Cheap Flight Tickets from Orlando (MCO) to Chicago (MDW), Starting at $500

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

$500

WN Southwest Airlines • nonstop • 4h 15m

Nov 21 – Nov 28

The cheapest round trip flight from Orlando to Chicago (MCO-MDW-MCO) is currently $500

🔍 Search Flights

Cheapest Direct Flight

$500

WN Southwest Airlines • nonstop • 4h 15m

Nov 21

The cheapest nonstop flight from Orlando to Chicago (MCO-MDW) is currently $500

🔍 Search Flights

Fastest Flight

4h 15m

The fastest nonstop flight from Orlando to Chicago (MCO-MDW) takes 4h 15m

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.

Nov 21 - Nov 28, Economy
WN
Orlando → Chicago
4h 15m
10:10 AM - 12:05 PM • nonstop
WN
Orlando → Chicago
4h 5m
7:50 AM - 11:35 AM • nonstop
$500
Southwest Airlines
Nov 21 - Nov 28, Economy
WN
Orlando → Chicago
4h 15m
1:00 PM - 2:55 PM • nonstop
WN
Orlando → Chicago
7h 5m
7:40 AM - 1:05 PM • 1 stop
$500
Southwest Airlines
Nov 21 - Nov 28, Economy
WN
Orlando → Chicago
4h 15m
4:35 PM - 6:30 PM • nonstop
WN
Orlando → Chicago
4h
6:10 PM - 9:50 PM • nonstop
$500
Southwest Airlines
Nov 21 - Nov 28, Economy
F9
Orlando → Chicago
5h 1m
5:46 PM - 7:47 PM • nonstop
F9
Orlando → Chicago
5h
5:12 PM - 9:12 PM • nonstop
$500
Frontier Airlines
Nov 21 - Nov 28, Economy
WN
Orlando → Chicago
4h 15m
10:30 PM - 12:25 AM • nonstop
WN
Orlando → Chicago
3h 55m
9:15 AM - 12:50 PM • nonstop
$500
Southwest Airlines
Nov 21 - Nov 28, Economy
DL
Orlando → Chicago
7h 19m
6:45 AM - 10:24 AM • 1 stop
DL
Orlando → Chicago
7h 2m
9:30 AM - 2:52 PM • 1 stop
$683
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 6:45 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 500
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 10:30 pm

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

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

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

Why Fareleaders for MCO to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Orlando to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MCO to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Orlando to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Orlando (MCO) to Chicago (MDW)
Terms and Conditions*