Oregon Holidays

Photo by Timothy Kilkenny

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Top Flight + Hotel Deals in Oregon

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
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on 30 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Beautiful hotel , breakfast was amazing

Reviewed on 30 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Wonderful hotel in a great location along the river. The view from Terrace 16 is amazing! Also, the pillows on the bed are really comfortable. I love this hotel and would recommend it to anyone.

Reviewed on 30 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
We enjoyed the accommodations and the helpful staff. Great location for exploring on foot.

Reviewed on 30 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Top hotels in Oregon

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street, Oregon, WI
Fully refundableReserve now, pay when you stay
The price is €78 per night from 5 Aug to 6 Aug
€78
5 Aug - 6 Aug
includes taxes & fees
9.2/10 Wonderful! (279 reviews)
Great gotel
"Very nice hotel, nice breakfast. Room has full kitchen"

Reviewed on 25 Jul 2025

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
9.4/10 Exceptional! (2,915 reviews)
"This was our third time staying in the Governor’s Club and would recommend it to anyone looking for a destination to just relax and enjoy the amenities. We were celebrating our anniversary and they surprised us with a complimentary bottle of champagne and strawberries! How lovely!"

Reviewed on 28 Jul 2025

Get rates
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 €71 per night from 12 Aug to 13 Aug
€71
12 Aug - 13 Aug
includes taxes & fees
7.8/10 Good! (1,024 reviews)
"Staff was ver friendly. The room was clean, spacious and comfortable. We will definitely return on our next visit."

Reviewed on 27 Jul 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 488 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.

Frequently asked questions

How much does an Oregon holiday package cost?
You'll find cheap prices from €718 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.

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