@gosmom, lol.
My daughter does live in the bay area. However, she wants a bigger house. I told her Novato is not priced that bad
compared to other places in the bay area.
She said no to Novato…but she still lives in the bay area. She may just have to get used to a small place. 
She went to Michigan. That was a good choice. Now she is never going to move to a cold weather place.
“Rent…his share…maybe $2,000 a month. Less would be better.”
For $1500, he can have half of a 2 bed/2 full bath in a luxury building in any neighborhood. We’re talking doorman, gym, pool, granite kitchen, etc. He can choose between a lake view or a two-minute walk to the L; with luck, he might even be able to get both.
We do still call it the Sears Tower around here. Easy commute if he lives near the Brown Line. The train is faster and more reliable than the bus, though he can certainly get there on many bus routes. He could walk there easily from the West Loop or a longer walk from River North.
I was in Lakeview for a year – Irving Park Rd, a long block west of Lake Shore Drive. It’s about (?) four blocks north of Wrigley Field. I had a buddy whose wife was doing her master’s at Northwestern, so I’d head up to Evanston now and then. But mostly I hung out between Lincoln Park and Lakeview (with Wrigleyville in between). Those three neighborhoods are pretty decent.
@Hanna, sounds good to me.
Oh - the tower is still called Sears!
To give some perspective, from Lincoln Park, my D has ~25 min commute by either el or bus to the West Loop. Public transportation is very easy to access.
I, then couple we, then family lived in Chicago for many years. We were Lincoln Park and Lakeview, condominium dwellers. I’m still partial to Lincoln Park, Old Town and DePaul personally. Lots going on. I’d be comfortable with my own kids in virtually any northside neighborhood from Streetville and Gold Coast all the way north to many areas of Rogers Park. Also, near west - Bucktown, WickerPark. Museum Campus area is another idea. The areas and prices vary greatly - it’s pretty easy to tell if you are in area that isn’t the safest. Best to start searching with a budget and some notion of the transport you need to get to work. We lived for over 10 years, even after starting a family, without a car.
Here is a useful guide to Chicago neighborhoods (click on the map to explore). I think the pictures chosen give a pretty good sense of how the neighborhoods differ from one another.
http://www.choosechicago.com/neighborhoods-and-communities/
Hanna may differ with me on this, but I don’t really think of the Gold Coast as my first choice for a young person’s area. I think of it as a lot of well-to-do empty nesters or older people who like the convenience of high-rise living and the access to North Michigan Avenue for shopping and restaurants. Streeterville will have more young people, but my sense is that most of them are going to be affiliated with either the Northwestern grad schools or the Northwestern medical complex which dominates the area.
Also note that the River North (and West Loop) areas are relatively new neighborhoods in terms of having nice places to live. The construction / rehabbing is relatively recent. River North in particular is very high priced IMO (though I’m sure you would do well on such an investment).
I would also note that one thing you’ll find is that some of the neighborhoods have “sub-neighborhoods.” So for example, my mother also lives in Lincoln Park about 0.5 mile from my daughter – but if you asked my mother where she lives, she’d say DePaul. Likewise, my daughter is moving to Lakeview, but to a “sub-neighborhood” she could call either Lakeview East or Boystown. Just so you are aware of this.
We just went through looking at a lot of these neighborhoods to help my daughter in buying her place. I hope this is helpful.
“But mostly I hung out between Lincoln Park and Lakeview (with Wrigleyville in between). Those three neighborhoods are pretty decent.”
Oh, here’s a perfect example! Wrigleyville is a “sub-neighborhood” of Lakeview. Though I can understand why someone might call them three different neighborhoods, it’s really just two - Lincoln Park and Lakeview.
It could be important for your son to be in a neighborhood with his “tribe” – is it hipster, bro, urbane, gay, etc.?
FWIW: South Loop, Museum Campus, and Gold Coast don’t seem to have any young adult lifestyle, except for young married couples of means. Skews older.
@Pizzagirl, very helpful. Thank you and thanks to all the posters.
Re Dyiu13’s comment: Good call. If this is of critical importance, I would suggest the following alignments …
Broadly speaking, hipster would align with Wicker Park / Bucktown / Ukrainian Village (though parts of Wicker Park are getting more upscale as we speak and “siphoning off” some who might have gone to Lincoln Park in the past).
Bro is a little more Lincoln Park (DePaul specifically) and Lakeview (Wrigleyville specifically).
Urbane would align with River North, possibly Streeterville.
Gay would lead to Boystown (though my daughter is moving there and she is a straight female - it just is particularly gay-friendly).
Having said that, those are general tendencies / alignments, not rules written in stone.
I really think your big “divide” is going to be whether you prefer newer/just-constructed/high-rise style apartment living that will have all the amenities (but may be a bit more soulless) or whether you prefer older/vintage/smaller/walk-up buildings where you will have plenty of charm and character in the buildings but the amenities may be a bit spottier.
I think Pizza has nailed it pretty close to what I know (many of our friends’ kids migrated from Michigan to Chicago) and several of our friends have get-away condo’s in the “gold coast” to be closer to the kids… which is fun, but more of an “oldster” area in my opinion. I used to use a friend’s condo for get-aways on Delaware “behind” the Hancock.
The nightlife for young single people is concentrated in Wrigleyville (more fratty), the north/Milwaukee area (more hipster), and Boystown (obviously).
River North, Wicker Park, or West Loop.
D lived in Lincoln Park when we were paying and is living in Lakeview now that she is paying. I have loved both neighborhoods.
Chicago looks about a third of the way home to me.
Chicago is laid out on a uniform grid that makes distances easy to calculate: 8 full city blocks to the mile, with each block counting for 100 on the address numbering system… Fullerton Avenue which runs east-west through the heart of Lincoln Park is 2400 North, so that’s exactly 3 miles north of Madison St. in the heart of the Loop. That would put Willis (Sears) Tower about 3 and 1/2 miles from the heart of the Lincoln Park neighborhood, walkable on a nice day but it would take a good hour or more with stoplights and such. I wouldn’t recommend it in winter. Old Town is around North Avenue, 1600 North or 2 miles north of the Loop. Lakeview centers on Belmont Ave., 3200 North or 4 miles from the Loop. Wrigleyville is the northern part of Lakeview centering on Addison St., 3600 north or 4.5 miles north of the Loop. Boystown is the eastern edge of Lakeview from roughly Diversey Parkway, 2800 North, to Addison, 3600 North.
Most young people coming to Chicago live either on the north Lakefront (Lincoln Park, Lakeview, Wrigleyville, Boystown, on up into Uptown, Andersonville, and East Rogers Park); or on the near Northwest Side (Wicker Park, Bucktown, Ukrainian Village, Logan Square); or in neighborhoods clustered around the Loop (Streeterville, Gold Coast, Near North, River North, West Loop). The rough rule of thumb used to be that the further north you go away from the Loop, the lower the rent, and the further west you go away from the Lake, the lower the rent. This was never precisely true because there were always some more upscale and more downscale pockets that ran contrary to the general pattern. It’s probably even less true now because some near Northwest areas like Wicker Park and Bucktown have become much pricier (relative to other parts of Chicago, but still a bargain compared to SF or NYC). But the old pricing logic still applies to many neighborhoods: Uptown and East Rogers Park are still much cheaper than Lakeview and Lincoln Park, Lakeview is cheaper than Lincoln Park or the Gold Coast, and the western parts of Lakeview and Lincoln Park are cheaper than the blocks closest to the Lake. Proximity to the L also influences prices, and is an important practical consideration for most new arrivals as walking is not a desirable mode of transportation in the winter months and many of these neighborhoods are too dense to make car travel practical or desirable for many purposes.
I think my son would probably live within 3 miles of the Sears Tower area. Definitely near an L stop. He is not a hipster. He doesn’t like to drive.
I like the prices of rents and condos compared to Manhattan. There is no comparison.
I will know in 2 to 3 months if the move is going to happen. If the move doesn’t happen, I learned a little about Chicago. I forgot a lot of stuff. I remember walking by the Northwestern Chicago campus 6 years ago.
I was in Lincoln Park. I walked by her coop. I was in Grant Park too.
Learning and remembering is all good.
I know a young professional who just closed on a Near North condo. Less expensive than Lincoln Park but only a few blocks away.