Chicago Hotels

Everything everyone has listed is terrific touristy stuff and certainly worth seeing.
But if you want to experience the actual culture of the city, find a street festival and go to the beach. You can google the street festivals and find one happening during your visit (if it's in the summer). Absolutely worth it!

Stay near or on Michigan Ave to give you access (someone mentioned the Gold Coast, and that would be great too). Just make sure you get out into the neighborhoods for the best boutique shopping and dining. Everything on the mag mile is a chain.

Visit Bucktown (Milwaukee/Damen/North Aves), Lincoln Park (start around Armitage/Halsted and walk north), and Wrigleyville (Addison/Clark) for certain.

Welcome to Chicago! :)

I usually tend toward boutique hotels, but I fell in love with the Hyatt Regency on the River several years ago, so now that's always where I stay. The first year, my mom had booked the weekend for my husband and I as a treat (I have family south of Chicago), that was also our first weekend away without our son. Well, my mum screwed up and booked the weekend PRIOR to what they'd thought. There was a pediatric nursing convention at the hotel at the time, and they were full up, and the whole durn CITY was full up (I forget what was going on, but our only other option was to turn around and drive 100 miles south). Long story short, the front desk person got us into a HALF a Presidential Suite for both nights for the same rate (the people booking the other half didn't need the entertaining area until monday, so they hadn't booked it). So we had over 1000 square feet of private concierge hotel room (with fold out couch that had an 18" deep mattress, shower and bath bigger than my bedroom, dining table for 20, 84" TV, etc.) all for our $99 a night rate. He'd booked the wrong date train tickets for his mother earlier that summer and was "paying it forward", because someone at AmTrack had gotten his mother onto that train in a private sleeper compartment. Hyatt won my perpetual business (and my husband's and father's and uncle's companies' business) because of that gentleman. LOL... hundreds of bookings from one kind act. Ever since, we've just always stayed in their basic rooms... but it doesn't matter, as they're fantastic. That LOVELY man saved the back of our laps on that one. Our entire stay that time, and each following has been some of the best we've ever had. And since I've spent half my life in hotel rooms, that says a lot.

It's also a pretty rockin' hotel.

http://www.chicagoregency.hyatt.com/hyatt/hotels/index.js...

Make sure to check out their deals and specials. I always hit up a lot of Blues in Chicago, but I also always get the tip from the concierge about where to go.

As far as food: Chophouse. Must. Absolutely must. There is NOTHING IN THE WORLD like cornfed beef, and the pigs in Illinois actually have wings. There are many many different chophouses in Chicago. I'm afraid I can't say which is best. I've had Harry Met Sally meals in every one I've been to.

I love the Hotel Burnham (Kimpton Resort) and the Ambassador East. Very cool historical buildings close to great shopping and restaurants. Ambassador has "The Tap Room" where Sinatra used to play in the day and celebrities all hung out there during that era. Last time I stayed at the Burnham (which is closer to the Gold Coast shopping, etc.) we stayed in Al Capone's "dentist office", rumored to be more of a secret business meeting place. Apparently it was an office building during that time. Great breakfast/brunch there and the service was extraordinary! Walk to shopping and Millenium park sculptures and Art Museum area. Love Chicago, have fun!

The lovely Intercontinental hotel on Michigan Avenue is expensive but you might find a deal if you book both hotel and flight together on Travelocity -- we did. It's a historic building (you can actually get an audio tour of it from the front desk) and gorgeous and in a great location. But yeah, pricey, if you can't find a deal.

Chicago is awesome. I second Bobbi's suggestions about activities. Don't forget the Art Institute too. The view from the Hancock Building is better than the higher view from the Sears Tower (has some new name I don't know...) because Hancock is by the lake and the Sears is over in the business district; there's nothing else you want to do around the Sears anyway. There is a kids' "museum" by the lake that my daughter found fun though it's not deep. If you have a girl, try American Girl Place - good food and fun if you can prevent your child from asking for anything.

Do get to the Field Museum of Natural History which is also next to the Adler Planetarium on the lakefront to the south of downtown. Take a bus all the way there from downtown, not the "El" (subway) -- a friend who's a local gave us that advice and said the El stop was in a not-great area but the bus took you much closer to the museums. Just a tip.

Navy Pier. Sears (Willis) Tower. Hancock Tower. Museum of Science and Industry. Field Museum. Lincoln Park Zoo. The air show if you're around the weekend after this one. Brookfield Zoo. Adler Planetarium. Grant Park and the Cloudgate Sculpture (better known as the Bean). Segway tours on the lakefront. Bikeriding on the lakefront. The Sea Dog speed boat tour at Navy Pier. Buckingham Fountain in Grant Park.

As far as eating, we love Ed Debevic's. The food is ok, but the atmosphere is fun! Grande Lux Cafe on Michigan Avenue is outta this world! Yum! Gino's East Pizza or Uno's deep dish pizza. That's a must. Have a Chicago-style hot dog somewhere downtown. Popcorn at Garrett's. See a play, go see the Cubs or Sox play baseball.

Have fun! We live here so I'm not so sure about hotels. We had friends stay at the Doubletree near Michigan Avenue recently, and also the Sheraton on the Chicago River. Both had good experiences.

Went to Chicago last year and stayed at the Palmer House hotel. Beautiful and had excellent service. It's near the theater district too so that was a plus for me.

Agree with Manda - stay away from the typical touristy stuff and you'll get a better feel of the real city. Two options for hotels that are not downtown or coast - Days Inn on Diversey or Belden Strattford on Lincoln Park West. Days Inn is located in the Lakeview neighborhood and Belden Strattford is located in the Lincoln Park Neighborhood. Belden Strattford is a beautiful art deco building - check out the photos on their website. It's also within walking distance of great restaurants, shops, and the lake. Also, if you want to stay away from the touristy steakhouses, your best bet is Gene and Georgetti's. It's been around since 1941 for a reason. Personally I think one of the city's greatest treasures is the architecture. If this is something you're interested in, there are many great tours, including a boat tour on the river http://www.cruisechicago.com/tours. Have a great trip. I've lived and traveled many places, but there is truly something special about the city. Heck, we don't live here for the weather!