Gateway Vacations from $723
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The Latest Gateway Vacation Packages
- Budget Inn Bend
Oct 17 - Oct 23Budget Inn Bend + Flight
Old Farm District6 nights2.5 star property7.0/10 - Good (86 reviews)Roundtrip • Chicago (CHI) - Redmond (RDM)ORD - RDM • 1 stop RDM - ORD • 1 stop$1,071$723found 16 hours agoper traveler - The Pines at Sunriver
Oct 17 - Oct 23The Pines at Sunriver + Flight
Sunriver6 nights3.0 star property9.4/10 - Exceptional (449 reviews)Roundtrip • Chicago (CHI) - Redmond (RDM)ORD - RDM • 1 stop RDM - ORD • 1 stop$1,176$815found 16 hours agoper traveler - Brasada Ranch
Oct 17 - Oct 23Brasada Ranch + Flight
Powell Butte6 nights4.0 star property9.4/10 - Exceptional (374 reviews)Roundtrip • Chicago (CHI) - Redmond (RDM)ORD - RDM • 1 stop RDM - ORD • 1 stop - The Lodge at Eagle Crest Resort
Oct 17 - Oct 23The Lodge at Eagle Crest Resort + Flight
Redmond6 nights3.5 star property7.6/10 - Good (1,011 reviews)Roundtrip • Chicago (CHI) - Redmond (RDM)ORD - RDM • 1 stop RDM - ORD • 1 stop$1,157$824found 16 hours agoper traveler - Canyon Rim at Eagle Crest
Oct 17 - Oct 23Canyon Rim at Eagle Crest + Flight
Redmond6 nights4.5 star property9.6/10 - Exceptional (138 reviews)"Friendly staff!"Reviewed July 25, 2026Roundtrip • Chicago (CHI) - Redmond (RDM)ORD - RDM • 1 stop RDM - ORD • 1 stop$1,262$911found 16 hours agoper traveler
Gateway Hotel Deals
Frequently Asked Questions
How much does a Gateway vacation package cost?
You can snap up a vacation package to this popular destination from $723 on Expedia. However, how much your vacation to Gateway costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Gateway?
If you're hoping to book a cheap Gateway vacation package, consider visiting in December, January and February. You'll typically find better prices on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Gateway?
With a well-organized travel plan, you can easily hit the most popular Gateway sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Gateway vacation for longer.
How to find the best Gateway package deals?
Use Expedia's filter tool to find some of the best Gateway package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Gateway package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Gateway vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can customize your Gateway getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Gateway?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Gateway trip.
Does Expedia offer Book Now, Pay Later Gateway vacation packages?
Your Gateway getaway should be an escape from your daily routine, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.