$114 Cheap flight deals from Chicago (CHI) to Sunnyvale (SJC)

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This Weekend's Flight Deals from Chicago to Sunnyvale

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, May 29 - Wed, Jun 3
MDW
Midway Intl.
SFO
San Francisco Intl.
$346 Roundtrip, found 3 days ago
$346
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, May 29 from Midway Intl. to San Francisco Intl., returning Wed, Jun 3, priced at $346 found 3 days ago
Sun, May 31 - Wed, Jun 3
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$346 Roundtrip, found 5 hours ago
$346
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, May 31 from O'Hare Intl. to San Francisco Intl., returning Wed, Jun 3, priced at $346 found 5 hours ago
Sat, May 30 - Tue, Jun 2
ORD
O'Hare Intl.
OAK
Oakland Intl.
$407 Roundtrip, found 5 days ago
$407
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sat, May 30 from O'Hare Intl. to Oakland Intl., returning Tue, Jun 2, priced at $407 found 5 days ago
Sun, May 31 - Mon, Jul 6
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$473 Roundtrip, found 1 day ago
$473
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, May 31 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Mon, Jul 6, priced at $473 found 1 day ago

Airfares from $114 One Way, $215 Round Trip from Chicago to Sunnyvale

Prices starting at $215 for return flights and $114 for one-way flights to Sunnyvale 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, Jul 22 - Sat, Jul 25
ORD
Chicago
SFO
San Francisco
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jul 22 from Chicago to San Francisco, returning Sat, Jul 25, priced at $215 found 3 days ago
Sat, Aug 22 - Sun, Aug 30
MDW
Chicago
SFO
San Francisco
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Chicago to San Francisco, returning Sun, Aug 30, priced at $248 found 4 days ago
Wed, Aug 12 - Tue, Aug 18
ORD
Chicago
SFO
San Francisco
$253 Roundtrip, found 18 hours ago
$253
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Chicago to San Francisco, returning Tue, Aug 18, priced at $253 found 18 hours ago
Wed, Sep 30 - Tue, Oct 6
MDW
Chicago
SFO
San Francisco
$253 Roundtrip, found 5 hours ago
$253
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Sep 30 from Chicago to San Francisco, returning Tue, Oct 6, priced at $253 found 5 hours ago
Wed, Aug 12 - Tue, Aug 18
ORD
Chicago
SFO
San Francisco
$253 Roundtrip, found 18 hours ago
$253
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Aug 12 from Chicago to San Francisco, returning Tue, Aug 18, priced at $253 found 18 hours ago

Sunnyvale economy flight packages

Price found within the past 48 hours. Click for updated prices.
Bay Landing San Francisco Airport Hotel
3.0-star property

Bay Landing San Francisco Airport Hotel

9/10 Wonderful! (4,872 reviews)

Jul 8 - Jul 14

6 night stay

Chicago (CHI) to San Francisco (SFO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $898, price is now $591 per person
$591
per person
found 1 day ago
It is great hotel. Clean, well maintained, nice gym facilities, great view, nice location.

Reviewed on May 21, 2026

The Stevenson Monterey
2.5-star property

The Stevenson Monterey

8.8/10 Excellent! (1,017 reviews)

Jul 18 - Jul 24

6 night stay

Chicago (CHI) to San Francisco (SFO)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,239, price is now $833 per person
$833
per person
found 11 hours ago
We stayed here for a quick overnight stop based on other reviews. The staff was so friendly and the room was clean and comfortable. Rooms are tiny and the bathroom was very small but fine for a short stay. You do hear a lot of street noise but with the window closed and air on you can’t hear anything. It is located on the edge of town next to a gas station and across from a Dennys but those were not a deterrent for us. It’s a quick drive to the Wharf. Great price too!

Reviewed on Apr 15, 2026

Treehouse Hotel Silicon Valley
5.0-star property

Treehouse Hotel Silicon Valley

9.8/10 Exceptional! (91 reviews)

Jul 1 - Jul 7

6 night stay

Chicago (CHI) to San Francisco (SFO)

American Airlines • Coach

San Francisco (SFO) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,785, price is now $1,923 per person
$1,923
per person
found 5 hours ago
Such a wonderful place to stay ; the pool is awesome !

Reviewed on Jul 28, 2025

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More About Flying To Sunnyvale from Chicago

Route Information for Flights from Chicago to Sunnyvale

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

Chicago to Sunnyvale

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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.