Long Weekend in Chicago - May

In My Humble Opinion
1

I’m in charge of putting together a weekend gathering for my sister/BIL, another couple, and me and my wife; just adults, in Chicago this May. The centerpiece will be seeing Hamilton either Friday or Saturday night but the rest of the weekend is open. My initial planning includes the Field Museum and/or the Art Institute. The White Sox are in town against the Blue Jays, which might appeal to some of the group (mostly me). Looks like there’s something called Mayfest going on but not sure if it’s worth a visit. Is the Willis Tower worth it?

We’ll probably try to catch some blues in a club somewhere, or the gospel brunch at the House of Blues. Any recommendations?

We will be staying at an AirBnB with full kitchen but I suspect we’ll have at least one nice dinner out at as a group. Something that represents Chicago, perhaps a steak house. I’m sure we’ll have deep dish at some point.

2

Skip the Willis Tower. If you want a view, get a cocktail in the Signature Room in the Hancock building.

I recommend a river architecture tour, weather should be plenty good enough for it.

For deep dish I recommend Pequods, but the real Chicago food to go for is an Italian beef sandwich (hot peppers, dipped).

Chicago does do steak pretty well, but it’s considered at least a little old fashioned. Lots of good food, I’d do a little research, you likely can get a great steak where you’re at. I’d do something unique to Chicago.

3

I second the architecture boat tour, great way to see the city from a unique perspective. You can take the red line south to 35th st. for the Sox game. I, for one, am underwhelmed by the Field museum, but then again I’m not really a museum guy. The House of Blues is cool, and if you’re looking for expensive steak, the restaurant next door is well regarded. (I thought the steak at the House of Blues was really good, btw.)

4

OP: Where are you staying? Will you have a car(s)?

Mayfest (or Maifest) is pretty fun. There are bands, German and the more usual street festival types, food, large beers. It is very family oriented during the earlier hours and a bit more party oriented later in the evening. If the weather is at all nice-ish, it will be crowded. There are huge event tents for the bands and vendors that attendees can run to in case of rain. The festival is at the CTA Brown Line stop for Western. Note that the event website hasn’t yet been updated for 2019.

Pritzker Pavilion, part of Millenium Park, is a great place to take in a live show (weather permitting) but it might be too early. They haven’t scheduled any performances for May but I’m not sure whether that schedule is final.
http://www.grantparkmusicfestival.com

I disagre about Pequods. I like it alright but it isn’t the cheesy, saucy, photogenic pie out-of-town visitors are expecting.

A beef is required eating, though. If hot peppers are not acceptable (it feels weird writing that), at least get sweet peppers. Hot peppers on a beef is always giardeiera, a relish of chopped veggies, usually lightly pickled in a salty, vinegary oil base. Get this on the side if you’re not sure. Al’s Beef on Taylor is a classic. You can also get a combo which is a beef sandwich with an Italian sausage. I very seldom get a combo, the subtle beef flavor is muddled. I do not condone cheese, garlic bread, or any other adulterants on an Italian beef sangwich.

5

Check out the many prior such threads. Not trying to shut down this discussion - just suggesting additional resources.

Where is the AirBnB located?

The Field just had a substantial redo - they moved their big T Rex from the main gallery to a separate gallery, and have a new huge skeleton (Gigantosaurus?) and various pt-beasts hanging from the ceiling. My son works there, and says both are pretty cool. When my other kid was recently in town, she said the Egypt exhibit was well worthwhile. If you like natural history museums, the Field is pretty cool. But if not - or if you’ve seen a bunch of other NH museums, you might want to go elsewhere.

Once you get to Grant Park, you can walk to Millenium Park, Navy Pier, Buckingham Fountain, the Art Institute, The Field, The Shedd Aquarium, and the Adler Planetarium. More than you can see in a day. You should get out to the Adler peninsula, or Northerly Island (Meigs), to get the money shot of the Chicago skyline. Take your own postcard photo.

I’d suggest looking into renting bikes, and riding up/down the lakefront trail. You can either rent the streetside bikes (Divvy?) or look to a bike shop that would rent something nicer. The 20-mile or so lakefront path is the closest Chicago comes to natural beauty. The north end gets REALLY crowded on weekend afternoons. But it could be funb to bike up to Lincoln Park Zoo, or down to the Museum of Science and Industry.

I also enjoy just walking up/down Michigan Ave - say from the Art Institute up to Oak Street Beach. IMO really the best view of Chicago.

Maybe check out the new riverwalk - very nice. On a nice day it shows Chicago at its best.

Yeah, the river architecture cruise is pretty much mandatory.

I find Navy Pier EXTREMELY missable. And I’m not a fan of the Chicago Historical Society (or whatever it is called now.)

My favorite music bar is Fitzgerald’s in Berwyn. Depending on where you are staying and who’s playing, it might be worthwhile.

I read a review recently about a new book on “offbeat” attractions in Chicago. Forget the title/author, but there have been many. You might check a few of them out to see if anything catches your attention.

6

Have you ever been to the Art Institute or Field before? Just observing, each is the kinda place you could spend a whole day - or several days - in. Just a heads up. I generally don’t care for exhaustive daylong museum visits, so I acknowledge I will miss all manner of stuff, and only try to see what I most want to see. With 3 couples, I suggest you readily split up, so everyone can see what they like best.

7

We don’t have our AirBnB yet, my wife generally takes care of those. We’ll be looking for a place close to downtown so we’re walking distance to most things.

I think the group can handle one museum for a few hours. I don’t think any of us have been to the major sights, at least not recently. I’m partial to the Field, but the AIC may win out.

Assuming the weather is nice the architecture cruise will be a winner. I also think we can easily spend a day walking/biking along the waterfront. We don’t need to stay together all day so that allows us to separate and gather as needed.

8

Make sure that if you do take a river tour, you take the one from the Chicago Architectural Foundation. That’s the gold standard. Also seconding the new river walk.

9

I’ll add my voice to the chorus recommending a river tour. And, yes, Chicago Architectural Foundation is the one to do.

My favorite deep dish pizza is Geno’s East, followed by Lou Malnati’s, Pizzeria Uno (or Due), and Giordano’s, in that order. But none of them are bad, and everyone has a different opinion. Not familiar with Pequod’s.
Don’t forget that Chicago thin crust is a thing too. A lot of people miss out because they’re going for the deep dish experience. Rosati’s and Aurelio’s (multiple locations of each) do a good thin, as well as half a million neighborhood places.

Definitely get an Italian Beef. My ranking is Mr. Beef, Al’s, Portillo’s, and - as a last resort - Buona. Again, plenty of local neighborhood joints will do as well.

You may also want to check out the Billy Goat Tavern on Lower Michigan Avenue. I love the cheeseburgers; they’re greasy and delicious. Many other people think they’re awful. But the place itself is a hoot. It’s a real time capsule. Virtually nothing has changed since 1964. If you’re lucky there’ll be a Sianis behnd the bar.

I like that you’re considering a ball game. You’ll probably be underwhelmed by Sox Park though (whatever they’re calling it these days). Wrigley Field offers tours when the Cubs are out of town. I highly recommend one.

10

Another endorsement for the architecture boat tour, and the Signature Room at (the building formerly known as) The Hancock. I also like to recommend the Untouchables Tour - a bus tour of gangster-oriented historical sites.

If you want a really good blues club downtown, I don’t think you can beat Buddy Guy’s. If you can’t find a good seat on the main floor, you can go upstairs where it’s less crowded and still watch the act on the big screen. Excellent Louisiana-style food, too.

For deep dish pizza, I recommend Lou Malnati’s to out-of-towners. It isn’t really hard-core deep, so rookies can handle it :wink: . For the mandatory Italian Beef, all those mentioned are excellent, but I think Portillo’s is probably the most tourist-friendly.

If you’re into such things, there are Segway tours up and down Lake Shore Drive. And of course don’t forget to take a selfie of your reflection in The Bean in Millennium Park.

11

I haven’t been to Chicago in several years, but yes to Italian Beef. I’ve been craving it so I have to figure out how to make it. The descriptions here are killing me!

I also agree with skipping Navy Pier.

12

Gene and Georgetti. Yes, it’s an old-fashioned Chicago steakhouse, ala carte and pricey, but it’s fantastic. I’ve been there a half dozen times in my former business travels and I plan on taking Mrs. White to Chicago one weekend specifically to have a meal there. Never been to the one in Rosemont, only the original one in Chicago…

13

Red alert, red alert! Air BNB is a very hot button issue here and likely to get hotter with local elections coming up. Chicago isn’t an Air BNB city and avoid any place with license ‘pending.’

14

Best advice I got from Dopers when I asked what to do when I went to Chicago was the architectural boat tour. Just do it. You’l be glad you did.

15

Not to hijack, but you can get Lou Malnati’s and Portillo’s delivered anywhere in the U.S. from this website. It’s a bit spendy, but I’ve had both and they travel pretty well (packed on dry ice). Just the thing to cure a bout of Chicago homesickness.

16

I highly recommend the Chicago Magic Lounge for a great evening out. Its in Andersonville on Clark St.

17

Thanks for this recommendation! I may have to splurge. :slight_smile:

18

I love Pequods but I would not call it deep dish pizza. More a pan pizza. Still great but not what people think of as Chicago Deep Dish.

For deep dish I’d recommend Pizzeria Uno or Pizzeria Due (same business, different locations but only about a block apart from each other).

19

If you’re going to see Hamilton, the Hamilton Exhibition will also be open by then. No idea if it’s going to be any good though.

20

Cool, I commented in the Hamilton thread that I would like to see the exhibit.

Thanks for all the food suggestions. It looks like my cousin who lives in Milwaukee may be coming down for one of the days and they know Chicago pretty well. So we may have some inside help.