No, there are. It was fairly sunny for a while today.
There are extraordinarily few sunny days in winter, and far fewer in Spring and Fall than you might think as well. I lived in Seattle for over 10 years, and I always felt like the nice weather was from about July 5th through the end of August, or maybe September if you were lucky. And while it doesn’t snow often, it is untrue that you won’t ever have to deal with snow. Of course since it snows relatively rarely, no one is prepared for it, so it’s a much bigger mess than it should be (I’ve also lived in places that get a ton of snow, so I am making a direct comparison).
Obviously everyone handles it differently, but I hated the weather almost immediately, and wanted to move within a year. I stayed primarily for career reasons, but since I finally made the decision to bail to somewhere with better weather (and worse career options), I’ve been immeasurably happier.
That said, for the most part if it weren’t for the weather, I think both Seattle and Portland are nice places. There are plenty of nits I could pick, but that’s true of anywhere.
Believe it!
There are no sunny days in winter.
There are no sunny days in spring.
There are no sunny days in the fall.
Yes, obviously, I am exagerrating–But only just a little, tiny bit. Basically, those 3 sentences are true.
I had a great situation when I lived there-- young, just out of college, a great job in my new profession, and lots of enthusiasm. But the weather ruined it for me.
Seriously—the constant damp and grey seeps into your body, and then seeps into your mind.
I became aware of it as it happened…that as soon as I woke up, looking out the window put me in a bad mood.
Thousands of songs have been written about blue skies, sunshine and happiness.
Zero songs have been written about grey skies, gloomy weather, and happiness.
I will never, never,never go back to Seattle again.
(Besides, there are too many Starbucks. Often right across the street from each other. It’s weird. 
)
I have lived in the PNW since the early 80’s, in Seattle proper for almost 10 years. The grey and gloomy weather seldom bothers me. Seattle has stunning natural beauty and boatloads of culture. It is true that socially it is polite but cool. It can take a long time to establish a social circle. The traffic in Seattle is truly awful. Portland is not as pretty and pulsing with life, but it’s more human scaled and a bit friendlier. When I was young and hip I preferred Seattle. Now that I’m older and hipper I would choose Portland.
See, I just haven’t seen this (Yet, I’ve only been here approx. 2.5 years). I did grow up in, and spend 41 years of my life in Alaska, but I was born in Auburn WA, and lived there until I was 10. I don’t remember unrelenting grey then, and I haven’t really noticed it now.
It’s winter now, so overcast days are more “the norm” but it doesn’t seem like this oppressive dark grey, and it’s NOT constant. There are a lot of times we’ll look out over the sound and it’ll be really pretty and you can see the ferries come in, and the mountain range etc. (however, you have to take my opinion with a grain of salt, probably a BIG one, I grew up where it’s dark most of the day for at least 6 months out of the year :D).
I’ve never lived in Portland, but my daughter did up until I moved here (well in the burbs that is), and I have gone through there, or stayed there many times for projects, and it does seem like a much prettier city than Seattle. The public transport seems better too. Their Max (I think it’s called) goes all over the place, whereas our light rail just has one route of about 13 stops, from the airport to Westlake.
Regarding the looks of the two cities, again, I’ve got a very limited knowledge of the entire city though, I work in Pioneer Square, which I’m told is kind of a yucky area.
I live on the light rail line, on one of the last stops south of town and it takes me only 35 mins to Pioneer Sq, about 40-45 to Westlake (the last stop). 40 if there are a buncha slow buses in the tunnel. So if you can get within walking distance to one of the stops, it’s not bad at all. One of my coworkers lives WAY south and takes the sounder commuter train. Two of my other coworkers live a few stops north of me, and their commute is only about 15 to 20 minutes.
Having spent five years in Chicago and the rest of my life in Seattle, I can say that Seattle is NOTHING like Chicago! No way, no how.
Of course there are. In fact, we just finished about two weeks of colder, clearer weather. Unusual for winter in the PNW, but the climate is changing, don’t you know. Bitching about the gray and the drizzle is what is expected, and I admit that our second winter here was a bit rough for me. But I’ve settled into things and keep busy. If you let the rain and gray keep you from living life, then you’ve got bigger problems than the weather.
Based on my experience, all the Seattleites will strongly recommend that you move to Portland and vice versa. In their city, it rains all the time and it’s full of junkies and there’s nothing to do.
Be warned. In the Seattle area, the four seasons are
Early Winter
Winter
Late Winter
Road Construction
That’s still better than Anchorage, which was: nine months of winter, three months of rough sledding.
The best way of describing the cloudiness out here is to relate that the local weather reports out here will include “chance of sunbreaks” as a normal update. That is, the possibility of the sun even making an appearance through the cloud cover at some point during a day is a remarkable, although not totally unheard of, occurence during the non-summer months.
The raininess is definitely overhyped: while it often rains, it’s usually a very light drizzle, and tends not to last more than an hour or so, but the gray is not. If you have any history of a Seasonal Affective Disorder, do not move to the PNW.
That being said, there’s nothing more gorgeous than the Puget Sound and environs when its nice out.
I’m also interested in moving to either city, in part due to their reputation as cycling friendly. Does anyone here have experience with cycling there?
Portland: Flat
Seattle: Hilly
The Seattle ferries do give you some options for cycling along wooded highways in Kitsap County, but peninsula drivers are notoriously oblivious to cyclists and pedestrians.
Seattle recently painted in a whole bunch of bike lanes that are really annoying and make no sense.
Cycling is a religion in this city. There are bike boulevards (I live on one) with traffic choke points and speed humps to slow down car traffic; there is the aforementioned paved trail that extends for 42 miles around the city, including along the river and over some of the bridges. There are bike shops everywhere and a lot of them do rentals.
I have not actually ridden a bicycle in Seattle proper, but it seems like a slightly more bike-hostile place than Portland. There are a few choke-points in the Seattle area where you prettymuch have to take arterials to get from A to B, Portland is generally a little more navigable as far as having low-traffic alternative routes.
One thing to note: we had about a week of cold and clear, dipping near 10F, and it was merely cold; then it warmed up just enough to call up the fog, and even though the thermometer was up some, it felt a lot colder. Typically, we have a January-summer for about a week, when the days go over 50 and the sky is mostly clear, but it is late this year.
If you still like snow, it is always less than an hour away – two in August.
Yes, if you live right on top of a light rail or Sounder station, and your work is also right on top of a station, you’ve got it made. It leaves you with a very narrow choice of places to live, though.
I live half an hour from the SeaTac end of the light rail line, and it’s a 45 minute ride to Westlake station. Add in a few minutes for catching the train, walking from the station to work, etc. and it really is a massively long commute. If you’re anywhere but directly South of the city, substitute ‘bus’ for ‘train’, and the same story applies.
TL,DR: Except for a very narrow slice near rail stations, traveling from the 'burbs to downtown via public transit is pretty gnarly.
(or BOATING, in the streets).
Preach it! 
That’s true, that’s why I said “if you can get near one of the stops”. I knew, before I accepted the job and moved to the states, that my new job was located near one of the light rail stops, I took the “shame train” WAY too often in Anchorage to do that again. Anyway, so when I started looking for an apartment, I purposely chose one near one of the south end stations, and like my coworker who commutes by Sounder, I can work on the train, which reduces my hours at work.
As to driving…Add in the horrendous parking fees, and it’s pretty awful too. I haven’t found that the commute is all THAT much worse than Anchorage (which oddly was okay in the morning "rush and ridiculous along the SAME damned route in the afternoon) time-wise that is. I won’t go into the drivers here.
Personally I like Portland better, especially looks-wise, I just realized why because of someone’s post further upthread. It’s flat. I don’t like how closed-in the Seattle area feels, all the hills just means you can’t SEE anywhere. I guess I like wide-open spaces, since the OP is coming from Chicago, he might too?