Search Deals on
Doss Vacation Packages

Build your package with 2 more options

Doss Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites San Antonio North - Windcrest by IHG

Holiday Inn Express & Suites San Antonio North - Windcrest by IHG

2.5 out of 5
Price was $586, price is now $490 per person
$490
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this business-friendly hotel in San Antonio. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions San Antonio Zoo and Aquarium and Morgan's Wonderland are located nearby.

Hotel Contessa

Hotel Contessa

4 out of 5
Price was $862, price is now $629 per person
$629
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this spa hotel in San Antonio. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions River Walk and San Antonio River are located nearby.
I can’t wait to visit again. Beautiful hotel, with an Old World Spanish feel.

Reviewed on Jul 15, 2026

Hyatt Regency Hill Country Resort and Villas

Hyatt Regency Hill Country Resort and Villas

4 out of 5
Price was $1,084, price is now $809 per person
$809
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this golf hotel in San Antonio. Enjoy free WiFi, 3 outdoor pools, and 5 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Aquatica San Antonio Waterpark and Hill Country Golf Club are located nearby.
The property is amazing for families, from popsicles to pop up games of kickball - they do so much more than just offering great pools

Reviewed on Jul 9, 2026

Menger Hotel

Menger Hotel

3.5 out of 5
Price was $754, price is now $604 per person
$604
per person
Sep 16 - Sep 20
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this historic hotel in San Antonio. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the pool and the bar in our reviews. Popular attractions River Walk and San Antonio River are located nearby.
Clean, comfortable room and a prime location. Walking distance to many San Antonio must sees. Valet parking was very convenient.

Reviewed on Jul 16, 2026

La Luz

La Luz

3 out of 5
Price was $643, price is now $521 per person
$521
per person
Sep 11 - Sep 14
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Stay at this aparthotel in San Antonio. Enjoy free WiFi, laundry facilities, and premium bedding. Popular attractions Alamo and River Walk are located nearby.
I love the location, the ease of having washer and dryer in the unit rather than just on the property. And how quick the honor was to respond to a couple simple issues and fixes we had while I was there.

Reviewed on Jun 28, 2026

Staybridge Suites San Antonio by IHG

Staybridge Suites San Antonio by IHG

3 out of 5
Price was $604, price is now $491 per person
$491
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this business-friendly hotel in San Antonio. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions San Antonio Zoo and Aquarium and North Star Mall are located nearby.
Good overall experience. Some parking lot construction and one elevator was not functional. Good breakfast and nice staff.

Reviewed on Jul 6, 2026

Mokara Hotel & Spa San Antonio

Mokara Hotel & Spa San Antonio

4.5 out of 5
Price was $1,083, price is now $904 per person
$904
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Book a stay at this luxury hotel in San Antonio. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions San Antonio River and River Walk are located nearby.
Great staff. Great location.

Reviewed on Jul 15, 2026

Landing Apartments San Antonio near Baptist Neighborhood Hospital

Landing Apartments San Antonio near Baptist Neighborhood Hospital

3 out of 5
Price was $804, price is now $676 per person
$676
per person
Sep 16 - Sep 20
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Stay at this apartment in San Antonio. Enjoy free parking, an outdoor pool, and an in-room coffeemaker. Popular attractions San Antonio River and Alamodome are located nearby.

Doss Vacation Packages 3-4 Night Stays

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

Menger Hotel

3.5 out of 5
Downtown San Antonio
Price was $754, price is now $604 per person
$604
per person
Sep 16 - Sep 20
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Hotel Contessa

Hotel Contessa

4 out of 5
Downtown San Antonio
Price was $862, price is now $629 per person
$629
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Hyatt Regency Hill Country Resort and Villas

Hyatt Regency Hill Country Resort and Villas

4 out of 5
Far West Side
Price was $1,084, price is now $809 per person
$809
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)
Mokara Hotel & Spa San Antonio

Mokara Hotel & Spa San Antonio

4.5 out of 5
Downtown San Antonio
Price was $971, price is now $761 per person
$761
per person
Sep 11 - Sep 14
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to San Antonio (SAT)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Tue, Oct 20 - Fri, Oct 30
ATL
Hartsfield-Jackson Atlanta Intl.
SAT
San Antonio Intl.
$231 Roundtrip, found 4 hours ago
$231
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Hartsfield-Jackson Atlanta Intl. to San Antonio Intl., returning Fri, Oct 30, priced at $231 found 4 hours ago
Sun Country Airlines
Fri, Jul 31 - Mon, Aug 3
MSP
Minneapolis - St. Paul Intl.
SAT
San Antonio Intl.
$233 Roundtrip, found 23 hours ago
$233
Roundtrip
found 23 hours ago
Select Sun Country Airlines flight, departing Fri, Jul 31 from Minneapolis - St. Paul Intl. to San Antonio Intl., returning Mon, Aug 3, priced at $233 found 23 hours ago
Frontier Airlines
Sun, Sep 27 - Mon, Sep 28
SEA
Seattle - Tacoma Intl.
SAT
San Antonio Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 27 from Seattle - Tacoma Intl. to San Antonio Intl., returning Mon, Sep 28, priced at $240 found 1 day ago
Frontier Airlines
Thu, Sep 10 - Sat, Sep 19
ORD
O'Hare Intl.
SAT
San Antonio Intl.
$248 Roundtrip, found 1 hour ago
$248
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to San Antonio Intl., returning Sat, Sep 19, priced at $248 found 1 hour ago