Cheap flights from MDW to MCO (Midway Intl. to Orlando Intl.)

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Cheap Flights from MDW to MCO starting at $85 One Way, $110 Round Trip

Prices starting at $110 for return flights and $85 for one-way flights to Orlando Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, May 8 - Fri, May 15
MDW
Chicago
MCO
Orlando
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 8 from Chicago to Orlando, returning Fri, May 15, priced at $110 found 6 days ago
Wed, May 20 - Tue, May 26
MDW
Chicago
MCO
Orlando
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 20 from Chicago to Orlando, returning Tue, May 26, priced at $144 found 1 day ago
Fri, May 15 - Mon, May 18
MDW
Chicago
MCO
Orlando
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 15 from Chicago to Orlando, returning Mon, May 18, priced at $148 found 2 days ago
Fri, May 15 - Wed, May 20
MDW
Chicago
MCO
Orlando
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 15 from Chicago to Orlando, returning Wed, May 20, priced at $152 found 2 days ago
Tue, May 19 - Wed, May 20
MDW
Chicago
MCO
Orlando
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 19 from Chicago to Orlando, returning Wed, May 20, priced at $154 found 2 days ago

Hotel Ideas near Orlando Intl.

Airport Hotels near Orlando Intl.

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport

3 out of 5
7160 N Frontage Rd Orlando FL
$92 nightly
The price is $103 total per night from May 3 to May 4
$103 total
May 3 - May 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
7.4/10 Good! (1,831 reviews)
Breakfast menu was excellent. Room was clean and air conditioner was great. Shuttle service to the airport was also very good and efficient.

Reviewed on Apr 29, 2026

La Quinta Inn & Suites by Wyndham Orlando Airport
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
$89 nightly
The price is $101 total per night from May 25 to May 26
$101 total
May 25 - May 26
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,893 reviews)
The pool was wonderful and the room was very clean

Reviewed on Apr 29, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from May 31 to Jun 1
$150 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (6,727 reviews)
Fabulous

Reviewed on Apr 29, 2026

Universal's Cabana Bay Beach Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
$107 nightly
The price is $121 total per night from May 20 to May 21
$121 total
May 20 - May 21
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (5,323 reviews)
While we were only there for 1 night, it was a great place to stay. The rooms are amazing and it was perfect for any family. Both the bed and sofabed were amazingly comfortable. The ONLY downside is if you like a firmer pillow, bring one as I felt they were almost too soft.

Reviewed on Apr 29, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from May 31 to Jun 1
$150 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (6,727 reviews)
Fabulous

Reviewed on Apr 29, 2026

Universal's Cabana Bay Beach Resort
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
$214 nightly
The price is $241 total per night from May 14 to May 15
$241 total
May 14 - May 15
Total with taxes and fees
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (9,718 reviews)
My family and I loved everything about this resort! Next time we visit Orlando again this is where we’ll be staying!!

Reviewed on Apr 29, 2026

The Grove Resort & Water Park Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Orlando Hotels With Airport Transportation

Quality Inn & Suites Orlando Airport

Quality Inn & Suites Orlando Airport

2.5 out of 5
2601 Mccoy Rd Orlando FL
$78 nightly
The price is $88 total per night from May 12 to May 13
$88 total
May 12 - May 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.8/10 (1,849 reviews)
Nice stay.

Reviewed on Apr 24, 2026

Quality Inn & Suites Orlando Airport
Sleep Inn & Suites Orlando International Airport

Sleep Inn & Suites Orlando International Airport

2.5 out of 5
1700 Mccoy Rd Orlando FL
$86 nightly
The price is $97 total per night from May 12 to May 13
$97 total
May 12 - May 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the ...
Sleep Inn & Suites Orlando International Airport
La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport

3 out of 5
7160 N Frontage Rd Orlando FL
$92 nightly
The price is $103 total per night from May 3 to May 4
$103 total
May 3 - May 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
7.4/10 Good! (1,831 reviews)
Breakfast menu was excellent. Room was clean and air conditioner was great. Shuttle service to the airport was also very good and efficient.

Reviewed on Apr 29, 2026

La Quinta Inn & Suites by Wyndham Orlando Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Orlando Hotels

Champions World Resort

Champions World Resort

2 out of 5
8660 W Irlo Bronson Memorial Hwy Kissimmee FL
Book a stay at this family-friendly hotel in Kissimmee. Enjoy 2 outdoor pools, a fitness center, and a 24-hour business center. Our guests praise the property ...
7.4/10 Good! (1,000 reviews)
Nice location. Small pool. Staff were friendly. There is a shuttle to Disneyworld, which was very convenient

Reviewed on Aug 10, 2021

Get rates
Champions World Resort
Galleria Palms Hotel

Galleria Palms Hotel

2.5 out of 5
3000 Maingate Ln Kissimmee FL
$83 nightly
The price is $94 total per night from May 26 to May 27
$94 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (3,701 reviews)
Quaint boutique hotel..quite happy with all it offered. Would stay again

Reviewed on Apr 29, 2026

Galleria Palms Hotel
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

3 out of 5
7470 W. Irlo Bronson Memorial Hwy. Kissimmee FL
$68 nightly
The price is $78 total per night from May 31 to Jun 1
$78 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (3,847 reviews)
La limpieza es malísima

Reviewed on Apr 29, 2026

Ramada by Wyndham Kissimmee Gateway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Orlando

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from May 31 to Jun 1
$150 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (6,727 reviews)

Families like: Outdoor pools, waterslide, game room, bowling alley

Travelers say...
Fabulous

Reviewed on Apr 29, 2026

Universal's Cabana Bay Beach Resort
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd Winter Garden FL
$125 nightly
The price is $141 total per night from May 6 to May 7
$141 total
May 6 - May 7
Total with taxes and fees
Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, 2 outdoor pools, and free water park access. Our guests praise the pool and the helpful ...
8.8/10 Excellent! (3,996 reviews)

Families like: Outdoor pools, free waterpark access, kitchen, playground

Travelers say...
We have been to this resort now five different years! We continue to go back because the price is very reasonable for the facility that you get! We will continue to go back as long as the price remains reasonable for what you get! We look forward to going there once a year for one to two weeks! It ...

Reviewed on Apr 29, 2026

Hilton Vacation Club Aqua Sol Orlando West
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 out of 5
18000 International Dr S. Orlando FL
$115 nightly
The price is $129 total per night from May 28 to May 29
$129 total
May 28 - May 29
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
7.2/10 Good! (295 reviews)

Families like: Outdoor pools, free waterpark access, playground, game room

Travelers say...
Beautiful place to stay with many activities that will keep you busy and entertained all day!!!

Reviewed on Apr 29, 2026

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MDW to MCO Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
MCO Address & GPS
Address:
One Airport Boulevard
Orlando FL, 32827-4399
United States
IATA Code:
MCO
Longitude:
-81.308301
Latitude:
28.432177
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from Chicago Airport to MCO?
Multiple companies operate nonstop flights from Chicago Airport to Orlando Intl. Airport, which is great news if the very idea of a stopover sends you into a tailspin. Check out the deals with Southwest Airlines and Frontier Airlines.
What is the shortest flight from Chicago Airport to Orlando Intl. Airport?
Leave those movies on your laptop for some other time, because the trip from Chicago to Orlando will be over in the blink of an eye. It can take as little as 2 hours and 35 minutes to fly from Midway Airport to Orlando Intl. Airport (MCO).
How many hours flight from Midway Airport to MCO?
The average flight time from MDW to MCO is a short and sweet 2 hours and 40 minutes. So, pack your gear and book your seat. There's nothing more exciting than a spur-of-the-moment getaway.
What airlines have the most flights from Chicago Airport to Orlando Intl. Airport?
While you'll find various airlines flying from MDW to Orlando Intl. Airport (MCO), there are a couple that stand out. Frontier Airlines (F9) is one of the most liked and offers 23 flights monthly. If you'd like some more options, take a look at the fares from Southwest Airlines (WN), which offers 147 flights from Chicago to Orlando each month.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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