Cheap Flight Tickets from Orlando (MCO) to Chicago (MDW), Starting at $419

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

$419

WN Southwest Airlines • nonstop • 4h 10m

Oct 30 – Nov 02

The cheapest round trip flight from Orlando to Chicago (MCO-MDW-MCO) is currently $419

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Cheapest Direct Flight

$419

WN Southwest Airlines • nonstop • 4h 10m

Oct 30

The cheapest nonstop flight from Orlando to Chicago (MCO-MDW) is currently $419

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Fastest Flight

4h 10m

The fastest nonstop flight from Orlando to Chicago (MCO-MDW) takes 4h 10m

Top Airlines Flying from Orlando to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta 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.

Oct 30 - Nov 02, Economy
WN
Orlando → Chicago
4h 10m
10:40 AM - 12:30 PM • nonstop
WN
Orlando → Chicago
3h 55m
5:10 AM - 8:45 AM • nonstop
$419
Southwest Airlines
Oct 30 - Nov 02, Economy
WN
Orlando → Chicago
4h 10m
8:10 AM - 10:00 AM • nonstop
WN
Orlando → Chicago
3h 55m
8:40 PM - 12:15 AM • nonstop
$419
Southwest Airlines
Oct 30 - Nov 02, Economy
WN
Orlando → Chicago
4h 10m
6:30 PM - 8:20 PM • nonstop
WN
Orlando → Chicago
8h 55m
1:20 PM - 7:55 PM • 1 stop
$424
Southwest Airlines
Oct 30 - Nov 02, Economy
WN
Orlando → Chicago
7h 5m
2:25 PM - 5:50 PM • 1 stop
WN
Orlando → Chicago
3h 55m
12:50 PM - 4:25 PM • nonstop
$424
Southwest Airlines
Oct 30 - Nov 02, Economy
DL
Orlando → Chicago
7h 38m
2:02 PM - 6:00 PM • 1 stop
DL
Orlando → Chicago
7h 6m
8:05 AM - 1:31 PM • 1 stop
$483
Delta Airlines
Oct 30 - Nov 02, Economy
DL
Orlando → Chicago
7h 33m
6:40 PM - 10:33 PM • 1 stop
DL
Orlando → Chicago
7h 8m
9:29 AM - 2:57 PM • 1 stop
$483
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 8:10 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 WN : USD 424
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 10:35 pm

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

What's the cheapest airline from mco to mdw?
Southwest Airlines offers the cheapest flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) for a one-way trip with a First cabin booking. You can secure your seat with 24 days of advance booking and enjoy a budget-friendly flight experience. Please note that prices may vary depending on the travel dates. For the best deals, consider booking in December or July.
What's the popular airline to fly from mco to mdw?
Southwest Airlines offers a convenient and luxurious option for flying from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) with a single stop. As a first-class passenger, you can enjoy suites and fine dining on this one-way trip. Booking in advance, 24 days prior to your departure, can help you secure the best fares. For budget-friendly flights, consider Southwest Airlines for your travel needs.
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 Thursday. Booking a flight on this day can help you save on airfares. Low fares are often available on Thursdays, making it a budget-friendly option for your one-way trip.
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 July, as it tends to have lower airfares compared to other summer months. Budget-friendly flights can be found during this period, making it an ideal time for a luxury First-class experience.
Which airline/airlines fly from mco to mdw?
The airlines that fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) include Southwest Airlines, Porter Airline, Sun Country Airlines, Delta Airlines, United Airlines, WestJet Airlines, American Airlines, Frontier Airlines, and Aeromexico. You can find low fares on these airlines for your one-way trip.
What are the cheapest flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW)?
You can find affordable airfares on Southwest Airlines (WN), with prices starting from £200. Book in advance to secure the best deals.
How can I book a one-way First Class ticket from MCO to MDW?
Visit fareleaders.com, a reputable airline agency, to compare airfares and book your ticket. You can also contact Southwest Airlines (WN) directly for assistance.
What is the advance booking period for a one-way trip on a luxury airline?
For a one-way First Class ticket, book at least 24 days in advance to ensure availability.
Can I find affordable airfares for my July trip on a reputable airline agency?
Yes, July is a great time to find cheap flights. Book in advance to secure the best deals on fareleaders.com.
How do I compare airfares and fares on fareleaders.com to find the best deals?
Use our airfare comparison tool to find the cheapest flights from MCO to MDW. You can also contact our customer support team for assistance.
What are the benefits of booking flights in advance through a trusted agency?
Booking in advance ensures availability and often results in cheaper fares. Contact Southwest Airlines (WN) or our customer support team to book your ticket.
How can I plan my trip from MCO to MDW with a reliable travel website?
Visit fareleaders.com, a reliable travel website, to plan your trip. Our website offers flight comparison tools and customer support to ensure a smooth journey.

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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