$61 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.

Fri, Dec 12 - Mon, Dec 15
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$305 Roundtrip, found 8 hours ago
$305
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from O'Hare Intl. to San Francisco Intl., returning Mon, Dec 15, priced at $305 found 8 hours ago
Fri, Dec 12 - Sun, Dec 14
MDW
Midway Intl.
SFO
San Francisco Intl.
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Midway Intl. to San Francisco Intl., returning Sun, Dec 14, priced at $310 found 2 days ago
Sat, Dec 13 - Tue, Dec 16
ORD
O'Hare Intl.
OAK
Oakland Intl.
$330 Roundtrip, found 6 days ago
$330
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Dec 13 from O'Hare Intl. to Oakland Intl., returning Tue, Dec 16, priced at $330 found 6 days ago
Sat, Dec 13 - Sun, Dec 14
MDW
Midway Intl.
OAK
Oakland Intl.
$365 Roundtrip, found 6 days ago
$365
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Midway Intl. to Oakland Intl., returning Sun, Dec 14, priced at $365 found 6 days ago

Airfares from $61 One Way, $122 Round Trip from Chicago to Alameda

Prices starting at $122 for return flights and $61 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 18 - Wed, Feb 25
ORD
Chicago
SJC
San Jose
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Chicago to San Jose, returning Wed, Feb 25, priced at $122 found 3 days ago
Tue, Feb 10 - Sat, Feb 14
ORD
Chicago
SFO
San Francisco
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 10 from Chicago to San Francisco, returning Sat, Feb 14, priced at $142 found 2 days ago
Tue, Feb 17 - Thu, Feb 19
ORD
Chicago
SFO
San Francisco
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select United flight, departing Tue, Feb 17 from Chicago to San Francisco, returning Thu, Feb 19, priced at $145 found 1 day ago
Wed, Jan 21 - Wed, Jan 28
ORD
Chicago
SFO
San Francisco
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jan 21 from Chicago to San Francisco, returning Wed, Jan 28, priced at $164 found 5 days ago
Sat, Jan 17 - Tue, Jan 20
MDW
Chicago
SFO
San Francisco
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $164 found 5 days ago

Alameda economy flight packages

Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort
3.0-star property

RiverPointe Napa Valley Resort

8.8/10 Excellent! (1,344 reviews)

Jan 24 - Jan 27

3 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $596, price is now $405 per person
$405
per person
found 1 day ago
The property was way overpriced for the studio, but the front desk could not have been nicer and the grounds were amazing and quiet.

Reviewed on Oct 13, 2025

Alila Napa Valley, a Hyatt Luxury Resort
5.0-star property

Alila Napa Valley, a Hyatt Luxury Resort

9.4/10 Exceptional! (110 reviews)

Jan 26 - Jan 30

4 night stay

Chicago (ORD) to Oakland (OAK)

Frontier Airlines • Non-stop • Coach

Oakland (OAK) to Chicago (ORD)

United • Non-stop • Coach
Save 100% on your flight
Price was $2,183, price is now $1,481 per person
$1,481
per person
found 1 day ago
MacArthur Place Hotel & Spa
4.0-star property

MacArthur Place Hotel & Spa

9.4/10 Exceptional! (847 reviews)

Jan 15 - Jan 19

4 night stay

Chicago (ORD) to Oakland (OAK)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,155, price is now $1,509 per person
$1,509
per person
found 1 day ago
A wonderful place to celebrate a special occassion. The spa experience was one of the best I have had and the dining and bar excellent! Our room was perfect with all the amentities we needed. Plus, close to great wine tasting and dining options. The staff really made us feel special too!

Reviewed on Nov 11, 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.