$76 Cheap flight deals from Chicago (CHI) to Alameda (SJC)

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This Weekend's Flight Deals from Chicago to Alameda

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, Jan 10 - Sun, Jan 11
MDW
Midway Intl.
SFO
San Francisco Intl.
$263 Roundtrip, found 3 days ago
$263
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Midway Intl. to San Francisco Intl., returning Sun, Jan 11, priced at $263 found 3 days ago
Sun, Jan 11 - Thu, Jan 15
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to San Francisco Intl., returning Thu, Jan 15, priced at $269 found 2 hours ago
Fri, Jan 9 - Sun, Jan 11
ORD
O'Hare Intl.
OAK
Oakland Intl.
$369 Roundtrip, found 8 hours ago
$369
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Fri, Jan 9 from O'Hare Intl. to Oakland Intl., returning Sun, Jan 11, priced at $369 found 8 hours ago
Fri, Jan 9 - Mon, Jan 12
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$391 Roundtrip, just found
$391
Roundtrip
just found
Select Bargain Flight flight, departing Fri, Jan 9 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Mon, Jan 12, priced at $391 just found

Airfares from $76 One Way, $164 Round Trip from Chicago to Alameda

Prices starting at $164 for return flights and $76 for one-way flights to Alameda 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, Feb 11 - Wed, Feb 18
ORD
Chicago
SFO
San Francisco
$164 Roundtrip, found 10 hours ago
$164
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Feb 11 from Chicago to San Francisco, returning Wed, Feb 18, priced at $164 found 10 hours ago
Thu, Feb 19 - Mon, Feb 23
MDW
Chicago
SFO
San Francisco
$182 Roundtrip, found 1 hour ago
$182
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Chicago to San Francisco, returning Mon, Feb 23, priced at $182 found 1 hour ago
Sat, Jan 17 - Tue, Jan 20
RFD
Rockford
SFO
San Francisco
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Rockford to San Francisco, returning Tue, Jan 20, priced at $223 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
SFO
San Francisco
$223 Roundtrip, found 1 hour ago
$223
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $223 found 1 hour ago
Tue, Mar 3 - Wed, Mar 4
ORD
Chicago
SFO
San Francisco
$224 Roundtrip, found 2 hours ago
$224
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Mar 3 from Chicago to San Francisco, returning Wed, Mar 4, priced at $224 found 2 hours ago

Alameda economy flight packages

Price found within the past 48 hours. Click for updated prices.
Calistoga Motor Lodge and Spa
4.0-star property

Calistoga Motor Lodge and Spa

8.6/10 Excellent! (305 reviews)

Feb 27 - Mar 3

4 night stay

Chicago (ORD) to Oakland (OAK)

Alaska Airlines • Non-stop • Coach

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $920, price is now $600 per person
$600
per person
found 14 hours ago
On-site spa, bikes available to ride to town and wineries, soaking in the mineral pools until late… perfect for a relaxing getaway.

Reviewed on Sep 14, 2025

Solage, Auberge Collection
5.0-star property

Solage, Auberge Collection

9.4/10 Exceptional! (679 reviews)

Feb 12 - Feb 17

5 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,938, price is now $1,939 per person
$1,939
per person
found 9 hours 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

Elm House Inn
2.5-star property

Elm House Inn

9.6/10 Exceptional! (1,410 reviews)

Feb 12 - Feb 16

4 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $891, price is now $618 per person
$618
per person
found 9 hours ago
Amazing Bed and Breakfast. The rooms were so nice, extremely comfortable bed, spacious bathrooms. The staff was AMAZING!!

Reviewed on Jul 28, 2025

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More About Flying To Alameda from Chicago

Route Information for Flights from Chicago to Alameda

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

Chicago to Alameda

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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.