Southwest Airlines Oakland to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from Oakland to Chicago. Compare airline ticket prices and book air tickets starting from $119 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Southwest Airlines, arrivals and departure details below.

Find Cheap Airfare Oakland (CA) — Chicago (IL) by Southwest 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 - $119, two-way – $204.

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Cheap Flights from Oakland to Chicago by Southwest Airlines

Look at the list of plane tickets for the most popular direct flights by Southwest Airlines, their prices start from $119. The fastest nonstop flight takes 4h. There’re no connecting flights.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $119 Find flight	6:50 am Oakland Oakland Int	12:55 pm Chicago Midway	4h 5m	Southwest Airlines	WN2804
from $119 Find flight	12:40 pm Oakland Oakland Int	6:40 pm Chicago Midway	4h 0m	Southwest Airlines	WN516
from $173 Find flight	3:00 pm Oakland Oakland Int	9:00 pm Chicago Midway	4h 0m	Southwest Airlines	WN1276
from $174 Find flight	10:30 am Oakland Oakland Int	4:30 pm Chicago Midway	4h 0m	Southwest Airlines	WN1401

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 05/19/2024

Southwest Airlines Flight Schedule Oakland to Chicago

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	Flight Details	Flight Time	Price
10:30 am — 4:30 pm	10:30 am — 4:30 pm WN1401 Southwest Airlines Oakland — Chicago	4h	Find flight from$174
12:40 pm — 6:40 pm	12:40 pm — 6:40 pm WN516 Southwest Airlines Oakland — Chicago	4h	Find flight from$119
3:00 pm — 9:00 pm	3:00 pm — 9:00 pm WN1276 Southwest Airlines Oakland — Chicago	4h	Find flight from$173
6:50 am — 12:55 pm	6:50 am — 12:55 pm WN2804 Southwest Airlines Oakland — Chicago	4h 5m	Find flight from$119

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 05/19/2024

Flight Information

There are 4 flights by Southwest Airlines from Oakland to Chicago every week with departures from Oakland Int, Convention Center Heliport, Oakland/Coliseum Stat. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:30 am to 6:50 am. Nonstop flight is 4h. The time difference between Oakland and Chicago is 2h.

The fastest flight 4h
Average flight time 4h
The earliest flight 10:30 am
The latest flight 6:50 am
Distance 1846 ml

The cheapest flight by Southwest Airlines that our users were able to find is $119. This airfare is economy class on one-way WN2804 flight for October 3, 2018 leaving Oakland Int in Oakland at 6:50 am, it includes all taxes and additional fees.

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Southwest Airlines Airplanes on the Route

List of the most popular Southwest Airlines airplanes flying from Oakland to Chicago:

Other Popular Airlines on the Route

Besides Southwest Airlines there are other 1 airline carriers between Oakland and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Oakland to Chicago.

Nonstop flights

There are 4 direct flights every day from Oakland. Airlines and fares are below:

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Connecting Flights

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

AS - Alaska Airlines

from $161

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How to book an air ticket yourself?

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