Saturday afternoon in Chicago

August 10, 2023 11:10 AM

What should I do as a Chicago first-timer if I have only a Saturday afternoon to kill? And where should I store my luggage if I'm not staying in a hotel there.

Hi! I'll be working at an event an hour south of Chicago next Friday, so I thought instead of flying out that night, I'd stay over till the following morning and give myself a day in Chicago (Saturday Aug 18). I was there once when I was a kid in the 90s, but not since. All I know to do is "The Loop" and "Magnificent Mile" but not sure what there is to see in these places, but want to keep it central and small. I also live in New York, so just looking around at/going up in tall buildings probably won't do much for me. That being said, walking many blocks isn't a problem.

I'll be leaving my accommodations Saturday morning with a carryon suitcase, catching a ride into the city, hanging out by myself probably 10am-5pm, then ubering to O'Hare for a 9pm flight (is this a reasonable time allowance for getting to O'Hare with possible traffic?).

First order of business--where can I leave my bag? Since I don't have a hotel in the city, I'm not able to leave it there. It looks like I can't leave it at Union Station unless I have an Amtrak ticket, which I don't.

What should I see? I like taking photos of pretty/cool stuff, historical architecture, art, light shopping (more into housewares and decor than clothing), not into sports. I don't need feel the need to hit all the top tourist spots, just looking for a nice chill afternoon without dashing all over town.

Where should I eat lunch? I wouldn't mind something in an interesting space or with an interesting view, but will be dressed very casually so wouldn't want to feel out of place. Agnostic about what to eat, and doesn't even have to be the best food ever, just something decent with a interesting vibe. Maybe also a cool bar to post up at if I need a break?

So yeah! Hit me with your recs, thanks!

posted by greta simone to Travel & Transportation around Chicago, IL (20 answers total)

but will be dressed very casually so wouldn't want to feel out of place

Chicago is the best place in the world for this. The city is completely and utterly without pretension. You will not be out of place anywhere but maybe a wedding, if you crash one, and even maybe not then.

I've lived here for almost 20 years and I still think the Architecture Foundation boat tours are one of the must do can't miss attractions. I'll go on one anytime an out of towner wants company.
posted by phunniemee at 11:30 AM on August 10, 2023 [13 favorites]

I have walked by a business downtown that will hold your bags for the day, but their website says they are only open from 10am to 2pm on Saturday.

A better option may be to check your bag at the Art Institute, which is certainly a good place for a nice chill afternoon. My favorite restaurant near there is The Gage. For a restaurant with a view, try Cindy's Rooftop.

The Architecture Foundation boat tour is also hard to beat. If you want something more unique, you could do a Brick of Chicago tour .
posted by Xalf at 11:49 AM on August 10, 2023 [3 favorites]

First time in the loop, I'd see the Cloud Gate sculpture and then visit the Art Institute nearby. The Field Museum or the Shedd Aquarium are also in the area and would easily fill more than one day. Alder Planetarium is right by the aquarium. There are good views of the lakeshore in this area, too, so walk if you can and the weather is nice.

There are various apps like luggage hero that you might use, but read the reviews of the app and of the place you pick.
posted by soelo at 11:54 AM on August 10, 2023 [1 favorite]

When I went a few years ago (pre-pandemic), I could have literally spent the entire week just walking through the Art Institute, which is absolutely world-class.

Seconding the architectural boat tour, it's much easier than trying to see all of the different buildings on foot and has some gorgeous views of the city.

Re: Millennium Park (where Cloud Gate/The Bean is), it looks like they're going to be doing renovations/new construction in the park starting next week for the next several months, so this may not be the best time to go there.
posted by Strange Interlude at 11:57 AM on August 10, 2023

I feel like there is either construction or event setup or tear down nearly every time I go to MP! They do seem to keep access to the bean open but getting there and leaving can be a headache, for sure.
posted by soelo at 12:00 PM on August 10, 2023

Nthing the architectural boat tour. Hope you have fun!
posted by wicked_sassy at 12:07 PM on August 10, 2023

The Art Institute did a big rehang/reorg just before the pandemic and I think it's really good (except they moved the Chagall windows to a really stupid place). With only a Saturday afternoon, you should go to the Art Institute. If you can sneak out and leave your bag, you can also take the Red Line to the Cermak/Chinatown stop for lunch - it's been years since I was there, sadly, so I don't have any specific recommendations, but a quick look at Eater or just the internet will provide lots of suggestions and it's tough to go really wrong.

I grew up outside Chicago and have spent many a happy day hitting the Art Institute and then going to Chinatown. Depending on your city confidence, you can just walk to Chinatown (I usually took the train back due to being full.) It's about two miles IIRC. Not a thrilling walk per se, but if you like walking in cities it's enjoyable.
posted by Frowner at 12:21 PM on August 10, 2023 [1 favorite]

You can sue LuggageHero or Bounce to store your stuff. Essentially, they're services where businesses agree to stash luggage for a nominal fee. They're all over the city now and you should be able to pick one that's relevativelt convenient for $5-10-ish.
posted by DirtyOldTown at 12:31 PM on August 10, 2023

You can walk into any business class hotel, hand your bags and $5 to the bellhop, and they'll take care of you.
posted by COD at 12:47 PM on August 10, 2023 [2 favorites]

I came in to say the same thing about luggage - if you have $5, the bellhop never asks if you are staying at the hotel. I would second (or 10h) the Art Institute and the architectural boat cruise. I am a sucker for going up in the tall buildings and I like the John Hancock the best for that. That said, I would tend to stay off Michigan Avenue/Magnificent Mile (other than the Hancock, if you want to go up high), because it has suffered from general retail malaise during COVID and feels like a sad mall.
posted by Mid at 12:58 PM on August 10, 2023 [1 favorite]

If you are from NY, I would skip the museums. The Art Institute is amazing, but you have MoMA, the Met and the Guggenheim in your backyard. Same for the Field and AMNH. The Architectural Foundation boat tour is a great idea. I would also visit the Chicago Cultural Center because it's a beautiful building. Also I would try to eat deep dish pizza.
posted by avocado_of_merriment at 1:27 PM on August 10, 2023

Good advice above about luggage. The architectural boat tour is nice, there is also a walking tour (it doesn't go UP into skyscrapers and include the atrium of Marshall Fields & the Tiffany Dome at the Cultural Center).
Pops for Champagne isn't a dive bar but if you like bubbles it's a nice place to sit & quaff some stars.
For your interests, I'm including this: Architectural Artifacts in RiverNorth just NW of the Magnificent Mile, accessible Red Line with a little walk. They also have a cafe coffeehouse bar.
Last, I'm not an uber person, so your reasons are your own; but since you're a walking person I'd like to mention it's far easier and cheaper to take the Blue Line directly to OHare from Clark & Lake, just south and across the river from the MagMile area.
posted by winesong at 1:50 PM on August 10, 2023

Response by poster: I don't want to drag luggage around on the train and I can expense the Uber since it's a work trip :)
posted by greta simone at 2:23 PM on August 10, 2023

That's Chicago's Air and Water Show weekend. Just sayin... it'll be jetty.

Also, I'm going to MeMail you. I might be able to assist.
posted by heyho at 2:26 PM on August 10, 2023 [2 favorites]

One thing I would set aside time for is to just . . . find a neighborhood and be in it. Walk around, look at the buildings, go to a diner, go to a dive bar, interact with people. This is what Chicago does really well.

On the North Side you could do this off of the Wilson stop on the Red Line, the Lincoln stop on the Brown Line, the Kedzie stop on the Brown Line, the Bryn Mawr stop on the Red Line, literally any other stop. (You couldn't pay me to hang out in Wicker Park and surrounding neighborhoods now, but your mileage may vary.)

In Pilsen you could stop at Damen or 18th Street. Further in the South Side maybe Bronzeville off the Green Line (Indiana, 47th) or Washington Park further down the line.

My point is, it is a nice city to just get your feet on the pavement and check out, and while I would never tell someone to limit themselves to the radial layout of the El, I would definitely recommend keeping to El stops for a one day jaunt.
posted by kensington314 at 2:40 PM on August 10, 2023 [2 favorites]

If you’re doing downtown, walk around the Tribune building and see all the bits of other buildings from around the world.
posted by alligatorpear at 6:00 PM on August 10, 2023

I understand why everyone suggests the Art Institute and boat tour but for my money (since you’re in NYC and museums and building tours wouldn’t be as big of a draw), it’d be a better use of your limited time to go to the Cultural Center. Every floor features so much beautiful Tiffany stuff and then you get to the top and there’s that stunning Tiffany dome. It’s breathtaking and my favorite place to go when I’m in Chicago. It’s close to millennium park too so you can throw that in.
posted by kitten kaboodle at 3:58 PM on August 11, 2023

NYC does have amazing art museums, but the AIC has American Gothic, and Nighthawks, and Sunday on la Grande Jatte, and so much more. Including a Van Gogh exhibit and also a Remedios Varo exhibit that looks off the freaking hook. If you are a lover of art museums I would definitely go!!
posted by Sublimity at 4:38 PM on August 11, 2023 [4 favorites]

If you’re staying at a chain hotel the night before you could always ask them to see if another nearby outpost of that chain hotel in the city can hold your bag (especially with business traveler status at that hotel chain). Or just asking to check would probably just work, as others have said, with a nice tip.
posted by Bunglegirl at 6:52 AM on August 12, 2023

Response by poster: Just following up to say leaving my luggage at ARTIC was super easy, and technically didn't even require admission since bag check was before the ticket entrance technically (on the Monroe-side entrance).

I dropped my bag there, went to Navy Pier to catch a boat tour which I really enjoyed, less so for all the buildings than for the history the excellent guide shared. Then headed back through the park to the museum, took a turn around the galleries that interested me most, and popped over to the airport. It was a nice day. Thanks for the recs.
posted by greta simone at 8:27 AM on September 1, 2023