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Southwest Vacations from ￥76,974

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    Save up to ￥109,000 when you book a flight and hotel together*

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The Latest Southwest Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Sep 4 - Sep 6

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    2 nights
    2.0 star property
    8.0/10 - Very Good (314 reviews)
    "Very responsive, great location, awesome hosts! 10/10 would recommend."
    Reviewed July 31, 2026
    Roundtrip • Chicago (ORD) - Pittsburgh (PIT)
    ORD - PIT • Nonstop PIT - ORD • Nonstop
    ￥103,905
    ￥76,974
    per traveler
    found 1 day ago
    Stay Pittsburgh
  • Exterior
    Oct 3 - Oct 8

    The Westin Pittsburgh, a Marriott Hotel + Flight

    Downtown Pittsburgh
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room."
    Reviewed August 3, 2026
    Roundtrip • Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT • 1 stop PIT - HND • 1 stop
    ￥475,635
    ￥372,042
    per traveler
    found 14 hours ago
    The Westin Pittsburgh, a Marriott Hotel
  • Room, 1 King Bed, Accessible | Premium bedding, pillowtop beds, desk, blackout drapes
    Oct 3 - Oct 8

    Wyndham Grand Pittsburgh Downtown + Flight

    Downtown Pittsburgh
    5 nights
    3.5 star property
    8.2/10 - Very Good (3,704 reviews)
    "Nice room, especially for the price. The shower water pressure could have been better and the valve on the commode leaked causing you to take the lid off of the tank to release a snag. Very convenient to PNC Park. Overall, I would highly recommend."
    Reviewed August 3, 2026
    Roundtrip • Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT • 1 stop PIT - HND • 1 stop
    ￥340,734
    ￥274,323
    per traveler
    found 14 hours ago
    Wyndham Grand Pittsburgh Downtown
  • Exterior
    Oct 3 - Oct 8

    Fairmont Pittsburgh + Flight

    Downtown Pittsburgh
    5 nights
    4.5 star property
    8.8/10 - Excellent (1,002 reviews)
    "Great hotel"
    Reviewed August 2, 2026
    Roundtrip • Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT • 1 stop PIT - HND • 1 stop
    ￥442,820
    ￥376,490
    per traveler
    found 14 hours ago
    Fairmont Pittsburgh
  • Terrace/patio
    Oct 3 - Oct 8

    Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight

    Downtown Pittsburgh
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,602 reviews)
    "Small room. But comfortable and clean. Modern bathroom with good waterpressure."
    Reviewed August 3, 2026
    Roundtrip • Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT • 1 stop PIT - HND • 1 stop
    ￥354,489
    ￥306,889
    per traveler
    found 14 hours ago
    Joinery Hotel Pittsburgh, Curio Collection by Hilton

Southwest Hotel Deals

Indoor pool

Hampton Inn & Suites Pittsburgh New Stanton

Hampton Inn & Suites Pittsburgh New Stanton
2.5 star property
8.2 km from Southwest
9.6 out of 10, Exceptional, (752 reviews)
"Clean, neat, and new,"
The price is ￥18,597
￥20,643 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn & Suites Pittsburgh New Stanton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Southwest
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.