$119 Cheap flight deals from Chicago (CHI) to Calistoga (OAK)

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This Weekend's Flight Deals from Chicago to Calistoga

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.

Sun, Dec 21 - Wed, Dec 31
ORD
O'Hare Intl.
OAK
Oakland Intl.
$581 Roundtrip, found 1 day ago
$581
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sun, Dec 21 from O'Hare Intl. to Oakland Intl., returning Wed, Dec 31, priced at $581 found 1 day ago
Sun, Dec 21 - Tue, Jan 6
ORD
O'Hare Intl.
STS
Sonoma County
$635 Roundtrip, found 5 days ago
$635
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Sun, Dec 21 from O'Hare Intl. to Sonoma County, returning Tue, Jan 6, priced at $635 found 5 days ago
Sun, Dec 21 - Wed, Dec 31
MDW
Midway Intl.
OAK
Oakland Intl.
$743 Roundtrip, found 1 day ago
$743
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Dec 21 from Midway Intl. to Oakland Intl., returning Wed, Dec 31, priced at $743 found 1 day ago

Airfares from $119 One Way, $242 Round Trip from Chicago to Calistoga

Prices starting at $242 for return flights and $119 for one-way flights to Calistoga were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
OAK
Oakland
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Oakland, returning Tue, Jan 20, priced at $242 found 2 days ago
Wed, Feb 18 - Wed, Mar 4
ORD
Chicago
OAK
Oakland
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Chicago to Oakland, returning Wed, Mar 4, priced at $248 found 1 day ago
Sat, Feb 14 - Wed, Mar 4
ORD
Chicago
OAK
Oakland
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Feb 14 from Chicago to Oakland, returning Wed, Mar 4, priced at $254 found 1 day ago
Wed, Feb 18 - Sat, Feb 28
ORD
Chicago
OAK
Oakland
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Chicago to Oakland, returning Sat, Feb 28, priced at $255 found 1 day ago
Wed, Jan 14 - Wed, Jan 28
ORD
Chicago
OAK
Oakland
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Oakland, returning Wed, Jan 28, priced at $257 found 6 days ago

Calistoga economy flight packages

Price found within the past 48 hours. Click for updated prices.
Dream catcher
2.5-star property

Dream catcher

5.6/10 (87 reviews)

Jan 17 - Jan 20

3 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Roundtrip • Coach
Price was $378, price is now $298 per person
$298
per person
found 11 hours ago
DoubleTree by Hilton Hotel Berkeley Marina
4.0-star property

DoubleTree by Hilton Hotel Berkeley Marina

8.2/10 Very Good! (3,745 reviews)

Jan 17 - Jan 20

3 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Roundtrip • Coach
Price was $588, price is now $404 per person
$404
per person
found 11 hours ago
Noisy- the laundry machine was running the whole evening

Reviewed on Nov 10, 2025

Homewood Suites by Hilton Oakland-Waterfront
3.0-star property

Homewood Suites by Hilton Oakland-Waterfront

7.8/10 Good! (664 reviews)

Jan 17 - Jan 20

3 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Roundtrip • Coach
Price was $489, price is now $381 per person
$381
per person
found 11 hours ago
Breakfast was ok, would have liked more turkey or beef breakfast sausage or bacon instead of pork. Not sure if this is a pet friendly hotel

Reviewed on Dec 12, 2025

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More About Flying To Calistoga from Chicago

Route Information for Flights from Chicago to Calistoga

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

Chicago to Calistoga

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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.