Help us plan 24-48 hours in Chicago
December 4, 2021 8:20 PM   Subscribe

My spouse and I plan to spend a day or two in Chicago, hopefully in the fall of 2022. Please help us make the most of it. We will arrive and leave by Amtrak. We will be there only a short time because we have other stops to make.

About us: Two women about 60 years old. One of us has moderate COPD without oxygen use but gets around pretty well. We have broad interests, but they include:
Dance performance
Gay and lesbian culture
Kayaking
Museums
Music (blues, jazz, folk and country)
Outdoor activities
Poetry
Quirky and offbeat things
Sailing lessons
Trains
Watching women's sports

We are thinking of taking a boat tour of the architecture. Is that good?

Is there any time of year that is good or bad for a for a visit?

Do you have any recommendations for:
Things to do?
Place to eat or drink?
Place to stay (hostel, vacation rental home or moderately priced hotel or motel)?

Anything else we should know?
posted by NotLost to Travel & Transportation around Chicago, IL (19 answers total) 12 users marked this as a favorite
 
Best answer: We are thinking of taking a boat tour of the architecture. Is that good?

Yes! I did this over a memorial day weekend some years back and still remember it fondly. It was mighty warm that weekend in the sun, but the boat catches a bit of the breeze in the front.
posted by mochapickle at 8:31 PM on December 4, 2021 [4 favorites]


Best answer: I've been to Chicago twice, each time for a weekend and did the architecture boat tour both times. I loved it. The tour included a lot of history about Chicago as well.

I also went to Oak Park for a Frank Lloyd Wright architecture tour and went to a taping of "Wait, Wait, Don't Tell Me."
posted by bendy at 8:33 PM on December 4, 2021 [2 favorites]


Best answer: I can recommend the Thorne Miniature rooms.
posted by bq at 8:36 PM on December 4, 2021 [3 favorites]


Best answer: There's a wonderful walking tour of the Tiffany glass architecture in a few buildings in Chicago. My friend and I can never make our dates match up with the tour so we basically make one of our own, but I really recommend seeing the Chicago Cultural Center building in particular, it's gorgeous.
posted by kitten kaboodle at 9:40 PM on December 4, 2021 [2 favorites]


Best answer: It might be out of your price range, but the Palmer House could be worth the splurge. Then again I haven't stayed there since the late 90's.
posted by vrakatar at 10:17 PM on December 4, 2021


Best answer: I always recommend Billy Goat's Tavern (Cheesburger, Pepsi, chips no fries) on the lower level of Wacker Avenue - not only for the SNL connection but also because they're good (if not particularly healthy for you ) burgers (they have steak too) and because of its location between the two newspapers - there are, for example, Mike Royko columns on the walls.

Second recommendation: skip the observation deck on the John Hancock tower, go to the bar one floor below instead. No admission, same view. Though you will need to pay for a drink of some kind.

There was an excellent 5-star Chinese restaurant somewhere on a walk I took on the "Miracle Mile" but I don't remember the name and I'm not finding it on Google Maps right now
posted by TimHare at 10:47 PM on December 4, 2021 [3 favorites]


Best answer: Visit Andersonville for quirky and offbeat things as well as gay and lesbian culture--and the Swedish Museum, which gives you a great overview of Chicago's Swedish history. If you like weird museums you'll also enjoy the Museum of Science and Industry and the surgical history museum in the Gold Coast.

The architecture tour is worth it--you can also kayak on the Chicago River, which might give you a similar experience, though I've never done it and am not sure how that's arranged.

There's lots of music, but if you're looking for blues and don't mind touristy then Kingston Mines is a fun place for Chicago blues and entertainment. The Green Mill is pretty famous for jazz. There's also a great band called the Red Line Blues Band that often plays at Jackson Station.

Exile in Bookville is a fantastic bookstore in the Fine Arts Building--the owners are wonderful and really care about books. Myopic Books in Wicker Park is among the best used bookstores in the country. Women and Children First in Andersonville is also good, if you go to that neighborhood.

There are so many good places to eat that you almost can't go wrong, but the Loop is a little bit less interesting, food-wise. To me, Chicago is very much about Mexican as well as Scandinavian culture, so my faves are Tre Kronor in North Park (Swedish breakfast--so good) and Taqueria Atotonilco in Pilsen (there's also one in Little Village, but Pilsen would be more fun to explore--also the Museum of Mexican Art is there). There are also plenty of Michelin-starred places to spend lots of money, if that's what you're into.

As for places to drink, a truly cozy place to grab a drink (with beautiful views) is the library lounge in the Athletic Association Hotel right across from Millennium Park/"the Bean."
posted by Miss T.Horn at 11:02 PM on December 4, 2021 [7 favorites]


Best answer: If the weather is poor, I’d give the boat architecture tour a pass. We chanced it in a cold, rainy day in mid-October, thinking "eh, the boat has indoor seating, it’ll be fine." When we arrived, they said the river was too high for the tour boat, but rather than cancel, they would give us a special alternate tour that went out on the lake. Since it was unpleasant out, everyone was gathered in the indoor portion of the boat, and it was so loud with conversation that we could not hear the tour guide valiantly attempting to describe things. My (80 year old) mom and I finally went up to the outdoor seats and, in the drizzle, tried to enjoy the tour. But since we were out on the lake, we could hardly see anything that was being described. We were relieved (and cold, and soaked) when it was over. The tour is generally beloved, so I’m sure it’s usually great — but definitely weigh the weather more than we did.
posted by kite at 11:03 PM on December 4, 2021 [4 favorites]


Best answer: Personally, if I only had a day to do something in Chicago, I'd spend all of it roaming the Art Institute.
posted by Thorzdad at 5:37 AM on December 5, 2021 [4 favorites]


Best answer: Personally, if I only had a day to do something in Chicago, I'd spend all of it roaming the Art Institute.

You could also spend an entire day in the Field Museum if that's more your speed.
posted by Johnny Assay at 6:04 AM on December 5, 2021


Best answer: Taqueria Atotonilco in Pilsen (there's also one in Little Village, but Pilsen would be more fun to explore--also the Museum of Mexican Art is there).

Highly recommend both restaurant and museum. We live in the suburbs and this is one of my favorite outings every year.
posted by Serene Empress Dork at 6:20 AM on December 5, 2021 [1 favorite]


Best answer: I always recommend Billy Goat's Tavern (Cheesburger, Pepsi, chips no fries) on the lower level of Wacker Avenue - not only for the SNL connection but also because they're good (if not particularly healthy for you ) burgers (they have steak too) and because of its location between the two newspapers - there are, for example, Mike Royko columns on the walls.

It's gone, moved some time ago. A friend actually found the sign that was on Michigan Ave. at a flea market.
posted by Max Power at 7:37 AM on December 5, 2021


Best answer: The Art Institute is truly one of the world's great art museums. You easily could spend all day there. Plus it is centrally located so lots of other things are nearby.

My favorite childhood museum was the Museum of Science and Industry which has an enormous model train layout. It is staggering large. The also apparently have a full sized Amtrack train from the 30s: the Pioneer Zephyr (I'll admit I don't know anything about this).

The museum over all is big and full of all sorts of things. I last visited when I was in my 30s and while not all of it held up to my childhood memories a lot of it did. According to their website it is accessible via the METRA Electric Line which would be another train opportunity for you.
posted by mmascolino at 8:24 AM on December 5, 2021 [1 favorite]


Best answer: Best time of year to visit depends heavily on your tolerance for heat/cold. I personally find the city unendurable in July/August, with the stifling heat and unrelenting humidity, but I am a wintertime person generally. A lot of people would RATHER DIE than face Chicago's January winds, but, you know. Personal taste.

I would also doublecheck you're not going to be there during Lollapalooza or Taste of Chicago or something similarly huge, because everywhere is packed and transit runs on special schedules (and has an unusually high number of drunk people, which doesn't bother me when it's just me, but I dislike when I have my kids with me and I'm trying to navigate a train full of drunks).

The architecture river tour is the bomb! You can time your visit to see something at the Joffrey Ballet. Agree with the Art Institute and the Field.
posted by Eyebrows McGee at 11:29 AM on December 5, 2021


Best answer: The Field Museum dinosaur exhibit is fantastic, you go through several rooms about how life / dinosaurs evolved before the room with the big skeletons and several about more modern creatures after and it’s fascinating and very well-done. I’ve been multiple times and keep learning things. The gem room is also fun and the special exhibits I’ve seen have been worth it.

Also n-thing the boat tour and art institute. Next time I’m there, I want to get Polish food and maybe find a supper club style restaurant. There’s a free stained glass museum at Navy Pier that’s good if that appeals (but you have to go to Navy Pier…)
posted by momus_window at 5:52 PM on December 5, 2021


Best answer: Chicago’s’ women’s basketball team the Sky won the championship this year. I don’t watch but it looks like playoffs end mid-October so it would depend on how early you visit in the fall. Our soccer team is the Red Stars and plays in a suburb that is not easy to get to on public transport (I’d say it’s not worth the effort unless you’re a big soccer fan). The men’s soccer team has been playing in the city lately, so I don’t know if that means the women will shift too, but it doesn’t look like it right now. Chicago has a lot of universities, so you could always look into the women’s sports schedules at DePaul, University of Chicago, etc.

There’s all kinds of museums to choose from in Chicago so it depends what you’re into and what you can’t see where you live. I typically choose a museum closer to the date so I know what the traveling exhibits are during my visit. The art institute is the one to go to if you like art. The permanent collection is more than you can see in one visit and they get good traveling exhibits. The other major ones were covered above, so pick your poison. There’s plenty of small museums as well like the Outsider Art museum, as just one example. Depending on the time of year, The National Museum of Mexican Art often has a neat Day of the Dead exhibit close to the holiday. There’s lots of murals and good food in Pilsen, while you’re there.

A bigger modern dance company is Hubbard Street Dance.

Chicago is a city of neighborhoods. With only a day you probably should stay and visit things near the Loop (where the skyscrapers are). But if you do venture out you can take a self “tour” on the EL of a few neighborhoods — this also gives you more train time. Most of the train lines are above ground so you’ll see the wider part of the city. Take the red line up to Andersonville, as recommended upthread for example. If you head south on the red line, there’s Chinatown, etc. if you’re really into trans and want to spend a day riding between neighborhoods you could get a small hotel in a neighborhood or near the Clark/Lake station where all the El lines meet/transfer. Again, with your time I’d probably focus mostly downtown though.

Generally try to avoid Navy Pier (it’s where we herd our tourists), and you’ll see the city by water on the boat tour. If it’s nice out I usually recommend people rent a bike and ride along the lakefront (the bike path is 18 miles) but with so little time I’d leave it off. Chicago style hot dogs are, in my opinion, more of a Chicagoan’s food than deep dish pizza. I don’t know anyone who eats it here who isn’t a tourist or is entertaining out of towers (except for Pequods). My fav big hot dog joint is Portillo’s, but there’s small ones dotted all over.
posted by Bunglegirl at 6:18 PM on December 5, 2021 [1 favorite]


Best answer: "Chicago style hot dogs are, in my opinion, more of a Chicagoan’s food than deep dish pizza."

Italian beef, or pistols at dawn, sirrah! (Wet and sweet, TYVM)
posted by Eyebrows McGee at 7:49 PM on December 5, 2021 [1 favorite]


Response by poster: Thank you for all the ideas! We have a lot to work from to narrow down. Glad to get so much support for the boat architecture tour.
posted by NotLost at 4:33 AM on December 6, 2021 [1 favorite]


Best answer: If you're taking Amtrak, you'll arrive into (the ugly part of) Union Station. Make sure to take a quick detour to see the Great Hall, which has recently been renovated. Look for the terrific "Night and Day" statues in the Hall.

From there, you're at the western edge of the Loop, less than a mile from the Art Institute and lakefront. There are tons of hotels nearby, so I would stay somewhere in the Loop for easy access to/from the train station, plus the riverwalk, etc. Definitely do one of the architecture tours. The original one given by the Chicago Architecture Foundation Center on Chicago's First Lady is the most historically rich and accurate. There are lots of other companies doing them, too, but many are less focused on the history and architecture.

You can also kayak along the river and lake - lots of options! The main part of the riverwalk can be very crowded with boats and such in the summer/early fall, but it provides a great perspective. There are a ton of companies that will rent you kayaks or do tours. If you're there on a Weds or Sat night, you can kayak during the Navy Pier fireworks. I've also heard you can now kayak to Chinatown, just a couple miles south of downtown, though I've never done it.

Weather-wise... it's the Midwest, so it's impossible to plan. Summer can be miserably hot and humid, or it can be perfectly pleasant - often in the same week. In general fall weather is pretty great in Sept and early October, though after that the chances of cold/rain/early snow go up.
posted by writermcwriterson at 9:08 AM on December 6, 2021


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