$74 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 17 - Tue, Jan 20
MDW
Midway Intl.
OAK
Oakland Intl.
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Midway Intl. to Oakland Intl., returning Tue, Jan 20, priced at $288 found 6 days ago
Sat, Jan 17 - Wed, Feb 4
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$360 Roundtrip, found 3 days ago
$360
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Jan 17 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Wed, Feb 4, priced at $360 found 3 days ago
Sun, Jan 18 - Sat, Jan 31
MDW
Midway Intl.
SFO
San Francisco Intl.
$403 Roundtrip, found 2 days ago
$403
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jan 18 from Midway Intl. to San Francisco Intl., returning Sat, Jan 31, priced at $403 found 2 days ago
Fri, Jan 16 - Sun, Jan 25
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$413 Roundtrip, found 1 hour ago
$413
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jan 16 from O'Hare Intl. to San Francisco Intl., returning Sun, Jan 25, priced at $413 found 1 hour ago

Airfares from $74 One Way, $144 Round Trip from Chicago to Alameda

Prices starting at $144 for return flights and $74 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.

Tue, Apr 7 - Mon, Apr 13
ORD
Chicago
SFO
San Francisco
$144 Roundtrip, found 4 days ago
$144
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Apr 7 from Chicago to San Francisco, returning Mon, Apr 13, priced at $144 found 4 days ago
Thu, Apr 30 - Tue, May 12
ORD
Chicago
OAK
Oakland
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Apr 30 from Chicago to Oakland, returning Tue, May 12, priced at $159 found 3 days ago
Tue, Mar 10 - Wed, Apr 1
MDW
Chicago
SFO
San Francisco
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Chicago to San Francisco, returning Wed, Apr 1, priced at $160 found 2 days ago
Wed, Mar 11 - Mon, Mar 16
ORD
Chicago
SJC
San Jose
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Mar 11 from Chicago to San Jose, returning Mon, Mar 16, priced at $173 found 3 days ago
Wed, Jan 28 - Fri, Jan 30
ORD
Chicago
SJC
San Jose
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 28 from Chicago to San Jose, returning Fri, Jan 30, priced at $177 found 3 days ago

Alameda economy flight packages

Price found within the past 48 hours. Click for updated prices.
MacArthur Place Hotel & Spa
4.0-star property

MacArthur Place Hotel & Spa

9.4/10 Exceptional! (847 reviews)

Feb 12 - Feb 16

4 night stay

Chicago (CHI) to Oakland (OAK)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,116, price is now $1,516 per person
$1,516
per person
found 15 hours 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

Claremont Resort & Club
5.0-star property

Claremont Resort & Club

8.8/10 Excellent! (1,003 reviews)

Feb 24 - Feb 28

4 night stay

Chicago (CHI) to Oakland (OAK)

Delta • Non-stop • Coach

Oakland (OAK) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,105, price is now $1,862 per person
$1,862
per person
found 1 day ago
50$/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

Farmhouse Inn
5.0-star property

Farmhouse Inn

9.4/10 Exceptional! (68 reviews)

Mar 1 - Mar 6

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • Coach

Oakland (OAK) to Chicago (ORD)

Delta • Coach
Price was $3,066, price is now $2,138 per person
$2,138
per person
found 1 day ago
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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.