$47 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.

Fri, May 10 - Tue, May 14
MDW
Midway Intl.
SFO
San Francisco Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 10 from Midway Intl. to San Francisco Intl., returning Tue, May 14, priced at $167 found 1 hour ago
Sat, May 11 - Mon, May 13
ORD
O'Hare Intl.
OAK
Oakland Intl.
$238 Roundtrip, found 16 hours ago
$238
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sat, May 11 from O'Hare Intl. to Oakland Intl., returning Mon, May 13, priced at $238 found 16 hours ago
Fri, May 10 - Mon, May 13
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$323 Roundtrip, found 9 hours ago
$323
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Fri, May 10 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Mon, May 13, priced at $323 found 9 hours ago
Sat, May 11 - Wed, May 15
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$332 Roundtrip, found 1 hour ago
$332
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 11 from O'Hare Intl. to San Francisco Intl., returning Wed, May 15, priced at $332 found 1 hour ago

Airfares from $47 One Way, $103 Round Trip from Chicago to Cupertino

Prices starting at $103 for return flights and $47 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.

Tue, May 21 - Wed, May 29
ORD
Chicago
SJC
San Jose
$103 Roundtrip, found 16 hours ago
$103
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Tue, May 21 from Chicago to San Jose, returning Wed, May 29, priced at $103 found 16 hours ago
Tue, May 21 - Wed, May 29
ORD
Chicago
OAK
Oakland
$110 Roundtrip, found 16 hours ago
$110
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Tue, May 21 from Chicago to Oakland, returning Wed, May 29, priced at $110 found 16 hours ago
Sun, May 26 - Thu, May 30
ORD
Chicago
OAK
Oakland
$179 Roundtrip, found 18 hours ago
$179
Roundtrip
found 18 hours ago
Select Sun Country Airlines flight, departing Sun, May 26 from Chicago to Oakland, returning Thu, May 30, priced at $179 found 18 hours ago
Sat, Sep 28 - Tue, Oct 1
ORD
Chicago
SFO
San Francisco
$183 Roundtrip, found 13 hours ago
$183
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Sat, Sep 28 from Chicago to San Francisco, returning Tue, Oct 1, priced at $183 found 13 hours ago
Sat, Sep 28 - Tue, Oct 1
ORD
Chicago
SFO
San Francisco
$189 Roundtrip, found 13 hours ago
$189
Roundtrip
found 13 hours ago
Select United flight, departing Sat, Sep 28 from Chicago to San Francisco, returning Tue, Oct 1, priced at $189 found 13 hours ago

Cupertino economy flight packages

Price found within the past 48 hours. Click for updated prices.
Aqua Breeze Inn
2.5-star property

Aqua Breeze Inn

7.6/10 Good! (1,001 reviews)

Jun 23 - Jun 29

6 night stay

Chicago (ORD) to San Jose (SJC)

United • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
per person
Great place so close to the boardwalk! Amazing view from the top deck with tables and chairs outside. Kids happy with the two bedrooms.

Reviewed on Apr 1, 2024

Howard Johnson by Wyndham Santa Cruz Beach Boardwalk
2.0-star property

Howard Johnson by Wyndham Santa Cruz Beach Boardwalk

7/10 Good! (1,000 reviews)

Jun 23 - Jun 29

6 night stay

Chicago (ORD) to San Jose (SJC)

United • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach
per person
There were two gentlemen with leaf blowers who spent too much time blowing leaves. I can forgive a quick clean up but this seemed to go on and on and on.... Otherwise the room was clean and warm. The refridge was set to freeze so out breakfast OJ was solid when we woke up. The front staff was kind and helpful. We'll be back.

Reviewed on Feb 24, 2022

Chaminade Resort & Spa
4.0-star property

Chaminade Resort & Spa

7.8/10 Good! (1,007 reviews)

Jun 23 - Jun 29

6 night stay

Chicago (ORD) to San Jose (SJC)

United • Non-stop • Coach

San Jose (SJC) to Chicago (ORD)

Spirit Airlines • Non-stop • Coach
per person
Awesome check in and later Chris on the front desk was extremely accommodating for sure. Restaurant was ok. Loud from sound acoustics. Servers were extremely warm and welcoming, food was good but not outstanding and service was initially very slow; 10 minutes before a server came over.

Reviewed on Nov 18, 2023

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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
1842 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Aer Lingus, Austrian, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Royal Jordanian, Finnair, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
3:56PM UTC
Latest Flight Arrival
7:38AM UTC

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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.