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Cheap flights from Chicago Midway Airport to Orlando from $52

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 9/21. 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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Find the cheapest flights from Chicago Midway Airport to Orlando

Cheap round-trip flights

Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$94Frontier
Find Deal
Sat, Sep 27 - Sun, Sep 28
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$95Frontier
Find Deal
Mon, Sep 8 - Fri, Sep 12
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$96Frontier
Find Deal
Mon, Sep 8 - Fri, Sep 12
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$97Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
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
Allegiant Air Logo
3:27 pm - 11:14 pmMDW-SFB
6h 47m1 stop
Allegiant Air Logo
9:55 pm - 12:02 pmSFB-MDW
15h 07m1 stop
$273Allegiant Air
Find Deal
Fri, Nov 14 - Sun, Nov 16
Allegiant Air Logo
12:50 pm - 9:06 pmMDW-SFB
7h 16m1 stop
Allegiant Air Logo
10:55 am - 7:00 pmSFB-MDW
9h 05m1 stop
$343Allegiant Air
Find Deal
Mon, Sep 8 - Fri, Sep 12
Logo
12:30 pm - 10:35 amMDW-SFB
21h 05m2 stops
Logo
9:55 pm - 12:02 pmSFB-MDW
15h 07m1 stop
$345
Find Deal
Thu, Nov 6 - Sun, Nov 9
Allegiant Air Logo
12:50 pm - 9:06 pmMDW-SFB
7h 16m1 stop
Allegiant Air Logo
10:55 am - 7:00 pmSFB-MDW
9h 05m1 stop
$347Allegiant Air
Find Deal
Mon, Sep 8 - Fri, Sep 12

Frontier flights from Chicago Midway Airport to Orlando

Our best Frontier deals on Chicago Midway Airport to Orlando flight tickets
Frontier
Sep 27
MDW10:51 amChicago Midway
2h 42m
MCO2:33 pmOrlando
Sep 28
MCO7:25 amOrlando
2h 53m
MDW9:18 amChicago Midway
$94
Find similar
Frontier
Sep 8
MDW8:19 amChicago Midway
2h 41m
MCO12:00 pmOrlando
Sep 12
MCO7:00 amOrlando
2h 53m
MDW8:53 amChicago Midway
$95
Find similar
Frontier
Sep 8
MDW8:19 amChicago Midway
2h 41m
MCO12:00 pmOrlando
Sep 12
MCO7:00 amOrlando
2h 53m
MDW8:53 amChicago Midway
$96
Find similar

Allegiant Air flights from Chicago Midway Airport to Orlando

Our best Allegiant Air deals on Chicago Midway Airport to Orlando flight tickets
Allegiant Air
Nov 14
MDW3:27 pmChicago Midway
6h 47m
1 stop
SFB11:14 pmOrlando Sanford Intl
Nov 16
SFB9:55 pmOrlando Sanford Intl
15h 07m
1 stop
MDW12:02 pmChicago Midway
$273
Find similar
Allegiant Air
Sep 8
MDW12:50 pmChicago Midway
7h 16m
1 stop
SFB9:06 pmOrlando Sanford Intl
Sep 12
SFB10:55 amOrlando Sanford Intl
9h 05m
1 stop
MDW7:00 pmChicago Midway
$343
Find similar
Allegiant Air
Sep 8
MDW12:50 pmChicago Midway
7h 16m
1 stop
SFB9:06 pmOrlando Sanford Intl
Sep 12
SFB10:55 amOrlando Sanford Intl
9h 05m
1 stop
MDW7:00 pmChicago Midway
$347
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Orlando 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 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 9/27

10:51 am-2:33 pm

Nonstop2h 42m

Orlando

Sun 9/28

7:25 am-9:18 am

Nonstop2h 53m

$94

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/8

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

$95

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 9/8

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

$96

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/12

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sun 9/14

7:25 am-9:18 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 - SFB

MDWSFB

Chicago Midway

Fri 11/14

3:27 pm-11:14 pm

1 stop6h 47m

Orlando Sanford Intl

Sun 11/16

9:55 pm-12:02 pm

1 stop15h 07m

$273

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 9/8

12:50 pm-9:06 pm

1 stop7h 16m

Orlando Sanford Intl

Fri 9/12

10:55 am-7:00 pm

1 stop9h 05m

$343

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 11/6

12:30 pm-10:35 am

2 stops21h 05m

Orlando Sanford Intl

Sun 11/9

9:55 pm-12:02 pm

1 stop15h 07m

$345

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 9/8

12:50 pm-9:06 pm

1 stop7h 16m

Orlando Sanford Intl

Fri 9/12

10:55 am-7:00 pm

1 stop9h 05m

$347

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

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 $197. If you’re not able to fly to Orlando in September, then July is your next best option. Flight prices from Chicago Midway Airport to Orlando during July average around $226.

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 $261. On the other hand, Sunday 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 $309.

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 $251. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $302.

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 $303 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 $236 on momondo.

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

There is only 1 cabin class 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 August 2025, prices for Chicago Midway Airport to Orlando flights are approximately 105% more expensive 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

$81

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 $81. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $161.
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)
Search flight deals

  • How far is Chicago Midway to Orlando by plane?

    Orlando is 982.0 mi away from Chicago Midway. Flights usually cover this in 2h 38m, 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
8,031 reviews
Search Spirit Airlines flights
FrontierPriceFrom $105Free CancellationRating
5.8
3,200 reviews
Search Frontier flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,979 reviews
Search Delta flights
SouthwestPriceFrom $215Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $248Free CancellationRating
7.4
8,943 reviews
Search United Airlines flights

  • Southwest Flights From Chicago Midway Airport to Orlando

    Across 44 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $393, with the best Southwest deals starting from $215 round-trip. 4,243 users have rated Southwest on momondo, with an average score of 8.0/10.

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.

An easier way to manage your Orlando trip

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Find better results for your trip to the United States

Fly into one of these airports located in Orlando

Airports listed have a maximum distance of 18.3 mi from Orlando
Orlando Airport
Orlando Sanford Intl Airport