Cheswick Vacations from $394

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Your Cheswick Vacation

The best way to experience this unique city is with a tailor-made Cheswick vacation package. Base yourself in the neighborhood of Lawrenceville, which is great for nightlife, bars and pubs and dining or choose someplace else — our package deals are all about you. Any trip to Cheswick needs a well-thought-out itinerary. Fill yours with leading attractions like Galleria at Pittsburgh Mills, Shady Side Academy and Harmarville Blade Runners Ice Complex. Stop dreaming and start traveling. Check out the many options on Expedia today and finally put your Cheswick vacation plans into action!

The Latest Cheswick vacation packages

Price found within the past 48 hours. Click for updated prices.
Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $488, price is now $394 per person
$394
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9.6/10 Exceptional! (89 reviews)
This might be the coolest place I have ever stayed. Rooms are small (used to be a hostel) but spotless as is the rest of the hotel. Great history behind this building. Very comfortable sitting in the great room conversing with others. The peacefulness was in large part due to this being a TV free hotel.

Reviewed on Nov 17, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,196, price is now $943 per person
$943
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $1,495, price is now $1,186 per person
$1,186
per person
Apr 23 - Apr 25
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $700, price is now $565 per person
$565
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Rooms need microwaves

Reviewed on Jan 28, 2026

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Discover the most popular places to visit in Cheswick

PNC Park showing a city

PNC Park

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh
Mario Lemieux statue

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

PPG Paints Arena

What to do in Cheswick

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$106
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$67
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

$49
per adult
Whiskey Rebellion & Prohibition Tour
See all activities in Cheswick

Cheswick 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
$107 nightly
The price is $122 total per night from Feb 12 to Feb 13
$122 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (3,383 reviews)
The stay was excellent because of the staff. We were there during a giant snowstorm. The city was basically shut down. Big credit to Cody at the front desk (who I think was stuck there with us) and the others who took care of us when nothing was normal. While standing in the lobby and looking at ...

Reviewed on Jan 27, 2026

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
$159 nightly
The price is $182 total per night from Feb 8 to Feb 9
$182 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,929 reviews)
Room was very nice. The staff was extremely accommodating. Always stay here when in Pittsburgh.

Reviewed on Jan 22, 2026

Omni William Penn Hotel
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd Coraopolis PA
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from Feb 8 to Feb 9
$70 total
Feb 8 - Feb 9
Total with taxes and fees
8/10 Very Good! (2,215 reviews)
Nice clean room and very courteous staff. Perfect stay for early flight out!

Reviewed on Jan 24, 2026

La Quinta Inn by Wyndham Pittsburgh Airport
See all 1,924 properties in Cheswick
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.

Find the Best Cheswick Vacation Packages

Cheswick Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
1,750
Top Sights
Pittsburgh Zoo and PPG Aquarium, Kennywood and Sandcastle Water Park

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Frequently asked questions

How much does a Cheswick vacation package cost?
You'll find cheap prices from $394 on Expedia for your Cheswick escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cheswick costs.
What are the cheapest months to go to Cheswick?
November, December and January are the best times to search for cheap Cheswick vacation packages. Traveling in quieter periods means you can generally find better prices on accommodations and flights.
How many days is enough for Cheswick?
With a well-organized schedule, you can easily visit the main Cheswick sights in a few days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Cheswick vacation for longer.
How to find the best Cheswick package deals?
Finding a cheap Cheswick package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Cheswick package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cheswick vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize your Cheswick escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cheswick?
If you're considering a spontaneous Cheswick vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cheswick vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Cheswick vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.