$120 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.

Sat, Jun 6 - Sat, Jun 20
ORD
O'Hare Intl.
OAK
Oakland Intl.
$466 Roundtrip, found 2 days ago
$466
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Jun 6 from O'Hare Intl. to Oakland Intl., returning Sat, Jun 20, priced at $466 found 2 days ago
Sat, Jun 6 - Sat, Jun 13
MDW
Midway Intl.
OAK
Oakland Intl.
$490 Roundtrip, found 5 days ago
$490
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jun 6 from Midway Intl. to Oakland Intl., returning Sat, Jun 13, priced at $490 found 5 days ago
Sat, Jun 6 - Mon, Jun 8
ORD
O'Hare Intl.
STS
Sonoma County
$748 Roundtrip, found 3 hours ago
$748
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Sat, Jun 6 from O'Hare Intl. to Sonoma County, returning Mon, Jun 8, priced at $748 found 3 hours ago

Airfares from $120 One Way, $269 Round Trip from Chicago to Calistoga

Prices starting at $269 for return flights and $120 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.

Thu, Sep 17 - Sat, Sep 19
MDW
Chicago
OAK
Oakland
$269 Roundtrip, found 12 hours ago
$269
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Chicago to Oakland, returning Sat, Sep 19, priced at $269 found 12 hours ago
Wed, Jun 24 - Tue, Jun 30
ORD
Chicago
OAK
Oakland
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Jun 24 from Chicago to Oakland, returning Tue, Jun 30, priced at $273 found 1 day ago
Thu, Sep 17 - Sat, Sep 19
MDW
Chicago
OAK
Oakland
$275 Roundtrip, found 12 hours ago
$275
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Chicago to Oakland, returning Sat, Sep 19, priced at $275 found 12 hours ago
Thu, Sep 17 - Sat, Sep 19
MDW
Chicago
OAK
Oakland
$279 Roundtrip, found 12 hours ago
$279
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Chicago to Oakland, returning Sat, Sep 19, priced at $279 found 12 hours ago
Tue, Aug 18 - Thu, Aug 20
ORD
Chicago
OAK
Oakland
$281 Roundtrip, found 2 days ago
$281
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Aug 18 from Chicago to Oakland, returning Thu, Aug 20, priced at $281 found 2 days ago

Calistoga economy flight packages

Price found within the past 48 hours. Click for updated prices.
Claremont Resort & Club
5.0-star property

Claremont Resort & Club

9/10 Wonderful! (1,007 reviews)

Jul 20 - Jul 23

3 night stay

Chicago (CHI) to Oakland (OAK)

American Airlines • Coach

Oakland (OAK) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,108, price is now $695 per person
$695
per person
found 18 hours ago
50$/night facility fee is charged for every night I stayed there. This was not clear to me at the time of booking. Overall a good hotel.

Reviewed on May 25, 2024

Solage, Auberge Collection
5.0-star property

Solage, Auberge Collection

9.6/10 Exceptional! (725 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • Coach

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,106, price is now $1,547 per person
$1,547
per person
found 1 day ago
We have been going to Solage since 2010. Back then it was the nicest property in Calistoga. The problem is that that management has upgraded since 2010, or so it feels like. Pros are the following: 1. Property is still manicured well with staff on site ensuring both cleanliness and aesthetic. 2. Spa is still pretty nice. 3. Service was solid, overall..not the best but still in the top 10-15% of hotels. Cons: 1. Property has not been remodeled in some time and it shows. While it’s well maintained, the technology is nonexistent and quite frankly outdated; 2. Solbar does not deserve a Michelin recommendation or star. It was so disappointing. For starters the bacon was clearly thrown in the deep fryer, not cooked on the griddled. The smashed potatoes they are known for weren’t crispy and it appeared as though the oil wasn’t changed for many days. The fruit bowl was clunky. If I’m paying $16.00 for a fruit bowl, you should take the time and peel the fruit, present it nicely and make it beautiful. It was not that, just thrown together with little to no care. Dining room was load with kids. This is supposed to be a relaxing retreat not kids running around like Disneyland. If I wanted that experience I would go to the OC. Needless to say I did not enjoy paying $150 for breakfast and have such an awful experience. 3. A few more comments on the room and being outdated and old. The property is pretty dingy. The common areas are not well maintained.

Reviewed on Dec 25, 2025

Home2 Suites by Hilton Alameda Oakland Airport
3.0-star property

Home2 Suites by Hilton Alameda Oakland Airport

9/10 Wonderful! (525 reviews)

Jul 5 - Jul 8

3 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $1,043, price is now $767 per person
$767
per person
found 1 day ago
Airport noise , if you deep sleeper then its perfect.

Reviewed on Mar 30, 2026

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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.