Cheswick Vacations from $442

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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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $574, price is now $442 per person
$442
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
Clean and very cozy

Reviewed on Feb 1, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $2,371, price is now $1,707 per person
$1,707
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Very friendly staff and clean room.

Reviewed on Feb 1, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $968, price is now $746 per person
$746
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $772, price is now $597 per person
$597
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,009 reviews)
Every staff member was absolutely the best !! I would stay there every time i visit Pittsburgh!

Reviewed on Feb 2, 2026

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Discover the most popular places to visit in Cheswick

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
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
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 Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$67
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

$59
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike 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
$120 nightly
The price is $136 total per night from Feb 12 to Feb 13
$136 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (3,391 reviews)
The room was very clean and all the staff was top notch for service. The valet parking was nothing more than organized chaos. There was a dance event at the hotel so that added to the loads of cars stacking up in front, but I guess if that’s all I have to point out then it wasn’t that bad. We’ll ...

Reviewed on Feb 1, 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 11 to Feb 12
$182 total
Feb 11 - Feb 12
Total with taxes and fees
9/10 Wonderful! (1,938 reviews)
Check-in was the quickest I have ever experienced at a hotel.

Reviewed on Feb 3, 2026

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
$110 nightly
The price is $126 total per night from Feb 12 to Feb 13
$126 total
Feb 12 - Feb 13
Total with taxes and fees
8.4/10 Very Good! (1,427 reviews)
Excellent

Reviewed on Jan 29, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,926 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 $442 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.