Helena Vacations

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Helena Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Urban Boutique Hotel

Urban Boutique Hotel

Downtown San Diego
Save 100% on your flight
$732
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Diego and Petco Park are located nearby.
I really loved that it was a small hotel and close to everything in Little Italy. Will totally stay there again!

Reviewed on Sep 24, 2026

The Sofia Hotel

The Sofia Hotel

Downtown San Diego
$735
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
Book a stay at this historic hotel in San Diego. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Diego and Petco Park are located nearby.
Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

Fisherman's Wharf
Save 100% on your flight
$756
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Francisco (SFO)
Book a stay at this business-friendly hotel in San Francisco. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 39 and Lombard Street are located nearby.
Bahia Resort Hotel

Bahia Resort Hotel

Central Mission Beach
Save 100% on your flight
$737
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
Book a stay at this business-friendly resort in San Diego. Enjoy breakfast (surcharge), 24-hour room service, and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego
Save 100% on your flight
$1,049
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy a rooftop terrace, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Petco Park and Port of San Diego are located nearby.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

Mission Bay
Save 100% on your flight
$918
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Diego (SAN)
Book a stay at this beach resort in San Diego. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Mission Bay and Mission Beach are located nearby.
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Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Oct 14 - Wed, Oct 21
SEA
Seattle - Tacoma Intl.
RDD
Redding Municipal
$301
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct 14 from Seattle - Tacoma Intl. to Redding Municipal, returning Wed, Oct 21, priced at $301 found 4 days ago
Alaska Airlines
Alaska Airlines
Alaska Airlines