In case you haven't figured it out, we're really hoping you come to our wedding. It order to make it as painless as possible, we'll be giving you lots of helpful info so you can get the most out of your trip to Chicago.
Choosing a hotel is something I used to agonize over. Now I only agonize over it if I can't bring my bike along. It can be difficult finding the right hotel for your tastes that is also conveniently located for the types of things you want to do. For now, I'll focus on giving you a few different price/location options. Perhaps later I'll try and demystify Chicago's sometimes great/sometimes awful public transit system so you can see the things you want to see without losing your shirt.
The hotels in Chicago are concentrated around the airports or just north of the Loop in the neighborhoods of River North, Near North, Gold Cost, and Streeterville.
View Marmalade in a larger map (A quick key to the symbols: beds=expensive hotels, yellow pins=bed & breakfasts, red pins=not quite as expensive hotels)
These hotels range in price from slightly expensive to very expensive.
Pros: close to lots of (expensive) shopping options, restaurants, and nightlife. Short bus ride or long walk to downtown museums, etc.
Cons: far from (less expensive) shopping options, restaurants, and nightlife.
If you're looking for something (a little) cheaper and in a more varied neighborhood, I've found a few different kinds of accommodations a little farther north in the Lincoln Park/Lakeview/DePaul neighborhoods.
Pros: close to (less expensive) shopping options, restaurants, and nightlife. Closer to some nice public beaches which are nice for relaxing even if it's too cold to swim.
Cons: only one El line (the Red Line) runs through these neighborhoods, so you'll be doing more walking, busing, or taxi-ing.
Diversey and Clark
933 West Belmont Avenue
Super 8 (a little farther north than most)
7300 N. Sheridan Parkway
Bed and Breakfasts
Windy City Urban Inn
607 West Deming Place
Hansen House Mansion
1020 w. Altgeld
Gold Coast Guest House
113 West Elm St.
This is just enough to get you started, enough to realize there's more out there than what shows up on the first page of a travelocity search. And in case you get too enthusiastic in your search, there are a few businesses with "hotel" in the name that are not what you're looking for (they charge by the hour).
If you find any of this info needs updating due to changing availability, let me know.