Chicago for 20th anniversary
 

Our 20th wedding anniversary is this March... and as usual, DH and I haven't planned anything. He had this crazy ideal to go to an all-inclusive place in the Caribbean (friends were just there over Christmas and we both love the idea of a low effort vacation!) but of course everything is booked and/or crazy expensive. So we are thinking about just a few days in Chicago (driving distance from home) and making it a more luxurious vacation than usual... we usually stay at someplace like Ivy Hotel or Hotel Indigo. Any suggestions for hotels with great suites/rooms? Or good, nicer than average restaurants? And maybe some splurge activities?

For your luxury hotel pick from the fivestar alliance (39 hotels). (I couldn't copy and paste). I would not plan on driving my own car into Chicago and paying for parking. My favorite for Iowa would be to park the car in Burlington IA at the Amtrak station (big free parking lot) and take the California Zephyr into Chicago. The train takes about 4.5 hours from Burlington to Chicago. When on time the train is in Burlington about 10:30AM (sometimes late).
There are many threads about what to see and do in Chicago. I'm hoping the search is still working.

Thanks Tom - I will take a look at five star alliance hotels... and my user name is now a misnomer - we moved to central Illinois six years ago! We do take the Amtrak up from our town - or leave a car at the end of the Metra line and take it up to Chicago.

My taste in restaurants tends to run more towards regional iconic and lower-end (for example, I went to Gino's East, Lou Malnati's, and Giordano's for deep-dish pizza; Mr. Beef and Al's #1 for Italian beef sandwiches; Red Apple for Polish grandma food buffet-style; and Portillo's and Gold Coast Dogs for Chicago-style hot dogs -- all of which I can heartily recommend), so my experiences will likely not be of much help. Chicago has a ton of fine restaurants, though, and the limited amount of research I did suggest there are loads of excellent high-end options in different styles of cuisine. Am thinking it's well worth doing some serious research on the subject before going.

Chicago City Greeters
 

Not a splurge activity, but Free! I've done two different tours with Chicago City Greeters who are volunteers. Check out their website and what kind of tours you might consider. You have to register ahead of time so they can match you up with a volunteer. On our trip last September, the volunteer also helped us choose a tapas restaurant.

My favorite hotel: The Four Seasons, old school classy.

Favorite restaurant: Gibsons Bar and Steakhouse, wonderful steaks and desserts.

Favorite activity: Field Museum of Natural History. Be sure and visit "Sue" the dinosaur.

We like the Kimpton hotels and Sienna Tavern has great food and a cool vibe.

For luxury, Four Seasons or The Peninsula. Less ezpensive but still top end, The Sofitel.And for the special dinner Spiaggia on N. Michigan Ave.

Booked a suite at the James Hotel - and got tickets to see the Broadway bound Pretty Woman!