Midway Vacations from $273

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The Latest Midway vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
per person
Oct 25 - Oct 27
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
9/10 Wonderful! (1,001 reviews)
Lovely and helpful front desk staff

Reviewed on Aug 16, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Convenient place to access stadium for games. Nice view of river

Reviewed on Aug 16, 2025

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 25 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,582 reviews)
Nice and great staff. Good location

Reviewed on Aug 13, 2025

Homewood Suites by Hilton Pittsburgh Southpointe

Homewood Suites by Hilton Pittsburgh Southpointe

3 out of 5
Save 100% on your flight
per person
Oct 25 - Oct 28
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Great experience beds and pillows comfortable room was clean the only issue was sink did not drain well at all so brushing your teeth had to go back and rinse the sink out after water drained out this location is quite and clean will stay here again

Reviewed on Aug 3, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 25 - Oct 27
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,205 reviews)
The staff is very friendly and accomodating. I love the hotel decor and offerings.

Reviewed on Aug 16, 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
$134 nightly
The price is $153 total per night from Aug 20 to Aug 21
$153 total
Aug 20 - Aug 21
Total includes taxes and fees
8/10 Very Good! (2,966 reviews)
"We loved this hotel! Unfortunately a big draw for us was the pool, however we were there on a busy day and the check in took too long for us to get a chance to experience the pool at all. We did end up making it back in time right before the kitchen closed and had a great meal. Would happily stay ..."

Reviewed on Aug 16, 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
$143 nightly
The price is $163 total per night from Aug 31 to Sep 1
$163 total
Aug 31 - Sep 1
Total includes taxes and fees
9/10 Wonderful! (1,600 reviews)
"Nice and great staff. Good location"

Reviewed on Aug 13, 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
$121 nightly
The price is $137 total per night from Aug 24 to Aug 25
$137 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,339 reviews)
"Bike rental was fun. Friday night restaurant was closed at 9:45 pm when advertised to be open until 10."

Reviewed on Aug 15, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,185 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.

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Frequently asked questions

How much does a Midway vacation package cost?
You'll find cheap prices from $273 on Expedia for your Midway break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Midway costs.
What are the cheapest months to go to Midway?
December, January and February are the best times to search for cheap Midway vacation packages. Choosing to travel in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Midway?
With a well-planned schedule, you can easily tick off the main Midway attractions in a few days. But if you prefer to discover hidden spots or go on day trips, think about booking your Midway vacation for longer.
How to find the best Midway package deals?
Start your search for a Midway package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Midway package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Midway adventure underway.
Is it cheaper to book a Midway vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a customized Midway vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Midway?
Score incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Midway escape.
Does Expedia offer Book Now, Pay Later Midway vacation packages?
Your Midway break should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.