$114 Cheap flight deals from Chicago (CHI) to St. Helena (OAK)

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This Weekend's Flight Deals from Chicago to St. Helena

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, Nov 14 - Tue, Nov 18
ORD
O'Hare Intl.
OAK
Oakland Intl.
$457 Roundtrip, found 3 days ago
$457
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Nov 14 from O'Hare Intl. to Oakland Intl., returning Tue, Nov 18, priced at $457 found 3 days ago
Fri, Nov 14 - Sun, Nov 16
MDW
Midway Intl.
OAK
Oakland Intl.
$642 Roundtrip, found 5 days ago
$642
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Midway Intl. to Oakland Intl., returning Sun, Nov 16, priced at $642 found 5 days ago
Sun, Nov 16 - Mon, Nov 24
ORD
O'Hare Intl.
STS
Sonoma County
$723 Roundtrip, found 1 day ago
$723
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Sun, Nov 16 from O'Hare Intl. to Sonoma County, returning Mon, Nov 24, priced at $723 found 1 day ago

Airfares from $114 One Way, $242 Round Trip from Chicago to St. Helena

Prices starting at $242 for return flights and $114 for one-way flights to St. Helena were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Dec 10 - Mon, Dec 15
ORD
Chicago
OAK
Oakland
$242 Roundtrip, found 4 days ago
$242
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Oakland, returning Mon, Dec 15, priced at $242 found 4 days ago
Wed, Dec 10 - Mon, Dec 15
ORD
Chicago
OAK
Oakland
$247 Roundtrip, found 4 days ago
$247
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Oakland, returning Mon, Dec 15, priced at $247 found 4 days ago
Fri, Jan 23 - Fri, Feb 6
ORD
Chicago
STS
Santa Rosa
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Jan 23 from Chicago to Santa Rosa, returning Fri, Feb 6, priced at $258 found 1 day ago
Thu, Feb 5 - Sun, Feb 8
ORD
Chicago
OAK
Oakland
$258 Roundtrip, found 22 hours ago
$258
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Thu, Feb 5 from Chicago to Oakland, returning Sun, Feb 8, priced at $258 found 22 hours ago
Tue, Jan 6 - Wed, Jan 14
ORD
Chicago
OAK
Oakland
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 6 from Chicago to Oakland, returning Wed, Jan 14, priced at $259 found 1 day ago

St. Helena economy flight packages

Price found within the past 48 hours. Click for updated prices.
Oakland Airport Executive Hotel
3.0-star property

Oakland Airport Executive Hotel

5.6/10 (2,183 reviews)

Dec 26 - Dec 30

4 night stay

Chicago (CHI) to Oakland (OAK)

United • Roundtrip • Coach
Price was $624, price is now $536 per person
$536
per person
found 12 hours ago
The staff is extremely friendly. The rooms are horrible. Our 1st room was literally infested with roaches. Roaches were in the bed. We didn't come in til 11pm or so and were so tired and had to deal with this. We tried calling around for another hotel but it was too late. The staff moved us to another room, no roaches but the sink was clogged. The carpet is soooooo filthy and the A/C was not working. Ive never been to Oakland before so I totally drop the ball on reading reviews before choosing a hotel.

Reviewed on Aug 25, 2024

Sonesta Emeryville - San Francisco Bay Bridge
3.0-star property

Sonesta Emeryville - San Francisco Bay Bridge

8.6/10 Excellent! (1,224 reviews)

Dec 26 - Dec 30

4 night stay

Chicago (CHI) to Oakland (OAK)

United • Roundtrip • Coach
Price was $651, price is now $542 per person
$542
per person
found 12 hours ago
The staff at this hotel is truly exceptional. They provided excellent customer service, and I had a wonderful conversation with the young lady who checked me in. I also had a pleasant interaction with one of the cleaning ladies. Both were incredibly friendly and welcoming. The hotel is very well-maintained, and parking is convenient. My vehicle is securely parked, which is a plus. I definitely plan to return in the future.

Reviewed on Oct 31, 2025

Lafayette Park Hotel & Spa
4.0-star property

Lafayette Park Hotel & Spa

9.4/10 Exceptional! (1,004 reviews)

Dec 26 - Jan 1

6 night stay

Chicago (ORD) to Oakland (OAK)

United • Roundtrip • Coach
Price was $1,304, price is now $1,100 per person
$1,100
per person
found 7 hours ago
Our stay was wonderful. The staff was very accommodating and attentive. We will definitely stay here again in the future.

Reviewed on Jul 19, 2024

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More About Flying To St. Helena from Chicago

Route Information for Flights from Chicago to St. Helena

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

Chicago to St. Helena

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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.