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

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Cheap Flights from MDW to MCO starting at $87 One Way, $171 Round Trip

Prices starting at $171 for return flights and $87 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.

Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
MCO
Orlando
$171 Roundtrip, found 15 hours ago
$171
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Chicago to Orlando, returning Tue, Jul 21, priced at $171 found 15 hours ago
Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
MCO
Orlando
$175 Roundtrip, found 15 hours ago
$175
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Chicago to Orlando, returning Tue, Jul 21, priced at $175 found 15 hours ago
Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
MCO
Orlando
$177 Roundtrip, found 15 hours ago
$177
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Chicago to Orlando, returning Tue, Jul 21, priced at $177 found 15 hours ago
Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
MCO
Orlando
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Chicago to Orlando, returning Tue, Jul 21, priced at $181 found 15 hours ago
Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
MCO
Orlando
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Chicago to Orlando, returning Tue, Jul 21, priced at $181 found 15 hours ago

Hotel Ideas near Orlando Intl.

Airport Hotels near Orlando Intl.

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
The price is $224 total per night from Jun 1 to Jun 2
$224 total
per night
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
9.4/10 Exceptional! (4,177 reviews)
"This hotel"

Reviewed on May 29, 2026

Hyatt Regency 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
The price is $88 total per night from May 31 to Jun 1
$88 total
per night
May 31 - Jun 1
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! (2,033 reviews)
"Mantenimiento al elevador unicamente"

Reviewed on May 28, 2026

La Quinta Inn & Suites by Wyndham Orlando Airport
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
8101 Aircenter Ct Orlando FL
The price is $100 total per night from May 31 to Jun 1
$100 total
per night
May 31 - Jun 1
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,018 reviews)
"Not a bad stay. Safe, secure and excellent service."

Reviewed on May 28, 2026

Sonesta Essential 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.

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
The price is $161 total per night from Jun 21 to Jun 22
$161 total
per night
Jun 21 - Jun 22
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! (5,605 reviews)
"Clean, approachable staff, very family friendly."

Reviewed on May 29, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
The price is $224 total per night from Jun 1 to Jun 2
$224 total
per night
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
9.4/10 Exceptional! (4,177 reviews)
"This hotel"

Reviewed on May 29, 2026

Hyatt Regency Orlando International Airport
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
The price is $169 total per night from May 31 to Jun 1
$169 total
per night
May 31 - Jun 1
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! (6,861 reviews)
"Recommend best resort"

Reviewed on May 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.

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
The price is $73 total per night from Jun 21 to Jun 22
$73 total
per night
Jun 21 - Jun 22
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 (1,854 reviews)
"I live locally and wanted a quiet 3-night staycation, but this place was a massive letdown. Positives first: the bed/pillows were heavenly soft, check-in was easy with no hidden fees, they have smoking rooms, and a pull-out couch. However, the property is at a loud, awkward intersection. The room ..."

Reviewed on May 25, 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
The price is $90 total per night from May 31 to Jun 1
$90 total
per night
May 31 - Jun 1
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 ...
8/10 Very Good! (1,546 reviews)
"Our room smelled like a motel. The bathroom was disgusting. The tub was dirty, behind the toilet was filthy."

Reviewed on May 26, 2026

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
The price is $88 total per night from May 31 to Jun 1
$88 total
per night
May 31 - Jun 1
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! (2,033 reviews)
"Mantenimiento al elevador unicamente"

Reviewed on May 28, 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
The price is $77 total per night from May 31 to Jun 1
$77 total
per night
May 31 - Jun 1
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 ...
9/10 Wonderful! (3,747 reviews)
"breakfast"

Reviewed on May 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
The price is $82 total per night from Jun 24 to Jun 25
$82 total
per night
Jun 24 - Jun 25
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! (3,853 reviews)
"Booked the room with the mindset that our vacation wasn't going to be at wherever we stayed. The room was very nice and was exactly what we needed. The staff was very helpful and were great. Looking for a great place to sleep that's comfortable and quiet. Would highly recommend. Close to getting ..."

Reviewed on May 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
The price is $169 total per night from May 31 to Jun 1
$169 total
per night
May 31 - Jun 1
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! (6,861 reviews)

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

Travelers say...
"Recommend best resort"

Reviewed on May 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
The price is $150 total per night from Jun 4 to Jun 5
$150 total
per night
Jun 4 - Jun 5
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! (3,943 reviews)

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

Travelers say...
"M"

Reviewed on May 28, 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
The price is $136 total per night from Jun 2 to Jun 3
$136 total
per night
Jun 2 - Jun 3
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 ...
7.4/10 Good! (529 reviews)

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

Travelers say...
"Las picinas"

Reviewed on May 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

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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