Town of Pines Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Town of Pines Vacation
Memorable adventures await when you book a Town of Pines vacation package. Whether you're a foodie, history enthusiast or just a traveler who appreciates new places, there's something for everyone in this lively city. Fill your itinerary with tours of Indiana Dunes National Park, Indiana Dunes State Park and Blue Chip Casino, some of the top attractions you shouldn't miss during your trip to Town of Pines. Whoever you're going away with and whatever your bank balance, your dream Town of Pines vacation is just a few clicks away with Expedia.
Top Town of Pines Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The people at the front desk were extremely helpful. Everyone was super kind & you never really have to leave the hotel.. plenty of shops and restaurants right there in the hotel!
Breakfast was not included, but there is breakfast on site.. there’s cheap breakfast and expensive breakfast all depends on what you are in the mood for. Wonderful stay over all!!!
Reviewed on Jun 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,740, price is now CA $1,285 per person
CA $1,285
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Great location, great space in the rooms!!
Reviewed on Jun 21, 2026
Town of Pines Hotel Deals
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jun 28 to Jun 29
CA $139
CA $161 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,935 reviews)
"The hotel and casino were very clean and well maintained. The pool area was a great getaway from gambling and pool staff were awesome evening concerts a plus!"
Reviewed on Jun 22, 2026
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Jun 29 to Jun 30
CA $126
CA $165 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very good! (2,143 reviews)
"Our experience was very good. Very attentive bell staff"
Reviewed on Jun 20, 2026
Quality Inn Near Interstate I94
18830 Laporte Rd New Buffalo MI
Fully refundable
The price is CA $128 per night from Jun 25 to Jun 26
CA $128
CA $135 total
Jun 25 - Jun 26
includes taxes & fees
8.4/10 Very good! (1,215 reviews)
"The room was very clean and breakfast was fine. I could not find the guide on the TV to figure out what was on when I did briefly watch the TV, but that may have been me."
Reviewed on Jun 21, 2026
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.
Discover the most popular places to visit in Town of Pines
Washington Park Zoo
Why not meet the animals who live at Washington Park Zoo during your trip to Michigan City? Visit the area's casinos or amble around its beautiful beaches.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
