Midway Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Midway

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 S$197 per night from 27 Jul to 28 Jul
S$197
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (2,934 reviews)
"Only problem was that I booked a room with two double beds and a sofa bed. When I got the email for upgrade, I did the room upgrade. Turned out the upgrade had one king and a sofa bed. The room was for 5 people. Two adults, and two kids. Had to end up getting a cot."

Reviewed on 6 Jul, 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 S$209 per night from 27 Jul to 28 Jul
S$209
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,533 reviews)
"Great stay!~ Would be happy to do it again."

Reviewed on 5 Jul, 2025

Omni William Penn Hotel
Drury Plaza Hotel Pittsburgh Downtown
Drury Plaza Hotel Pittsburgh Downtown
3 out of 5
745 Grant Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is S$174 per night from 13 Jul to 14 Jul
S$174
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (1,904 reviews)
Felt like they were your bffs
"Friendliest staff I’ve ever encountered on a trip."

Reviewed on 4 Jul, 2025

Drury Plaza Hotel Pittsburgh Downtown
See all 1,256 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.

Frequently asked questions

How much does a Midway holiday package cost?
You'll find cheap prices 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 holiday to Midway costs.
What are the cheapest months to go to Midway?
January, February and March are the best times to look for cheap Midway holiday packages. Travelling in quieter periods means you can typically find reduced prices on accommodation and flights.
How many days is enough for Midway?
Generally, a handful of days is enough to see the top sights during your Midway holiday. But if you'd like to have some time to relax or take day trips, think about extending your trip.
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 holiday as a package?
Expedia holiday 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 customised Midway holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Midway?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to holiday in Midway.
  2. Set your budget: Consider costs like flights, transportation and food when working out how much to put aside for your trip to Midway. Then, pick a hotel that fits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Determine how many days away: Start by making a list of all the activities and sights you want to experience in Midway. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Midway holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.