Town of Pines Holidays
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Top Flight + Hotel Deals in Town of Pines
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was €617, price is now €362 per person
€362
per person
20 Nov - 27 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The hotel staff were friendly and the room was quiet and clean. we had an issue with the room safe and it was fixed right away. the location was excellent for walking to all the attractions we wanted to see. Overall we were very happy with our stay.
Reviewed on 2 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €1,013, price is now €522 per person
€522
per person
20 Nov - 27 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Good location not far from all the big attractions. But it was noisy in the evening.
Reviewed on 29 Sept 2025
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was €833, price is now €449 per person
€449
per person
20 Nov - 27 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
The room was clean and comfortable and the restaurant was good.
Reviewed on 1 Oct 2025
The Emily Hotel
Downtown Chicago
Price was €1,240, price is now €672 per person
€672
per person
20 Nov - 27 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on 29 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was €849, price is now €480 per person
€480
per person
20 Nov - 27 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 26 Sept 2025
Top hotels in Town of Pines
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is €111 per night from 5 Oct to 6 Oct
€111
5 Oct - 6 Oct
includes taxes & fees
8.2/10 Very Good! (1,752 reviews)
"convenient"
Reviewed on 26 Sept 2025
Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is €106 per night from 5 Oct to 6 Oct
€106
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (1,537 reviews)
"No room cleaning for our 3 day stay. Garbage cans were very small since the room is not cleaned for your stay."
Reviewed on 26 Sept 2025
Quality Inn Near Interstate I94
18830 Laporte Rd, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is €69 per night from 14 Oct to 15 Oct
€69
14 Oct - 15 Oct
includes taxes & fees
8.2/10 Very Good! (1,029 reviews)
"Nice and quiet and peaceful"
Reviewed on 27 Sept 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
