
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $720, price is now CA $555 per person
CA $555
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Friendly staff. Bathroom needs more hooks to hang clothes and towels, carpet could use more vacuuming, telephone in the room didn’t work, after turning on tv you had to enter the guide button to watch live tv, and always one minute later it went back to wanting you to Chromecast and we had to reset the channel we were watching. The shower curtain was about 1-2 inches too short and every time one showered the floor would get wet unless we turned the shower head toward the wall. The elevator made a grinding noise but we got used to the noise when in the room. No coffee maker or coffee in room but the morning coffee and fruit was nice.
Room was big enough for a queen sized bed which was comfortable .The view was good.
The location was good if you are comfortable with public transportation. E/W bus 66 two blocks north, N/S bus 22 was 1/2 block away and N/S bus 156 was 1/2 block away. The L red train about 4 blocks away by walking alone. All in all I would recommend this hotel if you plan for it’s known limitations.
Reviewed on Jun 25, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,463, price is now CA $1,624 per person
CA $1,624
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $3,614, price is now CA $2,421 per person
CA $2,421
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (493 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 Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $2,819, price is now CA $2,098 per person
CA $2,098
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Town of Pines Hotel Deals

Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundable
The price is CA $165 per night from Jun 29 to Jun 30
CA $165
CA $192 total
Jun 29 - Jun 30
includes taxes & fees
9.4/10 Exceptional! (1,939 reviews)
"Excellent stay,clean, affordable,fun"
Reviewed on Jun 25, 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 $138 per night from Jun 29 to Jun 30
CA $138
CA $178 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very good! (2,144 reviews)
"Will be back"
Reviewed on Jun 23, 2026

Quality Inn Near Interstate I94
18830 Laporte Rd New Buffalo MI
Fully refundable
The price is CA $128 per night from Jun 28 to Jun 29
CA $128
CA $136 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very good! (1,216 reviews)
"Easy check in, good location, outdated bathroom. The furniture needs to be replaced in hotel room. The cover on the chair was kinda off putting makes you wonder why it needs a cover. Good a/c, quiet, the smallest pillows I’ve ever seen for a king sized bed but the bed was comfortable. Better breakfast ..."
Reviewed on Jun 24, 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.
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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.







