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

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Cheap Flights from MDW to MCO starting at $90 One Way, $189 Round Trip

Prices starting at $189 for return flights and $90 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.

Tue, Oct 6 - Wed, Oct 7
MDW
Chicago
MCO
Orlando
$189 Roundtrip, found 11 hours ago
$189
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Chicago to Orlando, returning Wed, Oct 7, priced at $189 found 11 hours ago
Tue, Sep 22 - Tue, Sep 29
MDW
Chicago
MCO
Orlando
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Chicago to Orlando, returning Tue, Sep 29, priced at $190 found 3 days ago
Tue, Jun 16 - Wed, Jun 24
MDW
Chicago
MCO
Orlando
$194 Roundtrip, found 19 hours ago
$194
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Tue, Jun 16 from Chicago to Orlando, returning Wed, Jun 24, priced at $194 found 19 hours ago
Tue, Jun 30 - Tue, Jul 7
MDW
Chicago
MCO
Orlando
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 30 from Chicago to Orlando, returning Tue, Jul 7, priced at $194 found 2 hours ago
Wed, Aug 19 - Tue, Aug 25
MDW
Chicago
MCO
Orlando
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Chicago to Orlando, returning Tue, Aug 25, priced at $195 found 5 days 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
$199 nightly
The price is $224 total per night from May 25 to May 26
$224 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 breakfast (surcharge). Our guests praise the pool and the restaurant ...
9.4/10 Exceptional! (4,164 reviews)
"Grea TY"

Reviewed on May 18, 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
$78 nightly
The price is $88 total per night from May 24 to May 25
$88 total
May 24 - May 25
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! (1,988 reviews)
"Personal muy empático y servicial."

Reviewed on May 21, 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
$89 nightly
The price is $100 total per night from May 25 to May 26
$100 total
May 25 - May 26
Total with taxes and fees
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! (1,002 reviews)
"Walking into the hotel it smelled amazing and looked nice and new. Getting to the third floor, it seemed like a different hotel. Air smelled stale, loud air conditions unit, dark hallways. The room was clean. The sheets didn’t fit the bed, so they kept rolling up. I had to screw the cable back into ..."

Reviewed on May 22, 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
$127 nightly
The price is $142 total per night from Jun 1 to Jun 2
$142 total
Jun 1 - Jun 2
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! (5,535 reviews)
"I recommend everything about this property. Not one wrong thing I can think of, well maybe the water temperature fluctuations in shower. Besides that very minimal inconvenience, this property is amazing in all aspects. Would definitely return and will recommend."

Reviewed on May 22, 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
$199 nightly
The price is $224 total per night from May 25 to May 26
$224 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 breakfast (surcharge). Our guests praise the pool and the restaurant ...
9.4/10 Exceptional! (4,164 reviews)
"Grea TY"

Reviewed on May 18, 2026

Hyatt Regency Orlando International Airport
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 25 to May 26
$241 total
May 25 - May 26
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! (9,923 reviews)
"We loved every second of our stay here, EXCEPT the outside doors slam so loudly and it is so hard to sleep early in the morning as doors are slamming from 5AM on."

Reviewed on May 21, 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
$65 nightly
The price is $73 total per night from Jun 11 to Jun 12
$73 total
Jun 11 - Jun 12
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 (1,848 reviews)
"There was NO airport shuttle and they said they never had one!"

Reviewed on May 18, 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
$75 nightly
The price is $84 total per night from May 24 to May 25
$84 total
May 24 - May 25
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 ...
8/10 Very Good! (1,537 reviews)
"Ok"

Reviewed on May 18, 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
$78 nightly
The price is $88 total per night from May 24 to May 25
$88 total
May 24 - May 25
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! (1,988 reviews)
"Personal muy empático y servicial."

Reviewed on May 21, 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
$77 nightly
The price is $87 total per night from Jun 2 to Jun 3
$87 total
Jun 2 - Jun 3
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 ...
9/10 Wonderful! (3,781 reviews)
"Kimberly at the front desk was very helpful. Was able to give an early check in and free breakfast was much appreciated."

Reviewed on May 21, 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
$72 nightly
The price is $82 total per night from Jun 22 to Jun 23
$82 total
Jun 22 - Jun 23
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! (3,843 reviews)
"vvgreat distance from DisneyWorld! staff was very njf"

Reviewed on May 21, 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
$150 nightly
The price is $169 total per night from May 25 to May 26
$169 total
May 25 - May 26
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! (6,809 reviews)

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

Travelers say...
"Room was clean and in working order. Staff were very accommodating and helpful. The grounds were clean and easy to navigate."

Reviewed on May 22, 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
$124 nightly
The price is $140 total per night from Jun 4 to Jun 5
$140 total
Jun 4 - Jun 5
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! (3,951 reviews)

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

Travelers say...
"Loved it. It had lots of things to do on the property. Poolside bar and activities were ok. No room service but of course there are so many delivery services avail."

Reviewed on May 18, 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
$121 nightly
The price is $136 total per night from May 25 to May 26
$136 total
May 25 - May 26
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 ...
7.4/10 Good! (468 reviews)

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

Travelers say...
"worst 90s rooms ever. they didnt even clean rooms just put towels on living area and even after requesting to replace bedsheets they didnt not do. our 7 night stay was really bad here"

Reviewed on May 20, 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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