Midway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
7.6/10 Good! (142 reviews)
Clean and quiet property in downtown Pittsburgh. Had some difficulty leaving the Allied garage because my QR code or the scanner wasn’t working, but otherwise a great stay. Will definitely stay again if I’m in the area.

Reviewed on Jul. 6, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9/10 Wonderful! (1,002 reviews)
Absolutely loved the hotel. The room was very spacious and had a fantastic view. The staff was great. The bar inside the hotel was relaxed and the bartender was awesome. There is so many dining options within walking distance from the hotel. During my stay they was doing the Picklesburgh Festival, and this did not impact my stay at all. It was a great stay, planning to do it again soon.

Reviewed on Jul. 11, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.6/10 Excellent! (819 reviews)
The room was not very clean

Reviewed on Jul. 7, 2025

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,003 reviews)
Staff was great!! A+

Reviewed on Jul. 1, 2025

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9.4/10 Exceptional! (803 reviews)
Did not like parking and having to walk far

Reviewed on Jul. 10, 2025

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Midway Hotel Deals

Wyndham Grand Pittsburgh Downtown
Wyndham Grand Pittsburgh Downtown
3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Jul 16 to Jul 17
CA $170
CA $194 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very Good! (2,881 reviews)
"The hotel was nice and clean and a short walking distance to the park and baseball stadium."

Reviewed on Jul. 8, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel
Omni William Penn Hotel
4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jul 27 to Jul 28
CA $196
CA $224 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,530 reviews)
"It was a very cool experience staying at this historic hotel. It's in a great area. The lobby is stunning. The room we stayed in was spacious but nothing fancy. Our bed was very uncomfortable - it caved into the middle. The friendly staff gave offered us a breakfast credit for the bad sleep. Overall ..."

Reviewed on Jul. 9, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Joinery Hotel Pittsburgh, Curio Collection by Hilton
4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 16 to Jul 17
CA $173
CA $198 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (1,323 reviews)
"Friendly and clean"

Reviewed on Jul. 10, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,254 properties in Midway
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Midway vacation package cost?
You can snap up a vacation package to this destination from CA $807 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.