Critique my Chicago trip, please!
April 27, 2023 7:16 PM   Subscribe

I’ll be headed to Chicago next week for the Moonrunners music festival and for various wanderings, shenanigans, and cultural enrichment. I have never been to Chicago, and - as a Planner - I am asking for help to make sure I am maximizing my vacation days. My itinerary, with questions, is below the fold.

We’ll (32F, 42M) be arriving Wednesday, in the early evening, and staying near the Clark/Lake station. Since we’ll be arriving late I hadn’t planned on much other than dinner, some light meandering, Art on the Mart, and a visit to Howl at the Moon, as I love dueling pianos bars. But, it seems sterile and gimmicky - even for a piano bar. Any suggestions for dinner in the area? Is Howl at the Moon worth going to, or is there a better option? We’re going to a music festival so more music isn’t necessary, I’m just a sucker for dueling pianos.

Thursday, we have the Architecture Boat Tour in the morning, and Second City in the evening. Between, I was thinking of hitting up the Wicker Park area for some thrifting and such, with an early dinner at Taxim before the show. A good Mediterranean meal is an integral part of the trip, so is Taxim the right place to do it? Is there somewhere else in the area with some authentic Polish cuisine we should try instead? Anywhere better to kill a few hours than Wicker Park?

Friday, we’ll be switching to a hotel near the Cermak-McCormick Place station. Ideally, we would drop the bags off at the hotel and then get some Divvy bikes and ride along the lakefront, visit Milenium Park, the Navy Pier, check out some street art (Wabash Arts Corridor, Hubbard St Murals), etc. This is the day that is the most open, so I’m looking for suggestions on good areas to visit just to walk around, stop in here and there for a beer, visit some shops, see some nice parks, etc. Any suggested itinerary for Friday would be ideal.

Saturday, no real plans. Perhaps Pilsen? Chinatown? We’ll go to the venue around 5 or 6, so I’m mainly looking for morning and early afternoon activities.

Sunday, same: no real plans until the show. I did notice that Lips drag brunch is right next to the hotel. Is that worth going to?

Monday, Arts Institute, and then catch a plane out. At this point we’ll probably be wiped out from two late nights, so that’s probably about all we can handle unless there’s something that can’t be missed that only happens on Mondays.

I’ll be thankful for any suggestions that you have, with a few keywords: craft beer, Polish food, Mediterranean food, views of and/or places to hang out next to the water, art (specifically modern and street), anything weird, anything uniquely Chicago, and just in general anything that two Californians should see.

Thank you!
posted by sacrifix to Travel & Transportation around Chicago, IL (26 answers total) 6 users marked this as a favorite
Howl at the moon is touristy as hell but it’s a blast and you’ll get your best bet of midwestern culture.

Take brown line up to lake view and Lincoln park. Walk around there!
posted by sandmanwv at 8:23 PM on April 27, 2023

If you do Pilsen the Mexican Museum of Art is there. You can walk around and see some of the murals in the area as well! It's not very big compared to other museums in the area but I've always enjoyed it when I've gone.
posted by AlexiaSky at 8:49 PM on April 27, 2023 [2 favorites]

You could also check out Greek Town, my Greek Orthodox inlaws prefer Greek Island restaurant, though there are opinions amongst the area about what is the best and when you should go.
For a light snack or lunch Artopolis is pretty good.
posted by AlexiaSky at 8:56 PM on April 27, 2023

The Polish restaurant you are looking for is Podhalanka in Wicker Park. To be fair, I probably haven't eaten there in 15 years, but if the previous decades are any indication it can't have changed much.
posted by HeroZero at 9:08 PM on April 27, 2023

One of the Intelligentsia coffee locations is very close to the Art Institute. Go there for my favorite coffee on Monday morning after your two late nights.
posted by Ms Vegetable at 10:27 PM on April 27, 2023

Brunch on Belmont at Ann Sather. Cindy's has amazing lake views and is a nice place for a cocktail should you visit the bean. For classic cheese(borger, borger) and SNL nostalgia, grab a burger at the Billy Goat. If the Cubs are in town, an afternoon at Wrigley is worth it. (Day games only.)
posted by cyndigo at 10:43 PM on April 27, 2023

A couple quick notes:
1) Don't underestimate the Art Institute - I'd consider it genuinely one of the great museums of the world. Maybe not the thing to do on your potentially tired and rushed last day.
2) I'd suggest a trip down to Hyde Park (you can bike down the lakefront on Divvy's) - there's the Oriental Institute, the small but interesting Smart Museum of Art (and the Renaissance Society?), and you might be interested in the FLW Robie House. Hyde Park, and the UofC campus, is a lovely bit of town to walk around.
3) Navy Pier is basically a tourist trap - you can skip that without regret.
4) There's a small museum of Outsider Art called 'Intuit' that will be pretty near some of your other planned meanderings.
posted by kickingtheground at 11:53 PM on April 27, 2023 [6 favorites]

Seconding the suggestion that you should consider spending more than a half-day in the Art Institute.

The Museum of Contemporary Art is definitely worth a visit if you enjoy modern art. Maybe go there instead of Navy Pier.

During my time in Chicago (which was admittedly over a decade ago) the standard answer for "best beer-lovers' bar in Chicago" was The Hopleaf. If you enjoy a craft brew it might be worth checking out.

If you do go down to Hyde Park on a nice day, be sure to spend some time walking around Promontory Point.
posted by Johnny Assay at 4:43 AM on April 28, 2023 [1 favorite]

The Art Institute is indeed one of the world's greatest art museums with such a large and broad collection. The museum is adjacent to Millennium Park that has the Cloud Gate which you know by the name "The Bean".
posted by mmascolino at 5:08 AM on April 28, 2023 [3 favorites]

I am not at all trying to be a Debbie Downer, I love my city! But a note of caution about being downtown after can be kind of empty while simultaneously threatening. Keep your wits about you and limit your time downtown or on the train after dark.

I recommend The Dearborn for drinks downtown...classy vibe with excellent service. Food is good too, and it's a short walk from Clark/Lake.

SMAK-TAK for Polish food! Sooo delicious, I should schedule my own visit again.

Also, if you have time, since it's farther away, but thrifting in Andersonville is great, and Mid East Bakery is a national treasure there. I used to live across the street! The food both in the Cafe and just the store are incredible. Best hummus in Chicago.

Have a great time! :)
posted by tiny frying pan at 6:41 AM on April 28, 2023 [3 favorites]

(Hopleaf mentioned above is also in Andersonville, steps from Mid East Bakery)
posted by tiny frying pan at 6:46 AM on April 28, 2023 [1 favorite]

This local is confused about the idea of thrifting in Wicker Park. There may be one or two thrift shops around but it’s a lot of national chains on Milwaukee now. Also, the pandemic left quite a few Wicker Park storefronts empty. It’s still fun to window shop but not the alternative utopia people maybe made it out to be a decade or two ago. If you go there you could get off the L at Division, walk a bit west (boutiques and restaurants) and then come back to Milwaukee and walk Northwest on Milwaukee until Damen. There’s a lot less to see on Milwaukee between Damen and California but Logan Square (Milwaukee between California and Logan L Stations) is another area you could walk around if you’re in the neighborhood. Lots of restaurants in neighborhoods only open at 4 Monday - Thursday (and lots closed Mondays) so check the hours if you have a specific place in mind.

On the weekend you could go to Chinatown and get dumplings or dim sum. I like the idea about Hyde Park. It can feel like a long bike ride from museum campus down to Hyde Park on a bike but the trail is nice. If you’re into biking along the lake, the view is better heading south toward the city so you see the skyscrapers pop up in front of you so you could start in Lincoln Park, eat at some of the suggestions above, maybe go to the (free) zoo then get a bike and ride south for pretty views.

Be careful biking on Chicago streets. It’s fine if you’re used to it but I’m amazed to see so many tourists riding on big/busy streets (Michigan Avenue!), with headphones, or looking at a map. Assume cars do not see you. The lakefront trail is very busy in the center, between Lincoln park and McCormick Place. People ride fast, runners with headphones sometimes stop or turn right into your path… follow lane markings and make way for faster riders.

The Cubs have 1:20pm games the 5, 6, and 7th which fun and very Chicago to do. Get a chicago hotdog with everything on it, and an Italian beef sandwich (in my opinion more authentic Chicago than deep dish pizza). If you’re near state/lake you will be close to the river walk, so go downstairs to the river from Wacker Drive and walk along it, maybe stop for a drink. Definitely skip Navy Pier, I can’t imagine what anyone would want to do there.

I like to have a plan too. My advice is to think of this as a menu and allow yourself to be flexible and change plans depending on the weather (spend nice days outside, save museums for worse weather), and your energy level. If the weather is nice you will see locals at rooftop bars or patios enjoying a drink.
posted by Bunglegirl at 7:33 AM on April 28, 2023 [3 favorites]

Taxim is great, and I do think Wicker is a good place to spend a few hours - but yeah, it does not really have the thrift stores you might want. Still fun to shop around (I love Topdrawer for stationery, Quimby's for comics), but it's more mall than thrift - think more Aesop and Diptyque and Urban Outfitters.

Hitting up Chinatown on Saturday is a great idea. There will be a wait at most food places, but it's worth it. I love MCCB, but there's truly so many options. You can walk around Ping Tom Park as well and look at the river. It's possible to take a water taxi to Chinatown via Wendella, I think.

I second MCA, Intuit (small but nice), and also the Hyde Park suggestions - Jackson Park is great and you might catch some cherry blossoms, Promontory Point is lovely.
posted by quadrilaterals at 7:46 AM on April 28, 2023 [1 favorite]

+1 on dedicating more time to the Art Institute. The collection is mind-boggling. Standing face-to-face with artwork (Nighthawks, Sunday on the Grand Jatte, etc) you've only seen in books is very powerful.

Chicago is a great city for architecture, and I enjoy just walking around neighborhoods to take it in. I gravitate toward the Lincoln Park area because that's where I grew up, but it does have a lot of great buildings. The architectural boat tour is worthwhile, but you're obviously pretty limited in what you can see. Riding bikes along the beach is nice, but if I were to give anything on your list a miss, it would be that.

One thing I did a while back was go to The Infinite Wrench. Recommended.
posted by adamrice at 7:55 AM on April 28, 2023

Chicago has a ton of craft breweries, maybe 100s. Everyone has their favorite so unless you have a special style of beer you love I suggest choosing a place that is convenient to or located in a neighborhood you’re visiting. Some serve food, those that don’t allow you to get delivery or bring in your own. Chicago is a city of neighborhoods, so explore areas outside of the loop/where you’re staying.

My own personal, biased opinion on Chicago beer and some neighborhoods you may be in:
Andersonville/Ravenswood: Hopleaf is a good restaurant and has tons of beers (67 taps). Great for variety and options., Half Acre has a nice big patio, Spiteful is nearby as well.

Wicker Park/Logan Square: Solemn Oath, Maplewood, Revolution (has a restaurant on Milwaukee), Hopewell, and my personal favorite beer and brewery in the city Metropolitan (which is very far from anything you will want to see).

Others: Goose Island is no longer locally owned and not near areas you want to see so I’d skip it unless you’re a huge fan. We have a nice cider brewery called Eris, which has a nice restaurant and outdoor seating but it’s also not near anything you will want to see. I mention it if you really love cider.
posted by Bunglegirl at 7:57 AM on April 28, 2023

A transit note: the Blue Line has closures Friday--Sunday between Addison and Western; so no service to California, Logan, or Belmont stations by the train. They have shuttle buses running express for those stops.
This is if you're thinking of wandering up to Logan square, which you don't mention in your itinerary , but just FYI.
posted by winesong at 9:15 AM on April 28, 2023 [1 favorite]

With your emphasis on art, I'd suggest making the Art Institute a two day thing. It is a large collection and while it is possible to walk through all of it in a single day, it's exhausting to do so and by about halfway through you may not be taking in the art as well as if you were rested.

The Museum of Contemporary Photography is nearby. Check what's going on at the Millennial Park as well.

Museum of Contemporary Art is good but very small so make sure the exhibit is something that'll tickle your fancy. For example, the last time I was there, the exhibit was underground comix from the local scene which just isn't my thing.

I think the boat architecture tours are a lot prettier with the sunset run than during the day.

If you appreciate spendy high end food, I've not been but have heard good things about Moody Tongue (which is also a brewery).
posted by Candleman at 11:50 AM on April 28, 2023

The Chicago Cultural Center is free, centrally located, and has decent public bathrooms. It's right across the street from Millennium Park. They offer tours of the building daily and there have art exhibits and events.

I don't know what the weather will be like when you're here but if it's hot, the CCC is a good place to cool down. One of my favorite things is to sit and admire the Tiffany dome (largest in the world) at the top of the building.
posted by Constance Mirabella at 7:30 PM on April 28, 2023

Response by poster: Thank you so much for your input so far!

Quick question, re: "Keep your wits about you and limit your time downtown or on the train after dark." How scary are we talking about here? Worse than downtown San Francisco after dark? I'm well versed in walking fast, not making eye contact, and keeping my head on a swivel.
posted by sacrifix at 8:58 AM on April 29, 2023

I don't think your going to have a problem safety wise. * The trains can be a bit intense on the CTA ,(I got on to a train recently at 9pmish where multiple people were smoking cigars in multiple cars with a litteral 90's boom box and it was obnoxious and dangerous to my asthma lungs) but I wasn't unsafe in a physical harm way. It was bad enough that the conductor left his spot yelled at them then threatened police but he went back to the front car and they went back to smoking, playing their music and I got off at my stop). I could have simply waited for the next train but i decided it wasn't worth the wait. I had a phone stolen out of my hand once in the 15 years I've lived here riding.

I don't think you'll be stressed out provided you know where you are going and know how to navigate big cities. There are risks, but that's that's true anywhere.

You may notice there are quite a few people who are homeless use the train as shelter. The blue line has the longest track followed by the red so those are preferred, the other lines not so much especially downtown. But I don't think this is much different from California.

Also if you find yourself uncomfortable it is very easy to get a taxi or Uber/ lyft to go place to place. So if it's late and you don't feel it just do what feels safest to you.

*I find I am fairly unconcerned to some of my friends about this stuff so ymmv.
posted by AlexiaSky at 9:40 AM on April 29, 2023

I had one of my favorite meals of my life at Cellar Door Provisions a few months ago. It was so, so good. Highly recommend it if you're looking for a dinner place at any point.
posted by Gadarene at 12:35 PM on April 29, 2023

I visited Chicago with a friend a couple of years ago and the Architecture river tour was a real highlight. We also loved the Field Museum of Natural History.
posted by feste at 5:43 PM on April 29, 2023 [1 favorite]

I was hinting about random recent violence downtown and also I ride the trains and they can be a bit weird and edgy mid afternoon and more intense after dark, usually more of a substance abuse/mental illness situation rather than armed robbers but those have happened occasionally across the CTA. As all cities go, just pay attention and don't plan 30 city block walks in the dark or the train at 3 am and you should be OK. I truly don't want people to be nervous to visit and hope I didn't overstate...but even I, a 20 some year resident, am practicing more situational awareness, if you will. Unfortunately you aren't perfectly safe anywhere. If you have any granular questions please MeMail me...I know most train lines downtown and spend most of my time on the Blue Line which is prob more unclean than dangerous. I'm sure you'll have a blast!
posted by tiny frying pan at 3:53 PM on April 30, 2023

If Industrial/Postpunk music is of interest, Martin Aktins is hosting an open house on the 6th and 7th.
posted by Candleman at 6:41 PM on April 30, 2023

Response by poster: As a follow up: I am terrible at following my own plans.

A few notes:
- Howl at the Moon was worth about 10 minutes of our time.
- Three Dots and a Dash would have been better if it wasn't completely jammed full of assholes, but we got two nice servings of blackout juice and excellent service.
- The architecture tour through the Chicago Architecture Center was definitely a highlight of the trip.
- Second City was so hilarious it was overwhelming, in a mostly good way.
- Cloud Gate was, as expected, unnecessary but we were in the neighborhood. The amount of security around it was a bit shocking. Getting wanded to see a shiny bean? WTF?
- Had some fantastic bao "buns" at Little Bad Wolf. The tofu was a bit of a let down, but the steak and pork were delicious. Also the lumpia.
- Hopyard, especially the back patio, was exactly what we were looking for.
- Wooly Mammoth, around the corner from Hopyard, was delightful, if you're into that sort of thing.
- Pilsen Yards had some aggressively friendly waitstaff, and was overpriced for what it was. We didn't end up sitting on the patio, as it was hot and we were hungover, but it was beautiful.
- The Art Institute was actually a bit underwhelming. Maybe I was just worn out from the trip, and a little bummed by the foggy rainy weather.
- Don't wear a confederate flag shirt to a folk punk festival.
- Little Foot puts on an amazing show, and is all around a good guy.
posted by sacrifix at 9:12 PM on May 11, 2023

Cloud Gate was, as expected, unnecessary but we were in the neighborhood. The amount of security around it was a bit shocking. Getting wanded to see a shiny bean? WTF?

It was recently vandalized. Also there has been some unruly behavior in that area the cops are hyper about but thanks for letting us know it's been stepped up security wise!
posted by tiny frying pan at 6:21 AM on May 12, 2023

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