First-Time Chicago Trip in December?

September 22, 2024 12:37 PM

I'm thinking of taking my two young-adult sons to Chicago the first week of December. Am I a fool?

We're coming from the PNW so have no experience with real cold/ice/snow. It would be a pretty quick 3 day trip centering on the Art Institute, a Bulls game, various holiday sights and all the food we can fit in. I intend to make our accommodations and flights cancelable in case of last-minute VERY BAD WEATHER.

If this has potential to be fun, can you recommend accommodations? We need three beds, and really would like at least two separate sleeping areas. I swear I've looked at every hotel and Airbnb in "the Loop." Perhaps I just need to increase how much I was hoping to spend, as part of the reason I was thinking December (aside from holiday sights) was off-season pricing.

Finally, we are not completely inexperienced travelers, but haven't done so in a few years. I lived in NYC ages ago so have some big city experience. What else do I need to know/think about/plan for? Thank you!!

posted by Cloudberry Sky to Travel & Transportation (18 answers total)

I'm not sure exactly which days you're looking at or what your anticipated price was, but a quick Priceline for that first weekend and 3 adults, 2 rooms turns up prices that seem pretty average to me. Insofar as Chicago has an off-season, December isn't it -- lots of people come into town for holiday stuff.

For Airbnbs you'll have better luck outside the Loop probably. I just don't think there are a ton of airbnbs down there.

Actually come to think of it, if you're just using "loop" as your location, that's probably artificially limiting yourself a bit anyway; neighborhoods like River North, Near North, Streeterville, UIC, South Loop, West Loop, or Printers' Row will all leave you very convenient to your proposed destinations but they won't come up in a search for just "Loop."
posted by We put our faith in Blast Hardcheese at 1:09 PM on September 22 [4 favorites]

Early December should be OK. January and February are the really bad times.
posted by maggiemaggie at 1:15 PM on September 22 [6 favorites]

It’s certainly possible for the weather to be less good in early December, but that’s still pretty early in the winter season. Chicago’s legendary winter usually waits for Jan or Feb.

It’s a good time to visit the Loop and Mag Mile. All the holidays lights will be up and it probably won’t be miserable outside.
posted by Huggiesbear at 1:15 PM on September 22 [1 favorite]

Oh. It’s a common tradition for midwesterners to visit in December to do their holiday shopping, and have lunch at the Walnut Room in the old Marshall Fields building. Off-season doesn’t start til January.
posted by Huggiesbear at 1:25 PM on September 22 [1 favorite]

I too am dubious that that's really an off season. Winters have had incredibly mild beginnings lately and while I of course can't rule out something major, I'd also personally feel confident making plans. Folks specifically going to do shopping also sounds very plausible, though weekdays in early December seem like they'd probably be safe enough.

For accommodations, how much are you currently hoping to spend? I rented through Kasa once, the South Loop location, and it was enjoyable and seemed reasonable given the location and free parking.
posted by teremala at 1:37 PM on September 22

chicagoan here! last december around that time, it hovered around 40 degrees. i don't know your specific cold tolerance, but i've been here five years (moved from florida) and decembers have gotten progressively milder. it absolutely will be fun. you can also look at hotels and airbnb in river north, south loop, west loop, and west town to stay near transit to the loop and united center.
posted by europeandaughter at 1:51 PM on September 22 [1 favorite]

Response by poster: I probably focused too much on cost, when I guess the question is really maybe more about good location and if you have personal knowledge of accommodations that are not just two beds in a room. This is surprisingly difficult to find with hotel searches. Open to airbnb-type, but prefer hotel. I would like it to be less than $300/night, but understand that may not be possible with our parameters, and I will open up my search to 2 rooms and just accept that my frugality has no place here! ;) Thank you for all the good info so far!
posted by Cloudberry Sky at 1:53 PM on September 22

I think you may be able to find something in your desired location/budget if you go with something like one of the Sonder aparthotels--they are not really better or more ethical than an Airbnb (some might argue less, since they're corporately owned), but they do fill a niche, and a general search brings up some possibilities in your price range. I have no personal experience with them, though, so you might want to crosscheck ratings on sites outside their own.
posted by carrienation at 2:40 PM on September 22

I thought of Sonder with your follow-up, too. I’m a Chicagoan but haven’t stayed in them here, but was perfectly happy in one in Mexico City. Weather will most likely be fine in early/mid December, for Chicago winter definitions of “fine.” It would be unusual if it were much below 30ish. Get a hot cocoa at Fairgrounds on the ground floor of the Athletic Association hotel and walk around Millenium Park/Lurie Gardens and then go to the Art Institute. Or do that backwards and take your cocoa to the second floor lobby of the hotel and sit by a fireplace. There’s one lovely winter afternoon.
posted by jeweled accumulation at 3:14 PM on September 22 [1 favorite]

Traveling with kids you want the Homewood Suites by Hilton. Someone has to take a sofa bed, but otherwise you get two separate sleeping areas for a pretty decent price. Looks like there is one in the Chicago loop now. Plus, you get a little kitchen and dining area so you can save money if you don't want to eat all three meals out. Look for the rooms described as "Suite, 1 bedroom", which means two rooms, one with the beds and the other with a sofa bed/living area plus slightly separated off kitchen/dining area.
posted by EllaEm at 3:15 PM on September 22

Do not stay in the loop if you can help it, it would be nicer and feel safer to stay elsewhere, imo. Anything you're trying to see while you're here will be accessible without staying downtown. If you give more specifics about what you want to see while here it might help with suggestions but I wouldn't want visitors to stay downtown, for cost, accessibility, and safety perception and convenience. I think we can do better for you!
posted by tiny frying pan at 5:08 PM on September 22

Native Chicagoan and former Portlander here!

WEATHER & TIME
Like people have said I don't think you have to worry about this. There's of course a chance that some incredible winter event or storm happens, but it's pretty unlikely this early in winter, and Chicago is actually prepared for this. If it's snowy or ice, traffic doesn't stop, things aren't closed. One thing you should know--it IS colder and windier by the lake, especially when you're by skyscrapers that funnel wind down the block. For this reason (and because it's a tourist trap) I would also suggest not going to Navy Pier in the winter.

Christmas is a HIGH season in Chicago--because of the shopping people mentioned but also because there's a lot of Christmas traditions, and the decorations are pretty magical. All the department stores decorate their windows, the water tower is lit up, the science museum has an exhibit of world christmas trees, and most notably, the kristkindl German markets are the best outside Europe (they are rated so, not my opinion).

NEIGHBORHOOD
While several people have mentioned not staying downtown, I would say if you're going to be for only a few days, I think biting the bullet and staying downtown IS the way to go. You can stay in neighborhoods nearby on the blue or red lines if you're comfortable taking public transit also, or paying $15 or so each way via uber/lyft to downtown.

Mostly I'd suggest you figure out what you want to see first and then book a hotel around it. Based on what you mentioned, I think you COULD save some money staying a little farther south than the loop--i.e. near the Art Institute. There's relatively less sights there but it's an easy commute to the United Center & Art Institute and only a few stops on the el. The best thing to know is 8 blocks in Chicago is a mile, so that can help you estimate how cold a walk might be. There is also an underground pedway for walking indoors but it can be a bit confusing!

ROOMS
Some of the independent hotels have multiple bed setups, though I think two separate rooms are going to be pricey! I know the Freehand has rooms with 4 beds. Priceline CAN be your friend in Chicago, but not if you need a very specific bed arrangement.

INDOOR SIGHTS
The Chicago Cultural Center is free, heated, and has some beautiful domes inside. It's just a great place to warm up. The Macy's (which was our Marshall Field's) and getting OUR version of Frango Mints, which have a different recipe! And it has an amazing Tiffany glass ceiling.
posted by jennybento at 5:34 PM on September 22 [5 favorites]

I spend that weekend in Chicago every year, there is a huge radiology conference (RSNA) then. It is usually 40K + attendees and you will see them around. But Chicago is a huge city and you'll be able to enjoy it despite. Last year it was balmy weather but some years it is very cold.
posted by sulaine at 7:32 PM on September 22

For various work related reasons I was just in and out of several Loop-area hotels; I found the Freehand to be very dirty and party-centric with a strong mold smell in our room (and, for future readers who might care more about that, quite Cool and happening); the Homewood Suites by contrast was very quiet, calm, and clean. We ended up with a suite with two double beds in one half and a sofa (maybe sofabed?) in the other; also a pretty reasonable kitchenette. Maybe a half hour walk to the Art Institute, or twenty minutes by direct train.
posted by elanid at 9:20 PM on September 22 [1 favorite]

Unpopular opinion: Tbh if your a tourist doing touristy things, staying anywhere other than downtown will be a pita. The loop is really not that bad these days! It's just touristy and kinda city-like in comparison to the rest of Chicago, which is unusually neighborhood-y compared to other large metropolitan cities. There's the Lake, all the gorgeous tall buildings, public transport to connect to everywhere else...

I remember when I first arrived in Chicago years ago I was very confused, because I kept walking around all these different places trying to figure out "where is the city"? Like literally, I would go somewhere and get off at a train station and walk a few blocks, and think "am I lost or something, because there are all these houses and trees and wide streets, and I'm meant to be in a city. where the hell is everything?" Anywhere other than downtown is a confusing place to be a tourist if you don't already know exactly where you are going and how to get there. It's easy to make a wrong turn and end up in a residential street with nothing but houses. Which is nice if you live here and are looking for your buddies apartment... but not so much fun if you are a visitor looking for a place to eat or people watch.

Whereas downtown might smell bad, but at least there's always something to look at and do. Besides, it rained this week. The city took it's shower.
posted by EllaEm at 7:59 AM on September 23

To be clear, while I was suggesting expanding the search outside "the Loop," I don't actually recommend staying far out! You don't want to spend your whole trip on trains and in cabs.

It's just that "The Loop," as far as a hotel search tool is concerned, is a very specific zone of just a handful of blocks. Generally when Chicagoans think of "downtown" that's going to include some or most of those neighborhoods I listed. For example, a lot of the Christmas/holiday stuff you'll want to see is technically in the "Gold Coast" neighborhood on a site like Priceline.
posted by We put our faith in Blast Hardcheese at 9:12 AM on September 23 [1 favorite]

For the first week in December under $300 a night should be doable based on what I see offhand in the Hilton app. Looking at basic hotels with suite setups (Hampton Inn & Suites, Homewood Suites, Embassy Suites) — Embassy Suites at least always has two sleeping areas, albeit one is a sofa bed. Prices vary depending on day of the week but it appears that most of these are in the $200-$300 range for that time period right now at the highest (some going down to under $200 over a weekend). Other hotel chains have similar classes of hotel.

We’ve had good luck in December at the Hampton on West Illinois (in River North) and the Embassy Suites on Columbus in Streeterville, only about a quarter mile further east. There’s also another Embassy Suites in River North proper just a few blocks north of the Hampton. Prices feel like they’ve about doubled since the pandemic, but that’s been true wherever and whenever I’ve looked for hotels since then…

And early December may see some snow but it’s not likely to be too bad temperature-wise. If there’s a 48-hour cancellation you can cancel if a significant storm front is approaching, otherwise go for it!
posted by sesquipedalia at 12:51 PM on September 23

I had a good stay at this Days Inn over a year ago. The prices look very budget friendly, enough that you might choose to book two.

In my experience, hotels are a better deal than AirBNB in Chicago these days. But look and see.
posted by dog-eared paperback at 3:09 PM on September 23 [1 favorite]