$79+ Flights from Chicago Midway Airport to Orlando

One-way flight from Chicago Midway to Orlando (ORL)

Highest demand for flights based on searches. 1% potential increase in price ($2 potential increase over avg. RT price).

Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

Average for round-trip flights in June 2025

Price to beat on a round-trip flight from Chicago Midway to Orlando (ORL).

Price to beat on a one-way flight from Chicago Midway to Orlando (ORL).

Find flight deals from Midway to Orlando

Cheapest flights from Midway to Orlando
Explore the most affordable flight options available from Midway to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

Sat 9/1312:51 pmMDW - MCO

Nonstop2h 38mFrontier

Sun 9/215:45 amMCO - MDW

Nonstop2h 54mFrontier

Deal found 6/16

$126

Tue 9/27:40 amMDW - MCO

Nonstop2h 30mSouthwest

Fri 9/58:40 pmMCO - MDW

Nonstop2h 45mSouthwest

Deal found 6/17

$158

Fri 8/229:32 amMDW - SFB

1 stop10h 12mAllegiant Air

Sun 8/246:55 pmSFB - MDW

1 stop14h 47mAllegiant Air

Deal found 6/16

$206

Sat 8/306:00 amMDW - MCO

1 stop7h 25mDelta

Sat 9/64:50 pmMCO - MDW

1 stop5h 22mDelta

Deal found 6/16

$207

Fri 7/1110:31 amMDW - MCO

1 stop9h 12mAllegiant Air

Mon 7/148:27 amMCO - MDW

1 stop6h 37mAllegiant Air

Deal found 6/16

$220

Wed 7/29:03 amMDW - SFB

3 stops28h 13mMultiple Airlines

Sun 7/611:29 amSFB - MDW

2 stops21h 53mMultiple Airlines

Deal found 6/17

$788

Best flights from Midway to Orlando
Discover carefully curated flight deals from Midway to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2025.

Sat 9/1312:51 pmMDW - MCO

Nonstop2h 38mFrontier

Sun 9/215:45 amMCO - MDW

Nonstop2h 54mFrontier

Deal found 6/16

$126

Tue 9/27:40 amMDW - MCO

Nonstop2h 30mSouthwest

Fri 9/58:40 pmMCO - MDW

Nonstop2h 45mSouthwest

Deal found 6/17

$158

Fri 8/229:32 amMDW - SFB

1 stop10h 12mAllegiant Air

Sun 8/246:55 pmSFB - MDW

1 stop14h 47mAllegiant Air

Deal found 6/16

$206

Sat 8/306:00 amMDW - MCO

1 stop7h 25mDelta

Sat 9/64:50 pmMCO - MDW

1 stop5h 22mDelta

Deal found 6/16

$207

Fri 8/11:11 pmMDW - MCO

1 stop24h 08mAllegiant Air

Fri 8/88:27 amMCO - MDW

1 stop6h 29mAllegiant Air

Deal found 6/17

$219

Wed 7/29:03 amMDW - SFB

3 stops28h 13mMultiple Airlines

Sun 7/611:29 amSFB - MDW

2 stops21h 53mMultiple Airlines

Deal found 6/17

$788

Last-minute flights from Midway to Orlando
Discover last-minute flight deals from Midway to Orlando. Data last updated June 18, 2025 and is based on user searches.

Fri 6/2710:34 amMDW - MCO

1 stop9h 09mAllegiant Air

Fri 7/48:27 amMCO - MDW

1 stop6h 37mAllegiant Air

Deal found 6/17

$250

Fri 6/2710:34 amMDW - SFB

1 stop12h 00mAllegiant Air

Sun 6/296:15 amSFB - MDW

2 stops26h 00mAllegiant Air

Deal found 6/16

$338

Fri 6/2710:34 amMDW - MCO

1 stop9h 09mMultiple Airlines

Tue 7/112:45 pmMCO - MDW

3 stops32h 38mMultiple Airlines

Deal found 6/17

$352

Sat 6/289:12 pmMDW - MCO

Nonstop2h 41mFrontier

Mon 6/306:22 pmMCO - MDW

Nonstop2h 55mFrontier

Deal found 6/16

$172

Sat 6/2811:50 amMDW - MCO

1 stop5h 20mSouthwest

Thu 7/109:50 pmMCO - MDW

Nonstop2h 50mSouthwest

Deal found 6/17

$268

Sat 6/281:09 pmMDW - MCO

1 stop4h 38mDelta

Tue 7/86:15 amMCO - MDW

1 stop4h 30mDelta

Deal found 6/17

$288

Wed 7/29:03 amMDW - SFB

3 stops28h 13mMultiple Airlines

Sun 7/611:29 amSFB - MDW

2 stops21h 53mMultiple Airlines

Deal found 6/17

$788

Tue 7/812:43 pmMDW - MCO

1 stop6h 08mDelta

Sat 7/195:30 amMCO - MDW

1 stop5h 15mDelta

Deal found 6/16

$208

Fri 7/1110:31 amMDW - MCO

1 stop9h 12mAllegiant Air

Mon 7/148:27 amMCO - MDW

1 stop6h 37mAllegiant Air

Deal found 6/16

$217

Fri 7/118:03 amMDW - MCO

2 stops13h 55mMultiple Airlines

Mon 7/148:27 amMCO - MDW

1 stop6h 37mMultiple Airlines

Deal found 6/16

$323

Tue 7/157:50 amMDW - MCO

Nonstop2h 35mSouthwest

Fri 7/186:35 amMCO - MDW

Nonstop2h 45mSouthwest

Deal found 6/17

$169

Thu 7/179:12 pmMDW - MCO

Nonstop2h 51mFrontier

Sun 7/201:10 pmMCO - MDW

Nonstop2h 56mFrontier

Deal found 6/16

$127

One-way flights from Midway to Orlando
Search for one-way flight options from Midway to Orlando. Find affordable one-way fares based on user searches. Data last updated June 18, 2025.

Wed 8/136:15 amMDW - MCO

Nonstop2h 30mSouthwest

Deal found 6/16

$79

Thu 7/249:12 pmMDW - MCO

Nonstop2h 51mFrontier

Deal found 6/15

$81

Mon 7/142:54 pmMDW - SFB

1 stop7h 44mAllegiant Air

Deal found 6/16

$98

Fri 8/11:11 pmMDW - MCO

1 stop6h 32mAllegiant Air

Deal found 6/17

$100

Mon 8/1812:43 pmMDW - MCO

1 stop6h 16mDelta

Deal found 6/16

$104

Mon 8/259:32 amMDW - MCO

2 stops21h 32mMultiple Airlines

Deal found 6/17

$136

Cheapflights Fare Finder

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 9/13

12:51 pm-4:29 pm

Nonstop2h 38m

Orlando

Sun 9/21

5:45 am-7:39 am

Nonstop2h 54m

$126

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 9/2

8:05 pm-11:40 pm

Nonstop2h 35m

Orlando

Fri 9/5

6:20 am-8:05 am

Nonstop2h 45m

$158

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 8/22

9:32 am-8:44 pm

1 stop10h 12m

Orlando Sanford Intl

Sun 8/24

6:55 pm-8:42 am

1 stop14h 47m

$206

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 8/30

6:00 am-2:25 pm

1 stop7h 25m

Orlando

Sat 9/6

4:50 pm-9:12 pm

1 stop5h 22m

$207

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 8/1

1:11 pm-2:19 pm

1 stop24h 08m

Orlando

Fri 8/8

8:27 am-1:56 pm

1 stop6h 29m

$219

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Wed 7/2

9:03 am-2:16 pm

3 stops28h 13m

Orlando Sanford Intl

Sun 7/6

11:29 am-8:22 am

2 stops21h 53m

$788

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 8/13

6:15 am-9:45 am

Nonstop2h 30m

$79

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 7/24

9:12 pm-1:03 am

Nonstop2h 51m

$81

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 7/14

2:54 pm-11:38 pm

1 stop7h 44m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 8/1

1:11 pm-8:43 pm

1 stop6h 32m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 12 results

The best insider tips for Chicago Midway Airport to Orlando flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Orlando trip

Airports

MDW

Use the 'L' train to reach MDW easily. The Orange Line stops directly at the airport, offering a quick 30-minute ride to the city center.

MCO

Skip renting a car at MCO; rideshares are affordable and convenient for exploring Orlando and reaching Disney resorts.

Our travel experts

Ramsey Qubein

Expert on MDW

Paul Rubio

Expert on MCO

Best time to book a flight from Midway to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Midway with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Orlando

How far ahead should I book a flight from Chicago Midway Airport to Orlando?

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Orlando, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Orlando?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando (average of $206). Flying from Chicago Midway Airport to Orlando in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to ORL?

It’s typically best to fly out from Chicago Midway Airport to Orlando at noon. Doing so could potentially save you 16% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Orlando?

Travelers seeking maximum savings on their Chicago Midway Airport to Orlando flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago Midway Airport to Orlando

The most flights from MDW to ORL are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Orlando by month

In terms of precipitation, rainfall in Orlando ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Orlando when rainfall is around 2.4 in.

Temperature in Orlando by month

If weather is an important factor for your trip to Orlando, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

Reviews of airlines servicing Orlando

To help decide which airline to fly from Chicago to Orlando, see what other customers have to say about Southwest, Delta and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

8.0

Very good

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta

8.0

Very good

7,964 reviews

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Allegiant Air

7.3

Good

722 reviews

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Frontier

5.9

Fair

3,301 reviews

8.0

Very good