Alaska Airlines Orlando to Chicago Flights

Return flight: Chicago – Orlando
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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Alaska Airlines flights from Orlando to Chicago. Compare airline ticket prices and book air tickets starting from $225 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Alaska Airlines, arrivals and departure details below.

Find Cheap Airfare Orlando (FL) — Chicago (IL) by Alaska Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in december: one-way - $225, two-way – $386.
Direct flights
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Cheap Flights from Orlando to Chicago by Alaska Airlines

Look at the list of plane tickets for the most connecting flights by Alaska Airlines, their prices start from $225. There’re no direct flights. The fastest connecting flight – 11h 59m.
Price Departure Arrival Flight Time Airline Flight
from $226
Find flight
7:00 am
Orlando
Orlando Int.
 11:59 pm
Chicago
O'Hare International
 17h 59m
layover
7h 25m - Seattle
 Alaska Airlines
AS395
AS538
from $302
Find flight
10:00 am
Orlando
Orlando Int.
 11:59 pm
Chicago
O'Hare International
 14h 59m
layover
4h 26m - Seattle
 Alaska Airlines
AS347
AS538
from $225
Find flight
8:40 am
Orlando
Orlando Int.
 11:59 pm
Chicago
O'Hare International
 16h 19m
layover
1h 43m - Portland
3h 7m - Seattle
 Alaska Airlines
AS527
AS1008
AS538
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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/04/2024
Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:00 am — 11:59 pm
5:06 pm — 8:26 pm AS347 Alaska Airlines
Orlando — Seattle
4h 26m stop
6:06 pm — 11:59 pm AS538 Alaska Airlines
Seattle — Chicago
14h 59m
including layover
Find flight
from$302
7:00 am — 11:59 pm
7:00 am — 10:21 am AS395 Alaska Airlines
Orlando — Seattle
7h 25m stop
6:06 pm — 11:59 pm AS538 Alaska Airlines
Seattle — Chicago
17h 59m
including layover
Find flight
from$226
7:00 am — 5:59 pm
7:00 am — 10:35 am AS395 Alaska Airlines
Orlando — Seattle
1h 10m stop
11:45 am — 5:59 pm AS352 Alaska Airlines
Seattle — Chicago
11h 59m
including layover
Find flight
from$273
8:40 am — 11:59 pm
8:40 am — 12:09 pm AS527 Alaska Airlines
Orlando — Portland
1h 43m stop
1:52 pm — 2:53 pm AS1008 Alaska Airlines
Portland — Seattle
3h 7m stop
6:00 pm — 11:59 pm AS538 Alaska Airlines
Seattle — Chicago
16h 19m
including layover
Find flight
from$225
8:40 am — 11:59 pm
8:40 am — 12:09 pm AS527 Alaska Airlines
Orlando — Portland
2h 51m stop
3:00 pm — 4:00 pm AS3358 Alaska Airlines
Portland — Seattle
2h stop
6:00 pm — 11:59 pm AS538 Alaska Airlines
Seattle — Chicago
16h 19m
including layover
Find flight
from$225
*Departure and arrival times are local. Last updated on 12/04/2024

Flight Information

There are 6 flights by Alaska Airlines from Orlando to Chicago every week with departures from Orlando Int., Walt Disney World, Herndon. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:00 am to 8:40 am. Nonstop flight is 11h 59m. The time difference between Orlando and Chicago is 1h.

  • The fastest flight 11h 59m
  • Average flight time 16h 19m
  • The earliest flight 10:00 am
  • The latest flight 8:40 am
  • Distance 995 ml

The cheapest months for traveling to Chicago are january (from 225 $), november (from 778 $).

The cheapest flight by Alaska Airlines that our users were able to find is $225. This airfare is economy class on one-way AS527 flight for January 22, 2025 leaving Orlando Int. in Orlando at 8:40 am, it includes all taxes and additional fees.

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Alaska Airlines Airplanes on the Route

List of the most popular Alaska Airlines airplanes flying from Orlando to Chicago:

Other Popular Airlines on the Route

Besides Alaska Airlines there are other 8 airline carriers between Orlando and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Orlando to Chicago.

Nonstop flights

There are 16 direct flights every day from Orlando. Airlines and fares are below:

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Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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