As much as I don't 'enjoy' existing in this godforsakenfrozen-tundralandia, I can live with residing in Chester Park, lo these many years.

Gary pro: Lotus Inn

Chester Park has a weather station so I can get info that actually reflects conditions at my house, plus the a lake view and central Duluth location! Plus, I never see my friends who moved to Gary; they never come to downtown shows anymore.

Gary/New Duluth:
Pros - easy access to Jay Cooke State Park, Magney-Snively, SHT (without annoying road walks), Mission Creek, Oliver Bridge, St. Louis River.

My guess is the housing is cheaper too and you may even get more than a postage sized yard if you so desire.

Cons - feels like it is a long distance drive from the rest of Duluth (though for some this could be a pro); no grocery store, one bus line and limited schedule on same.

East Hillside/Chester Park:
Pros - close to downtown and all sorts of grocery stores, shopping and restaurants and venues for entertainment; Chester Creek (the park), Hartley, Hawk Ridge, the Lake; easy access to the DTA on multiple routes.

Cons - housing prices seem a bit high compared to other parts of town, parties on every other block during some times of the year, lack of yard (if inclined that way), densely populated.

Now I want to see the listing!

Messina & Associates listing

Plus ... it's a freakin' church!

There's definitely plenty of room for your brood, too! AND, I love the idea of you guys living in a church!

My Chicago friends looked at that but couldn't swing the financials. Heating would be my concern, too. I see the roof is new. I'd throw lots of house shows with that kind of space. Good Luck with whatever scenario you pursue!

They are all very nice places to live, IMHO.  I'd live wherever I would be closest to work, friends, etc.  The closer to those things, the better.  I hate having to go far.

That place is awesome!

Gary Pros:
Downtown is only about 15 minutes away. That's like forever in Duluth commute time but zip for people used to Twin Cities, Chicago, Milwaukee, etc.  

Bridgeman's opens this summer.

Daily views of Bardon's Peak and Ely's Peak.

Raptors circling and cruising

Skatepark at the elementary school.

More SHT, mt. bike, ski and Munger trails than you'll know what to do with.

Oliver bridge 1.  Way cool double decker Dickensian looking rail/highway bridge.

Oliver bridge 2.  Be back home sipping your Sunday off-sale from the El Dorado before Lakesiders even reach Superior.

Hugo's Pizza.

Midway/Beck's Road exit cuts 20 mins. off Twin Cities trips.  This is a godsend when the first tournament game kicks off at 9 on some windswept field in Blaine ... or your kid remembers in Cloquet that cleats and shin pads are under the bench in the front porch.

As for the commute, I grew up in Lester Park and I thought it was close to everything. But now I go out there and it seems like I'm driving forever. SO perspective is important I agree on that.  

Another plus that I don't think anyone else mentioned is Gary weather.  They are often outside of the "Colder by the Lake" pocket and it can be 10-15 or more degrees warmer there in Spring/Summer/Fall.  

I'd stay in the Hillside if I were you but ... I agree there's a real choice to be considered.

Proximity of grocery store is another factor.  What is Super One from Gary?  15 minutes in good weather?  And you can forget about a hop-skip-and-jump to the co-op, if that's where you get most of your vittles you are going to have to plan ahead.  Every time.

Seriously? The Co-op?

...if so, the DTA runs from Gary to DT and right to the Co-op...(#2 & #13 I believe.) 
Look at is as... An adventure with the kids!

People seem to forget there's a library in West Duluth too.

Regardless, the DT branch is right on the DTA route to the Co-op! 
Two errands in one!

BYOB (Bring your own bags!)

PLUS - There's the whole Ride Free deal going on during the Road Construction period through October.

And, it's flat out there (plus the trails) - you (all) can ride a bike forever! Or Bike and Bus!

You could end up as the DTA spokes-family! HAHAHAA

Uh oh... I totally understood what ruby2sd4y was saying....

I will +1 Erin on the Gary Milkhouse.  Decent selection and friendly service.  Also doubles as a neighborhood hitchin post for meet-ups and news sharing.  Still ... Gary feels really far out to me.  Ultimately this is obviously going to hinge on what is best for you as a family since, even though I have my own opinion, I don't see any way to say that either neighborhood is fundamentally better than the other overall.  Location location location.  It's so important they say it 3 times in business.

I'm not a fan. I don't understand why anyone likes it here. I have lived in Gary for three years now and I absolutely hate it here. The only pros I came up with was its a tiny bit cheaper to live here, the staff at the Milk House is awesome and Hugo's is kind of amazing. 

Forget about the bus, it takes nearly an hour just to get downtown I don't even want to think about going to the mall or beyond DT via bus. 

It seems like parents don't give a crap about parenting here because all the kids run amok without paying attention to their surroundings, so half the time you nearly kill some 3 year old out riding their bike down the middle of the street.

Also, it's not like you are taking a long-ass drive out to quiet country living, the train yard and foundry are really loud basically all the time, and a lot of the houses are really close to each other so you don't have much privacy in your own yard and you can't have parties without your neighbors getting bothered (meaning me).

Well I could rant all night but I think you get the gist of it. Heed my advice. Don't move here. It just sucks.

Alternatively, I have lived in Spirit Valley and I looovovvveeedd living there! It's like the perfect place to live -- specifically south of Grand and Central avenues.

I've lived in Gary for 6 years now and I enjoy it.  I get a great deal on housing, it's quiet most of the time (with the exception of the train rumbling), the Milkhouse w/ car wash and Hugo's are awesome and the people in general are friendly and willing to help if they see you need it.  There are a lot of kids/families in the area, so you do have to be cautious of children in the streets, but in a residential area, you shouldn't be traveling over 25 mph anyways.  I-35 is only 5 minutes up Midway and Proctor is just a short drive away.  The Wal-Mart/Target in Superior are accessible and you don't have to manage the mess up on the hill.

As far as the drive, which seems to be everyone's major complaint, the first time I drove out there it felt like forever.  It just kept going and going and going.  Now, it seems like nothing.  It's 7 minutes to get on I-35 North.  I don't think 7 minutes to connect to downtown is that unreasonable.  Certainly it's comparable or better than Chester Park area.  It's 15 minutes to Downtown Duluth and 17 minutes to Superior.  For me, that was very manageable.  If you want yard space and space between houses, then you should live out in the country, where your commute will be at least 25-30 minutes.

I've only lived in East Hill/Chester, but to me it has a just-right mix of proximity (to downtown, retail hubs, nightlife), nature trails (Chester Bowl and Tischer within walking distance) and scenery. The only detractor I sense is the area's shift toward student rentals, which will only continue as years pass. The 300-foot rule won't survive to protect homeowners forever (nor should it). So if that's something that you find even a little bothersome, probably best to look elsewhere.

Claire, its because my husband doesn't want to move, It's not for lack of trying to move to my favorite neighborhoods in D town (our rent is rediculously cheap too I can't find anything better for $550 or even $650 all included is the problem). Plus he's super lazy and he's a nerd which means he doesn't like change. I was also in a pissy mood that day because my upstairs neighbors are inconsiderate jerks and left their garbage out for animals to get into then didn't pick it up for a couple days. So I guess if you like Gary thats just fine, I personally don't care for it at all.

At least you have a great restaurant nearby, Vietnamese Lotus.