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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
5 Nov - 9 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
This was property was centrally located next to everything that a first time visitor would like to experience. The access to the parks, museums, the Riverwalk and dining options makes for an enjoyable trip. The only downside was having to wait a considerable time for the elevators. Having 5 elevators and not all running at the same time, led to long wait times for a popular hotel with many guests.

Reviewed on 17 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Nov - 7 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Nov - 9 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug 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
2 Nov - 7 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great view of the lake and city

Reviewed on 18 Aug 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (260 reviews)
Fantastic experience. Staff was friendly and accommodating. Highly recommend

Reviewed on 15 Aug 2025

Top hotels in Town of Pines

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
9.2/10 Wonderful! (1,469 reviews)
"Great time"

Reviewed on 17 Aug 2025

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

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is €134 per night from 25 Aug to 26 Aug
€134
25 Aug - 26 Aug
includes taxes & fees
8/10 Very Good! (1,666 reviews)
Great Stay!!!
"Wonderful casino/hotel. Very tight... meets US federal military/intelligence bases and National Labs (e.g. Fermi, Argonne, Sandia, Ft. Bragg) standards of infrastructure and customer service and care."

Reviewed on 16 Aug 2025

Blue Chip Casino Hotel and Spa
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

2.5 out of 5
18830 Laporte Rd, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is €77 per night from 25 Aug to 26 Aug
€77
25 Aug - 26 Aug
includes taxes & fees
8.2/10 Very Good! (1,017 reviews)
"proximity to the highway, Rate excellent"

Reviewed on 17 Aug 2025

Quality Inn Near Interstate I94
See all 1,567 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.

Frequently asked questions

How much does a Town of Pines holiday package cost?
You'll find cheap prices from €780 on Expedia for your Town of Pines getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Town of Pines costs.
What are the cheapest months to go to Town of Pines?
Travel in the low season and you're likely to score cheap Town of Pines holiday packages. Keep in mind that school holiday periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Town of Pines?
The ideal length of your Town of Pines holiday depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the leading sights and explore some hidden gems along the way.
Is it worth booking a holiday package to Town of Pines?
It's no wonder a Town of Pines holiday is on the to-do list of many travellers. Major attractions like Lake View Beach are just the start of things to keep you busy here.
How to find the best Town of Pines package deals?
Start your search for a Town of Pines package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Town of Pines package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Town of Pines adventure underway.
Is it cheaper to book a Town of Pines holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a customised Town of Pines holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Town of Pines?
Secure incredible discounts by booking your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Town of Pines trip.
How to plan a trip to Town of Pines?

  1. Pick your travel dates: The things you plan to do in Town of Pines and your preferred season will help you decide when to go.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Town of Pines. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a more upscale getaway.
  3. Decide how long to go away for: Now that you know more about Town of Pines, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Town of Pines holiday package.

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