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Flight Deals from Oakland to Chicago from $118

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Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

Incredible Deals

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Up to 1 stop
    $281
  • Up to 2 stops
    $246
  • Nonstop
    $236

Airlines

  • Alaska Airlines
    $247
  • Delta Air Lines
    $423
  • Southwest Airlines
    $236
  • United Airlines
    $571

Cabin Class

  • Economy
    $236

Arrival Airports

  • Chicago Metropolitan Area
    $246
  • Chicago Midway Airport
    $236
  • Chicago O Hare Airport
    $296

Layover Airports

  • Chicago Midway Airport
    $246
  • Chicago O Hare Airport
    $247
  • Norman Y. Mineta San Jose International Airport
    $247
  • Oakland International Airport
    $246
  • Phoenix Sky Harbor International Airport
    $246
  • Portland International Airport
    $287
  • Salt Lake City International Airport
    $423
  • San Diego International Airport
    $247
  • San Francisco International Airport
    $276
  • Seattle Tacoma International Airport
    $380

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

Southwest Airlines Logo
Southwest Airlines

08/15/26

OAK
4h
Direct

08/16/26

MDW
Southwest Airlines Logo
Southwest Airlines

08/22/26

MDW
4h 25m
Direct

08/22/26

OAK
$236
Southwest Airlines Logo
Southwest Airlines

08/01/26

OAK
6h 5m
MDW

08/02/26

CHI
Southwest Airlines Logo
Southwest Airlines

08/08/26

CHI
4h 30m
PHX
OAK

08/08/26

OAK
$246
Alaska Airlines Logo
Alaska Airlines

08/15/26

OAK
9h
SAN
ORD

08/15/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/19/26

CHI
4h 58m
SAN
SJC

08/19/26

OAK
$247
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Alaska Airlines Logo
Alaska Airlines

08/12/26

OAK
8h 46m
SAN
ORD

08/12/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/18/26

CHI
4h 51m
SAN
SJC

08/18/26

OAK
$247
Alaska Airlines Logo
Alaska Airlines

08/11/26

OAK
8h 46m
SAN
ORD

08/11/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/12/26

CHI
4h 51m
SAN
SJC

08/12/26

OAK
$247
Alaska Airlines Logo
Alaska Airlines

08/18/26

OAK
8h 46m
SAN
ORD

08/18/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/19/26

CHI
4h 58m
SAN
SJC

08/19/26

OAK
$247
Alaska Airlines Logo
Alaska Airlines

08/05/26

OAK
8h 46m
SAN
ORD

08/05/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/19/26

CHI
4h 58m
SAN
SJC

08/19/26

OAK
$247
Alaska Airlines Logo
Alaska Airlines

08/20/26

OAK
8h 46m
SAN
ORD

08/20/26

CHI
Alaska Airlines Logo
Alaska Airlines

09/03/26

CHI
7h 24m
SAN
SFO

09/03/26

OAK
$276
Southwest Airlines Logo
Southwest Airlines

08/01/26

OAK
6h 5m
MDW

08/02/26

CHI
Southwest Airlines Logo
Southwest Airlines

08/08/26

CHI
2h 35m
SFO

08/08/26

OAK
$281
Alaska Airlines Logo
Alaska Airlines

08/01/26

OAK
11h 25m
PDX
ORD

08/02/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/15/26

CHI
5h 56m
SAN
SJC

08/15/26

OAK
$287
Alaska Airlines Logo
Alaska Airlines

08/15/26

OAK
7h
SAN

08/15/26

ORD
Alaska Airlines Logo
Alaska Airlines

08/22/26

ORD
7h 5m
SAN

08/22/26

OAK
$296
Alaska Airlines Logo
Alaska Airlines

08/21/26

OAK
8h 46m
SAN
ORD

08/21/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/24/26

CHI
5h 5m
SAN
OAK

08/24/26

OAK
$330
Alaska Airlines Logo
Alaska Airlines

08/29/26

OAK
12h 33m
SAN
ORD

08/29/26

CHI
Alaska Airlines Logo
Alaska Airlines

09/05/26

CHI
7h 24m
SAN
SFO

09/05/26

OAK
$348
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Alaska Airlines Logo
Alaska Airlines

08/30/26

OAK
8h 46m
SAN
ORD

08/30/26

CHI
Alaska Airlines Logo
Alaska Airlines

09/03/26

CHI
7h 24m
SAN
SFO

09/03/26

OAK
$353
Alaska Airlines Logo
Alaska Airlines

08/09/26

OAK
9h 47m
PDX
ORD

08/10/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/12/26

CHI
4h 51m
SAN
SJC

08/12/26

OAK
$358
Alaska Airlines Logo
Alaska Airlines

08/19/26

OAK
9h 48m
SEA
ORD

08/19/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/24/26

CHI
5h 5m
SAN
OAK

08/24/26

OAK
$380
Alaska Airlines Logo
Alaska Airlines

07/31/26

OAK
9h 47m
PDX
ORD

08/01/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/20/26

CHI
4h 52m
SAN
SFO

08/20/26

OAK
$380
Alaska Airlines Logo
Alaska Airlines

08/22/26

OAK
10h 29m
SEA
ORD

08/23/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/29/26

CHI
4h 58m
SAN
SJC

08/29/26

OAK
$386
Alaska Airlines Logo
Alaska Airlines

08/26/26

OAK
9h 48m
SEA
ORD

08/26/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/31/26

CHI
4h 58m
SAN
SJC

08/31/26

OAK
$386
Alaska Airlines Logo
Alaska Airlines

08/25/26

OAK
9h 48m
SEA
ORD

08/25/26

CHI
Alaska Airlines Logo
Alaska Airlines

08/28/26

CHI
4h 51m
SAN
SJC

08/28/26

OAK
$400
Delta Air Lines Logo
Delta Air Lines

08/17/26

OAK
12h 19m
SLC
ORD

08/17/26

CHI
Delta Air Lines Logo
Delta Air Lines

08/18/26

CHI
4h
SLC
SJC

08/18/26

OAK
$423
Delta Air Lines Logo
Delta Air Lines

08/16/26

OAK
12h 19m
SLC
ORD

08/16/26

CHI
Delta Air Lines Logo
Delta Air Lines

08/18/26

CHI
4h
SLC
SJC

08/18/26

OAK
$486
Delta Air Lines Logo
Delta Air Lines

08/14/26

OAK
9h
SLC
ORD

08/14/26

CHI
Delta Air Lines Logo
Delta Air Lines

08/18/26

CHI
4h
SLC
SJC

08/18/26

OAK
$488
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Delta Air Lines Logo
Delta Air Lines

08/23/26

OAK
25h 19m
SLC
ORD

08/24/26

CHI
Delta Air Lines Logo
Delta Air Lines

08/27/26

CHI
4h 12m
SLC
OAK

08/27/26

OAK
$502
United Airlines Logo
United Airlines

08/18/26

OAK
8h 46m
SAN
ORD

08/18/26

CHI
United Airlines Logo
United Airlines

08/22/26

CHI
2h 36m
SFO

08/22/26

OAK
$571
United Airlines Logo
United Airlines

08/05/26

OAK
8h 46m
SAN
ORD

08/05/26

CHI
United Airlines Logo
United Airlines

08/17/26

CHI
2h 36m
SFO

08/17/26

OAK
$571
United Airlines Logo
United Airlines

08/15/26

OAK
9h
SAN
ORD

08/15/26

CHI
United Airlines Logo
United Airlines

08/19/26

CHI
2h 36m
SFO

08/19/26

OAK
$571
United Airlines Logo
United Airlines

08/04/26

OAK
8h 46m
SAN
ORD

08/04/26

CHI
United Airlines Logo
United Airlines

08/11/26

CHI
2h 36m
SFO

08/11/26

OAK
$571
United Airlines Logo
United Airlines

08/12/26

OAK
8h 46m
SAN
ORD

08/12/26

CHI
United Airlines Logo
United Airlines

08/17/26

CHI
2h 38m
SFO

08/17/26

OAK
$571
United Airlines Logo
United Airlines

08/01/26

OAK
11h 25m
PDX
ORD

08/02/26

CHI
United Airlines Logo
United Airlines

08/07/26

CHI
2h 37m
SFO

08/07/26

OAK
$614

Top Deals on flights from Oakland to Chicago

Oakland, US (OAK) - Chicago, US (CHI)

Southwest Airlines Logo
Southwest Airlines

Aug 15

OAK
4h
Direct

Aug 16

MDW

as low as

$118

Oakland, US (OAK) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Aug 15

OAK
7h
SAN

Aug 15

ORD

as low as

$128

Oakland, US (OAK) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 27

OAK
6h 59m
SLC

Jul 27

ORD

as low as

$213

Oakland, US (OAK) - Chicago, US (CHI)

 Logo

Jul 2

OAK
6h 15m
LAX

Jul 3

MDW

as low as

$344

Oakland, US (OAK) - Chicago, US (CHI)

 Logo

Oct 20

OAK
7h 15m
SAN

Oct 20

ORD

as low as

$370

Oakland, US (OAK) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jul 2

OAK
8h 22m
SEA

Jul 2

ORD

as low as

$388

Oakland, US (OAK) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jul 30

OAK
17h 15m
SLC

Jul 31

ORD

as low as

$686

Good to Know

Essential information to help you plan your flight from Oakland to Chicago

Cheapest Flight

$118

The lowest price we found in the last two weeks, departing Aug 15 and returning Aug 16

Airline WN4h ‧ economy

Fastest Flights

$236

The fastest flight that we found in the last two weeks, departing Aug 15 and returning Aug 22

Airline WN4h ‧ economy

Cheapest Flight Round-trip

$236

Cheapest price found in the last 14 days, departing Aug 15 and returning Aug 22

Airline WN4h ‧ economy

Cheapest Flight One-way

$118

Cheapest price found in the last 14 days, departing Aug 15

Airline WN4h ‧ economy

Cheapest Layover airport

$128

The cheapest layover airport to Chicago is currently $128

Airline AS1 stop ‧ 7h ‧ economy

Best Arrival airport

$128

The best arrival airport to Chicago is currently $128

Airline AS1 stop ‧ 7h ‧ economy

Best Departure airport

$128

The best departure airport to Chicago is currently $128

Airline AS1 stop ‧ 7h ‧ economy

Cheapest Airline

$128

The cheapest airline to Chicago is currently $128

Airline AS1 stop ‧ 7h ‧ economy

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