Chicago in October for Anniversary

This is such a loaded, generic question. I've (and a few other Chicago people on this board) provided so much information over the years between this and F&DB. My first recommendation is to use search and filter Chicago threads. My second recommendation is to hit r/AskChicago and r/chicagofood subs on Reddit. If you need further guidance, think you have to provide more information - i.e. are you willing to explore neighborhoods that doesn't include "downtown" (I'd assume you're speaking to The Loop, River North and Streeterville)?

I hear The Bear has really good Michelin quality food. Just dont accept the kitchen tour

Eat at Bavette’s Bar and Boeuf

Wanted to add the outdoor experience at Miru at the Regency hotel was pretty killer. The view and weather was amazing coupled with some great Japanese food.

If you’re into architecture, the Frank Lloyd Wright walking homes tour was great (if the weather’s nice).

Art Institute or Field Museum

Chicago 360

Steppenwolf if you like theater

Second City for improv/sketch comedy

There’s usually a good Broadway tour with some kind of residency

Dinner at Ciccio Mio. In river north - perfect spot for anniversary nice dinner

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If your into good food Monteverde and Rose Mary are both very good.

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Agreed, though I will add Monteverde dinner service is one of the more difficult reservations in Chicago. It's one a lot of people stay awake for when they release at midnight the month in advance. Definitely easier to get in for lunch if OP prefers that route. Rose Mary is significantly easier to snag. What ever the choice, Joe Flamm and Sarah Grueneberg are fantastic chefs and people.

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But, I will say, that when I was there a couple weeks ago we did talk to multiple locals that said it was very unfortunate how the Loop was affected and how everything shuts down early now to be safe. I never felt like the Loop was much of an after hours place anyway so IDK how much it has truly changed, but there is absolutely no reason to feel unsafe anywhere the average tourist or even for lack of better term white person in Chicago would go.

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Think there are two sides to this.

The Loop has always sucked, in my opinion. Whether before or after COVID, most, including myself, take the 'L' (or Metra, if you live in the suburbs) for work and leave when the day is over. The couple exceptions, of course, is the Riverwalk and parks to the east. Especially during the summer months, the Riverwalk has a lively stretch of beer gardens and restaurants, while Millennium has concerts and movie nights. Admittedly, though, areas like the Riverwalk align much closer to River North than The Loop. In general, I can't remember the last time I voluntarily went into The Loop - it's a neighborhood chalked with office buildings and chains, that largely becomes a ghost town after the 9-5.

That all said, and despite my opinion of The Loop, it was affected by COVID. Commercial real estate is a mess (not dissimilar from other cities) and there has been an increase in crime. CPD enforces curfews for teenagers, especially, because of some of the large-scale 'disturbances' they create during the summer months.

My advice for weekend visitors, on this board and in my personal life, has always been to explore Chicago's neighborhoods - it's the lifeblood of this city and there are so, so many fantastic neighborhoods that you don't need to be on edge (i.e. Lincoln Park, Logan Square, Andersonville). If you don't want to venture far, maybe stick to River North, West Loop and Gold Coast, but, generally, I don't think there's much reason to be in The Loop unless you're going to The Bean, Grant Park and the Riverwalk.

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Hoopsgalore I just booked the Pendry for a quick anniversary celebratory weekend in sept. Is it close enough to the river / river north?

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Absolutely. You're only a block from Upper Wacker, which gives you incredibly easy access to the Riverwalk and bridges that go across to Mag Mile / River North, and a couple blocks to Millennium Park.

Also, it's a quick walk to every train line, whether it's Lake (Red ), Clark/Lake (Blue), and State/Lake (All other lines). Encourage you to use that to your advantage and explore some neighborhoods. Some popular neighborhoods that weekend visitors would feel comfortable visiting are West Loop, Gold Coast, Lincoln Park, Lake View, Wicker Park, and Logan Square.