Southwest Airlines Chicago to Oakland Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to Oakland. Compare airline ticket prices and book air tickets starting from $86 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 Chicago (IL) — Oakland (CA) 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 - $86, two-way – $147.

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Cheap Flights from Chicago to Oakland by Southwest Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by Southwest Airlines, their prices start from $86. The fastest nonstop flight takes 4h 35m. The fastest connecting flight — 6h 10m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $117 Find flight	8:25 am Chicago Midway	11:25 am Oakland Oakland Int	5h 0m	Southwest Airlines	WN830
from $117 Find flight	1:30 pm Chicago Midway	4:20 pm Oakland Oakland Int	4h 50m	Southwest Airlines	WN1562
from $117 Find flight	10:05 am Chicago Midway	12:40 pm Oakland Oakland Int	4h 35m	Southwest Airlines	WN3488
from $119 Find flight	7:00 pm Chicago Midway	9:40 pm Oakland Oakland Int	4h 40m	Southwest Airlines	WN3372
from $119 Find flight	4:25 pm Chicago Midway	7:05 pm Oakland Oakland Int	4h 40m	Southwest Airlines	WN1298
from $119 Find flight	8:25 am Chicago Midway	11:05 am Oakland Oakland Int	4h 40m	Southwest Airlines	WN2381
from $119 Find flight	11:25 am Chicago Midway	2:05 pm Oakland Oakland Int	4h 40m	Southwest Airlines	WN1019
from $135 Find flight	1:15 pm Chicago Midway	3:55 pm Oakland Oakland Int	4h 40m	Southwest Airlines	WN3042
from $171 Find flight	6:35 pm Chicago Midway	9:15 pm Oakland Oakland Int	4h 40m	Southwest Airlines	WN561
from $183 Find flight	7:05 pm Chicago Midway	9:55 pm Oakland Oakland Int	4h 50m	Southwest Airlines	WN1068
from $231 Find flight	6:05 pm Chicago Midway	8:55 pm Oakland Oakland Int	4h 50m	Southwest Airlines	WN4681
from $231 Find flight	9:15 am Chicago Midway	12:10 pm Oakland Oakland Int	4h 55m	Southwest Airlines	WN441
from $86 Find flight	9:05 pm Chicago Midway	2:08 pm+1 день Oakland Oakland Int	19h 3m layover 13h 33m - Las Vegas	Southwest Airlines	WN537 G41031

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 05/06/2024

Southwest Airlines Flight Schedule Chicago to Oakland

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
10:05 am — 12:40 pm	10:05 am — 12:40 pm WN3488 Southwest Airlines Chicago — Oakland	4h 35m	Find flight from$117
11:25 am — 2:05 pm	11:25 am — 2:05 pm WN1019 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
1:15 pm — 3:55 pm	1:15 pm — 3:55 pm WN3042 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$135
1:30 pm — 4:20 pm	1:30 pm — 4:20 pm WN1562 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$117
4:25 pm — 7:05 pm	4:25 pm — 7:05 pm WN1298 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
6:05 pm — 8:55 pm	6:05 pm — 8:55 pm WN4681 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$231
6:35 pm — 9:15 pm	6:35 pm — 9:15 pm WN561 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$171
7:00 pm — 9:40 pm	7:00 pm — 9:40 pm WN3372 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
7:05 pm — 9:55 pm	7:05 pm — 9:55 pm WN1068 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$183
8:25 am — 11:25 am	8:25 am — 11:25 am WN830 Southwest Airlines Chicago — Oakland	5h	Find flight from$117
8:25 am — 11:05 am	8:25 am — 11:05 am WN2381 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
9:15 am — 12:10 pm	9:15 am — 12:10 pm WN441 Southwest Airlines Chicago — Oakland	4h 55m	Find flight from$231
10:20 am — 2:40 pm	10:20 am — 11:55 am WN526 Southwest Airlines Chicago — Denver 1h stop 12:55 pm — 2:40 pm WN2180 Southwest Airlines Denver — Oakland	6h 20m including layover	Find flight from$131
11:50 am — 4:15 pm	11:50 am — 12:55 pm WN965 Southwest Airlines Chicago — Lake Saint Louis 50m stop 1:45 pm — 4:15 pm WN2107 Southwest Airlines Lake Saint Louis — Oakland	6h 25m including layover	Find flight from$131
12:55 pm — 6:30 pm	12:55 pm — 3:00 pm WN4727 Southwest Airlines Chicago — Las Vegas 2h stop 5:00 pm — 6:30 pm WN4665 Southwest Airlines Las Vegas — Oakland	7h 35m including layover	Find flight from$287
2:55 pm — 11:26 pm	2:55 pm — 5:00 pm WN1660 Southwest Airlines Chicago — Las Vegas 4h 56m stop 9:56 pm — 11:26 pm NK711 Spirit Airlines Las Vegas — Oakland	10h 31m including layover	Find flight from$164
2:55 pm — 11:10 pm	2:55 pm — 5:00 pm WN1660 Southwest Airlines Chicago — Las Vegas 4h 40m stop 9:40 pm — 11:10 pm WN1288 Southwest Airlines Las Vegas — Oakland	10h 15m including layover	Find flight from$165
4:20 pm — 9:10 pm	4:20 pm — 7:15 pm WN1914 Southwest Airlines Chicago — Phoenix 50m stop 8:05 pm — 9:10 pm WN803 Southwest Airlines Phoenix — Oakland	6h 50m including layover	Find flight from$131
5:55 am — 10:05 am	5:55 am — 7:40 am WN2397 Southwest Airlines Chicago — Denver 35m stop 8:15 am — 10:05 am WN4695 Southwest Airlines Denver — Oakland	6h 10m including layover	Find flight from$131
5:55 am — 11:40 pm	5:55 am — 7:40 am WN2397 Southwest Airlines Chicago — Denver 14h 15m stop 9:55 pm — 11:40 pm WN1421 Southwest Airlines Denver — Oakland	19h 45m including layover	Find flight from$140
6:00 am — 11:26 pm	6:00 am — 8:05 am WN1269 Southwest Airlines Chicago — Las Vegas 13h 51m stop 9:56 pm — 11:26 pm NK711 Spirit Airlines Las Vegas — Oakland	19h 26m including layover	Find flight from$98
6:00 am — 5:24 pm	6:00 am — 8:05 am WN1269 Southwest Airlines Chicago — Las Vegas 7h 45m stop 3:50 pm — 5:24 pm NK939 Spirit Airlines Las Vegas — Oakland	13h 24m including layover	Find flight from$98
9:05 pm — 2:08 pm +1 day	9:05 pm — 11:05 pm WN537 Southwest Airlines Chicago — Las Vegas 13h 33m stop 12:38 pm — 2:08 pm G41031 Allegiant Air Las Vegas — Oakland	19h 3m including layover	Find flight from$86
9:05 pm — 10:18 am +1 day	9:05 pm — 11:05 pm WN537 Southwest Airlines Chicago — Las Vegas 9h 40m stop 8:45 am — 10:18 am NK562 Spirit Airlines Las Vegas — Oakland	15h 13m including layover	Find flight from$96
7:00 am — 11:26 pm	7:00 am — 10:10 am WN1308 Southwest Airlines Chicago — Boston 6h 50m stop 5:00 pm — 8:20 pm NK641 Spirit Airlines Boston — Las Vegas 1h 36m stop 9:56 pm — 11:26 pm NK711 Spirit Airlines Las Vegas — Oakland	18h 26m including layover	Find flight from$152

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

*Departure and arrival times are local. Last updated on 05/06/2024

Flight Information

There are 12 flights by Southwest Airlines from Chicago to Oakland every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Oakland Int, Convention Center Heliport, Oakland/Coliseum Stat.

Departures start from 10:05 am to 9:55 am. Nonstop flight is 4h 35m. The time difference between Chicago and Oakland is 2h.

The fastest flight 4h 35m
Average flight time 4h 40m
The earliest flight 10:05 am
The latest flight 9:55 am
Distance 1846 ml

The cheapest flight by Southwest Airlines that our users were able to find is $86. This airfare is economy class on one-way WN537 flight for December 5, 2018 leaving Midway in Chicago at 9:05 pm, 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 Chicago to Oakland:

Other Popular Airlines on the Route

Besides Southwest Airlines there are other 7 airline carriers between Chicago and Oakland. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Oakland.

Nonstop flights

There are 13 direct flights every day from Chicago. Airlines and fares are below:

NK - Spirit Airlines

from $69

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Connecting Flights

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

AA - American Airlines

from $99

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AS - Alaska Airlines

from $102

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F9 - Frontier Airlines

from $82

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DL - Delta Air Lines Inc.

from $96

Find
UA - United Airlines

from $94

Find
NK - Spirit Airlines

from $83

Find
AM - Aeromexico

from $249

Find

See more connecting flights

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