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arnobg

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Me and my fiance are taking a 3-4 day trip to Chicago at the end of May, we have Southwest miles to burn and they are a good value for the points.

We have not yet been to Chicago so we aren't so familiar with the downtown areas. We want to stay somewhere where we can walk to a lot of options for local food, pubs, breweries, etc. Other things we are interested in doing while there is checking out the Shedd Aquarium, Willis Tower, Goose Island Brewery, possibly go to a ball game at Wrigley.

Looking for any advice of hotels/areas to stay to be most accessible to all of this, especially the being able to walk around from the hotel part if possible. Obviously looking for the "safe" areas to walk around if it is at night too. Open to any pubs/breweries close too if there's suggestions!
 
I'm an ex-Chicago peep. Any hotel on Michigan Avenue, north of the river and south of Oak street (essentially, the Magnificent Mile) will be accessible and safe. Look into anything within 3-4 blocks of that strip to the west, as well. My favorite place to stay when I go there is the Omni. It's pricey but it is in the ideal location and is a nice place. I also liked the location of the House of Blues hotel when I stayed there, and it was a decent place. I have stayed at other nice hotels in that area, but they all kind of merge together in my memory. The Hilton Garden was nice. Whatever the hotel with the Capital Grill in it (I forget the name) was nice.


My word of advice is to avoid the older hotels that are listed as 4 stars (Drake, Knickerbocker, etc.). They are beautiful old buildings and are neat to go visit the lobby/bar, but the rooms are small and outdated (at least when I have stayed at those places).

EDIT: Apparently the hotel with the Capital Grill is the Hyatt.

DOUBLE EDIT: I just remembered also staying at the Holiday Inn inside of the Merchandise Mart once (but it was 12-15 years ago) and like that place...a little bit more of a walk to Michigan Avenue, but I think it was more reasonably priced than the hotels right on the Mag Mile.
 
I'm an ex-Chicago peep. Any hotel on Michigan Avenue, north of the river and south of Oak street (essentially, the Magnificent Mile) will be accessible and safe. Look into anything within 3-4 blocks of that strip to the west, as well. My favorite place to stay when I go there is the Omni. It's pricey but it is in the ideal location and is a nice place. I also liked the location of the House of Blues hotel when I stayed there, and it was a decent place. I have stayed at other nice hotels in that area, but they all kind of merge together in my memory. The Hilton Garden was nice. Whatever the hotel with the Capital Grill in it (I forget the name) was nice.


My word of advice is to avoid the older hotels that are listed as 4 stars (Drake, Knickerbocker, etc.). They are beautiful old buildings and are neat to go visit the lobby/bar, but the rooms are small and outdated (at least when I have stayed at those places).

Thanks for the advice, the Magnificent Mile is actually exactly where I was browsing hotels! I was looking the the Magnificent Mile Marriott, I will look into the others you noted.

What is parking like at these downtown hotels? Considering getting a rental car when I arrive, would it be cheaper/better to cab/subway everywhere? We will fly into MDW
 
I was stranded once overnight in Chicago due to a cancelled flight and got a last minute deal on a room at hotel Allegro. It was a walkable distance from a number a breweries and gastropubs, as well as a big shopping center. The area seemed pretty safe to me. The GF was tired so I tooled around a bit and got lost. Some homeless dude literally escorted be back to my hotel. Probably not the best idea, maybe i just didnt get stabbed cause I gave him a tip

Definitely one of the fanciest and coolest modern designed hotels I've been in. Not just the common areas, but the rooms too. It looks like the regular rates on Kayak arent much more expensive than what we did.
 
And as far as Wrigley and Goose Island...those are in the same neighborhood but considerably north of where you probably want to be. But if you are on Michigan Avenue, the Red Line of the L is only a few blocks away (on State Street) and it has a stop that is nearly inside of Wrigley Field. It is relatively cheap to travel by L, so that neighborhood is accessible from downtown very easily.

Do yourself a huge favor. If you are going to travel north on the Red Line up to places like Wrigley, make a point of eating a meal at the Chicago Pizza and Oven Grinder Co. The name is a bit deceiving, this is not a pizza joint. It is an old tavern style restaurant with amazing food. You want a pizza pot pie with meat and mushrooms. You will find yourself making plans to get some frozen to bring home with you...they are that good. If memory serves though, bring cash...they didn't take plastic last time I was there.
 
Thanks for the advice, the Magnificent Mile is actually exactly where I was browsing hotels! I was looking the the Magnificent Mile Marriott, I will look into the others you noted.

What is parking like at these downtown hotels? Considering getting a rental car when I arrive, would it be cheaper/better to cab/subway everywhere? We will fly into MDW

A. I stayed at that Marriott once, a long time ago. It was not bad and it is right in the heart of where you want to be.

B. I think parking is reasonable if you get it with the room ($40 for a weekend, maybe?). Once there, I suggest never touching your car again until you leave. Use the Red Line "L" where possible and cabs where not.

EDIT: just saw that you are flying in and talking of renting a car. Skip the rental car, in my opinion. You can get downtown from either airport via the "L" system. It is cheap but takes a while (maybe 30 minutes). Or you can drop $50 (again going of memory on that rate) and get a cab.
 
Thanks for the advice, the Magnificent Mile is actually exactly where I was browsing hotels! I was looking the the Magnificent Mile Marriott, I will look into the others you noted.

What is parking like at these downtown hotels? Considering getting a rental car when I arrive, would it be cheaper/better to cab/subway everywhere? We will fly into MDW

If you're flying in and doing things in the city, DO NOT get a rental car. Train will take you from the airport downtown, and get you close to anywhere you want to go within the city. Uber, cabs, and buses cover the rest. Parking at a hotel downtown will be $30+ per night (often valet only), and anywhere in the city you go you will need to pay to park as well.

I've spend the night at the Sheraton Grand Chicago and would do it again. I also put my parents up at the Palmer House Hilton, and would recommend that as well. Room sizes in the Palmer House vary, it's one of the old hotels previously mentioned, but I don't think you'll be disappointed, and if you're doing things right, you won't be spending a whole lot of time in the hotel room anyway.
 
Attached to the Hotel Allegro is 3-2-1 which has amazing food. the rabbit I got there back in 2001 will never be forgotten. That was for a college class trip and the only hotel i have ever stayed in there as my bother lives in the area. We ran around that area stopping at the small galleries. There were a bunch and they all had free wine. We saw a play at the goodman theater. I'm sure almost every hotel will have some sort of parking for it's guests. You may just want to give a call. Get all the insurance on your rental, you will most likely need it if you park along the road any where in the city.

Revolution brewing co is worth checking out, but I feel it's worth mentioning that you won't be far from 3 floyds.
 
I've spend the night at the Sheraton Grand Chicago and would do it again. I also put my parents up at the Palmer House Hilton, and would recommend that as well. Room sizes in the Palmer House vary, it's one of the old hotels previously mentioned, but I don't think you'll be disappointed, and if you're doing things right, you won't be spending a whole lot of time in the hotel room anyway.

My ex-wife's company has an account with the Palmer (their building is across the street) and we stayed there a number of times. Excellent location and great hotel.

I generally send folks to The Talbott but a number of friends have stayed at the ACME and loved it.

As mentioned, unless you are a masochist, do not rent a car for Chicago. So many reasons but the parking and the STRONG possibility you will find yourself going in circles if you try to use GPS downtown (less so with smartphone GPS with cell tower triangulation). The eL is pretty idiot proof and cabs are not too expensive because downtown is so compact.
 
I am actually planning a trip there in May-July, as well. Places that I really try to see while there:

1. Chicago Pizza and Oven Grinder Co, as mentioned before, I think is the best meal in town.
2. Buddy Guy's Legends. A great blues bar a bit south of the Loop. I will skip it this time because I will have kids with me.
3. Shedd's Aquarium. In my opinion this is the best of the "museums" down there, but I'm not much of an artsy person.
4. Wrigley Field. I'm a huge baseball fan and spent many afternoons at Cubs games when I lived up that way. Even if you don't go to a game, that neighborhood is a great place to walk around and bar hop.
5. The Lego Store. Yes, this is silly and I'm a nerd, but I love that place. I don't remember where they moved it to, though, as it used to in the Nordstrom Building...maybe in the Water Tower Mall now?
6. American Girl Store. OK, I don't actually like this one, but my two daughters will be with me and that is like the highlight of littlest one's life, so I like to see her there.

Now you've got me all excited to go there.

EDIT: and if you've never been to the top of the Sears Tower (Wilis Tower, whatever) or the Hancock Building, it is worth it to do that once. There is a bar/lounge near the top of the Hancock, if I remember correctly. I also remember a glass of Chivas costing around $20 at said lounge...but the view is awesome.
 
Revolution brewing co is worth checking out, but I feel it's worth mentioning that you won't be far from 3 floyds.

Even though I only live about 10 minutes from 3-Flyods I cannot honestly recommend it for visitting on a short trip to Chicago. Even post-remodel, it is a pain to get in any time after 4 PM almost any day. The shortest wait I have had in the last 6 months was 20 minutes. My exception would be if you can slip in at opening time on Saturday or Sunday...might still be a line, though.
 
Awesome info thanks guys! No rental car it is, currently looking at the Omni, Marriott, Hilton DoubleTree all in Magnificent Mile.
 
Even though I only live about 10 minutes from 3-Flyods I cannot honestly recommend it for visitting on a short trip to Chicago. Even post-remodel, it is a pain to get in any time after 4 PM almost any day. The shortest wait I have had in the last 6 months was 20 minutes. My exception would be if you can slip in at opening time on Saturday or Sunday...might still be a line, though.

I have never waited there, but I have only been by myself and able to belly up to the bar. Though your right, it's probably not worth the trouble. I just hate when i'm that close to a infamous brewery and didn't even know about it. like going to ben and jerry's and not knowing you just drove by the Alchemist.

Anyway, enjoy Chicago OP!
 
If you are staying on the Mag Mile and want to get classic Chicago Style Deep Dish and a Pint, Gino's East (River North location on LaSalle St.) opened up a brewery at this location. Not the best micro brews I've ever had, but they were decent and certainly added to the experience.

Depending on where you are on Michigan ave, it should be walking distance for you as myself, Wife and kids, 10 and 12 all walked over there from our hotel.

I would also suggest hitting up Revolution, make sure you get signed up for the tour quick though, if you want to go on it. They fill up quick.
 
Some pretty good points have been made here as far a s places to visit. The EL is your friend, particularly the Red Line and Blue Line. Red Line going north gets you to Lincoln Park, Wrigleyville, and Andersonville quite well. The Blue Line going north will get you to the Bucktown and Wicker Park. Bucktown/Wicker is the upcoming/gentrified area with several hot restaurants and shops. Piece Pizza has an in-house brewery and serve a couple of decent beers. They're right off the Blue Line at North Ave. Revolution Brewing is just north of that near the California Ave stop on the Blue Line.
The safe parts of town have already been mentioned. Try to stay Downtown or North of it. There's very little for visitors on the South and West Sides of the city. Although, University Village, the east end of Pilsen and Bridgeport have a couple of up and coming places. You could cab it there if you find something to your liking.
As with any major city you'll need to be on your toes and trust your instincts. No matter where you are there are opportunistic knuckleheads. Keep your smartphone stowed, your wallet in an upper/chest area coat pocket, and a small amount of cash in your pocket.
If you run into issues, the coppers here are quite helpful despite what the media wants you believe.
 
Some pretty good points have been made here as far a s places to visit. The EL is your friend, particularly the Red Line and Blue Line. Red Line going north gets you to Lincoln Park, Wrigleyville, and Andersonville quite well. The Blue Line going north will get you to the Bucktown and Wicker Park. Bucktown/Wicker is the upcoming/gentrified area with several hot restaurants and shops. Piece Pizza has an in-house brewery and serve a couple of decent beers. They're right off the Blue Line at North Ave. Revolution Brewing is just north of that near the California Ave stop on the Blue Line.
The safe parts of town have already been mentioned. Try to stay Downtown or North of it. There's very little for visitors on the South and West Sides of the city. Although, University Village, the east end of Pilsen and Bridgeport have a couple of up and coming places. You could cab it there if you find something to your liking.
As with any major city you'll need to be on your toes and trust your instincts. No matter where you are there are opportunistic knuckleheads. Keep your smartphone stowed, your wallet in an upper/chest area coat pocket, and a small amount of cash in your pocket.
If you run into issues, the coppers here are quite helpful despite what the media wants you believe.

I second all of that. I rode the Red Line every day to work for years. I still carry my wallet in my front pocket as a result. Pick pockets troll the L. Pickpockets have a ***** of a time getting a wallet from your front pocket.
 
Really good info in this thread. I'm looking at moving to the Chicago Metro area next summer if the SWMBO gets into grad school at DePaul or Elmhurst. I'll be quitting my current stable and secure (but boring and much loathed) job and following along for a new chapter in our lives. I'll be potentially looking for a job in the brewing industry in the area, so this is really helpful for me.
So if any of you fine folks run a brewery and are looking to hire an industrially inexperienced but knowledgeable homebrewer... hi :D

Also, what are wages like in the area? I'm basically just looking for enough to get by until she graduates with her degree, then I'll be looking for more of a career.

Thanks for the thread and the info all! and sorry OP, I don't intend to thread jack... think of it more as a hitchhiker :D
 
Really good info in this thread. I'm looking at moving to the Chicago Metro area next summer if the SWMBO gets into grad school at DePaul or Elmhurst. I'll be quitting my current stable and secure (but boring and much loathed) job and following along for a new chapter in our lives. I'll be potentially looking for a job in the brewing industry in the area, so this is really helpful for me.
So if any of you fine folks run a brewery and are looking to hire an industrially inexperienced but knowledgeable homebrewer... hi :D

Also, what are wages like in the area? I'm basically just looking for enough to get by until she graduates with her degree, then I'll be looking for more of a career.

Thanks for the thread and the info all! and sorry OP, I don't intend to thread jack... think of it more as a hitchhiker :D

When I lived there the wages were relatively high but so was the cost of living. Netted out, I'd still say it is a relatively expensive place to live, despite the higher wages.

I'm a DePaul grad, by the way.
 
When I lived there the wages were relatively high but so was the cost of living. Netted out, I'd still say it is a relatively expensive place to live, despite the higher wages.

I'm a DePaul grad, by the way.

Yeah I kind of figured that was the case. Sounds like I'll basically be a hermit for 2 years haha, but it'll be an adventure until we get settled somewhere.
 
Yeah I kind of figured that was the case. Sounds like I'll basically be a hermit for 2 years haha, but it'll be an adventure until we get settled somewhere.

Your primary issues are:

Housing cost are high
Taxes in cook county are insane
taxes in other counties are merely loathsome
Park cost can be stupid

Not knowing the COL in Pullman, if it is anything like eastern Washington, you are in for a shock.

Are you up for "big city" living? If not, consider North West Indiana. Commute from NWI to anything close to downtown is faster than the same quality/school district in IL This is assuming kids. Not kids, no big dogs, take the city and ping me if you need neighborhood details
 
Your primary issues are:

Housing cost are high
Taxes in cook county are insane
taxes in other counties are merely loathsome
Park cost can be stupid

Not knowing the COL in Pullman, if it is anything like eastern Washington, you are in for a shock.

Are you up for "big city" living? If not, consider North West Indiana. Commute from NWI to anything close to downtown is faster than the same quality/school district in IL This is assuming kids. Not kids, no big dogs, take the city and ping me if you need neighborhood details

If you are young (anything in your twenties), I say just say "screw it" and find a way to live in the city. If you are like me, you'll never live in a big city like that again. I wouldn't trade my years living in the city for anything, despite being a small town guy who now dwells in the urban sprawl of the Detroit suburbs. Chicago is amazing when you're young and don't have kids. Just do it.
 
Your primary issues are:

Housing cost are high
Taxes in cook county are insane
taxes in other counties are merely loathsome
Park cost can be stupid

Not knowing the COL in Pullman, if it is anything like eastern Washington, you are in for a shock.

Are you up for "big city" living? If not, consider North West Indiana. Commute from NWI to anything close to downtown is faster than the same quality/school district in IL This is assuming kids. Not kids, no big dogs, take the city and ping me if you need neighborhood details

PM sent, thanks!
 
I ended up booking the Omni on Magnificent Mile. It is fully refundable up until 24 hours prior so if I change my mind I'm set. I'll try to hit some of the places you guys mentioned for food.
 
Onkel, what is Edgewater like these days? I lived there the longest when I was in the city (the rest of the time was in Lakeview, just outside of Wrigleyville). I had a really nice place, for reasonably cheap, just off the Northrop stop of the Red Line (if I remember right). The neighborhood was "transitional" back then...meaning I felt safe walking at night, but would not feel good about my wife doing so (we were not together at that time). We were just south of Loyola's Rogers Park campus.


That was about 12 years ago, though. Wonder if that neighborhood ever turned the corner.
 
I ended up booking the Omni on Magnificent Mile. It is fully refundable up until 24 hours prior so if I change my mind I'm set. I'll try to hit some of the places you guys mentioned for food.

You'll be happy with the Omni, I think. I haven't stayed there in a few years but you are certainly where you want to be, and the hotel was very nice last time I stayed there. Even had a nice pool and restaurant/bar.
 
Onkel, what is Edgewater like these days? I lived there the longest when I was in the city (the rest of the time was in Lakeview, just outside of Wrigleyville). I had a really nice place, for reasonably cheap, just off the Northrop stop of the Red Line (if I remember right). The neighborhood was "transitional" back then...meaning I felt safe walking at night, but would not feel good about my wife doing so (we were not together at that time). We were just south of Loyola's Rogers Park campus.


That was about 12 years ago, though. Wonder if that neighborhood ever turned the corner.
Lakeview and most of Wrigleyville are great now. Young, vibrant and occasionally very Indian (Wriggleyville). Wriggleville struggles with high vacancy rates still from the crash (to many condo's built on spec right before the crash).

Parts of Lakeview are still awaiting the full effects of "gentrification" but it is more grotty student housing than crack den in the lesser areas.

Ex-wife lives north of Loyola in Rogers park on the lake and the neighborhood could not be nicer.
 
Lakeview and most of Wrigleyville are great now. Young, vibrant and occasionally very Indian (Wriggleyville). Wriggleville struggles with high vacancy rates still from the crash (to many condo's built on spec right before the crash).

Parts of Lakeview are still awaiting the full effects of "gentrification" but it is more grotty student housing than crack den in the lesser areas.

Lakeview was very well to do back then. Edgewater Beach is the neighborhood I was curious about.
 
Lakeview was very well to do back then. Edgewater Beach is the neighborhood I was curious about.

Not familiar enough as I skip right over it on the way to Rogers Park on the Lake Shore. Sorry. Imagine gong from NWI to Rogers Park and you can see the quandary. I get a glimpse as I make the turn to Sheridan but until I am on Sheridan, I get no feel for the neighborhoods.
 
Lou Malnati's
Heaven on Seven
River architecture tour
Signature room at the Hancock Tower
Great bar-hopping in Wrigleyville
Avoid Navy Pier like the plague
Bring walking shoes and work your way from south Wabash up to Lincoln Park
 
If you are young (anything in your twenties), I say just say "screw it" and find a way to live in the city. If you are like me, you'll never live in a big city like that again. I wouldn't trade my years living in the city for anything, despite being a small town guy who now dwells in the urban sprawl of the Detroit suburbs. Chicago is amazing when you're young and don't have kids. Just do it.

This advice is valid for most BUT city living has compromises some of us might not be willing to make regardless of age. I have not lived in a large city in the US but I have in Europe. I did not have dogs and my job was a single streetcar line ride to my office.

I firmly believe city life is something most folks should experience but circumstance have to line up. I am a redneck by nature but would move to the DC area if the right DoD job came along. I have non-stop offers for Houston but...emr, Houston. Chicago holds no appeal for me. Seattle, DC, Boston....maybe.

So to each their own.
 
Lou Malnati's
Heaven on Seven
River architecture tour
Signature room at the Hancock Tower
Great bar-hopping in Wrigleyville
Avoid Navy Pier like the plague
Bring walking shoes and work your way from south Wabash up to Lincoln Park

This..emphasizing the river tour and the plague-like avoidance of Navy Pier. Add a museum or two if you are into that with Science and Industry on the top of the list.
 
My opinion of Navy Pier is a bit softer than the others, but I wouldn't go out of my way unless you really have no idea what you want to do and there is a free trolly from Mich Ave to the Pier, which I believe there normally is during summer months.

River tour > lake tour. If you are going to do only one, do the river tour. I'm kind of a history nerd and I just thought of something else really neat that I took for granted because I walked past it every day...embedded in the south exterior wall of the Tribune building (on Mich Ave, near the river) are stones from famous places all over the world (Gettysburg, etc. - I think they were from all over the world, maybe just US). I find that sort of thing neat...if you are in that area. My inner history nerd also loved seeing the vacant lot across the street from the Chicago Pizza and Oven Grinder Co. (I know, I'm obsessed) because it was the site of the St. Valentine Day Massacre (Al Capone) and the trees in the lot have plaques commemorating it...oh, and the theater where Dillinger was shot is still standing, and was still showing movies when I lived there. It is in Lincoln Park, just off the Red Line at Fullerton...damn it, I want to go now.
 
+1 on the river architecture tour, did that last year and really enjoyed it.

Restaurant recommendations:
~Purple Pig - right on MM really good food (pork blade steak or the milk braised pork shoulder), and good atmosphere (both inside and out)
~Girl & The Goat - meat packing district, really tasty and creative small plates. One of my favorite places to go
~Little Goat - same owner as above, fun place for breakfast
~Aviary - for some crazy and super scify drinks
~Frontera Grill - really good Mexican food
~Glazed and Infused - awesome donuts (maple bacon ftw!)
 
Chicago's a great place. I've lived here for 4 years and have never been bored. Anyone with any style or interest can find something fun to do here. All depends upon what you're looking for.

Hotel- my recommendation is to make a list of the things you want to do and see where you'll be spending most of your time. Avoid south of 7th St. Dont get me wrong; there are some great places down south loop, but the options are limited and spread thin. You'll spend a lot of time walking or riding in cabs.

If it were me, I'd focus on River North as your homebase. Lots of bars of varies styles (look at a map along Hubbard St). Great restaurants scattered all throughout. Great proximity to Michigan Ave shopping if you are into that. Easy to get across to the Loop. Convenient access to the Red Line and up to Wrigley.

Pizza - my absolute favorite is Pizzeria Uno on Wabash and Ohio. (Pizzeria Due is essentially the same restaurant, they just opened up another location a few blocks). Next would be Pizzanos and then Exchequer (not on most people's pizza radar but they have a solid deep dish). Personally, I don't much care for Gino's and Lou Malnatis, but everyone has their own preference.

Transportation - take the L into town. DO NOT DRIVE. It'll take you longer to get downtown and you'll spend $30-50 a night on parking (if you do get a car, make sure the parking garage allows in/out access. Many places charge you every time you exit). Instead, save that money for cab fare to help you get home at 3am instead of messing with the L or a bus. Also, don't be intimidated by the bus. They'll help you get to more of the city on the cheap.

Beer- I'd save Laguintas for another trip...just too far out of the way. I wasn't much impressed with Goose Island in Wrigley. It is basically a restaurant with a microbrewery in the back. I may have just caught them on an off day. I've never been to their location don't even know what the scene is like, but I am a fan of Revolution beers. Anti-hero is one of my top 3 IPAs. Lots of bars downtown serve local brews so you'll get plenty of variety. One of the great things about this city, IMO.

Food - There are tons of options here and really just depends upon what you're taste buds are calling for. The West loop is home to quite a few great place, some requiring tickets or reservations 6 months in advance. If you're over there, stop into Haymarket for a pint or two. Au Cheval has a fried bologna sandwich that is awesome. Great burger too.

There's some thought starters for ya. As you research spots and get closer to the trip feel free to ping me. I'll be happy to give my thoughts. As I said at the beginning, it all depends upon what type of trip you're looking for. What works for me may not work for you or the next guy.
 
Onkel, what is Edgewater like these days? I lived there the longest when I was in the city (the rest of the time was in Lakeview, just outside of Wrigleyville). I had a really nice place, for reasonably cheap, just off the Northrop stop of the Red Line (if I remember right). The neighborhood was "transitional" back then...meaning I felt safe walking at night, but would not feel good about my wife doing so (we were not together at that time). We were just south of Loyola's Rogers Park campus.


That was about 12 years ago, though. Wonder if that neighborhood ever turned the corner.

Edgewater and East Rogers Park turned a corner for the most part. I've worked that area the past 2 years and find that the gentrification that started in Andersonville has crept north to as far as Morse Ave. There are still some dicey bits west of Clark St. though. The Loyola area is decent since the University has bought a lot of the properties on Winthrop and Kenmore. Broadway, south of Devon has had a bit of revitalization. Not a lot of visitor/tourist things to do there though. The beaches along the lake front, all the way up to Howard St, are nice in the summer.

To the OP: Find a new Fodor's Guide to the city. I find those to have some of the best info. Fodor's will give you some very good ideas where to go and visit. The museums are always a treat! Even though it's on the South side, the Museum of Science and Industry is very cool. The University of Chicago and President Obama's house (no political comments please) is not too far from there. It's reachable by cab.

Some folks with tell you to have the deep dish pizza. I say find out from the locals who has the best thin crust and go from there. Deep dish is for tourists! lol

Most of all have fun on your visit! You'll find the people here to be down to earth and almost too helpful for a large city. There's an awful lot to do here!
 
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