So. It looks like an international trip isn't going to happen this year. Instead, we thought we'd just go to Chicago for a few nights. We've never been, and I have no idea where we should be thinking about staying. Since it's going to be our anniversary trip, we don't mind spending more money than we usually would...so are there any really special hotels you'd recommend? (Also interested in nice restaurants, recommended shows, activities, etc.) If someone could point me in the right direction, I'd be so grateful!

We were really happy with The Fitzpatrick two summers ago. There is a nice Irish pub in the basement with decent pub food. Also went to Mike Ditka's steakhouse, but just to the bar. Food looked good. My friends swear by an Italian place called Papa Milano's on State Street.
Also stayed at the Hilton in the past and been happy with it.

Most hotels are in the North Michigan Avenue area or in The Loop. What types of amenities do you want and what's your budget?

Because there are lots of conventions and large events, the rates will vary greatly by date. The top hotels are The Ritz, Peninsula, Four Seasons and Park Hyatt.

If you want an older hotel with character, try The Drake, Intercontinental, Allerton or the Palmer House. For something with a view, The Swissotel, Fairmont or Westin River North. Other hotels that get high marks are the Sofitel and Burnham.

The Trump hotel also opened recently, but I haven't heard too much about it.

For activities and restaurants, check www.metromix.com.

Thank you so much for the input and the link. Since our transportation costs won't be too high, and we've shortened the length of our trip to (probably) three nights, we don't mind splurging on a nicer hotel than we typically choose.

Out of the Ritz, Four Seasons, Peninsula, and Westin, is one of their locations significantly more desirable than the others?

I love the Amalfi. It's my Fav for Chicago. It's off Michigan Ave but within walking distance from most of the major sights. They offer breakfast on each floor at the elevators and a manager's cocktail party each evening FREE. I love the rooms and the beds are to die for. Aveda products and a killer restaurant across the street. Harry Carrey's they have great food and it's a fun place to hang out.

On the north end of Michigan Avenue, you'll find the Peninsula, Park Hyatt, Ritz, Four Seasons Westin-Michigan and Drake on consecutive blocks. So, there's no real difference in the location.

The Westin River North is about 10 blocks south on Dearborn Street at the River and 1 block from the Amalfi.

Second the Amalfi - a special place. The others are posh as you'd expect, and all locations are fine. Would a view be important to you, though -- perhaps of the lake and skyline? That puts a slightly different twist on it.

Papa Milanos is gone, putting up condos. Carmine's right on Rush is very good food and outside patio is best for watching people. River cruise a must. Navy Pier fireworks, Riva is restaurant right on the pier, good seafood. Trolley run from Michigan Ave to Navy Pier. A nice walk but a couple miles. Millinieum Park. Bike ride on LSD.

Still doing our research...

Cassandra, which hotel(s) would you recommend for great views?

I would go with The Peninsula as its the best in the city.
http://chicago.peninsula.com/pch/index.shtml

If you want the best hotel with lake views, The Ritz- Carlton(A Four Seasons Hotel) would be the best choice. Both of these hotels are in the best location.
http://www.fourseasons.com/chicagorc/

Sjince I am going to be in Chicago for six nights in July, I read this post with interest. We have reservations at the Fairmont. Can anyone give some feedback on this hotel?

Had a great stay at the Park Hyatt...great bathroom! ha

The hotel also has a private driver to take you anywhere withing 5 miles of hotel but walking was definitely our preferred mode of transportation.

Had some great meals and a place right next door to Park Hyatt on the northside is Bistro 110...liked the atmosphere, menu and location.

Can't comment on the other hotels, but we stayed at the Peninsula for my birthday weekend a few years ago and it was wonderful.

I haven't stayed there yet, but The Whitehall in August is going for $92/night through Expedia. Others on here say its great. You can hear from laurelee, her post on here is: Self Planned Chicago Food Tour

We just got back from Hotel Monaco, where we had an excellent deal on a two room suite (not awful . It was wonderful, and I would certainly recommend it. Great location.

Travelzoo says Hotel Burnham is 50% off, too.

You know, people are mostly talking large, large high end hotels that are North.

IMHO, the River is the best area for "doing".

So I would decide by the "kind" of couple of days you are spending. If you want to go out frequently- to a play or show???

Swissotel is farther from the walk, but if you want a view where you can see the coast all the way to the curve going South- that's the one.

I like the hotels on the Riverwalk area (Chicago River) and the smaller hotels- boutique ones mentioned- better myself. So it depends what kind of a room you really want, and if you are going to spend all your time in it.