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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 9/29. 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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0 bags

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Find the cheapest flights from Chicago Midway Airport to Orlando (MDW-MCO)

Cheap round-trip flights

Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
5:35 am - 7:23 amMCO-MDW
2h 48mnonstop
$96Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$97Frontier
Find Deal
Mon, Sep 22 - Fri, Sep 26
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$98Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$99Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
Frontier Logo
5:35 am - 7:23 amMCO-MDW
2h 48mnonstop
$102Frontier
Find Deal
Sat, Sep 13 - Mon, Sep 15
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$103Frontier
Find Deal
Fri, Sep 12 - Fri, Sep 19
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$104Frontier
Find Deal
Fri, Sep 5 - Fri, Sep 12
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$105Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 21
Frontier Logo
5:28 pm - 9:10 pmMDW-MCO
2h 42mnonstop
Frontier Logo
8:25 am - 10:21 amMCO-MDW
2h 56mnonstop
$106Frontier
Find Deal
Mon, Oct 13 - Sat, Oct 18
Frontier Logo
5:28 pm - 9:10 pmMDW-MCO
2h 42mnonstop
Frontier Logo
7:50 am - 9:47 amMCO-MDW
2h 57mnonstop
$107Frontier
Find Deal
Fri, Oct 17 - Thu, Oct 23

Frontier flights from Chicago Midway Airport to Orlando Airport

Our best Frontier deals on Chicago Midway Airport to Orlando Airport flight tickets
Frontier
Sep 5
MDW9:48 amChicago Midway
2h 40m
MCO1:28 pmOrlando
Sep 8
MCO5:35 amOrlando
2h 48m
MDW7:23 amChicago Midway
$96
Find similar
Frontier
Sep 22
MDW8:19 amChicago Midway
2h 41m
MCO12:00 pmOrlando
Sep 26
MCO7:00 amOrlando
2h 53m
MDW8:53 amChicago Midway
$97
Find similar
Frontier
Sep 19
MDW9:48 amChicago Midway
2h 40m
MCO1:28 pmOrlando
Sep 21
MCO7:25 amOrlando
2h 53m
MDW9:18 amChicago Midway
$98
Find similar

Southwest flights from Chicago Midway Airport to Orlando Airport

Our best Southwest deals on Chicago Midway Airport to Orlando Airport flight tickets
Southwest
Aug 27
MDW1:30 pmChicago Midway
2h 40m
MCO5:10 pmOrlando
Sep 11
MCO8:40 pmOrlando
2h 45m
MDW10:25 pmChicago Midway
$243
Find similar
Southwest
Aug 27
MDW4:30 pmChicago Midway
5h 45m
1 stop
MCO11:15 pmOrlando
Sep 11
MCO7:35 amOrlando
2h 45m
MDW9:20 amChicago Midway
$253
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Orlando Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/5

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Mon 9/8

5:35 am-7:23 am

Nonstop2h 48m

$96

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/22

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Fri 9/26

7:00 am-8:53 am

Nonstop2h 53m

$97

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/19

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sun 9/21

7:25 am-9:18 am

Nonstop2h 53m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/26

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sun 9/28

7:25 am-9:18 am

Nonstop2h 53m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 9/13

10:51 am-2:33 pm

Nonstop2h 42m

Orlando

Mon 9/15

5:35 am-7:23 am

Nonstop2h 48m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/12

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

$103

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/5

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

$104

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/15

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Sun 9/21

7:25 am-9:18 am

Nonstop2h 53m

$105

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

Orlando

Sat 10/18

8:25 am-10:21 am

Nonstop2h 56m

$106

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 10/17

5:28 pm-9:10 pm

Nonstop2h 42m

Orlando

Thu 10/23

7:50 am-9:47 am

Nonstop2h 57m

$107

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Orlando from

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

The cheapest month to fly to Orlando Airport from Chicago Midway Airport is in January. Flight prices, which tend to average around $252, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Orlando Airport from Chicago Midway Airport during July instead. Flights to Orlando Airport in July, while not as cheap as those in January, still average around $257.

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

The cheapest day to depart from Chicago Midway Airport to Orlando Airport is on a Tuesday. Travelers who choose to depart for Orlando Airport on a Tuesday will often find tickets for as low as $260. The most expensive day to fly to Orlando Airport is Monday, with ticket prices averaging around $310.

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

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Orlando Airport when you can find flight prices for as low as $252. Flying to Orlando Airport in the afternoon is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $303.

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 Airport?

You are more likely to see cheaper flights to Orlando Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando Airport for around $302 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando Airport from Chicago Midway Airport for as low as $236 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 Airport flights?

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

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

As of August 2025, prices for Chicago Midway Airport to Orlando Airport flights are approximately 47% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Orlando Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Orlando Airport 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 Airport (MDW to MCO) flight deals and tips

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

Best Price Found

$108

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Orlando Airport from Chicago Midway Airport in the past 72 hours is $108. The best round-trip flight deal from Chicago Midway Airport to Orlando Airport found on momondo in the last 72 hours is $158.
The fastest flight from Chicago Midway Airport to Orlando Airport takes 2h 30m
Direct flights go from Chicago Midway Airport to Orlando Airport every day.
Search flight deals

  • How far is Chicago Midway to Orlando by plane?

    There are 990.5 mi between Chicago Midway and Orlando. In terms of flight time, this usually takes a little over 2h 40m.

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

    Prices for flights from Chicago Midway Airport to Orlando Airport are updated daily.

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

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

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

    The necessary travel and health documents for your Orlando Airport 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 Airport?

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

Best airlines flying from Chicago Midway Airport to Orlando Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Orlando Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,981 reviews
Search Delta flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
United AirlinesPriceFrom $248Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights

  • Southwest Flights From Chicago Midway Airport to Orlando Airport

    The lowest priced Southwest flight from Chicago Midway Airport to Orlando Airport from the last 72 hours was $214. Generally, Southwest has 44 flights on this route every week with an average price of $393. Southwest is rated 8.0/10 by our users.

Traveling to a place near Orlando?

Book flights to Orlando if you plan to visit one of these locations
Kissimmee
Lake Buena Vista
Cocoa Beach
Ocala
Ormond Beach
Winter Haven
Cape Canaveral
Bay Lake
The Villages
Sanford
New Smyrna Beach
Titusville
Mount Dora
Daytona Beach Shores
Davenport
Palm Coast
Cocoa
Sebring
Palm Bay
Altamonte Springs

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Orlando. Millions of users trust and use momondo every year so you are in good hands.

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 helps you find the best flight between Chicago and Orlando by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Orlando from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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