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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Allentown North by IHG

Holiday Inn Express Allentown North by IHG

2.5 out of 5
Price was $415, price is now $327 per person
$327
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Book a stay at this business-friendly hotel in Allentown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PPL Center and Dorney Park & Wildwater Kingdom are located nearby.
Roached and bed bugs left

Reviewed on Nov 8, 2026

New Season Royals

New Season Royals

2 out of 5
Save 100% on your flight
Price was $2,250, price is now $1,225 per person
$1,225
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Stay at this hotel in Chester. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Harrah's Casino and Racetrack and Subaru Park are located nearby.

Orchard Way

Orchard Way

2 out of 5
Save 100% on your flight
Price was $2,702, price is now $1,823 per person
$1,823
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Stay at this hotel in Lansdowne. Enjoy free parking, laundry facilities, and Netflix. Popular attractions Rittenhouse Square and Xfinity Mobile Arena are located nearby.

The Windsor Suites

The Windsor Suites

4 out of 5
Save 100% on your flight
Price was $651, price is now $476 per person
$476
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
Book a stay at this business-friendly hotel in Philadelphia. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pennsylvania Convention Center and Rittenhouse Square are located nearby.

YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
Save 100% on your flight
Price was $1,111, price is now $836 per person
$836
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Stay at this hotel in Philadelphia. Enjoy free WiFi, premium bedding, and bathrobes. Popular attractions Pennsylvania Convention Center and Rittenhouse Square are located nearby.
It was our first time staying here! We loved it! Felt like more of a home than a hotel and we had a ton of space in our room! Microwave with mini fridge is amazing so we could enjoy meals we had more than once! Loved the location and we had a wonderful time! Staff was quick at responding when we had questions! Thank you!

Reviewed on Oct 31, 2026

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Price was $1,967, price is now $1,509 per person
$1,509
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Book a stay at this luxury hotel in Philadelphia. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Rittenhouse Square and Pennsylvania Convention Center are located nearby.

Grand Eastonian Hotel & Suites

Grand Eastonian Hotel & Suites

3.5 out of 5
Price was $478, price is now $372 per person
$372
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Book a stay at this business-friendly hotel in Easton. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions One Centre Square and Crayola Experience are located nearby.

Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Save 100% on your flight
Price was $693, price is now $541 per person
$541
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
Book a stay at this business-friendly hotel in Philadelphia. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rittenhouse Square and Pennsylvania Convention Center are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Windsor Suites

The Windsor Suites

4 out of 5
Center City
Save 100% on your flight
Price was $651, price is now $476 per person
$476
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
New Season Royals

New Season Royals

2 out of 5
Save 100% on your flight
Price was $2,250, price is now $1,225 per person
$1,225
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Orchard Way

Orchard Way

2 out of 5
Save 100% on your flight
Price was $2,702, price is now $1,823 per person
$1,823
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
South Philadelphia
Save 100% on your flight
Price was $1,111, price is now $836 per person
$836
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Conwell Inn

The Conwell Inn

2.5 out of 5
North Philadelphia
Price was $706, price is now $556 per person
$556
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)
Orchard Way

Orchard Way

2 out of 5
Price was $6,191, price is now $4,319 per person
$4,319
per person
Dec 28 - Jan 4
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Hotel Anna & Bel

Hotel Anna & Bel

4 out of 5
North Philadelphia
Save 100% on your flight
Price was $1,825, price is now $1,342 per person
$1,342
per person
Dec 24 - Dec 30
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Philadelphia (PHL)
The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was $1,967, price is now $1,509 per person
$1,509
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Philadelphia (PHL)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Wed, Jan 20 - Tue, Feb 9
ATL
Hartsfield-Jackson Atlanta Intl.
PHL
Philadelphia Intl.
$62 Roundtrip, found 1 hour ago
$62
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Jan 20 from Hartsfield-Jackson Atlanta Intl. to Philadelphia Intl., returning Tue, Feb 9, priced at $62 found 1 hour ago
Frontier Airlines
Wed, Nov 11 - Wed, Nov 11
SJU
Luis Munoz Marin Intl.
PHL
Philadelphia Intl.
$108 Roundtrip, found 4 hours ago
$108
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Luis Munoz Marin Intl. to Philadelphia Intl., returning Wed, Nov 11, priced at $108 found 4 hours ago
Frontier Airlines
Wed, Dec 2 - Sat, Dec 12
TPA
Tampa Intl.
PHL
Philadelphia Intl.
$115 Roundtrip, found 10 hours ago
$115
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Tampa Intl. to Philadelphia Intl., returning Sat, Dec 12, priced at $115 found 10 hours ago
Allegiant Air
Fri, Feb 12 - Mon, Feb 15
PIE
St. Petersburg-Clearwater Intl.
PHL
Philadelphia Intl.
$124 Roundtrip, found 3 hours ago
$124
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Fri, Feb 12 from St. Petersburg-Clearwater Intl. to Philadelphia Intl., returning Mon, Feb 15, priced at $124 found 3 hours ago