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Long Island Vacation Packages

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Long Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was $425, price is now $361 per person
$361
per person
Apr 21 - Apr 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Scarborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Big 20 Bowling Center and Nonesuch River Golf Club are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,833, price is now $1,528 per person
$1,528
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $1,322, price is now $1,109 per person
$1,109
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,279, price is now $1,091 per person
$1,091
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $471, price is now $402 per person
$402
per person
Apr 21 - Apr 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maine Mall and Nonesuch River Golf Club are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,366, price is now $1,180 per person
$1,180
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
Price was $461, price is now $399 per person
$399
per person
Apr 21 - Apr 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Nonesuch River Golf Club are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,198, price is now $1,044 per person
$1,044
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.

Long Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was $425, price is now $361 per person
$361
per person
Apr 21 - Apr 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,833, price is now $1,528 per person
$1,528
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,322, price is now $1,109 per person
$1,109
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,279, price is now $1,091 per person
$1,091
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Long Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Price was $676, price is now $564 per person
$564
per person
Apr 29 - May 4
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,129, price is now $907 per person
$907
per person
Apr 29 - May 4
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,082, price is now $883 per person
$883
per person
Apr 29 - May 4
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $918, price is now $768 per person
$768
per person
Apr 29 - May 4
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$175 Roundtrip, found 11 hours ago
$175
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $175 found 11 hours ago
Bargain Flight
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $203 found 4 days ago
Delta
Fri, Mar 6 - Wed, Mar 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Mar 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Mar 11, priced at $209 found 4 days ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Mar 17 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Mar 25, priced at $219 found 3 days ago