Town of Pines Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 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

Town of Pines Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,450 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 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! (1,468 reviews)
"Great view of the woods and the deer, And the sky view was nice, not many city lights"

Reviewed on 19 Aug, 2025

Get rates
Four Winds Casino Resort – New Buffalo
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 S$117 per night from 3 Sept to 4 Sept
S$117
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Mid week escape.
"Easy, convenient to our areas of interest. Clean."

Reviewed on 21 Aug, 2025

Quality Inn Near Interstate I94
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 S$191 per night from 1 Sept to 2 Sept
S$191
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,669 reviews)
"Excellent place to relax! Staff were very friendly, especially the lady that checked us in."

Reviewed on 19 Aug, 2025

Blue Chip Casino Hotel and Spa
See all 1,572 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 S$696 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.