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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €618, price is now €391 per person
€391
per person
6 Sept - 11 Sept
found 20 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!

Reviewed on 12 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,541, price is now €895 per person
€895
per person
25 Sept - 30 Sept
found 21 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,407, price is now €842 per person
€842
per person
6 Sept - 11 Sept
found 23 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,408, price is now €874 per person
€874
per person
20 Sept - 25 Sept
found 20 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Parking Situation is kind of difficult, if you are staying at the Hotel parking should be included.

Reviewed on 12 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was €787, price is now €499 per person
€499
per person
6 Sept - 11 Sept
found 20 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Loved the size of our room and how clean it was.

Reviewed on 9 Jul 2026

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
The price is €91 per night from 28 Jul to 29 Jul
€91
28 Jul - 29 Jul
includes taxes & fees
9.4/10 Exceptional! (2,000 reviews)
"Exceptional. Roomy. Clean. Friendly."

Reviewed on 11 Jul 2026

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 €117 per night from 9 Aug to 10 Aug
€117
9 Aug - 10 Aug
includes taxes & fees
8.4/10 Very good! (2,208 reviews)
"We were staying in the old part of the property. I wouldn’t stay there again. The air conditioning unit was loud and rattled, there was a strong sewer smell in the room one morning. Be sure to stay in the newer tower."

Reviewed on 11 Jul 2026

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 refundable
The price is €110 per night from 14 Jul to 15 Jul
€110
14 Jul - 15 Jul
includes taxes & fees
8.4/10 Very good! (1,239 reviews)
"Our room was so CLEAN! The staff was super friendly. Location was easy to access."

Reviewed on 11 Jul 2026

Quality Inn Near Interstate I94
See all 1,624 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 €391 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.

Explore a world of travel with Expedia

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