Very OT--Chicago hotels

the chinatown hotel. it's quite luxurious, and by luxurious i mean it smells awful, is nearly impossible to find, and is all around great.

http://www.expedia.com/pub/agent.dll/qscr=dspv/htid=1118357

Take her to David Burke's. It's not Italian, it's a steakhouse, but it's really really f-ing good.

The Omni is nice and in a decent spot on Michigan, if you plan to do some shopping and the usual tourist stuff. The Hilton is good, and at the other end of Michigan right across from Grant Park. I've stayed at the House of Blues as well, it's good.

The Sheraton is real nice, its about 150 a night but its got the best beds and if you get the right room a great view of Downtown.

I would recommend checking out a place called Club Quarters, they are a kind of unique Hotel concept, primarily geared towards business travelers, therefore weekend rates are very good for the location (either in Central Loop or on Wacker and Michigan). Another one worth checking out are either W Hotel, and the Hyatt on Wacker. Otherwise I don't have too much hotel experience in the city, being from here and all that.

For Italian, I would highly recommend a place called Volare. It is kind of tucked back in the River East neighborhood, not as expensive as some of the places you would normally find in the tourist areas, but for the price is very delicious. Another one to check out is Osteria Via Stato. I have never been (but am going on Friday night) and my wife claims its a great place.

On the off chance you end up in Lincoln Park/Lakeview, my favorite Italian place in Chicago is Sapori Trattoria, on Halsted. Its a little bit farther from where you will be visiting most likely, but is reasonably priced and very excellent food.

Best hotel in Chicago. Pricing is a little high :) But seriously, if you do get a chance to stay there on a discount, it's a great experience.

I second the nod for the Omni. I also recommend the Hilton on Michigan Avenue. If you don't want to be on Michigan Ave (but why wouldn't you as a Michigan fan?), then the Palmer House (Hilton I believe) is a nice place. The Drake Hotel is also a nice place and is also located on Michigan...

As far as nice Italian places go, there will be no shortage in the city... There is a pretty high price range. I've been to Spiaggia before. That is a nice place to take the lady and it's right in the middle of the mag mile. The Italian Villiage is in the loop. IIRC, they have a couple levels and each level is a different Italian place. Each level ranges in price too... Have fun! Don't forget to get an Italian beef loaded with giardiniera...

Can't wait to move back to Chicago.

Penninsula

There are many nice hotels in Chicago to stay at. You should be able to find reasonable deals.

It really depends where you want to stay, on where to reccommend.

For a tourist, you will either want to stay near or on Michigan ave or in the Gold Coast. Do not be seduced by low rates in the loop as it is dead on the weekends.

Many great hotels from the pricey: four seasons, penninsula, sofitel; to next tier down: hyatt regency, westin, marriott

I like to stay at Westins and there is one around the 800 block of Michigan ave.

As far as italian restaurants, there are some great choices. If you don't mind a short cab ride, I would reccomend Tuscany or Rosebud in Little Italy on Taylor. There are several other neighborhood places as well, but if you are going to get in a cab you might as well go to little italy in my opinion.

Good luck and spend lots of money here.

you will have a better experience staying closer to the action. The Hyatt Regency and Swishotel is about as far south as you will want to go. You are still within easy striking distance of the museum campus if so inclined, but night life/day life/vibe will be much better for you.

Make sure you grab a burger at the Billy Goat (the original) on lower Michigan ave, just north of the river (basically under the Wrigley bldg). Whenever I have friends in town I always bring them there and they are never disappointed.

the peninsula is the jam

i usually stay at the w on west adams, but rooms can be a bit small for a vacation type trip

with the Kimpton boutique hotel chain when I was in Washington DC. Its a bit more decorative than your typical hotel room and they are generally located in old renovated downtown buildings. Maybe its not considered fancy, but its definitely different. They have pretty good weekend rates too.

It looks like Chicago has the Hotel Monaco and the Burnham Hotel and Allegro. I have no idea what they are near to in the city though.

http://www.kimptonhotels.com/hotels/hotels-chicago.aspx

I appreciate it.

On another note; if anyone is staying in the Detroit area, check out the Townsend Hotel (in Birmingham). We stayed there Valentine weekend and all I can say is it's worth every penny. Their restaurant, the Rugby Grille is amazing, best roasted chicken I have ever had. Ever.

Damn, I should have utilized the MGo for my trip to Boston in June. Good thinkin', TIMMMAAY. I spent a good 4 hours trying to find the perfect hotel taking into consideration price/location/"niceness" of the hotels. I found that a place like the Marriott was $350 a night!!! I found a decent place, not far from the Marriott for much cheaper.

put in a low bid (30 to 40% lower than published rates) for a 5* in the Mag mile/ Gold Coast area and see what happens. I got the JW Marriot in Orlando for $150 a night in March, when the Marriott.com price was $299.

In terms of actual hotels, The Parc Hyatt on N.Michigan is awesome, and the W Lakeshore is really nice (smallish rooms, but great bar/ restaurant). The Sofitel was also pretty nice.

1) Stay at the James Hotel if it's in your price range (quick check on Orbitz for a few weeks from now had it basically the same price as the two you were looking at).

2) For Italian and not big loud rambunctous places, I'd look at Piccolo Sogno, A Tavola, and Gioco. And if you can blow big bucks on dinner, then Spiaggia is the only way to go.

Also, are you coming in the near future, or is this several months out when it's warmer? Some Italian places have great outdoor dining, but obviously that's not an option the next few months.

One comment, stay away from the Italian Village restaurants. I found them to be very uninspired and kind of pricey for what you got. Chitown is of course correct about Carmine's and Rosebuds, those are can't miss (though trend a little pricier).

Stayed there once, it was really nice. Kind of a small feel, plus a really nice free happy hour, tons of good food and good wine. I would recommend it if its not more than the other ones.

If you want to trek up to check out Wrigley Field/the Clark Street scene on either night you could start out with dinner at Mia Francesca on Clark just north of School. Great Food and very reasonably priced. BYOB too if you want to grab a nice bottle of wine to take with you - I think they charge like $5 corking fee, but worth it to save a little cash and still have some nice wine with a good meal. You could even take the El train to get to the neighborhood from downtown.

Sofitel has amazing beds and is right near (but not on) Michigan Ave. I used to work in Chicago for a major consulting firm and they always put clients up at the Sofitel, Peninsula or Palmer House. The Westin River North is not too bad either; it's where I generally stay.

Second that Carmine's and Rosebud are good places and are near the Gold Coast/Michigan Ave. area you'll probably be. I'd also recommend getting drinks in the Signature Lounge at the top of the WaterTower hotel -- it's expensive but worth the view. Second City is a comedy club/show and is another good activity.