Midway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Midway vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 31 - Jan 6

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    6 nights
    2.0 star property
    8.0/10 - Very good (346 reviews)
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,426
    CA $1,136
    per traveller
    found 17 hours ago
    Stay Pittsburgh
  • Dec 31 - Jan 6

    The Oaklander Hotel, Autograph Collection + Flight

    Oakland
    6 nights
    4.5 star property
    9.2/10 - Wonderful (855 reviews)
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,869
    CA $1,475
    per traveller
    found 17 hours ago
    The Oaklander Hotel, Autograph Collection
  • Dec 31 - Jan 6

    The Westin Pittsburgh, a Marriott Hotel + Flight

    Downtown Pittsburgh
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,000 reviews)
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,959
    CA $1,580
    per traveller
    found 17 hours ago
    The Westin Pittsburgh, a Marriott Hotel
  • Dec 18 - Dec 21

    Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight

    Downtown Pittsburgh
    3 nights
    4.0 star property
    8.4/10 - Very good (1,711 reviews)
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,664
    CA $1,418
    per traveller
    found 1 day ago
    Joinery Hotel Pittsburgh, Curio Collection by Hilton
  • Dec 18 - Dec 21

    Hampton Inn & Suites Pittsburgh-Downtown + Flight

    Downtown Pittsburgh
    3 nights
    2.5 star property
    9.4/10 - Exceptional (1,367 reviews)
    "This is the perfect hotel for those visiting downtown Pittsburgh with a car. It's easy to get to and has ample free self-parking; come in and out as you please. Located a stone's throw from the Allegheny Riverside path, and right next to the Strip district, you can easily walk to restaurants and shops. Both the National Aviary and the Duquesne Incline are less than a 10 minute drive. Our corner room was huge, with windows overlooking the city and river. Gorgeous! Yes, it's a big-chain corporate..."
    Reviewed November 10, 2026
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,674
    CA $1,438
    per traveller
    found 1 day ago
    Hampton Inn & Suites Pittsburgh-Downtown

Midway Hotel Deals

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.

Frequently Asked Questions

How much does a Midway vacation package cost?

You can snap up a vacation package to this destination from CA $1,136 on Expedia. However, how much your vacation to Midway costs will depend on factors like the season, hotel choice and length of stay.

What are the cheapest months to go to Midway?

January, February and March are great times to look for cheap Midway vacation packages. Choosing to travel in quieter periods means you can typically find better prices on flights and accommodations.

How many days is enough for Midway?

With a well-organized schedule, you can easily tick off the top Midway attractions in a handful of days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Midway vacation for longer.

How to find the best Midway package deals?

Use Expedia's handy filters to help you find some fabulous Midway package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Midway package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.

Is it cheaper to book a Midway vacation as a package?

You can enjoy significant savings on your Midway break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Midway?

If you have your Midway travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.

How to plan a trip to Midway?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Midway.
  2. Set your budget: Consider expenses like flights, transportation and food when calculating how much to set aside for your trip to Midway. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
  3. Decide how long to go for: Now that you're more familiar with Midway, you can work out the right length of your vacation. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Midway vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.