$70 Cheap flight deals from Chicago (CHI) to Pleasant Hill (OAK)

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This Weekend's Flight Deals from Chicago to Pleasant Hill

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.

Sat, Nov 15 - Mon, Nov 17
MDW
Midway Intl.
SFO
San Francisco Intl.
$297 Roundtrip, found 23 hours ago
$297
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to San Francisco Intl., returning Mon, Nov 17, priced at $297 found 23 hours ago
Sun, Nov 16 - Mon, Nov 17
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$426 Roundtrip, just found
$426
Roundtrip
just found
Select Alaska Airlines flight, departing Sun, Nov 16 from O'Hare Intl. to San Francisco Intl., returning Mon, Nov 17, priced at $426 just found
Sat, Nov 15 - Sat, Nov 15
ORD
O'Hare Intl.
OAK
Oakland Intl.
$480 Roundtrip, found 4 days ago
$480
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Oakland Intl., returning Sat, Nov 15, priced at $480 found 4 days ago
Fri, Nov 14 - Mon, Nov 17
RFD
Greater Rockford
SFO
San Francisco Intl.
$591 Roundtrip, found 6 days ago
$591
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 14 from Greater Rockford to San Francisco Intl., returning Mon, Nov 17, priced at $591 found 6 days ago

Airfares from $70 One Way, $140 Round Trip from Chicago to Pleasant Hill

Prices starting at $140 for return flights and $70 for one-way flights to Pleasant Hill were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jan 8 - Mon, Jan 12
MDW
Chicago
SFO
San Francisco
$140 Roundtrip, found 9 hours ago
$140
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Chicago to San Francisco, returning Mon, Jan 12, priced at $140 found 9 hours ago
Thu, Jan 22 - Mon, Jan 26
ORD
Chicago
SFO
San Francisco
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Chicago to San Francisco, returning Mon, Jan 26, priced at $140 found 1 day ago
Wed, Dec 10 - Tue, Dec 16
ORD
Chicago
SFO
San Francisco
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Dec 10 from Chicago to San Francisco, returning Tue, Dec 16, priced at $207 found 5 days ago
Wed, Dec 3 - Wed, Dec 10
ORD
Chicago
SFO
San Francisco
$226 Roundtrip, found 3 hours ago
$226
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to San Francisco, returning Wed, Dec 10, priced at $226 found 3 hours ago
Mon, Jan 26 - Thu, Jan 29
RFD
Rockford
SFO
San Francisco
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Jan 26 from Rockford to San Francisco, returning Thu, Jan 29, priced at $239 found 2 days ago

Pleasant Hill economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Yountville
4.0-star property

Hotel Yountville

9.6/10 Exceptional! (1,007 reviews)

Dec 27 - Jan 1

5 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Coach

Oakland (OAK) to Chicago (CHI)

Alaska Airlines • Coach
Save 100% on your flight
Price was $2,513, price is now $1,783 per person
$1,783
per person
found 13 hours ago
this is a perfect place to spend some days in Napa , Hotel is

Reviewed on May 24, 2025

Stanly Ranch, Auberge Collection
5.0-star property

Stanly Ranch, Auberge Collection

9.4/10 Exceptional! (156 reviews)

Dec 27 - Jan 1

5 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Coach

Oakland (OAK) to Chicago (CHI)

Alaska Airlines • Coach
Save 100% on your flight
Price was $4,313, price is now $2,867 per person
$2,867
per person
found 13 hours ago
Amazing resort and service

Reviewed on Jul 18, 2025

Carneros Resort and Spa
5.0-star property

Carneros Resort and Spa

9.2/10 Wonderful! (347 reviews)

Dec 27 - Jan 1

5 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Coach

Oakland (OAK) to Chicago (CHI)

Alaska Airlines • Coach
Save 100% on your flight
Price was $3,677, price is now $2,686 per person
$2,686
per person
found 13 hours ago
The property was located in a very quiet area. It is very evident in some locations of the resort that service is extremely important. The Hilltop & Boonfly Café were consistently on top of service. The restaurant Farm lost points with us after a follow-up call was not received pertaining to reservation availability. The cottages themselves were very cute and had excellent amenities. The fireplace, fire pit, and outdoor tub/shower were so unique to our cottage experience. The cleanliness of the outdoor pillows, the curtains, and rugs were not pleasing. The outdoor rugs and cushions in the outdoor seating areas, particularly, near Farm were filled with pet hair & the floor rugs need to either be cleaned or replaced. The overall disappointing piece of the resort was the cleanliness. Even the hot tub had grime. With the amount of money paid to book the resort along with monies spent at the resort, there needs to be some revamping of the care.

Reviewed on Apr 3, 2021

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More About Flying To Pleasant Hill from Chicago

Route Information for Flights from Chicago to Pleasant Hill

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

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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.