Cheap Flights from Chicago, IL to Oakland, CA from $69

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On Cheapflightsplus.com you will find 13 direct and 325 connecting flights from Chicago to Oakland. You can compare airfare deals from 8 airlines and multiple travel sites from $69, book and save on cheap plane tickets and last minute offers. Also check out CHI-OAK flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to Oakland Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $69 (one-way), $118 (round-trip).

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Best Flights from Chicago to Oakland Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Oakland with the lowest price of $69. The fastest direct flight takes 4h 35m and the fastest connecting – 6h 10m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $69 Find flight	20:05 Chicago O'Hare International	22:50 Oakland Oakland Int	4h 45m	Spirit Airlines	NK1209
from $117 Find flight	08:25 Chicago Midway	11:25 Oakland Oakland Int	5h 0m	Southwest Airlines	WN830
from $117 Find flight	10:05 Chicago Midway	12:40 Oakland Oakland Int	4h 35m	Southwest Airlines	WN3488
from $117 Find flight	13:30 Chicago Midway	16:20 Oakland Oakland Int	4h 50m	Southwest Airlines	WN1562
from $119 Find flight	08:25 Chicago Midway	11:05 Oakland Oakland Int	4h 40m	Southwest Airlines	WN2381
from $119 Find flight	11:25 Chicago Midway	14:05 Oakland Oakland Int	4h 40m	Southwest Airlines	WN1019
from $119 Find flight	16:25 Chicago Midway	19:05 Oakland Oakland Int	4h 40m	Southwest Airlines	WN1298
from $119 Find flight	19:00 Chicago Midway	21:40 Oakland Oakland Int	4h 40m	Southwest Airlines	WN3372
from $135 Find flight	13:15 Chicago Midway	15:55 Oakland Oakland Int	4h 40m	Southwest Airlines	WN3042
from $171 Find flight	18:35 Chicago Midway	21:15 Oakland Oakland Int	4h 40m	Southwest Airlines	WN561
from $83 Find flight	15:08 Chicago O'Hare International	20:05 Oakland Oakland Int	6h 57m layover 0h 49m - Los Angeles	Spirit Airlines	NK731 NK955
from $85 Find flight	16:20 Chicago O'Hare International	20:35 Oakland Oakland Int	6h 15m layover 0h 46m - Las Vegas	Spirit Airlines	NK245 NK695

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 24, 2024

Flight Schedule Chicago (Illinois) to Oakland (California)

Full flight schedule will help you in detecting at what time planes fly from Chicago to Oakland. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
08:25 — 11:25	08:25 — 11:25 WN830 Southwest Airlines Chicago — Oakland	5h	Find flight from$117
08:25 — 11:05	08:25 — 11:05 WN2381 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
09:15 — 12:10	09:15 — 12:10 WN441 Southwest Airlines Chicago — Oakland	4h 55m	Find flight from$231
10:05 — 12:40	10:05 — 12:40 WN3488 Southwest Airlines Chicago — Oakland	4h 35m	Find flight from$117
11:25 — 14:05	11:25 — 14:05 WN1019 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
13:15 — 15:55	13:15 — 15:55 WN3042 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$135
13:30 — 16:20	13:30 — 16:20 WN1562 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$117
16:25 — 19:05	16:25 — 19:05 WN1298 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
18:05 — 20:55	18:05 — 20:55 WN4681 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$231
18:35 — 21:15	18:35 — 21:15 WN561 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$171
19:00 — 21:40	19:00 — 21:40 WN3372 Southwest Airlines Chicago — Oakland	4h 40m	Find flight from$119
19:05 — 21:55	19:05 — 21:55 WN1068 Southwest Airlines Chicago — Oakland	4h 50m	Find flight from$183
20:05 — 22:50	20:05 — 22:50 NK1209 Spirit Airlines Chicago — Oakland	4h 45m	Find flight from$69
05:15 — 11:03	05:15 — 07:49 AA2429 American Airlines Chicago — Dallas 1h 16m stop 09:05 — 11:03 AA890 American Airlines Dallas — Oakland	7h 48m including layover	Find flight from$99
06:00 — 17:24	06:00 — 08:05 WN1269 Southwest Airlines Chicago — Las Vegas 7h 45m stop 15:50 — 17:24 NK939 Spirit Airlines Las Vegas — Oakland	13h 24m including layover	Find flight from$98
06:00 — 23:26	06:00 — 08:05 WN1269 Southwest Airlines Chicago — Las Vegas 13h 51m stop 21:56 — 23:26 NK711 Spirit Airlines Las Vegas — Oakland	19h 26m including layover	Find flight from$98
07:05 — 12:05	07:05 — 10:07 AA475 American Airlines Chicago — Phoenix 48m stop 10:55 — 12:05 AA5800 American Airlines Phoenix — Oakland	7h including layover	Find flight from$99
09:23 — 20:12	09:23 — 11:37 NK357 Spirit Airlines Chicago — Las Vegas 7h 5m stop 18:42 — 20:12 G41031 Allegiant Air Las Vegas — Oakland	12h 49m including layover	Find flight from$94
09:23 — 17:24	09:23 — 11:37 NK357 Spirit Airlines Chicago — Las Vegas 4h 13m stop 15:50 — 17:24 NK939 Spirit Airlines Las Vegas — Oakland	10h 1m including layover	Find flight from$99
10:30 — 20:38	10:30 — 13:05 NK737 Spirit Airlines Chicago — Los Angeles 6h 12m stop 19:17 — 20:38 NK955 Spirit Airlines Los Angeles — Oakland	12h 8m including layover	Find flight from$101
11:20 — 20:38	11:20 — 13:53 NK1739 Spirit Airlines Chicago — Los Angeles 5h 24m stop 19:17 — 20:38 NK955 Spirit Airlines Los Angeles — Oakland	11h 18m including layover	Find flight from$86
13:30 — 18:00	13:30 — 16:14 DL1644 Delta Air Lines Inc. Chicago — Salt Lake City 46m stop 17:00 — 18:00 DL3600 Delta Air Lines Inc. Salt Lake City — Oakland	6h 30m including layover	Find flight from$100
13:50 — 22:15	13:50 — 16:43 AA1882 American Airlines Chicago — Phoenix 4h 34m stop 21:17 — 22:15 AA418 American Airlines Phoenix — Oakland	10h 25m including layover	Find flight from$99
14:40 — 07:10 +1 day	14:40 — 17:46 NK1167 Spirit Airlines Chicago — Phoenix 12h 19m stop 06:05 — 07:10 WN2101 Southwest Airlines Phoenix — Oakland	18h 30m including layover	Find flight from$98
15:08 — 20:05	15:08 — 17:56 NK731 Spirit Airlines Chicago — Los Angeles 49m stop 18:45 — 20:05 NK955 Spirit Airlines Los Angeles — Oakland	6h 57m including layover	Find flight from$83
15:48 — 23:26	15:48 — 18:01 NK245 Spirit Airlines Chicago — Las Vegas 3h 55m stop 21:56 — 23:26 NK711 Spirit Airlines Las Vegas — Oakland	9h 38m including layover	Find flight from$88
16:20 — 20:35	16:20 — 18:20 NK245 Spirit Airlines Chicago — Las Vegas 46m stop 19:06 — 20:35 NK695 Spirit Airlines Las Vegas — Oakland	6h 15m including layover	Find flight from$85
16:27 — 08:51 +1 day	16:27 — 19:01 NK731 Spirit Airlines Chicago — Los Angeles 12h 29m stop 07:30 — 08:51 NK949 Spirit Airlines Los Angeles — Oakland	18h 24m including layover	Find flight from$86
17:40 — 23:59	17:40 — 20:18 AS51 Alaska Airlines Chicago — Seattle 1h 27m stop 21:45 — 23:59 AS356 Alaska Airlines Seattle — Oakland	8h 19m including layover	Find flight from$103
18:42 — 10:20 +1 day	18:42 — 20:57 F91263 Frontier Airlines Chicago — Las Vegas 11h 53m stop 08:50 — 10:20 WN1963 Southwest Airlines Las Vegas — Oakland	17h 38m including layover	Find flight from$82
18:42 — 17:24 +1 day	18:42 — 20:57 F91263 Frontier Airlines Chicago — Las Vegas 18h 53m stop 15:50 — 17:24 NK939 Spirit Airlines Las Vegas — Oakland	24h 42m including layover	Find flight from$82
20:00 — 17:24 +1 day	20:00 — 21:59 UA599 United Airlines Chicago — Las Vegas 17h 51m stop 15:50 — 17:24 NK939 Spirit Airlines Las Vegas — Oakland	23h 24m including layover	Find flight from$94
21:00 — 10:18 +1 day	21:00 — 23:15 NK457 Spirit Airlines Chicago — Las Vegas 9h 30m stop 08:45 — 10:18 NK562 Spirit Airlines Las Vegas — Oakland	15h 18m including layover	Find flight from$95
21:05 — 14:08 +1 day	21:05 — 23:05 WN537 Southwest Airlines Chicago — Las Vegas 13h 33m stop 12:38 — 14:08 G41031 Allegiant Air Las Vegas — Oakland	19h 3m including layover	Find flight from$86
08:00 — 19:01	08:00 — 10:38 AS23 Alaska Airlines Chicago — Seattle 1h 27m stop 12:05 — 13:10 AS700 Alaska Airlines Seattle — Portland 3h 54m stop 17:04 — 19:01 AS2563 Alaska Airlines Portland — Oakland	13h 1m including layover	Find flight from$102
08:00 — 19:01	08:00 — 10:38 AS23 Alaska Airlines Chicago — Seattle 2h 37m stop 13:15 — 14:09 AS2063 Alaska Airlines Seattle — Portland 2h 55m stop 17:04 — 19:01 AS2563 Alaska Airlines Portland — Oakland	13h 1m including layover	Find flight from$102
11:07 — 19:26	11:07 — 12:55 NK478 Spirit Airlines Chicago — Denver 50m stop 13:45 — 14:44 NK939 Spirit Airlines Denver — Las Vegas 3h 12m stop 17:56 — 19:26 G41031 Allegiant Air Las Vegas — Oakland	10h 19m including layover	Find flight from$95
12:15 — 23:32	12:15 — 14:30 DL2818 Delta Air Lines Inc. Chicago — Detroit 3h 44m stop 18:14 — 20:40 DL2538 Delta Air Lines Inc. Detroit — Salt Lake City 1h 45m stop 22:25 — 23:32 DL1182 Delta Air Lines Inc. Salt Lake City — Oakland	13h 17m including layover	Find flight from$104
12:26 — 23:32	12:26 — 14:46 DL3742 Delta Air Lines Inc. Chicago — Detroit 3h 28m stop 18:14 — 20:40 DL2538 Delta Air Lines Inc. Detroit — Salt Lake City 1h 45m stop 22:25 — 23:32 DL1182 Delta Air Lines Inc. Salt Lake City — Oakland	13h 6m including layover	Find flight from$96
14:37 — 23:32	14:37 — 16:59 DL2875 Delta Air Lines Inc. Chicago — Detroit 1h 15m stop 18:14 — 20:40 DL2538 Delta Air Lines Inc. Detroit — Salt Lake City 1h 45m stop 22:25 — 23:32 DL1182 Delta Air Lines Inc. Salt Lake City — Oakland	10h 55m including layover	Find flight from$96

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

*Departure and arrival times - local. Updated on April 24, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Oakland depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Oakland is 2970 miles. Time difference between the cities is 2h. Airplanes depart 01:40 to 22:40 from 7 Chicago airports and arrive 01:40 to 22:40 to 3 Oakland airports. Average flight time is 4h 40m.

The fastest flight 4h 35m
Average flight time 4h 40m
The earliest flight 01:40
The latest flight 22:40
Distance 1846 ml

What is the lowest airfare Chicago to Oakland?

The cheapest plane ticket found by our users is $69. This airfare is for economy class on one-way NK1209 flight by Spirit Airlines for October 5, 2018 which leaves O'Hare International in Chicago at 20:05 am and arrives at Oakland Oakland Int at 22:50.

Economy class

$69

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Business class

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First class

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Popular Airlines on the Route

The flight Chicago — Oakland is served by 8 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by American Airlines - 64 departures per week at the price of from $ 99 . And the most expensive tickets are offered by American Airlines airline - from $ 672.

Direct flights

There are 13 nonstop flights on the route. The fastest direct flight is WN3488 by Southwest Airlines takes 4h 35m and the cheapest is NK1209 by Spirit Airlines for $69.

WN - Southwest Airlines

from $117

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NK - Spirit Airlines

from $69

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Connecting Flights

There are 325 flights with layovers on the route. The fastest connecting flight is WN2397 by Southwest Airlines takes 6h 10m and the cheapest is NK1209 by Spirit Airlines for $82.

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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WN - Southwest Airlines

from $86

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DL - Delta Air Lines Inc.

from $96

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UA - United Airlines

from $94

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NK - Spirit Airlines

from $83

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AM - Aeromexico

from $249

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See more connecting flights

Airports

You can fly from Chicago to Oakland from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

O'Hare International-ORD

from $69
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Midway-MDW

from $86
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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Oakland airports

Oakland Int-OAK

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Oakland/Coliseum Stat-OBT

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Convention Center Heliport-JCE

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Airplanes

There are flights to Oakland from Chicago by 8 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Canadair Regional Jet 700

from $96

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Airbus A319

from $96

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Airbus A321

from $99

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Boeing 737

from $99

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Boeing 737-900 (winglets)

from $103

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Boeing 717

from $104

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Boeing 737-800 (winglets)

from $104

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Canadair Regional Jet 900

from $108

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Boeing 737-900

from $108

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McDonnell Douglas MD-88

from $114

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Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Chicago — Las Vegas

from $508

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Chicago — Tampa

from $63

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Chicago — Los Angeles

from $181

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Chicago — Orlando

from $62

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Chicago — New York

from $74

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Chicago — Dallas

from $70

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Chicago — San Antonio

from $59

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Chicago — Atlanta

from $76

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Chicago — Miami

from $66

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Chicago — Denver

from $61

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Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Chicago — London

from $60

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Chicago — Manchester

from $58

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Chicago — Zurich

from $61

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Chicago — Cancun

from $72

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Chicago — Dublin

from $59

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Chicago — Madrid

from $72

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Chicago — Rome

from $79

Find
Chicago — Paris

from $61

Find
Chicago — Tel Aviv

from $628

Find
Chicago — Mumbai

from $74

Find

All flights from Chicago | All flights to Oakland

How to book a plane ticket yourself?

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