Town of Pines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,031 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on Jul. 30, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
I booked a room with the water view, when I checked in I asked before I get the key, Is it a water view. They told me it is. I show up in my room and it’s not the room I booked. I called the front desk and they’re telling me we apologize all of the rooms are booked with the water view. They also said booking a water view room doesn’t guarantee a water view room even though I paid extra for a water view room! Never going to stay there again for sure.

Reviewed on Aug. 3, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Ready to book your vacation to Town of Pines?

 

Choose your dates

Town of Pines Hotel Deals

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
The price is CA $144 per night from Sep 1 to Sep 2
CA $144
CA $181 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,639 reviews)
"My bestie and I have been staying at the Blue Chip for 10 plus years. The staff is so friendly, accommodating and all around excellent."

Reviewed on Aug. 2, 2025

Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 4 to Sep 5
CA $135
CA $157 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (1,436 reviews)
"Everybody was very friendly and helpful. Our room was the cleanest hotel room I've ever stayed in and was lovely!"

Reviewed on Aug. 2, 2025

Four Winds Casino Resort – New Buffalo
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

2.5 out of 5
18800 Harbor Country Drive, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Sep 2 to Sep 3
CA $107
CA $115 total
Sep 2 - Sep 3
includes taxes & fees
6.6/10 (1,008 reviews)
"Aside from my issue at check in i had a great time"

Reviewed on Aug. 2, 2025

Baymont by Wyndham New Buffalo
See all 1,573 properties in Town of Pines
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.

Washington Park Zoo

Frequently asked questions

How much does a Town of Pines vacation package cost?
You'll find cheap prices from CA $931 on Expedia for your Town of Pines getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Town of Pines costs.
What are the cheapest months to go to Town of Pines?
Plan your trip for the low season and you're likely to find cheap Town of Pines vacation packages. Bear in mind that public holidays and major events and festivals can impact prices, so do your research before booking.
How many days is enough for Town of Pines?
With a well-planned schedule, you can easily visit the most popular Town of Pines sights in a few days. But if you prefer to venture off the beaten track or go on day tours, think about booking your Town of Pines vacation for longer.
Is it worth booking a vacation package to Town of Pines?
It's no wonder a Town of Pines vacation is on the to-do list of many travellers. Well-known attractions like Lake View Beach are just the beginning of things to see and do here.
How to find the best Town of Pines package deals?
Finding a cheap Town of Pines package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Town of Pines package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Town of Pines vacation as a package?
You can enjoy significant savings on your next Town of Pines escape by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Town of Pines?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Town of Pines escape.
How to plan a trip to Town of Pines?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to visit Town of Pines.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to airfares and activities. Your hotel will likely be the biggest expense during your trip to Town of Pines.
  3. Decide how long to go for: Now that you're up to speed on Town of Pines, you can work out the ideal length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Town of Pines vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.