Cheap Flight Tickets from Orlando (MCO) to Chicago (MDW), Starting at $287

Good to Know: Cheapest and Fastest MCO - MDW Flights

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

Cheapest Round Trip Flight

$297

WN Southwest Airlines • 1 stop • 17h

Sep 11 – Sep 11

The cheapest round trip flight from Orlando to Chicago (MCO-MDW-MCO) is currently $297

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Cheapest One way Flight

$483

DL Delta Airlines • 1 stop • 10h 47m

Aug 12

The cheapest one way flight from Orlando to Chicago (MCO-MDW) is currently $483

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Cheapest Direct Flight

$287

WN Southwest Airlines • nonstop • 4h 5m

Sep 11

The cheapest nonstop flight from Orlando to Chicago (MCO-MDW) is currently $287

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Fastest Flight

4h 5m

The fastest nonstop flight from Orlando to Chicago (MCO-MDW) takes 4h 5m

Top Airlines Flying from Orlando to Chicago

Delta Airline, DL

Delta Airlines

Southwest Airlines-WN

Southwest Airlines

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

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

Sep 11 - Sep 11, Economy
WN
Orlando → Chicago
17h
6:10 AM - 3:30 PM • 1 stop
WN
Orlando → Chicago
3h 55m
7:50 PM - 11:25 PM • nonstop
$297
Southwest Airlines
Sep 11 - Sep 11, Economy
WN
Orlando → Chicago
11h 45m
6:10 AM - 12:15 PM • 1 stop
WN
Orlando → Chicago
3h 55m
7:50 PM - 11:25 PM • nonstop
$297
Southwest Airlines
Sep 10 - Sep 11, Economy
WN
Orlando → Chicago
4h 5m
8:15 AM - 10:00 AM • nonstop
WN
Orlando → Chicago
3h 55m
9:10 AM - 12:45 PM • nonstop
$297
Southwest Airlines
Sep 11 - Sep 11, Economy
DL
Orlando → Chicago
10h 6m
5:30 AM - 10:36 AM • 1 stop
DL
Orlando → Chicago
10h 26m
3:40 PM - 11:06 PM • 1 stop
$447
Delta Airlines
Sep 11 - Sep 11, Economy
DL
Orlando → Chicago
8h 41m
6:15 AM - 10:36 AM • 1 stop
DL
Orlando → Chicago
8h 56m
4:30 PM - 11:06 PM • 1 stop
$447
Delta Airlines
Sep 11 - Sep 11, Economy
DL
Orlando → Chicago
7h 16m
7:00 AM - 10:36 AM • 1 stop
DL
Orlando → Chicago
10h 52m
4:30 PM - 12:22 AM • 1 stop
$577
Delta Airlines

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

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

FAQs on Orlando to Chicago Flights

What are the airports in Orlando?
MCO
What’s the most popular airline flying from MCO to MDW?
The most popular airline flying from Orlando to Chicago are
Can I fly from MCO to MDW non-stop?
Yes, you can fly MCO to MDW non-stop on
Which airlines fly nonstop between Orlando and Chicago?
The non-stop flights between Orlando and Chicago are .
What’s the earliest departure time from MCO to MDW Airport?
The earliest flight leaves MCO at 5:30 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Orlando to Chicago 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 MCO to MDW?
Read the fare rules of the Orlando to Chicago 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 Orlando and Chicago?
operate flights between Orlando and Chicago
How long does a flight from Orlando to Chicago take?
It takes approximately 3 hour to fly non-stop from MCO to MDW, which is 989.7 miles by air.
Which airlines provide the cheapest flights from Orlando (MCO) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from MCO were found on DL : USD 525
Do I need a passport to fly between MCO and MDW?
No
What’s the latest departure time from MCO to MDW ?
The last flight leaves MCO at 8:55 pm

Essential Information for Booking Flights from Orlando (MCO) - AI Insights

What's the cheapest airline from mco to mdw?
You can find affordable flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) on Southwest Airlines. For a round-trip economy ticket, consider booking in advance to take advantage of low fares. Please note that the cheapest airfares may vary depending on your travel dates and availability.
What's the popular airline to fly from mco to mdw?
You can fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) on Southwest Airlines. This is a 0-stop flight, suitable for your group of 3 passengers. Booking in advance will help you secure the best airfare options. For round-trip flights, consider booking at least 33 days prior to your desired travel date.
What's the cheapest day of the week to fly from mco to mdw?
The cheapest day to fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) is Wednesday. This flight option offers a budget-friendly airfare solution, ideal for travelers looking to save on their round-trip airfares.
What's the cheapest month to fly from mco to mdw?
The cheapest month to fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) is November. This is based on historical data, which suggests that airfares tend to be lower during this time of year. You can expect to find budget-friendly flights with airlines such as those operating out of MCO, offering savings on fares.
Which airline/airlines fly from mco to mdw?
The airlines that fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) include Delta Airlines, Frontier Airlines, American Airlines, Aeromexico, Porter Airline, Avianca, Volaris Airline, Allegiant, JetBlue Airways, and WestJet Airlines. You can find low fares on these airlines for your round-trip journey from MCO to MDW.
What is the cheapest airfare from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW)?
The cheapest airfare from MCO to MDW can be found on Southwest Airlines, with prices starting at £200. Book your flight 33 days in advance for the best deals.
Can I book my flight 33 days in advance?
Yes, you can book your flight up to 33 days in advance through FareLeaders.com. Simply enter your travel dates and destinations to find available flights.
How do I find the best airline for my round trip journey?
At FareLeaders.com, we offer a range of airlines that operate on round-trip journeys, including Southwest Airlines, Delta Airlines, Frontier Airlines, American Airlines, and more. Compare prices and schedules to find the best fit for your needs.
Is it possible to get a discount on my airfare booking?
Yes, we offer exclusive discounts and promotions on airfares through our agency. Sign up for our newsletter or follow us on social media to stay informed about the latest deals.
What is the process of booking flights through your agency?
Booking flights through FareLeaders.com is easy. Simply enter your travel dates, destinations, and number of passengers, and we will provide you with a list of available flights and prices. You can then book online or contact our customer service team for assistance.
How can I plan my July travel itinerary using your website?
To plan your July travel itinerary on FareLeaders.com, simply enter your travel dates and destinations in the search bar. We will provide you with a list of available flights and prices, as well as tips and recommendations for making the most of your trip.
Can I book multiple bookings at once?
Yes, you can book multiple bookings at once through our website or by contacting our customer service team directly. We offer competitive pricing on all flights, so be sure to compare prices across airlines to find the best deals.

Orlando (MCO) to Chicago (MDW): Airport Information

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

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