Trail Creek Holidays from NZ$3,594

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Top Holiday Package Deals in Trail Creek

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NZ$4,995, price is now NZ$3,594 per person
NZ$3,594
per person
2 Apr - 9 Apr
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay

Reviewed on 9 Jan 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$5,057, price is now NZ$3,805 per person
NZ$3,805
per person
2 Apr - 9 Apr
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on 8 Jan 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,942, price is now NZ$3,756 per person
NZ$3,756
per person
2 Apr - 9 Apr
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room

Reviewed on 5 Jan 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$5,065, price is now NZ$3,854 per person
NZ$3,854
per person
2 Apr - 9 Apr
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on 25 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$7,111, price is now NZ$5,493 per person
NZ$5,493
per person
2 Apr - 9 Apr
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on 6 Jan 2026

Our pick of the best Trail Creek 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
Fully refundableReserve now, pay when you stay
The price is NZ$215 per night from 12 Jan to 13 Jan
NZ$215
12 Jan - 13 Jan
includes taxes & fees
8.2/10 Very Good! (1,900 reviews)
Even though it was a room that has not been updated yet, it was just fine Enjoyable trip.

Reviewed on 7 Jan 2026

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 NZ$170 per night from 12 Jan to 13 Jan
NZ$170
12 Jan - 13 Jan
includes taxes & fees
9.2/10 Wonderful! (1,667 reviews)
Great hotel BUT if you want to do online gaming since michigan allows please be aware you CANT get location verification thus cant play online!

Reviewed on 5 Jan 2026

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 NZ$120 per night from 22 Jan to 23 Jan
NZ$120
22 Jan - 23 Jan
includes taxes & fees
6.8/10 (1,018 reviews)
Great stay

Reviewed on 27 Dec 2025

Baymont by Wyndham New Buffalo
See all 1,664 properties in Trail Creek
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 Trail Creek holiday package cost?
You can pick up a holiday package to this top destination from NZ$3,594 on Expedia. But how much your holiday to Trail Creek costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Trail Creek?
You can generally find lower prices and better availability in January, February and November. Take a look at our cheap Trail Creek holiday packages and you could score some great off-season deals.
How many days is enough for Trail Creek?
Typically, a handful of days is enough to check out the top attractions during your Trail Creek holiday. But if you prefer to have more time to chill out or go on day trips, consider extending your trip.
How to find the best Trail Creek package deals?
Bagging a cheap Trail Creek package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Trail Creek package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Trail Creek holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can tailor your Trail Creek trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Trail Creek?
If you're planning a spontaneous Trail Creek trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Trail Creek?

  1. Pick your travel dates: The things you plan to do in Trail Creek and your favourite season will help you decide when to travel.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Trail Creek. Then, choose a hotel that fits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to get to in Trail Creek. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, lock in the ideal Trail Creek holiday package for you.

Discover the most popular places to visit in Trail Creek

Lighthouse Place Premium Outlets

You can enjoy retail therapy at Lighthouse Place Premium Outlets during your visit to Michigan City. Visit the area's casinos or amble around its beautiful beaches.

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