Christmas in Chicago?

October 5, 2008 4:01 PM

Christmas in Chicago: Cosy and romantic - but where should we stay? Where should we eat? What's open, and what's cool?

So, me and the s.o. are going to spend Christmas in Chicago. It's our first Christmas spent together, and apart from our respective families, so it's kind of a big deal. We need it to be not just a getaway, but a special, memorable thing.

About us: We are late twenties/early thirties, we like music, architecture, good food, good wine, cool stuff, old stuff. We fly in on the 22nd of December and we plan to stay five nights in the city before traveling on to visit friends in Michigan. It'll be just the two of us. I'm trying to choose a hotel, restaurants and fun activities. I have this kind of Mad Men idea of winter in Chicago with beautiful old skyscrapers, comfy chairs and well-mixed drinks. In London we've stayed in, and loved, the Rookery, but we also had a really cool time at the Barbican. We like to stay and hang out in places that have a sense of history and story to them; not necessarily old, but interesting. I spent a few weeks in Chicago - in the summertime - years ago, and I've pored over the other Chicago threads which have given me some ideas. For example, a hot toddy in the Duke of Perth is definitely on the agenda, and I'm going to try (and probably fail) to get reservations in Alinea. But there's still lots of stuff I feel I need to check up on.

Hotel-wise (and going on previous threads) , I'm leaning towards the W in the City, but I'm not sure. Hotel Sax is another option. The Burnham looks beautiful but is probably slightly out of our budget. The Hard Rock Hotel tempts me with its beautiful 1920's building and free internet access, but is it super-cheesy? Other contenders include the Dana Hotel, which is new, the Amalfi, and the Rafaello. (caution: lots of auto-playing music in those hotel links)

Oh, and ideally we would like a hotel with a pool, but it seems to me that that would involve some compromises on location and other coolness. A nice lobby, a comfy and fairly spacious room, and being in a good location are more important.

Other stuff: I don't know what to expect from Christmas in the U.S.! Where I'm from, almost everything is shut on Christmas day and St Stephen's day, and the time between Christmas and New Years is a kind of quiet family time. Will the art galleries and museums be open? How about the shops and restaurants? Cinemas and theatre? Will we be able to get dinner reservations for Christmas day, or should we make sure we have a hotel with a restaurant/room service? Will it be possible to dine out at all without reservations? Will all the bars be packed, or empty? Or shut? Is there cool Christmas stuff we shouldn't miss?

We've got a moderate budget - I found deals on most of the above hotels at around $130-$160 a night, and about that's as much as we can pay. We'll eat cheese and bread one day so we can afford some amazing meal the next day, and we're willing to splash out a little for really special things. But cheap also = good and we don't want to waste our hard-earned cash. Hivemind, help me plan a really great, romantic Christmas!

posted by tiny crocodile to travel & transportation (8 comments total)

First things first: Hotel.

I love the W City Center, which is the one you linked to, but let me be clear - it's hardly cozy. It used to be a gentleman's club and is decorated with gentle nods to that history. The lobby was recently redone to make it feel even more like a nightclub - and after work the music starts pumping a bit. It's a gorgeous building, but not where I would want to stay for a holiday. BUT - it's very close to transport, if not all the pretty things that will be going on near Michigan avenue.

The Hard Rock is pretty cheesy, but again, the building is gorgeous.

If I had to choose one of the ones you've listed I would go with Hotel Burnham because it's a Kimpton and they rock. And, well it's the Burnham! See if you can scrimp together the few extra bucks for it.

I've never had a bad stay at the Intercontinental so if you can find a good deal, you may want to consider that. Architecturally important, amazing pool and right in the heart of Michigan Avenue.

Chicago rarely closes up. There will be some things that are dark on the holiday, but there's also still stuff to be done. I've spent more than my fair share of holiday afternoons or evenings in a cinema and/or at a theater event. The holiday proper will be the most quiet time, but there are restaurants and such open.

There's lots of silly and wonderful holiday stuff to be done. There's the holiday express trains that run on various routes of the CTA's el train. It's silly but charming.

I've only been there for one Christmas in the last eight years so I'll let others cover the rest of what's to do - but hope the hotel info helps some.
posted by FlamingBore at 5:00 PM on October 5

Regarding the hotels you've mentioned: The W in the city has very nice, VERY small rooms (at least the base level rooms) I don't think the location is exactly what you want though, it is a bit south and west of the parts of the loop that your (very well written) description mentions. It's still close, but your hotel view is more likely to be parking garage or nondescript building.

The Burnham is in fact beautiful - we stayed there after our wedding. Other alternatives that you might want to consider are the Hotel Monaco and the Swissotel.

The Hotel Monaco has great rooms in a good location (if you can get a suite somehow even more so). If I remember correctly most of their rooms have very deep window seats - like 3 feet deep, more than enough for two people to sit up there and enjoy the view. The Monaco will also provide you with a fish if you would like a pet for the duration of your stay - free of charge.

The Swissotel has beautiful views and a pool/health club near the top floor. It's a decent location between the "Mag Mile" area and the downtown parks.

From a second hand report the Hard Rock was "nice, but too hip for me". Assuming you are not my father in law that may not be a concern.

You might have luck with priceline, since you can't really go wrong with any of the 4/5 star hotels in those areas. We got a room at the Swissotel in December two years ago for under $100. If you google around you can find the appropriate characteristics to pick that will narrow it down to just a few hotels and let you put in multiple bids by changing your criteria slightly.

You should be able to find enough open on every day - bars, restaurants, etc. You may have to travel out to some of the nearby neighborhoods, but I would highly recommend that anyway. I can't think of anything right now that is can't miss, but you might want to walk along Michigan avenue and enjoy all the lights (just don't do it the 2-3 days before Christmas because everyone will be doing their last minute shopping).

Have fun!
posted by true at 5:01 PM on October 5

I'm intrigued by the Intercontinental and will definitely check it out. I should probably also have said that I find really big hotels sometimes a bit impersonal and intimidating. But I guess not all of them are.

The holiday express train sounds cool!
posted by tiny crocodile at 5:32 PM on October 5

I just took a look at rates - and you can get a king in the historic tower (where you want to be) for about $150 a night for the 24th through the 30th. Not sure when you're planning, but that seems like a great deal to me. Good luck.
posted by FlamingBore at 6:34 PM on October 5

I don't know if you've looked at the Palmer House Hilton as a place to stay, but it definitely qualifies as romantic, if it's not too expensive.

As for things to do, the quintessential Chicago Christmas activities include eating at the Walnut Room in what USED to be Marshall Fields, but is now a Macy's. Also, the window displays outside the department store are traditionally fun to walk by.

Might want to go ice skating in the rink which is in Millennium Park.

If you're into art and will be there on a Thursday, that is usually the free night at the Art Institute Museum, after 5:00.

Happy travels. Enjoy our town!
posted by achmorrison at 6:57 PM on October 5

Me and my sister do a Chicago hotel bar hop every Christmas. We start at the Drake Hotel for some appetizers and cocktails, then just wander around and hit all the hotel bars. If you enjoy cocktailing it's a great way to see Chicago during the holidays, which is beautiful. We usually do a drink at a place then march on, so it lets you see a lot of the city on foot. We change up the exact locations every year, but it always starts at the Drake and ends up at Pippens (which is a regular bar that closes at 4am)

Several years in the middle we have swung by Bistro 110 for dinner.

I hate to specifically give restaurants/bars to go to as there are so many wonderful ones, but there is something special about starting a hop at the historic Drake and finishing late at night at rowdy late night bar(Pippens)
posted by travis08 at 8:21 PM on October 5

I stayed at the Raffaello and found it VERY overpriced. The rooms were small and they tried to charge you for every little thing. Also, it wasn't AS well located as some of the others that you've mentioned. I would avoid it. The Hard Rock, by comparison, was very sleek, well-located and beautiful. Like True mentions, it is a bit "hip."
posted by brynna at 10:40 AM on October 6

Thanks everyone - every answer was really helpful. We got a really good deal on a fairly high-end room in the Hard Rock Hotel in the end so we went with that - but it was great to have lots of information and choice. Definitely trying the hotel bar hop. Thanks you guys.
posted by tiny crocodile at 1:57 PM on October 10