$119 Cheap flight deals from Chicago (CHI) to Pleasanton (SJC)

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This Weekend's Flight Deals from Chicago to Pleasanton

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jul 10 - Tue, Jul 14
MDW
Midway Intl.
SFO
San Francisco Intl.
$378 Roundtrip, found 4 days ago
$378
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jul 10 from Midway Intl. to San Francisco Intl., returning Tue, Jul 14, priced at $378 found 4 days ago
Sat, Jul 11 - Sun, Jul 12
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$428 Roundtrip, found 3 days ago
$428
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 11 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Sun, Jul 12, priced at $428 found 3 days ago
Fri, Jul 10 - Sat, Jul 11
ORD
O'Hare Intl.
OAK
Oakland Intl.
$432 Roundtrip, found 4 hours ago
$432
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Fri, Jul 10 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 11, priced at $432 found 4 hours ago
Sat, Jul 11 - Sat, Jul 18
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$454 Roundtrip, found 1 hour ago
$454
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 11 from O'Hare Intl. to San Francisco Intl., returning Sat, Jul 18, priced at $454 found 1 hour ago

Airfares from $119 One Way, $237 Round Trip from Chicago to Pleasanton

Prices starting at $237 for return flights and $119 for one-way flights to Pleasanton were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 22 - Wed, Sep 23
RFD
Rockford
SFO
San Francisco
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 22 from Rockford to San Francisco, returning Wed, Sep 23, priced at $237 found 2 days ago
Sat, Sep 19 - Thu, Sep 24
MDW
Chicago
SFO
San Francisco
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Sep 19 from Chicago to San Francisco, returning Thu, Sep 24, priced at $245 found 4 days ago
Tue, Aug 18 - Mon, Aug 24
ORD
Chicago
SFO
San Francisco
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Chicago to San Francisco, returning Mon, Aug 24, priced at $246 found 1 day ago
Wed, Sep 2 - Tue, Sep 8
ORD
Chicago
OAK
Oakland
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Sep 2 from Chicago to Oakland, returning Tue, Sep 8, priced at $257 found 3 days ago
Sat, Aug 15 - Sat, Aug 22
ORD
Chicago
SJC
San Jose
$260 Roundtrip, found 2 days ago
$260
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Aug 15 from Chicago to San Jose, returning Sat, Aug 22, priced at $260 found 2 days ago

Pleasanton economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Meritage Resort and Spa
4.0-star property

The Meritage Resort and Spa

8.2/10 Very Good! (1,008 reviews)

Aug 13 - Aug 17

4 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,254, price is now $846 per person
$846
per person
found 1 day ago
I wasn’t extremely impressed with this property. Honestly I wasn’t overly impressed with Napa Valley as a whole.. But regarding the property it seemed old and outdated. House keeping only came by request which is a bit off putting when you have to remember to call in the middle of a winery event every day. The front desk confirmed that I covered my full stay minus the resort fee on Expedia at the time of booking so no extra charges are due at the time of arrival and that they would not be charging my method of payment. Only to find out they still immediately charged my card over $4500 so I had to clarify that on my second day. They reversed the charge with a wait of 7-10 business days but what if I didn’t have over $100k in my account!!? What if I was a 21 year old looking to propose to my wife and actually needed access to the over $4500 that they tied up. Napa’s over hype does cost money!! They fixed their mistake and offered $100 food credit that we didn’t even bother to use.. Over all I’m not impressed and I will not be returning to Napa Valley or that hotel anytime soon..

Reviewed on Jul 5, 2026

White House Napa
4.0-star property

White House Napa

9.2/10 Wonderful! (630 reviews)

Aug 13 - Aug 17

4 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,465, price is now $939 per person
$939
per person
found 1 day ago
Everything was wonderful. We had some issues with our room code but they were able to gives us a new code right away with a quick phone call. They did their best to make sure we were comfortable. It is a beautiful property and the staff was very kind and did their best to make sure we had everything we wanted and needed. I highly recommend for a beautiful getaway.

Reviewed on Jul 2, 2026

Claremont Resort & Club
5.0-star property

Claremont Resort & Club

9/10 Wonderful! (1,023 reviews)

Aug 12 - Aug 17

5 night stay

Chicago (ORD) to Oakland (OAK)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,569, price is now $1,014 per person
$1,014
per person
found 24 hours ago
My room was clean but my floor was squeaky. My bed had throw pillows on it that didn’t look so clean and new, but other than that, it was a pretty good experience.

Reviewed on Jul 5, 2026

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Pleasanton packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
White House Napa
4.0-star property

White House Napa

9.2/10 Wonderful! (630 reviews)

Aug 4 - Aug 8

4 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,307, price is now $987 per person
$987
per person
found 10 hours ago
Everything was wonderful. We had some issues with our room code but they were able to gives us a new code right away with a quick phone call. They did their best to make sure we were comfortable. It is a beautiful property and the staff was very kind and did their best to make sure we had everything we wanted and needed. I highly recommend for a beautiful getaway.

Reviewed on Jul 2, 2026

Carneros Resort and Spa
5.0-star property

Carneros Resort and Spa

9.2/10 Wonderful! (375 reviews)

Aug 4 - Aug 8

4 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $8,267, price is now $6,163 per person
$6,163
per person
found 10 hours ago
Great spot

Reviewed on Jul 4, 2026

Vineyard Estate w/ Pool, Spa & Bocce Ball + Mins to Wineries & Park Lawndale Manor by Avantstay
3.0-star property

Vineyard Estate w/ Pool, Spa & Bocce Ball + Mins to Wineries & Park Lawndale Manor by Avantstay

No reviews

Aug 4 - Aug 8

4 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,846, price is now $3,728 per person
$3,728
per person
found 10 hours ago

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Pleasanton first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Emeryville - San Francisco Bay Bridge
3.0-star property

Sonesta Emeryville - San Francisco Bay Bridge

8.6/10 Excellent! (1,546 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,203, price is now $1,114 per person
$1,114
per person
found 9 hours ago
Clean room

Reviewed on Jul 4, 2026

Courtyard San Francisco Larkspur Landing/Marin County
3.0-star property

Courtyard San Francisco Larkspur Landing/Marin County

8.8/10 Excellent! (834 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,541, price is now $1,421 per person
$1,421
per person
found 9 hours ago
Convenient, comfortable, clean, love the pool, very pretty environment, most of staff very helpful.

Reviewed on Jun 29, 2026

Residence Inn by Marriott Oakland Downtown
3.5-star property

Residence Inn by Marriott Oakland Downtown

9.4/10 Exceptional! (545 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,264, price is now $1,216 per person
$1,216
per person
found 9 hours ago
Hotel room was very nice, bartender was also great.

Reviewed on Jun 9, 2026

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More About Flying To Pleasanton from Chicago

Route Information for Flights from Chicago to Pleasanton

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Pleasanton

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.