Cheap Flight Tickets from Chicago (MDW) to Orlando (MCO), Starting at $233

Good to Know: Cheapest and Fastest MDW - MCO Flights

Useful information for finding best airline tickets from Chicago Midway International to Orlando International on your next trip.

Cheapest Round Trip Flight

$233

WN Southwest Airlines • 1 stop • 27h 20m

Jan 15 – Jan 18

The cheapest round trip flight from Chicago to Orlando (MDW-MCO-MDW) is currently $233

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Cheapest Direct Flight

$278

WN Southwest Airlines • nonstop • 4h 5m

Jan 15

The cheapest nonstop flight from Chicago to Orlando (MDW-MCO) is currently $278

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Fastest Flight

3h 55m

The fastest nonstop flight from Chicago to Orlando (MDW-MCO) takes 3h 55m

Top Airlines Flying from Chicago to Orlando

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Chicago (MDW) to Orlando (MCO)

Compare and book low fare round-trip air tickets from Chicago to Orlando. Ideal for travelers with confirmed return itineraries.

Jan 15 - Jan 18, Economy
WN
Chicago → Orlando
27h 20m
3:30 PM - 9:10 AM • 1 stop
WN
Chicago → Orlando
23h 25m
7:45 PM - 8:50 AM • 1 stop
$233
Southwest Airlines
Jan 15 - Jan 18, Economy
WN
Chicago → Orlando
3h 55m
11:00 AM - 2:35 PM • nonstop
WN
Chicago → Orlando
23h 25m
7:45 PM - 8:50 AM • 1 stop
$242
Southwest Airlines
Jan 15 - Jan 18, Economy
WN
Chicago → Orlando
15h 40m
10:10 AM - 8:50 PM • 1 stop
WN
Chicago → Orlando
23h 25m
7:45 PM - 8:50 AM • 1 stop
$246
Southwest Airlines
Jan 15 - Jan 18, Economy
WN
Chicago → Orlando
4h 5m
7:40 AM - 11:25 AM • nonstop
WN
Chicago → Orlando
4h 15m
9:25 PM - 11:20 PM • nonstop
$278
Southwest Airlines
Jan 15 - Jan 18, Economy
DL
Chicago → Orlando
19h
6:00 AM - 6:40 PM • 1 stop
DL
Chicago → Orlando
37h 21m
8:19 PM - 6:00 PM • 2 stops
$390
Delta Airlines
Jan 15 - Jan 18, Economy
DL
Chicago → Orlando
15h 40m
6:00 AM - 4:40 PM • 1 stop
DL
Chicago → Orlando
13h 21m
6:00 AM - 1:01 PM • 1 stop
$398
Delta Airlines

Fly from Chicago to Orlando with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Orlando? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Orlando Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to MCO?
The most popular airline flying from Chicago to Orlando are
Can I fly from MDW to MCO non-stop?
Yes, you can fly MDW to MCO non-stop on
Which airlines fly nonstop between Chicago and Orlando?
The non-stop flights between Chicago and Orlando are .
What’s the earliest departure time from MDW to MCO Airport?
The earliest flight leaves MDW at 5:05 am and lands in MCO - Orlando International
What are the airports in Orlando?
MCO
Can I make changes to my Chicago to Orlando flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to MCO?
Read the fare rules of the Chicago to Orlando air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Orlando?
operate flights between Chicago and Orlando
How long does a flight from Chicago to Orlando take?
It takes approximately 3 hour to fly non-stop from MDW to MCO, which is 989.7 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Orlando (MCO) ?
In the past couple of days, the cheapest tickets to MCO from MDW were found on DL : USD 390
Do I need a passport to fly between MDW and MCO?
No
What’s the latest departure time from MDW to MCO ?
The last flight leaves MDW at 7:10 pm

Hotels in Orlando (MCO)

5 hotels near Orlando International — compare rates from top booking sites.

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5.0-star hotel 5-star hotel

Hampton Inn And Suites Orlando-north/Altamonte Spr

📍 161 North Douglas Avenue, Altamonte Springs, Florida 32714

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5.0-star hotel 5-star hotel

Reunion Resort By 1791 Vacation Experience

📍 Check-in At: 7543 Osceola Polk Line Road, Davenport, Florida 33896

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5.0-star hotel 5-star hotel

Gaylord Palms

📍 6000 Osceola Parkway, Kissimmee, Florida 34746

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5.0-star hotel 5-star hotel

Lighthouse Key Resort & Spa

📍 8545 W Irlo Bronson Hwy, Kissimmee, Florida 34747

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5.0-star hotel 5-star hotel

Orange Lake Resort By Holiday Inn Club Vacation

📍 8505 W Irlo Bronson Memorial Hwy, Kissimmee, Florida 34747

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Hotel Deals in Orlando (FL)
Ramada by Wyndham Kissimmee Gateway
Wyndham Hotels & Resorts

Ramada by Wyndham Kissimmee Gateway

7.9/10
★★★☆☆ Hotel 500.0 rooms
✓ Free WiFi ✓ Breakfast

📍 7470 West Irlo Bronson Mem Hwy, Orlando (FL), Florida

Great care is taken to ensure guests experience comfort through top-notch services and amenities.Remain linked during your visit by utilizing the complimentary internet access available. Discovering …

Check-in 03:00 PM  ·  Check-out 11:00 AM

$36/night
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Palazzo Lakeside Hotel
Independent

Palazzo Lakeside Hotel

8.4/10
★★★☆☆ Hotel
✓ Breakfast

📍 4944 W Irlo Bronson Memorial Hwy, Kissimmee, FL, Orlando (FL), Florida

$39/night
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Kompose Boutique Resort @ Theme Parks

Kompose Boutique Resort @ Theme Parks

8.9/10
✓ Free WiFi ✓ Breakfast
$40/night
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Nobile Hotel Parkway at Celebration Orlando Very Close to Disney Theme Parks
No chain

Nobile Hotel Parkway at Celebration Orlando Very Close to Disney Theme Parks

7.9/10
★★★☆☆ Hotel
✓ Free WiFi ✓ Breakfast

📍 3104 Parkway Blvd, Orlando (FL)

Check-in 04:00 PM  ·  Check-out 11:00 AM

$55/night
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Howard Johnson by Wyndham Orlando Lake Buena Vista South
Wyndham Hotels & Resorts

Howard Johnson by Wyndham Orlando Lake Buena Vista South

7.6/10
★★☆☆☆ Motel 107.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5055 W Irlo Bronson Memorial Hwy, Orlando (FL), Florida

Great care is taken to ensure guests experience comfort through top-notch services and amenities.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. Whe…

$56/night
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Best Western Orlando Gateway Hotel
Best Western International

Best Western Orlando Gateway Hotel

8.0/10
★★☆☆☆ Hotel 298.0 rooms
✓ Free WiFi ✓ Breakfast

📍 7299 Universal Boulevard, Orlando (FL), Florida

At Best Western Orlando Gateway Hotel, exceptional service and top-notch amenities create a memorable experience for guests.Complimentary internet access is available in the hotel to ensure you stay …

Check-in 04:00 PM  ·  Check-out 11:00 AM

$59/night
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Wyndham I-Drive Avanti Resort & Conference Center
Wyndham Hotels & Resorts

Wyndham I-Drive Avanti Resort & Conference Center

7.6/10
★★★★☆ Hotel 650.0 rooms
✓ Free WiFi ✓ Breakfast

📍 6515 International Drive , Orlando (FL), Florida

Wyndham I-Drive Avanti Resort & Conference Center provides flawless service and all the necessary facilities for visitors.Stay connected with your associates, as complimentary Wi-Fi is available duri…

Check-in 4:00 PM  ·  Check-out 11:00 AM

$62/night
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Holiday Inn & Suites Orlando SW - Celebration Area By IHG
InterContinental Hotels Group

Holiday Inn & Suites Orlando SW - Celebration Area By IHG

8.0/10
★★★☆☆ Hotel 444.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5711 West Irlo Bronson Memorial Highway, Orlando (FL), Florida

Great care is taken to ensure guests experience comfort through top-notch services and amenities. Remain linked during your visit by utilizing the complimentary internet access available.Services off…

Check-in 04:00 PM  ·  Check-out 11:00 AM

$63/night
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Quality Inn & Suites Kissimmee near Main Gate
Choice Hotels

Quality Inn & Suites Kissimmee near Main Gate

8.2/10
★★★☆☆ Hotel 179.0 rooms
✓ Free WiFi ✓ Breakfast

📍 7785 W. Irlo Bronson Memorial, Orlando (FL), Florida

Quality Inn & Suites Kissimmee by The Lake offers top-notch services and amenities, ensuring guests experience utmost comfort.Share your photos and respond to emails at your convenience, thanks to th…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$64/night
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Chicago (MDW) to Orlando (MCO): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Orlando International , Orlando, US
Distance 990 miles

More Flight Options for Chicago (MDW) and Orlando (MCO)

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