1. Markarth


2. Whiterun
3. Solitude
4. Riften
5. Windhelm

1. Solitude- It's really nice, reminds me of the imperial city, and has cool people.
2. Whiterun- Has tons of cool people, Balgruuf's the coolest jarl and Lydia, Dragonsreach is awesome, central hub of the game etc.
3. Riften- Thieves guild is cool the whole autumn feel is nice and it has plenty of cool people.
4. Markarth- As cool as dwemer ruins are, the architecture just doesn't really fit into a living city as well as a dungeon. Plus there aren't many cool people in markarth.
5. Windhelm- Always snowing(gloomy), full of stormcloaks, Ulfric(such a jerk) , racist nords and oppressed dunmer. On the positive side the architecture of windhelm is really cool.

1. Solitude: This definitely felt like a city, although because of game limitations, it's a bit depopulated to really be one. I like the easy-access locations of the stores, and the house here is nice too.

2. Whiterun: All of the stores are easily accessible, and you get the sense that this really is a city, with the walls, the seemingly large (but not really) population, and the castle at the top of the hill.

3. Riften: I think this Reach has the most visually pleasing landscape, but the town still isn't very convenient to navigate for me yet (I don't have time to play Skyrim much).

4. Windhelm: I really like the ancient Nordic look, but like Markarth, it is somewhat confusing to navigate, or it was initially. I think I'm getting it now.

5. Markarth: a bit confusing in my opinion, but very interesting architecture. It seems eerily imposing, doesn't it?

While I'm at it, here are some others from memory:

6. Falkreath: this one I like better than Markarth, but I don't think it qualifies for the top five list. It seems very homely, and has a small town feel. I like the surrounding green pine forests too.

7. Riverwood: For similar reasons to Falkreath, I appreciate this village, and it's easy to get around, with nice scenery in the Reach.

8. Morthal: A neat town with swamp-like terrain, I like it.

9. Winterhold: Not a city so much as a depopulated town with mainly destroyed and dilapidated houses around. It's borderline out of commission, if it weren't for the importance of the College.

I just wish with Solitude, we could actually go in the sewers.

1. Solitude. Beautiful design, pulls off the Medieval city feel excellently. From the execution when you first enter, to the shouts coming from the marketplace, it's the sort of city I love spending time in!
2. Whiterun. It's a sentimental favorite, being the first city I ever visited in TES. Jarl Balgruuf is easily my favorite Jarl, and the lore behind the city (especially Dragonsreach) is superb.
3. Riften. Again, the marketplace is extremely well done. The thieves trying to steal around the city are a great touch, although they seem a little too frequent.
4. Windhelm. It feels to cold and unwelcoming - its climate doesn't help that, but the towering stone walls and the fact that I still have difficulty navigating it puts me off.
5. Markarth. It's layout feels strange, and makes the city seem a bit small. Personally, I just don't like the city. Vlindrel Hall is a beautiful home though, and I love the Forsworn Conspiracy quest.

1/ Windhelm - beautiful architecture, Dunmer and Argonians live here ( even though they're regarded as second class), market area is easily accessible. Interesting quests. And it's closest to my home : the tower in the college of Winterhold

2/ Markarth - beautiful Dwemer architecture, waterfalls

3/ Solitude- pleasant city, nice people overall, a bit too "imperialish"

4/ Whiterun - boring, with the exception of dragonsreach visually uninteresting. Positive is location of some shops and central location

5/ Riften - nice surroundings but city itself is boring, almost never come here.

out of the 5 major cities:
1. Riften, because thats where i work
2. Solitude, because all those rich punks live there and i get all their money
3. Whiterun, trading centre, love it
4. Windhelm, ugly city but better than markarth
5. Markarth, because the MOMENT i step into the city, 5min later, *thrown into jail*

If it was to include the past Winterhold and Blackreach, i really want to see how winterhold looked. Dont forget, 100 years ago, winterhold and solitude are the biggest cities in skyrim. But gamesas decided to kill winterhold because of 'LORE' reasons, which actually i believed to be 'laziness'

I'm sorry for bringing the thread off-topic, but what kind of lore reasons are you talking about?

1) Markarth- Mostly because it reminds me of Rivendale from LotR.
2) Black Reach- Minus the random lonely giant and the hundreds of Falmors. But, by far the most gorgeous and eerie place in all of Skyrim.
3) Solitude- Its huge, but I personally think they could have designed it better. Seeing as how it is the capital.
4) Windhelm- I love the house you get there, but, I do wish they gave us a quest to rebuild the city into something much more vast. Like allowing us to build a quarter for all the other races?
5) Riften- Maven Black-Briar ruins everything about Riften for me. I ultimately despise Maven. If I got to kill anyone one my personal killing list, She'd be the first one on it. Next would be Rikkie.

Me too. Maybe in DLC?
We can only hope

1: Whiterun. Nice central location. Has the Balmora Factor in its favor too. All the buildings have such wonderful ornate wood carving too. And it also happens to be the city whose default Jarl has the most of his crap together too.
2: Markarth. Dwarven stuff is fun. Plus, its surrounding hold is the fields for the Official Dragonborn Pastime.
3: Windhelm. It's just kinda... eh to me. Not really sweet, but not really bleck.
4: Solitude. It just seems... empty. It's supposed to be the capital, the seat of Imperial power in the province... and there's hardly anyone there it seems.
5: Riften. It just looks boring. The Rift itself is quite colorful, but the city itself is just boring feeling.

1. Markarth- I love the Dwemer layout, it's easily one of the most beautiful places in the game with the waterfall. And the forsworn conspiracy was pretty good IMO

2. Riften- I tend to like Riften because when you're visiting the city, you can never be quite sure what you'll encounter. Usually I see theives getting attacked by guards, but recently I witnessed a man murdered randomly by a volley of arrows...not sure if it's quest related

3. Whiterun- Center of the landmass, always visiting and it's constantly in the MQ. Sky forge is interesting as well

4. Solitude- It's not like I don't enjoy the beautiful and actually city like city of solitude, it's just that I don't find any reason for it to top the other three

5. Windhelm- again, I still like windhelm. I love visiting Ulfric and hearing his speech. Not to mention that I broke into a guy's house and found out he was the butcher, before I knew there was a butcher...I still haven't done the quest but I found a journal that makes him seem quite guilty.

1. Markarth. The moment I exited a certain temple after a certain night to remeber and saw the city from above, I gasped in awe, and for the first time felt like I'm truly playing an ES game. Learning to navigate my way around the city is another story, but it only adds to its special charm.

2. Morthal. Another eerie, a little Morrowindish place. And I have very warm feelings for the Jarl of Morthal - she showed up in my wedding, and later on I met her WALKING alone all the way from Riften to Morthal, so I accompanied and guarded her. Also, she gave me some good laugh during Dimplomatic Immunity quest.

3. Riften. It has a strong "personality". Not a very adorable personality, yet a distinctive one.

4. Solitude. The closest thing to a "city" in Skyrim. Lots of interesting people in there, rich history (Wolf Queen) and related quests.

5. Whiterun. What a bore.

6. Windhelm. I hate that place. Up to now I keep getting lost there, even Markarth is so much more easier to navigate than Windhelm, plus I feel claustrophobic in Windhelm. The local quest is (or at least was when I was doing it) terribly bugged and a straight rip-off from a certain Dragon Age 2 quest. And last but not least, Ulfric resides there.