$109 Cheap flight deals from Chicago (CHI) to Capitola (SJC)

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This Weekend's Flight Deals from Chicago to Capitola

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, Sep 5 - Sat, Sep 19
ORD
O'Hare Intl.
MRY
Monterey Peninsula
$414 Roundtrip, found 4 days ago
$414
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sat, Sep 5 from O'Hare Intl. to Monterey Peninsula, returning Sat, Sep 19, priced at $414 found 4 days ago
Sun, Sep 6 - Sun, Sep 13
ORD
O'Hare Intl.
SJC
Norman Y. Mineta San Jose Intl.
$490 Roundtrip, found 3 days ago
$490
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sun, Sep 6 from O'Hare Intl. to Norman Y. Mineta San Jose Intl., returning Sun, Sep 13, priced at $490 found 3 days ago

Airfares from $109 One Way, $217 Round Trip from Chicago to Capitola

Prices starting at $217 for return flights and $109 for one-way flights to Capitola 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, Sep 30 - Mon, Oct 5
ORD
Chicago
SJC
San Jose
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, Sep 30 from Chicago to San Jose, returning Mon, Oct 5, priced at $217 found 1 hour ago
Wed, Sep 30 - Mon, Oct 5
ORD
Chicago
SJC
San Jose
$220 Roundtrip, found 1 hour ago
$220
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, Sep 30 from Chicago to San Jose, returning Mon, Oct 5, priced at $220 found 1 hour ago
Thu, Nov 19 - Mon, Nov 23
ORD
Chicago
SJC
San Jose
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Thu, Nov 19 from Chicago to San Jose, returning Mon, Nov 23, priced at $247 found 1 hour ago
Thu, Nov 19 - Mon, Nov 23
ORD
Chicago
SJC
San Jose
$248 Roundtrip, found 1 hour ago
$248
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Chicago to San Jose, returning Mon, Nov 23, priced at $248 found 1 hour ago
Sun, Oct 18 - Thu, Oct 22
ORD
Chicago
SJC
San Jose
$250 Roundtrip, found 1 hour ago
$250
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Oct 18 from Chicago to San Jose, returning Thu, Oct 22, priced at $250 found 1 hour ago

Capitola economy flight packages

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel
2.0-star property

The LEEF Hotel

8.6/10 Excellent! (817 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Los Angeles (LAX)

Frontier Airlines • Coach

Los Angeles (LAX) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $780, price is now $385 per person
$385
per person
found 1 day ago
⚠️ FAIR WARNING to anyone thinking about booking a stay at THE LEEF. We stayed for 3 days/2 nights. The room itself is cute, and while there’s no microwave—which is inconvenient—it wasn’t a huge deal. What IS a huge deal is that we found TWO ROACHES in our room on the very first night. I reported it the following morning, but they weren’t able to provide us with a different room. Instead, I was offered cleaning services for that day and one day of free parking (aka $10) as compensation. However, on the next morning - checkout day, we found TWO MORE ROACHES. Four roaches during a two-night stay is absolutely unacceptable. A hotel should be able to provide guests with a clean, pest-free room, and the fact that we continued finding roaches after reporting the issue is disgusting. And don’t expect much when it comes to customer service. The so-called “lobby” is essentially just a screen with a virtual representative. When you have an actual issue that requires assistance, it makes the experience even more frustrating. I genuinely hope no one else has to worry about accidentally bringing roaches home with them after staying here. Do yourself a favor: if you value cleanliness and want a pest-free stay, DON’T STAY AT THE LEEF.

Reviewed on Aug 31, 2026

SIRTAJ - Beverly Hills
4.0-star property

SIRTAJ - Beverly Hills

8.2/10 Very Good! (1,006 reviews)

Oct 15 - Oct 18

3 night stay

Chicago (CHI) to Los Angeles (LAX)

Frontier Airlines • Roundtrip • Coach
Price was $963, price is now $467 per person
$467
per person
found 1 day ago
In general the property is fine. It was clean, the bed was comfortable and the shower was hot. It also has a great location. I had to book in a rush and I almost cancelled the reservation mid flight. The reviews I read were awful. The property did not reflect that in my opinion. Parking is expensive. There is ongoing construction, and a dumpster was right outside my first floor window. Fortunately, I was in LA for work so I did not have to bear the noise during the day. When I returned each evening construction had stopped for the day. Noise, overnight, in the building was nominal. The hotel is very no frills. There is no food nor a bar onsite, although a water machine is in the lobby. I would not stay with my family, as the rooms are very small. Overall the property is great for a single business traveller.

Reviewed on Sep 3, 2026

Four Seasons Hotel San Francisco
5.0-star property

Four Seasons Hotel San Francisco

9.4/10 Exceptional! (1,003 reviews)

Oct 9 - Oct 16

7 night stay

Chicago (CHI) to San Francisco (SFO)

Southwest Airlines • Coach

San Francisco (SFO) to Chicago (CHI)

Frontier Airlines • Coach
Price was $7,553, price is now $3,817 per person
$3,817
per person
found 1 day ago

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Capitola packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn LAX Los Angeles Airport
3.0-star property

Hilton Garden Inn LAX Los Angeles Airport

8.2/10 Very Good! (2,177 reviews)

Oct 11 - Oct 17

6 night stay

Chicago (CHI) to Los Angeles (LAX)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,165, price is now $856 per person
$856
per person
found 24 hours ago

Venice V Hotel
3.0-star property

Venice V Hotel

9.2/10 Wonderful! (794 reviews)

Oct 11 - Oct 17

6 night stay

Chicago (CHI) to Los Angeles (LAX)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,681, price is now $1,221 per person
$1,221
per person
found 24 hours ago
Room was small, elevator slow asl. No gym or pool. But at least they charge you 30 dollars a day for towels and a speaker that you can’t keep. Only reason 4 stars because it was clean and the staff were nice.

Reviewed on Sep 2, 2026

Foghorn Harbor Inn
3.0-star property

Foghorn Harbor Inn

7.8/10 Good! (1,186 reviews)

Oct 11 - Oct 17

6 night stay

Chicago (CHI) to Los Angeles (LAX)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,241, price is now $947 per person
$947
per person
found 24 hours ago

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Capitola first class flight packages

Price found within the past 48 hours. Click for updated prices.
Gjelina Hotel
2.0-star property

Gjelina Hotel

9.6/10 Exceptional! (97 reviews)

Oct 18 - Oct 21

3 night stay

Chicago (ORD) to Los Angeles (LAX)

Delta • Non-stop • FirstClass

Los Angeles (LAX) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $1,744, price is now $1,461 per person
$1,461
per person
found 1 day ago

1 Hotel West Hollywood
5.0-star property

1 Hotel West Hollywood

8.8/10 Excellent! (1,020 reviews)

Oct 18 - Oct 21

3 night stay

Chicago (ORD) to Los Angeles (LAX)

Delta • Non-stop • FirstClass

Los Angeles (LAX) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $11,439, price is now $8,636 per person
$8,636
per person
found 1 day ago

The Maybourne Beverly Hills, Maybourne
5.0-star property

The Maybourne Beverly Hills, Maybourne

9.6/10 Exceptional! (324 reviews)

Oct 18 - Oct 21

3 night stay

Chicago (ORD) to Los Angeles (LAX)

Delta • Non-stop • FirstClass

Los Angeles (LAX) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $4,953, price is now $4,155 per person
$4,155
per person
found 1 day ago

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More About Flying To Capitola from Chicago

Route Information for Flights from Chicago to Capitola

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

Chicago to Capitola

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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.