 pm - 9:25 pmMDW-MCO
2h 35mnonstop
Southwest Logo
7:30 am - 9:20 amMCO-MDW
2h 50mnonstop
$144Southwest
Find Deal
Sat, Nov 8 - Tue, Nov 11
Southwest Logo
7:00 am - 2:15 pmMDW-MCO
6h 15m2 stops
Southwest Logo
8:40 pm - 10:25 pmMCO-MDW
2h 45mnonstop
$146Southwest
Find Deal
Sat, Sep 20 - Thu, Sep 25
Allegiant Air Logo
9:32 am - 8:44 pmMDW-SFB
10h 12m1 stop
Allegiant Air Logo
10:55 am - 3:02 pmSFB-MDW
5h 07m1 stop
$195Allegiant Air
Find Deal
Fri, Aug 22 - Mon, Aug 25
Allegiant Air Logo
9:32 am - 8:44 pmMDW-SFB
10h 12m1 stop
Allegiant Air Logo
6:55 pm - 8:42 amSFB-MDW
14h 47m1 stop
$196Allegiant Air
Find Deal
Fri, Aug 22 - Sun, Aug 24
Allegiant Air Logo
7:07 pm - 9:47 amMDW-SFB
13h 40m1 stop
Allegiant Air Logo
8:10 am - 2:04 pmSFB-MDW
6h 54m1 stop
$204Allegiant Air
Find Deal
Fri, Aug 15 - Mon, Aug 18

Frontier flights from Chicago Midway Airport to Orlando

Our best Frontier deals on Chicago Midway Airport to Orlando flight tickets
Frontier
Jul 18
MDW8:35 amChicago Midway
2h 45m
MCO12:20 pmOrlando
Jul 25
MCO1:10 pmOrlando
2h 56m
MDW3:06 pmChicago Midway
Frontier
Jul 28
MDW8:35 amChicago Midway
2h 45m
MCO12:20 pmOrlando
Jul 31
MCO6:23 pmOrlando
2h 59m
MDW8:22 pmChicago Midway
Frontier
Aug 11
MDW8:35 amChicago Midway
2h 45m
MCO12:20 pmOrlando
Aug 16
MCO6:23 pmOrlando
2h 59m
MDW8:22 pmChicago Midway

Southwest flights from Chicago Midway Airport to Orlando

Our best Southwest deals on Chicago Midway Airport to Orlando flight tickets
Southwest
Aug 14
MDW6:45 pmChicago Midway
2h 35m
MCO10:20 pmOrlando
Aug 19
MCO7:10 amOrlando
2h 45m
MDW8:55 amChicago Midway
Southwest
Aug 30
MDW11:40 amChicago Midway
6h 40m
1 stop
MCO7:20 pmOrlando
Sep 4
MCO5:40 pmOrlando
2h 45m
MDW7:25 pmChicago Midway
Southwest
Nov 8
MDW5:50 pmChicago Midway
2h 35m
MCO9:25 pmOrlando
Nov 11
MCO7:30 amOrlando
2h 50m
MDW9:20 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 cheapest month to fly to Orlando?

The month of September is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $173. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago Midway Airport to Orlando during August average around $182.

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 $266. 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 $316.

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 $249. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $304.

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 weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $308 when searching 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 $229 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.

Can stopping save me money on Chicago Midway Airport to Orlando flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Orlando flight.

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

As of July 2025, prices for Chicago Midway Airport to Orlando flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Orlando

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

Cheap Chicago Midway Airport to Orlando (MDW to ORL) 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

$44

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Orlando

2 airports
The best one-way flight to Orlando from Chicago Midway Airport in the past 72 hours is $44. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $103.
The fastest flight from Chicago Midway Airport to Orlando takes 2h 30m
Direct flights go from Chicago Midway Airport to Orlando every day.
There are 2 airports near Orlando: Orlando (MCO), Orlando Sanford Intl (SFB)

  • How far is Chicago Midway to Orlando by plane?

    Orlando is 982.0 mi away from Chicago Midway. Flights usually cover this in 2h 30m, 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 $63Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
FrontierPriceFrom $103Free CancellationRating
5.9
3,271 reviews
Search Frontier flights
DeltaPriceFrom $196Free CancellationRating
8.0
7,951 reviews
Search Delta flights
SouthwestPriceFrom $224Free CancellationRating
8.0
4,249 reviews
Search Southwest flights
United AirlinesPriceFrom $248Free CancellationRating
7.4
8,846 reviews
Search United Airlines flights
  • Southwest Flights From Chicago Midway Airport to Orlando

    Across 51 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $396, with the best Southwest deals starting from $224 round-trip. 4,249 users have rated Southwest on momondo, with an average score of 8.0/10.

  • Frontier Flights From Chicago Midway Airport to Orlando

    Frontier (5.9/10 from 3,271 reviews) operates around 2 flights from Chicago Midway Airport to Orlando in any given week. The average Frontier airfare for this route is around $215, with deals from around $103 rare but found on momondo. Referenced prices are for round-trip Chicago Midway Airport to Orlando flight searches in the last 72 hours.


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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1 adult
Tue 7/15
Tue 7/22

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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