Trail Creek Holidays from NZ$3,146

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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 Holiday Package Deals in Trail Creek

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,303, price is now NZ$3,146 per person
NZ$3,146
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$6,133, price is now NZ$4,038 per person
NZ$4,038
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$5,140, price is now NZ$3,607 per person
NZ$3,607
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special

Reviewed on 11 Nov 2025

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was NZ$4,753, price is now NZ$3,402 per person
NZ$3,402
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (983 reviews)
Everything was good

Reviewed on 17 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,630, price is now NZ$4,802 per person
NZ$4,802
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

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$213 per night from 1 Dec to 2 Dec
NZ$213
1 Dec - 2 Dec
includes taxes & fees
8.2/10 Very Good! (1,817 reviews)
Yes

Reviewed on 14 Nov 2025

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$157 per night from 25 Nov to 26 Nov
NZ$157
25 Nov - 26 Nov
includes taxes & fees
9.2/10 Wonderful! (1,604 reviews)
The only complaint I have is the sound system for the karaoke. And that was the whole reason for me to come. I was disappointed

Reviewed on 14 Nov 2025

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$125 per night from 25 Nov to 26 Nov
NZ$125
25 Nov - 26 Nov
includes taxes & fees
6.8/10 (1,000 reviews)
Awesome

Reviewed on 14 Nov 2025

Baymont by Wyndham New Buffalo
See all 1,668 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$3,146 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.