Help me plan 4 nights in Chicago

Yeah, West Loop has lots of great dining options! That’s one of the hip eating areas of the city, for sure. You’ll probably want to cab it out there, but it’s about a 2-mile-and-change walk to the start of the Fulton Market area from the Hilton Chicago. So definitely walkable if you don’t mind strolling for 40 minutes to an hour.

I agree…unless you know the place you want to go is a 10-15 minute walk or less probably best to take a taxi/Uber (I won’t try to get visitors to deal with the mass transit system). Of course, if you (general “you”) just love to walk then sure…can be done.

That said, walking the Mag Mile is a thing to do so I’d say that is worth a stroll.

And I agree…West Loop/Fulton Market has all the really hip restaurants (legit very good too). Not easy to get into some either so plan ahead…way ahead in some cases. Plenty of other great restaurants in River North and the Gold Coast too though (Gold Coast is starts at the north edge of River North). Chicago has more than its fair share of really good restaurants.

Hell, in Saveur Magazine’s first city-centered issue, they named Chicago their favorite food town in the US. (This was back in 2007. I certainly don’t think it’s gotten any worse. I think this is a great food city.)

This!

That Hilton used to have special rates on the weekends (they called them “Bounceback Weekends” and included a good breakfast… we’d upgrade to the buffet and enjoy the omelettes, meats, and the mountainous displays of fresh fruit).

It’s really a quick walk to those great museums, etc. We used to do it in the middle of winter with two strollers, and it was no big deal. We’d also walk north across the bridge and shop on Michigan Avenue (I hate the Mag. Mile nickname… I don’t consider a bunch of stores worthy of a superlative).

And if we got tired, we could take a bus “home”! Plenty of them just run up and down Michigan Ave.

Hey, I’ll bet your elderly mom would love Grahan Cracker Comics, fifty feet off Michigan, across from the Art Institute. Fun, smart staff, and excellent budget bins.

Apparently the south mile of Michigan Ave has the moniker “The Cultural Mile” according to some signs in the city, but I have never heard that appellation in the wild. To tell the truth, though, I don’t really say “Magnificent Mile” or really “Mag Mile.” I might use the latter, but more likely just “north Michigan” if there is enough context.

To be fair, it is more than just the stores. There is some great architecture there too like the Wrigley Building and the Tribune Tower and the John Hancock (to name a few).

Thanks, I’ll take that into consideration…

So the mass transit (ie: the loop part etc, and underground/elevated tracks), is that really complicated? We’ve been fine with New York. San Francisco, Portlands light rail etc. Seems less to walk if using those too.

Oh, not at all. You can easily use public transport for any of the locations we mentioned. It just didn’t occur to me now that the only transport I use is either my car or Lyft.

The trains are very easy to use but know there are a lot of stairs either up or down to use them. Some have elevators but I have never seen those actually work. The trains come when they will…no need to look for a schedule. Just go and wait for the next one to show up (usually within 10 minutes).

Busses will get you anywhere but I have found them to be very unreliable lately. In theory one should show up every (say) 15 minutes but I’ve waited 30+ minutes without one showing (even when my apps say they are perpetually 5 minutes away…very annoying). The next time two show up at the same time.

On the upside, Michigan Avenue where that Hilton is, has busses galore running by and if all you want to do is ride up Michigan Ave then most any of them will suffice. If in doubt, ask the driver if they go where you want to go. They almost always know the answer.

Also, I am not sure how to pay for mass transit for those from out of town. I have my card I use as a resident but not sure what visitors do. Doubtless there is an answer for this, I just don’t know what it is. (I think the busses still accept cash but they will not give change.)

All the El stations should have both Ventra tickets and Ventra cards available. I have like a half dozen of them around the house because every time I seem to need one, I don’t have it on me and just buy a new one. It sounds like you might be able to make payments with contactless bank cards too? I’m not sure if I’m reading that right, but a little Googling around suggests that Apple Pay and contactless CCs should, indeed, work. I don’t know when this happened. That’s pretty cool if that’s correct.

Anyhow, all the info is here:

Excellent, we’ll be falling off a plane (First Class from UK, so plenty of champagne will be consumed), so the train/subway into the city is the plan. Hope it’s not that complicated to work out.

Train to the city is super easy. There’s only one and it only goes one way (the airport is the end of that line assuming you are arriving at O’Hare airport).

So you’ll be flying into O’Hare, I assume. The El has its terminus station in the airport. It’s a bit of a walk, and if you’re coming from the UK, you got all that fun customs stuff to do. But just follow the signs. The El is underground (rather than elevated) there, so you’ll be in a subway terminal, and there are plenty of machines should you decide to buy a Ventra card (I think the only advantage of buying a card now would be if you want to buy a multi-day discounted pass instead of paying as you go.) You then just get off at Jackson (about 40/45 minutes) and can walk to your hotel (15 min) or transfer to the Red Line to go one stop south and have a shorter walk (about 5 min).

It is worth noting that the 720 S Michigan Hilton Hotel is big as a convention space. I have been there many times for conventions. No idea if there will be one when the visit happens or of it matters. Just something to note.

It’s a nice hotel.

Nothing better than a day game at Wrigley.

We got recommendations from friends several years ago before seeing “Hamilton” - a few of them independently recommended The Gage, which is right across the street from the Art Institute. It’s very nice - and the extremely convenient location to everything you’re doing (again) may assuage your wallet since you’ll save on another cab.

We’ve had two very nice meals at Catch 25, both the food and the service were great.

Last year I stayed at the La Quinta on Franklin and I’ll be staying there again when I go in April. Nothing special about it, but it’s affordable, the room was spacious and comfy, and the location was good. They were also helpful when I wound up in the hospital and missed checkout - they packed all my luggage into my suitcases and held onto it until fellow Doper Folly was able to bring them to me at the hospital.

My agenda, currently, looks something like this;

Tuesday: Arrive early afternoon, late lunch at JP Graziano, check into hotel, Sears Tower, thin crust pizza for dinner, go to sleep early since we’ll have been up since 1 AM

Wednesday: Breakfast at Lou Mitchell’s, MSI, bus tour or ???, dinner at Italian Village

Thursday: Brunch at Manny’s, lake cruise, Art Institute, dinner at ???, Second City revue

Friday: Breakfast at ???, Field Museum, Shedd Aquarium, dinner at Chicago Pizza & Oven Grinder company

Saturday: Breakfast at ???, fly home

I haven’t planned anything for lunch because we’ll probably just get quick bites, but mom definitely wants a hot dog and I intend to shove as many Italian beef sandwiches into my face as I can. Last time I tried the beefs at Portillo’s and Al’s; loved the former, the latter was interesting but the Greek spices really weren’t what I was looking for.

Further aside on hotel (not going to labour the point much further though), is that the Hampton Inn on East Huron Street is $200 cheaper for the stay, much better location (even to the train from airport), and while Diamond on Hilton for a bit longer, I don’t value it much in the US, the lounges (which the Chicago Hilton doesn’t have) are mostly crap, so it’s a breakfast credit. I had a lovely upgrade at the Parc 55 in SF, but I think decent upgrades tend to be great for a single night midweek, and not forthcoming for 5 day stays. So I’d rather have a breakfast via HI and no hope of upgrade.

My real question, is “is there a reason I shouldn’t stay at that Hampton Inn at that location”? It is too noisy or something, too much in the busy area? The arguments for are compelling.