AI Trip Planner
Plan a trip with
credit card points
Pick origin + destination + month → see best award flights, top hotels bookable on points, attractions, signature events, and the cards whose welcome bonus would cover the trip. 41 US origin airports, no bank link required.
US
Portland, OR
Coffee, breweries, food trucks, weird in the best way
Pay in cash
$1,650
$250 flight + $1,400 hotel
Pay with points
95,000 pts
+ $10 taxes & fees
Best card for this trip
Chase World of Hyatt
60K + free Cat 1-4 cert = 4 nights at Hyatt Centric (~$1,000 value)
Weather in June
☀️ Peak season — ideal time to visit
Air temp
53°–74°F
12°–23°C
Rainfall
low
Crowds
Peak
Dry warm — peak Rose Festival.
Flights — JFK → PDX
EconomySouthwest Rapid Rewards
JFK → PDX — check direct flights from JFK. Southwest into PDX — best for west-coast riders
13K/20K/30K
roundtrip · Wanna Get Away (dynamic)
+ $10 taxes
Alaska Mileage Plan
JFK → PDX — check direct flights from JFK. Alaska hub — strong PDX route network
25,000
roundtrip
+ $12 taxes
Top hotels for your points
Picked for best points value — Hyatt has the only fixed award chart left in major US hotels, so your points stretch the furthest here. Tap each option below for why it stands out.
Hyatt Centric Downtown Portland
Hyatt·Walkable, budget urbanCat 3 — central, near Powell's Books.
12K/15K/18K
off / std / peak · Hyatt Cat 4
$280/night cash
5 nights = 75,000 pts (~$1,400 value)
Hyatt Regency Portland
Hyatt·Conferences, transit accessCat 4 — at Convention Center, MAX light rail.
12K/15K/18K
off / std / peak · Hyatt Cat 4
$300/night cash
5 nights = 85,000 pts (~$1,500 value)
More hotels on points
The Nines
Marriott Bonvoy·Boutique luxuryTop of Macy's building, iconic atrium.
50,000/night
$400/night cash
5 nights = 250,000 pts (~$2,000 value)
Trip Strategy — open these cards and the trip is mostly free
Open World of Hyatt (60K + free Cat 1-4 cert) + Sapphire Preferred (75K UR). Covers 4 nights Hyatt Centric + RT flight + food trucks.
60K + free Cat 1-4 cert = 4 nights at Hyatt Centric (~$1,000 value)
$95/yr annual fee
Your out-of-pocket budget for this trip
🚗 MAX light rail PDX→downtown ($2.80) + walking + bikes · vs. $1,650 full cash trip
What to see & do in Portland, OR
Powell's City of Books
SightWorld's largest indie bookstore — 1.6M books, full city block. Can spend hours.
Multnomah Falls
Day trip30 min east — 620-ft waterfall in Columbia River Gorge. Iconic photo.
Food Truck Pods
Food500+ food carts citywide — Cartopia (SE), Alder St (downtown), Hawthorne pods.
Pittock Mansion
Sight1914 French Renaissance estate with downtown + Mt Hood views from forest perch.
Saturday Market
Only hereOldest outdoor crafts market in US — Saturdays + Sundays March-Dec at waterfront.
Voodoo Doughnut + Blue Star
FoodVoodoo for novelty (bacon maple bar); Blue Star for craft donuts. Compare yourself.
Events to know about
- May · Jun
Portland Rose Festival
HappeningLate May - mid-June — Grand Floral Parade, dragon boat races.
- Jul
Waterfront Blues Festival
July 4th weekend — major blues acts on Willamette River.
- Sep
Time-Based Art Festival
Mid-September — contemporary performance art.
- Aug
Pickathon
Early August music festival in Happy Valley — indie roots music.