53.
Great Dining Experience
SPQR boasts amazing food and terrific service. You can easily make a meal with the wide variety of small plates/starters. The ingredients are fresh, local, and seasonal. The wine list is extensive. But the professional, friendly staff is helpful in guiding you through the offerings. I love sitting at the chef's bar and watching one tasty dish after another come out of the tiny kitchen. Note that the dining room is small and can be noisy. Definitely get reservations.
Friendly Neighborhood Sushi Spot
Amasia is on the corner of Noe & Henry, just blocks from Market St. The interior is light and airy. Hide-san, the sushi chef-owner, presides behind the bar and turns out fresh, tasty, sushi. There's a variety of rolls and many a veggie option. Amasia also boasts a wide variety of premium sakes. If you're lucky, Hide-san's wife, Shoko-san, will entertain patrons with a set from her koto, a traditional Japanese stringed instrument. One note: sometimes it can take a while for the sushi to come out, so order a couple of appetizers, a few drinks, and relax.
Must See in Chicago
The Art Institute is a definite stop in Chicago. The museum has a respectable collection, and the new Modern Wing is beautiful.
A Great, Easy Cultural Cruise
Chicago is full of amazing architecture, and the Architecture River Cruise is a great way to see it from the river. There are a few operators, but the one run by the Chicago Architecture Foundation is informative and professional. You ride on the top deck of an open-air boat while a CAF docent explains the history and significance of the buildings on the tour. The tour is 90 minutes long. It's an easy way to ease into your Chicago visit. Plus there's a full bar belowdecks!
Serene and Relaxing
The Dana is a small, boutique hotel with modern decor. The rooms are nicely furnished and the staff is friendly. The Dana is conveniently located downtown, only 2 blocks from the Red Line, and 2 blocks from Michigan Ave. There's also a roofdeck bar that gets hopping at night. The crowd is mostly straight, but gay-friendly. Overall, a relaxing spot to base your visit to Chicago.
Great Neighborhood Bar
North End is a nice change of pace from Sidetrack and Roscoe's. It's a great sports bar with friendly staff and decent drinks. And, of course, lots of big screen tv's to watch all the sports you would want. It's got a couple of bars and pool tables. Definitely worth checking out.
Huge, Awesome Bar!
My Chicago friend calls Sidetrack "The Bar That Ate Halsted." It just gets bigger and bigger! They apparently keep buying adjacent properties and expanding their space. But it's still packed with way-cute boys who are all really friendly. Watch out for the slushy drinks: a couple of those on a sunny afternoon can put you under fast!