Town of Pines Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Town of Pines

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
€849
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Great stay

Reviewed on 13 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
€1,460
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,079
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Súper cerca a todas las atracciones de Chicago

Reviewed on 12 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,122
per person
23 Nov - 29 Nov
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Only negative was light water pressure at the shower, everything else was top notch. Great location, large immaculate rooms, great beds and nice bar and breakfast.

Reviewed on 13 Oct 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€877
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)

Top hotels in Town of Pines

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
€92
20 Oct - 21 Oct
includes taxes & fees
9.4/10 Exceptional! (2,273 reviews)
"."

Reviewed on 13 Oct 2026

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

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
€105
27 Oct - 28 Oct
includes taxes & fees
8.4/10 Very good! (2,380 reviews)
"Staff very friendly and knowledgeable."

Reviewed on 13 Oct 2026

Blue Chip Casino Hotel and Spa
Spring House Inn

Spring House Inn

303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
€104
1 Nov - 2 Nov
includes taxes & fees
Spring House Inn
See all 1,592 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.

Stay near popular Town of Pines attractions

Pines Park

After visiting Pines Park, make a plan to see the other sights and activities in Town of Pines. While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a Town of Pines holiday package cost?
You'll find cheap prices from €849 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.