Midway Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Midway Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Suites Pittsburgh South by IHG
CA $1,018
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,017 reviews)
I liked the location of the hotel. Rooms have very old carpets, when you step in barefoot in bathroom you will see linen from carpet in the bathroom. Bedsheets had blood stains, they did not bother to replace them
Reviewed on Aug 11, 2026
Stay Pittsburgh
Downtown Pittsburgh
CA $1,338
per person
Oct 30 - Nov 2
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8/10 Very good! (314 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.
Reviewed on Aug 9, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,423
per person
Oct 30 - Nov 2
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,581 reviews)
It took 20 minutes to check in bc only 1 person was at the desk. Bars were understaffed and out of items. Location was great and staff was friendly
Reviewed on Aug 12, 2026
Ready to book your vacation to Midway?
Midway Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $172
CA $196 total
Sep 2 - Sep 3
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $166
CA $189 total
Aug 23 - Aug 24
includes taxes & fees
9.4/10 Exceptional! (2,138 reviews)
"Very nice property right on the river."
Reviewed on Aug 12, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $291
CA $332 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (2,036 reviews)
"."
Reviewed on Aug 10, 2026
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 $1,018 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?
- 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.
- 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.
- 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.
- 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.
