Oregon Holidays from NZ$3,234

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The Latest Oregon Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was NZ$4,009, price is now NZ$3,234 per person
NZ$3,234
per person
5 Sept - 11 Sept
found 22 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
It needs to be refreshed it’s drab and dreary and doesn’t look clean my bathroom was dangerous I don’t need a handicap accessible but there are no bars to hang on to getting in and out of shower just depressing and breakfast a joke 1 morning no protein at all

Reviewed on 13 July 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,324, price is now NZ$3,433 per person
NZ$3,433
per person
5 Sept - 11 Sept
found 22 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on 13 July 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,833, price is now NZ$3,853 per person
NZ$3,853
per person
5 Sept - 11 Sept
found 22 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Great Experience

Reviewed on 14 July 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was NZ$4,532, price is now NZ$3,677 per person
NZ$3,677
per person
5 Sept - 11 Sept
found 22 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (2,239 reviews)
Great location near Park, museums, restaurants, River Walk, and theaters. Kudos to Gail and Alex at the Concierge Desk -- they were so very helpful, patient and kind.

Reviewed on 14 July 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,526, price is now NZ$3,710 per person
NZ$3,710
per person
5 Sept - 11 Sept
found 22 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
I don’t think there is anything to complain about! The staff was amazing, the rooms beyond clean, the rooms are super neat in shape also! Love the location, was able to walk to anything. Super clean neighborhood and overl excellent experience! Will be back for sure!

Reviewed on 14 July 2026

Oregon Holiday

Our pick of the best Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street Oregon WI
Fully refundable
The price is NZ$151 per night from 13 Aug to 14 Aug
NZ$151
13 Aug - 14 Aug
includes taxes & fees
9.4/10 Exceptional! (437 reviews)
"The hot tub is amazing"

Reviewed on 12 July 2026

Sleep Inn & Suites Oregon - Madison
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$290 per night from 2 Aug to 3 Aug
NZ$290
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (4,005 reviews)
"Lots of great things at this place. The only reason we docked a point is because we felt the staff in the bar were bit condescending after they realized that i was not drinking. Obviously, their choice to run their joint as they wish, but it didn’t sit well with us."

Reviewed on 14 July 2026

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 9 Aug to 10 Aug
NZ$135
9 Aug - 10 Aug
includes taxes & fees
8/10 Very good! (1,366 reviews)
"Breakfast was subpar — several options, but looked very unappetizing. The room was a disaster. We walked in and it stunk of mildew & cat urine. It was awful! The sheets had stains, towels had stains, hair in the shower, and pubic hair on the toilet tank. Just disgusted. We were doing to ask for a ..."

Reviewed on 12 July 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 496 properties in Oregon
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 Oregon attractions

Legend at Bergamont

Designed by two-time US Open Champion Andy North, this championship course earned Golf Digest's "Top 10 New Courses" honour. Visitors enjoy resort amenities including pool, tennis, and panoramic clubhouse views.
See properties

Frequently asked questions

How much does an Oregon holiday package cost?
You'll find cheap prices from NZ$3,234 on Expedia for your Oregon break. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Oregon costs.
What are the cheapest months to go to Oregon?
If you're hoping to score a cheap Oregon holiday package, consider travelling in January, July and November. You're likely to find lower prices on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Oregon?
The ideal duration for your Oregon holiday depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
How to find the best Oregon package deals?
Bagging a cheap Oregon package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oregon package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oregon holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalised Oregon holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Oregon?
If you're considering an impromptu Oregon holiday, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Oregon?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Oregon.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Oregon.
  3. Decide how long to go for: Now that you know more about Oregon, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose an Oregon holiday package that brings all your bookings together.

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.