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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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