Alaska Airlines Orlando to Chicago Flights

Return flight: Chicago – Orlando

Cheapflightsplus.com will find cheap Alaska Airlines flights from Orlando to Chicago. Compare airline ticket prices and book air tickets starting from $273 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 may: one-way - $273, two-way – $468.
Direct flights
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Below is a detailed 2024 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
4:00 pm — 4:26 am
+1 day
4:00 pm — 6:03 pm AS339 Alaska Airlines
Orlando — San Diego
4h 41m stop
10:44 pm — 4:26 am UA240 United Airlines
San Diego — Chicago
13h 26m
including layover
Find flight
from$370
4:00 pm — 12:16 pm
+1 day
4:00 pm — 6:03 pm AS339 Alaska Airlines
Orlando — San Diego
12h 12m stop
6:15 am — 12:16 pm UA913 United Airlines
San Diego — Chicago
21h 16m
including layover
Find flight
from$442
4:00 pm — 2:06 pm
+1 day
4:00 pm — 6:03 pm AS339 Alaska Airlines
Orlando — San Diego
13h 57m stop
8:00 am — 2:06 pm UA2137 United Airlines
San Diego — Chicago
23h 6m
including layover
Find flight
from$442
4:00 pm — 4:50 am
+1 day
4:00 pm — 6:03 pm AS339 Alaska Airlines
Orlando — San Diego
4h 47m stop
10:50 pm — 4:50 am AS4462 Alaska Airlines
San Diego — Chicago
13h 50m
including layover
Find flight
from$963
4:00 pm — 2:07 pm
+1 day
4:00 pm — 6:03 pm AS339 Alaska Airlines
Orlando — San Diego
13h 57m stop
8:00 am — 2:07 pm AS6641 Alaska Airlines
San Diego — Chicago
23h 7m
including layover
Find flight
from$963
4:50 pm — 5:06 am
+1 day
4:50 pm — 7:36 pm AS1305 Alaska Airlines
Orlando — San Francisco
3h 33m stop
11:09 pm — 5:06 am UA995 United Airlines
San Francisco — Chicago
13h 16m
including layover
Find flight
from$414
4:50 pm — 4:27 am
+1 day
4:50 pm — 7:36 pm AS1305 Alaska Airlines
Orlando — San Francisco
2h 59m stop
10:35 pm — 4:27 am UA1217 United Airlines
San Francisco — Chicago
12h 37m
including layover
Find flight
from$414
4:50 pm — 6:02 am
+1 day
4:50 pm — 7:36 pm AS1305 Alaska Airlines
Orlando — San Francisco
4h 23m stop
11:59 pm — 6:02 am UA214 United Airlines
San Francisco — Chicago
14h 12m
including layover
Find flight
from$415
4:50 pm — 6:40 am
+1 day
4:50 pm — 7:36 pm AS1305 Alaska Airlines
Orlando — San Francisco
4h 54m stop
0:30 am — 6:40 am UA680 United Airlines
San Francisco — Chicago
14h 50m
including layover
Find flight
from$419
4:50 pm — 6:02 am
+1 day
4:50 pm — 7:36 pm AS1305 Alaska Airlines
Orlando — San Francisco
4h 23m stop
11:59 pm — 6:02 am UA2264 United Airlines
San Francisco — Chicago
14h 12m
including layover
Find flight
from$419
5:45 pm — 4:55 am
+1 day
5:45 pm — 8:51 pm AS727 Alaska Airlines
Orlando — Portland
2h 24m stop
11:15 pm — 4:55 am UA745 United Airlines
Portland — Chicago
12h 10m
including layover
Find flight
from$397
5:45 pm — 6:52 am
+1 day
5:45 pm — 8:51 pm AS727 Alaska Airlines
Orlando — Portland
4h 5m stop
0:56 am — 6:52 am UA1269 United Airlines
Portland — Chicago
14h 7m
including layover
Find flight
from$402
6:50 pm — 6:55 am
+1 day
6:50 pm — 10:03 pm AS19 Alaska Airlines
Orlando — Seattle
2h 42m stop
0:45 am — 6:55 am AS20 Alaska Airlines
Seattle — Chicago
13h 5m
including layover
Find flight
from$273
6:50 pm — 6:49 am
+1 day
6:50 pm — 10:03 pm AS19 Alaska Airlines
Orlando — Seattle
2h 54m stop
0:57 am — 6:49 am UA1195 United Airlines
Seattle — Chicago
12h 59m
including layover
Find flight
from$397
7:15 am — 6:55 am
+1 day
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
14h 20m stop
0:45 am — 6:55 am AS20 Alaska Airlines
Seattle — Chicago
24h 40m
including layover
Find flight
from$278
7:15 am — 11:35 pm
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
7h 10m stop
5:35 pm — 11:35 pm AS26 Alaska Airlines
Seattle — Chicago
17h 20m
including layover
Find flight
from$300
7:15 am — 6:30 pm
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
1h 50m stop
12:15 pm — 6:30 pm AS22 Alaska Airlines
Seattle — Chicago
12h 15m
including layover
Find flight
from$368
7:15 am — 7:55 pm
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
3h 24m stop
1:49 pm — 7:55 pm UA670 United Airlines
Seattle — Chicago
13h 40m
including layover
Find flight
from$397
7:15 am — 4:59 am
+1 day
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
12h 55m stop
11:20 pm — 4:59 am UA619 United Airlines
Seattle — Chicago
22h 44m
including layover
Find flight
from$401
7:15 am — 6:49 am
+1 day
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
14h 32m stop
0:57 am — 6:49 am UA1195 United Airlines
Seattle — Chicago
24h 34m
including layover
Find flight
from$401
7:15 am — 4:18 pm
+1 day
7:15 am — 10:25 am AS9 Alaska Airlines
Orlando — Seattle
21h 45m stop
8:10 am — 4:18 pm UA263 United Airlines
Seattle — Chicago
34h 3m
including layover
Find flight
from$404
*Departure and arrival times are local. Last updated on 05/15/2024

Flight Information

There are 22 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 4:00 pm to 7:15 am. Nonstop flight is 12h 10m. The time difference between Orlando and Chicago is 1h.

  • The fastest flight 12h 10m
  • Average flight time 14h 12m
  • The earliest flight 4:00 pm
  • The latest flight 7:15 am
  • Distance 995 ml

The cheapest flight by Alaska Airlines that our users were able to find is $273. This airfare is economy class on one-way AS19 flight for October 5, 2018 leaving Orlando Int. in Orlando at 6:50 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Alaska Airlines there are other 2 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 2 direct flights every day from Orlando. Airlines and fares are below:

See more direct flights

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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