Bend — November 12 to 19

Two adults and the baby on a lap. Every price below is the total for all three of us, round trip, with a carry-on included. Same flight out in every case — the only real choice is which flight home.
Checked live · August 26, 2026

Getting there · Thursday Nov 12

There is only one sensible way out. Everything else either connects too tightly to be worth it or lands near midnight.

Alaska, through Seattle

Only good option
7:00 AM
Newark (EWR)
6 hr 16 min · Boeing 737 · Alaska 299
10:16 AM
Seattle (SEA)
1 hr 12 min in Seattle
11:28 AM
Seattle (SEA)
1 hr 15 min · Boeing 737 MAX 9 · Alaska 275
12:43 PM
Redmond (RDM)
8 hr 43 min door to door · lands 12:43 PM, so we get the whole afternoon in Bend

Coming home · Thursday Nov 19

Redmond is a small airport — only a handful of flights leave each day, and just three of them get us home at a decent hour. Here they are, cheapest first.

Option A — the early one

Cheapest
$1,027all three
5:20 AM
Redmond (RDM)
58 min · Embraer 175 · Alaska 2043
6:18 AM
Portland (PDX)
1 hr 32 min in Portland
7:50 AM
Portland (PDX)
5 hr 20 min · Boeing 737 MAX 9 · Alaska 294
4:10 PM
Newark (EWR)
7 hr 50 min · home by 4:10 PM — the earliest we can be back
The cost of it: a 5:20 AM flight means leaving the house around 3:45 AM with the baby.
Saves $244 against either of the others.

Option B — the relaxed one

+$244
$1,271all three
6:00 AM
Redmond (RDM)
1 hr 20 min · Embraer 175 · Alaska 2313
7:20 AM
Seattle (SEA)
2 hr 35 min in Seattle
9:55 AM
Seattle (SEA)
5 hr 28 min · Boeing 737 MAX 9 · Alaska 293
6:23 PM
Newark (EWR)
9 hr 23 min · home by 6:23 PM
A long, unhurried break in Seattle — room to feed and change the baby without watching the clock.

Option C — the late start

+$244
$1,271all three
7:40 AM
Redmond (RDM)
1 hr 18 min · Embraer 175 · Alaska 2114
8:58 AM
Seattle (SEA)
⚠ 57 min in Seattle — tight
9:55 AM
Seattle (SEA)
5 hr 28 min · Boeing 737 MAX 9 · Alaska 293
6:23 PM
Newark (EWR)
7 hr 43 min · home by 6:23 PM — the shortest travel day of the three
Two hours and twenty minutes more sleep than Option A, and the same arrival as Option B.
57 minutes to connect. Alaska to Alaska in the same terminal with bags checked through, so it should hold — but if that first flight is late, the next one home is the 5:41 PM redeye.

The choice, side by side

Out of bedLeave RedmondLayoverHomeTravel timePrice
A · early~3:45 AM5:20 AM1 hr 32 min4:10 PM7 hr 50 min$1,027
B · relaxed~4:30 AM6:00 AM2 hr 35 min6:23 PM9 hr 23 min$1,271
C · late start~6:10 AM7:40 AM57 min6:23 PM7 hr 43 min$1,271
B and C are the same flight across the country — Alaska 293, landing 6:23 PM — for the same money. The only difference is whether we leave Redmond at 6:00 AM and wait 2½ hours in Seattle, or leave at 7:40 AM and connect in 57 minutes.

What we are not booking, and why

Cheaper fares do exist. None of them are flights we would actually want.
FareWhat it actually is
$817Same great morning flight out — but the flight home leaves at 3:37 PM, sits 5 hr 40 min in Portland, and lands at 6:30 AM the next day.
$927Home flight connects in 48 minutes and lands at 11:59 PM.
$1,053American out of JFK — 53-minute connection in Phoenix.
$1,105Delta out of JFK — 45-minute connection in Salt Lake City.
$1,206United through San Francisco. Lands 37 minutes earlier than Alaska, costs $179 more, and the connection is exactly one hour.
$1,638United through Denver — 59-minute connection, and the priciest on the board.

We also tried moving the dates

Flying out a different day changes nothing — the price is identical from Nov 9 through Nov 15. Coming home on a different day is worse in every direction.
Fly homeAdvertisedActually workable
Wed Nov 18$817NothingThe best that day connects in 57 minutes and there is no backup.
Thu Nov 19$927$1,027Our date. The best on the board.
Fri Nov 20$1,027More than $1,027Starts above where Nov 19 finishes.
Sat Nov 21$838$1,347+$320. The cheap fares are a redeye and a midnight landing.
Sun Nov 22$838$1,283+$256, for three more days.
Prices move daily and Redmond has very few seats. Fares were verified live on August 26, 2026.