My Wife and I are thinking of Visiting Chicago in Mid May. First timers to Chicago so we want to see the City. Like to go out and have fun, dinners etc. Have seen the Drake, Hyatt, Westin in vacation packages but not familiar with the locations in Chicago. So If you could help with the areas and what there is to do this might help us figure out where to stay. And if you have any advice on hotels there that would also be great.

Thank you

Drake,Westin are on/adjacent to Michigan Ave, shopping area with restaurants nearby in Syreeterville and River North. Park Hyatt is also there, but Hyatt Regency is just south of the Chicago Riiver, still OK though.

The Magnificent Mile is the primary shopping district of Michigan Avenue from the Chicago River north to Oak Street. However, creative marketers stretch the boundaries several blocks east and west. ;-)

The Loop is the area just south of the river bounded by the L track on Lake, Wabash, Wells and Van Buren. Again, the term is subject to interpretation. The farthest points in the two areas are only about two miles apart, so you can easily walk anywhere within them.

The area to the west of Michigan Ave is River North and to the east is Streeterville. The Magnificent Mile (and River North) have a larger concentration of restaurants and tourist attractions while The Loop has more offices, the live theatres and museums.

Almost any hotel north of the river would be fine and The Loop would be a close second choice depending on what you want to do.

Chicago is a big convention destination, so hotel rates are very sensitive to supply and demand. If your dates are flexible, you'll be able to find a better deal. The National Restaurant show is the first weekend of May with around 50,000 people expected. Chicago will host a NATO summit May 18-20. No one really knows what to expect except that many hotels will be booked, security will be tight and some areas will be inaccessible. There will also likely be several demonstrations.

If you’re driving, you’d be wise to park your car when you arrive and leave it until you depart. Most hotels charge around $50/day parking, however you can find less-expensive (around $25-30/day) places at www.chicagoparking.com or www.chicago.bestparking.com.

If you'll be relying on public transit, you can purchase passes at the O'Hare and Midway rail stations. A 1-day pass is $5.75 and allows unlimited rides on all CTA trains and buses for a 24-hour period. A 3-day pass is $14. For complete transportation info, check the CTA site at www.transitchicago.com. You'll find maps, a trip planner and how to track trains and buses with your smart phone.

For restaurants, pubs and other happenings, check www.chicagoreader.com or www.chicagomag.com. You can search for restaurants on both sites by neighborhood, price or cuisine.

I like the River North and Streeterville areas as well, especially for first-time visitors. I've stayed in the Hyatt Regency on East Wacker and the Westin on Clark, both "won" on Hotwire (Chicago is a great city to use Hotwire and Priceline, if it's just two of you). The location of both was great for what we were doing. If I chose between the two I'd pick the Westin for the rooms, though the Hyatt might have a slightly better location for me. But there are tons of hotels in those areas. Using TripAdvisor reviews to decide (throwing out the absolutely glowing reviews and the reviews from people who would NEVER be satisfied ) has worked well for me.

DW and I are arriving on the Empire Builder late afternoon 5/17.
We are leaving on the Lakeshore Limited at 9:30PM. Any chance of a GTG after 5PM?

We rented an apartment, but that was for four, and we liked it. You might want to take a look at my trip report: click on my name to find it.