Dayton Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Dayton Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
HomeAwhile
Price was $833, price is now $664 per person
$664
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PWM)
Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Nonesuch River Golf Club are located nearby.
The Docent’s Collection – Thompson Block
Downtown Portland
Save 100% on your flight
Price was $1,983, price is now $1,415 per person
$1,415
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) 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.
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $2,038, price is now $1,552 per person
$1,552
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) 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.
Inn By The Sea
Save 100% on your flight
Price was $1,976, price is now $1,553 per person
$1,553
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) 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.
Comfort Inn & Suites Scarborough - Portland
Price was $938, price is now $747 per person
$747
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) 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.
Portland Regency Hotel & Spa
Downtown Portland
Price was $1,382, price is now $1,118 per person
$1,118
per person
May 22 - May 28
found 13 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Top Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
28.21 km from city center
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
26.44 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Portland Harbor Hotel
468 Fore Street Portland ME
28.88 km from city center
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 ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
29.14 km from city center
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
29.64 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
28.42 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
16.3 km from city center
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
24.72 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
DoubleTree by Hilton Hotel Portland
363 Maine Mall Rd South Portland ME
21.94 km from city center
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. ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
29.39 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Aloft Portland Downtown Waterfront ME
379 Commercial Street Portland ME
28.53 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Hyatt Place Portland Downtown - Old Port Square
433 Fore St Portland ME
28.95 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Ramada Plaza by Wyndham Portland
155 Riverside St Portland ME
25.41 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jun 2 - Tue, Jun 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Sat, Jun 6 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Tue, Apr 14 - Mon, Apr 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Thu, Apr 30 - Tue, May 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$306 Roundtrip, found 3 days ago
$306
Roundtrip
found 3 days ago
Wed, Mar 11 - Sat, Mar 14
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$317 Roundtrip, found 3 days ago
$317
Roundtrip
found 3 days ago