$70 Cheap flight deals from Chicago (CHI) to Cupertino (SJC)

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This Weekend's Flight Deals from Chicago to Cupertino

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, Nov 15 - Mon, Nov 17
MDW
Midway Intl.
SFO
San Francisco Intl.
$297 Roundtrip, found 13 hours ago
$297
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to San Francisco Intl., returning Mon, Nov 17, priced at $297 found 13 hours ago
Fri, Nov 14 - Tue, Nov 18
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$402 Roundtrip, just found
$402
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to San Francisco Intl., returning Tue, Nov 18, priced at $402 just found
Sat, Nov 15 - Mon, Nov 17
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$451 Roundtrip, found 14 hours ago
$451
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Mon, Nov 17, priced at $451 found 14 hours ago
Fri, Nov 14 - Tue, Nov 18
ORD
O'Hare Intl.
OAK
Oakland Intl.
$457 Roundtrip, found 4 days ago
$457
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Fri, Nov 14 from O'Hare Intl. to Oakland Intl., returning Tue, Nov 18, priced at $457 found 4 days ago

Airfares from $70 One Way, $142 Round Trip from Chicago to Cupertino

Prices starting at $142 for return flights and $70 for one-way flights to Cupertino 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, Jan 8 - Mon, Jan 12
MDW
Chicago
SFO
San Francisco
$142 Roundtrip, found 18 hours ago
$142
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Chicago to San Francisco, returning Mon, Jan 12, priced at $142 found 18 hours ago
Wed, Dec 17 - Thu, Jan 8
ORD
Chicago
SJC
San Jose
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Dec 17 from Chicago to San Jose, returning Thu, Jan 8, priced at $185 found 3 days ago
Wed, Dec 10 - Tue, Dec 16
ORD
Chicago
SFO
San Francisco
$207 Roundtrip, found 4 days ago
$207
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Wed, Dec 10 from Chicago to San Francisco, returning Tue, Dec 16, priced at $207 found 4 days ago
Mon, Jan 26 - Thu, Jan 29
RFD
Rockford
SFO
San Francisco
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jan 26 from Rockford to San Francisco, returning Thu, Jan 29, priced at $239 found 1 day ago
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
SFO
San Francisco
$239 Roundtrip, found 5 hours ago
$239
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Jan 17 from Chicago to San Francisco, returning Tue, Jan 20, priced at $239 found 5 hours ago

Cupertino economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Silicon Valley
4.0-star property

Sonesta Silicon Valley

9/10 Wonderful! (1,634 reviews)

Dec 24 - Dec 31

7 night stay

Chicago (CHI) to San Jose (SJC)

United • Roundtrip • Coach
Price was $693, price is now $498 per person
$498
per person
found 1 day ago
This was a nice property. The staff were pleasant and the check in was quick. The bed was good and the sheets were nice. The grounds and lobby were clean, the restaurant was nice and the food was decent (unfortunately, no free breakfast as it appeared on orbitz site). I would give this place a 7 (not a a 9.0 Wonderful rating like Orbitz has listed). No room cleaning and we were there 4 nights (not a huge deal, but we had to take our own garbage and ask for new towels). The pool and hot tub were both dirty. The hot tub was out of chemical balance and the pool needed the skimmer fixed. The prorperty is under construction, but they did shut down by 6pm which was fine for us. It was super loud at check in on a Thursday and if we weren't staying mostly over a weekend we would have been pretty frustrated.

Reviewed on Oct 11, 2025

@ Marbella Lane - 4BR Siliconvalley Gempool House
3.0-star property

@ Marbella Lane - 4BR Siliconvalley Gempool House

No reviews

Dec 27 - Dec 29

2 night stay

Chicago (CHI) to San Jose (SJC)

Southwest Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $2,026, price is now $1,657 per person
$1,657
per person
found 1 day ago
Shashi Hotel Mountain View Palo Alto
5.0-star property

Shashi Hotel Mountain View Palo Alto

9.4/10 Exceptional! (1,078 reviews)

Dec 29 - Jan 2

4 night stay

Chicago (ORD) to San Jose (SJC)

Southwest Airlines • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach
Price was $732, price is now $631 per person
$631
per person
found 19 hours ago
Good facilities like steam room and sauna

Reviewed on Sep 20, 2025

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More About Flying To Cupertino from Chicago

Route Information for Flights from Chicago to Cupertino

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

Chicago to Cupertino

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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.