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Cheap flights from Chicago Midway Airport to Orlando from $51

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 11/8. 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

Enter your travel dates to find the best prices.
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
$101Frontier
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Mon, Dec 15 - Fri, Dec 19
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
Frontier Logo
7:04 pm - 9:04 pmMCO-MDW
3h 00mnonstop
$102Frontier
Find Deal
Mon, Dec 15 - Sun, Dec 21
Frontier Logo
3:52 pm - 7:40 pmMDW-MCO
2h 48mnonstop
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
$103Frontier
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Fri, Dec 12 - Fri, Dec 19
Frontier Logo
11:36 am - 3:16 pmMDW-MCO
2h 40mnonstop
Frontier Logo
8:59 pm - 11:30 amMCO-MDW
15h 31m1 stop
$105Frontier
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Sat, Nov 8 - Wed, Nov 12
Frontier Logo
3:27 pm - 7:09 pmMDW-MCO
2h 42mnonstop
Frontier Logo
8:59 pm - 11:30 amMCO-MDW
15h 31m1 stop
$106Frontier
Find Deal
Fri, Nov 14 - Sat, Nov 15
Frontier Logo
5:30 pm - 9:18 pmMDW-MCO
2h 48mnonstop
Frontier Logo
2:34 pm - 4:30 pmMCO-MDW
2h 56mnonstop
$107Frontier
Find Deal
Thu, Nov 20 - Thu, Nov 27
Multiple Airlines Logo
5:30 pm - 9:18 pmMDW-MCO
2h 48mnonstop
Multiple Airlines Logo
11:04 am - 5:15 pmMCO-MDW
7h 11m1 stop
$126Multiple Airlines
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Thu, Nov 20 - Mon, Nov 24
Allegiant Air Logo
4:12 pm - 11:03 pmMDW-SFB
5h 51m1 stop
Allegiant Air Logo
7:50 am - 4:45 pmSFB-MDW
9h 55m1 stop
$234Allegiant Air
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Mon, Nov 10 - Fri, Nov 14
Allegiant Air Logo
2:57 pm - 10:56 pmMDW-SFB
6h 59m1 stop
Allegiant Air Logo
9:55 pm - 12:02 pmSFB-MDW
15h 07m1 stop
$266Allegiant Air
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Fri, Nov 7 - Sun, Nov 9
Allegiant Air Logo
12:52 pm - 8:02 pmMDW-SFB
6h 10m1 stop
Allegiant Air Logo
8:05 am - 1:21 pmSFB-MDW
6h 16m1 stop
$274Allegiant Air
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Mon, Nov 17 - Fri, Nov 21

Frontier flights from Chicago Midway Airport to Orlando

Our best Frontier deals on Chicago Midway Airport to Orlando flight tickets
Frontier
Dec 15
MDW3:10 pmChicago Midway
2h 48m
MCO6:58 pmOrlando
Dec 19
MCO7:58 pmOrlando
3h 00m
MDW9:58 pmChicago Midway
$101
Find similar
Frontier
Dec 15
MDW3:10 pmChicago Midway
2h 48m
MCO6:58 pmOrlando
Dec 21
MCO7:04 pmOrlando
3h 00m
MDW9:04 pmChicago Midway
$102
Find similar
Frontier
Dec 12
MDW3:52 pmChicago Midway
2h 48m
MCO7:40 pmOrlando
Dec 19
MCO7:58 pmOrlando
3h 00m
MDW9:58 pmChicago Midway
$103
Find similar

Southwest flights from Chicago Midway Airport to Orlando

Our best Southwest deals on Chicago Midway Airport to Orlando flight tickets
Southwest
Oct 31
MDW2:25 pmChicago Midway
2h 35m
MCO6:00 pmOrlando
Oct 31
MCO7:25 pmOrlando
2h 45m
MDW9:10 pmChicago Midway
$177
Find similar
Southwest
Oct 31
MDW6:55 amChicago Midway
5h 50m
1 stop
MCO1:45 pmOrlando
Oct 31
MCO7:25 pmOrlando
2h 45m
MDW9:10 pmChicago Midway
$187
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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 October 27, 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

Mon 12/15

3:10 pm-6:58 pm

Nonstop2h 48m

Orlando

Fri 12/19

7:58 pm-9:58 pm

Nonstop3h 00m

$101

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 12/15

3:10 pm-6:58 pm

Nonstop2h 48m

Orlando

Sun 12/21

7:04 pm-9:04 pm

Nonstop3h 00m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 12/12

3:52 pm-7:40 pm

Nonstop2h 48m

Orlando

Fri 12/19

7:58 pm-9:58 pm

Nonstop3h 00m

$103

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 11/8

11:36 am-3:16 pm

Nonstop2h 40m

Orlando

Wed 11/12

8:59 pm-11:30 am

1 stop15h 31m

$105

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 11/14

3:27 pm-7:09 pm

Nonstop2h 42m

Orlando

Sat 11/15

8:59 pm-11:30 am

1 stop15h 31m

$106

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 11/20

5:30 pm-9:18 pm

Nonstop2h 48m

Orlando

Thu 11/27

2:34 pm-4:30 pm

Nonstop2h 56m

$107

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 11/20

5:30 pm-9:18 pm

Nonstop2h 48m

Orlando

Mon 11/24

11:04 am-5:15 pm

1 stop7h 11m

$126

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 11/10

4:12 pm-11:03 pm

1 stop5h 51m

Orlando Sanford Intl

Fri 11/14

7:50 am-4:45 pm

1 stop9h 55m

$234

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/7

2:57 pm-10:56 pm

1 stop6h 59m

Orlando Sanford Intl

Sun 11/9

9:55 pm-12:02 pm

1 stop15h 07m

$266

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 11/17

12:52 pm-8:02 pm

1 stop6h 10m

Orlando Sanford Intl

Fri 11/21

8:05 am-1:21 pm

1 stop6h 16m

$274

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 August is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $202. If you’re not able to fly to Orlando in August, then September is your next best option. Flight prices from Chicago Midway Airport to Orlando during September average around $213.

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 $262. 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 $300.

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 $248. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $299.

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 $298 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 $243 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 October 2025, prices for Chicago Midway Airport to Orlando flights are approximately 100% 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

$89

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 $89. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $180.
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)
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
8,112 reviews
Search Spirit Airlines flights
FrontierPriceFrom $99Free CancellationRating
5.8
3,123 reviews
Search Frontier flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,996 reviews
Search Delta flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Orlando

    Across 50 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $398, with the best Southwest deals starting from $212 round-trip. 4,238 users have rated Southwest on momondo, with an average score of 8.0/10.

  • Frontier Flights From Chicago Midway Airport to Orlando

    Frontier (5.8/10 from 3,123 reviews) operates around 2 flights from Chicago Midway Airport to Orlando in any given week. The average Frontier airfare for this route is around $207, with deals from around $99 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.

An easier way to manage your Orlando trip

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Wed 11/26
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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