Town of Pines Vacation Packages
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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.
Pendry Chicago
Downtown Chicago
Price was CA $1,583, price is now CA $1,072 per person
CA $1,072
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,981, price is now CA $1,277 per person
CA $1,277
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,719, price is now CA $1,181 per person
CA $1,181
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,092, price is now CA $1,458 per person
CA $1,458
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Amazing hotel and staff!
Reviewed on May 5, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,705, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Town of Pines Hotel Deals
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from May 18 to May 19
CA $121
CA $159 total
May 18 - May 19
includes taxes & fees
8.4/10 Very Good! (2,051 reviews)
Clean and well lit
Reviewed on May 4, 2026
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from May 12 to May 13
CA $121
CA $141 total
May 12 - May 13
includes taxes & fees
9.4/10 Exceptional! (1,854 reviews)
Great stay
Reviewed on May 4, 2026
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
The price is CA $162 per night from May 11 to May 12
CA $162
CA $188 total
May 11 - May 12
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Notice it wasn’t as nice as previous stays. No hot chocolate, not much for breakfast, etc. BUT woke up to mice and mice poop took it over the edge.
Reviewed on May 5, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
