boxtonmom1014

3 of my girl friends and I are planning a December trip to Chicago for my 40th. We're probably looking to drink wine, see some sites (depending on temps!), eat good food, and enjoy each other and the city.

I'm trying to figure the best place to stay.I'm not a big shopper so that part isn't as important. Do we want to be more central like the Mag Mile, or do something more like Old Town?

Citylghts

The Mag Mile is Michigan Avenue between the river and Oak Street. To the east is Streeterville and to the west is River North. These areas have the largest concentration of hotels and restaurants. Play with your dates on one of the hotel sites to find a hotel with the amenities you want.

December usually isn't that cold.

exiledprincess

With there being four in that party and the fact that they mention Old Town in particular, I'll wager that the OP is thinking about going the route of a vacation rental, instead of a hotel, in Chicago.

If that is the case, well, you have a lot of research ahead of you. Choosing a vacation rental isn't as easy as picking a hotel. In order for the vacation rental to be legal, it has to be licensed by the City of Chicago. Then, if it is in an apartment building or a condominium building, you have to check with the building management or condominium association if they even allow that type of occupancy (the majority don't). The City and the owners/condo assn. boards are really cracking down on these unlicensed units. You don't want to be caught in the middle of a situation like that.

If you've passed those two issues, then you get down to the nitty-gritty details. Sometimes those vacation rental owners get a little too optimistic about describing the actual location of those units. They aren't exactly in the area which they describe. You have to check up on the area to confirm.

You have to check out what type of public transportation is available to you by these. Make certain that you have an OWL bus route nearby (meaning it runs 24/7) because some routes only run on weekdays - some mostly during rush hours. Otherwise, you'll be spending a lot on cab fare (or alternative transportation).

On the other hand, you don't want one sitting right next to an 'L line - for obviously reasons.

If you were planning on eating in during this stay (although I don't think you are), you need to check what amenities the immediate area has (i.e., grocery stores, convenience stores, maybe even drugstores, etc.).

As the above poster mentioned, the largest majority of hotels are concentrated in the Loop, River North and on/near the Magnificent Mile - with lesser amounts in Streeterville, the Gold Coast, Lincoln Park and Lakeview - as well as a few stragglers in other areas.

Remember, these first three are considered "central" because the CTA's busses and 'L lines are somewhat nearby. You'll be traveling to the attractions, better dining and entertainment options via public transportation.

Again, Chicago doesn't get the really bone-chilling cold until mid-January to late February. December isn't too bad.

ChgoGal

Hi, Boxtonmom.

Old Town is fine for an evening, but I'd stay near the Mag Mile. The River North-area hotels are well-located. Places like the Homewood Suites (at 40 E Grand, not the one labelled 'mag mile') or the Hilton Garden Inn on Grand, the Palomar or the Kinzie, will put you and your girlfriends in the center of many of nice restaurants and sights.

In December, I'd maybe keep an eye out for the Bruce Norris play at Steppenwolf, called 'Domesticated.' Would be nice for you and the ladies to have an early dinner at a restaurant called Summer House, then wander down Halsted to the theater. That would be a nice night.
http://summerhousesm.com/?loc=chicago

Or in Old Town, you could see a scripted, comedy show at Second City and have dinner somewhere there.

Hopefully December will be nice this year for you. Usually, Decembers are fine. I've lived here nearly 20 years, and the weather doesn't really turn miserable until the first week of January.

You'll be spoiled for choice in restaurants, but maybe sort your plans first, and then we can chime in with restaurants that are somewhat convenient.

Good luck with the hotel rates!

HappyTrvlr

Old Town had great dining, no hotels. It is a short walk from the Gold Coast so hotels at northern end of Michigan Ave would get you close to Old Town.