Cheap Flight Tickets from Orlando (MCO) to Chicago (MDW), Starting at $163

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

$164

DL Delta Airlines • 1 stop • 8h 39m

Sep 23 – Sep 23

The cheapest round trip flight from Orlando to Chicago (MCO-MDW-MCO) is currently $164

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Cheapest Direct Flight

$163

WN Southwest Airlines • nonstop • 4h 5m

Sep 23

The cheapest nonstop flight from Orlando to Chicago (MCO-MDW) is currently $163

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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

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.

Sep 23 - Sep 23, Economy
DL
Orlando → Chicago
8h 39m
5:30 AM - 9:49 AM • 1 stop
DL
Orlando → Chicago
10h 18m
1:55 PM - 9:13 PM • 1 stop
$164
Delta Airlines
Sep 23 - Sep 23, Economy
WN
Orlando → Chicago
9h 10m
7:10 AM - 12:00 PM • 1 stop
WN
Orlando → Chicago
6h 55m
5:20 PM - 10:35 PM • 1 stop
$177
Southwest Airlines
Sep 23 - Sep 23, Economy
WN
Orlando → Chicago
8h 50m
11:20 AM - 3:50 PM • 1 stop
WN
Orlando → Chicago
18h 35m
8:35 PM - 8:50 AM • 1 stop
$177
Southwest Airlines
Sep 23 - Sep 23, Economy
WN
Orlando → Chicago
10h 20m
9:00 AM - 2:20 PM • 1 stop
WN
Orlando → Chicago
18h 25m
8:40 PM - 8:45 AM • 1 stop
$177
Southwest Airlines
Sep 23 - Sep 23, Economy
DL
Orlando → Chicago
7h 14m
6:15 AM - 9:49 AM • 1 stop
DL
Orlando → Chicago
10h 18m
1:55 PM - 9:13 PM • 1 stop
$213
Delta Airlines
Sep 23 - Sep 23, Economy
DL
Orlando → Chicago
7h 29m
8:05 AM - 11:54 AM • 1 stop
DL
Orlando → Chicago
7h 37m
6:25 PM - 12:22 AM • 1 stop
$291
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 164
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 7:15 pm

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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