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I don't want to be responsible for you dying but my the company I work for has an office at the edge of the loop in the old post office. Lots of great restaurants and bars in the area. I highly recommend Bereket Turkish restaurant. The Turkish pizza was amazing. If you want a top notch bar, I suggest Kumiko, it's a little bit out of the loop.

You can stay anywhere in the downtown area and be fine. Just make sure you’re near a train stop which will help you navigate some of the neighborhoods. A lot of the bars in downtown are stale and for tourists or high-end. If you head up to Lincoln Park there are some more relaxed bars, but for a bachelor party may not be ideal. Cubs game would be cool on Saturday, try and get bleacher tickets. You may want to check to see if there is a train that goes to Green Bay. If you’re on a bus for a reason, then that’s fine, but amtrack or Metra may get you up there faster and more comfortable.

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For those of you who know, what’s the best place to stay in the city for a couple nights of dinner and going out?

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Grab a hotel in River North, The Loop, or along Magnificent Miles. Greatest concentration of hotels, across all price ranges, in the city. There are some hotels in West Loop (i.e. The Hoxton and Nobu) and the neighborhoods (i.e. The Robey + Hyatt Place in Wicker, Hotel Zachary in Wrigley, etc.), but you won't find the cheapest prices.

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For those of you who know, what’s the best place to stay in the city for a couple nights of dinner and going out?

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Getting a hotel in any of the three I mentioned above gives you flexibility. You can go to some of the clubs in River North, if bottle service is your thing, or easy to get on the train and go to other neighborhoods for your standard bar crawl.

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Is there an area with a good concentration of bars? The Cubs will be in town. Is wrigleyville the play on Saturday?

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Obviously, River North is pretty popular because it's where most of the clubs are. Know that's not for everyone, so will just give you a quick run of a couple neighborhoods for doing a bar crawl:

Depending on your age, Old Town gets pretty wild at night - big stretch of Wells is loaded with recent college grads. There's also a piece of Division, on the border of Old Town / Gold Coast, that has a concentration of 4-5 bars that are all pretty fun. Similar vibes to Wells.

Wicker is a mix of young professionals and recent college grads. Can get a bit ratchet at night, but Lottie's is a great bar, at all hours, and Paradise Park is one of the better day drinking spots in the city for larger groups. There's always a few bachelorette parties there.

Logan Square is close to Wicker - slightly more put together because there are more families than Wicker, but still a generous mix with young professionals. IMO, best overall neighborhood in Chicago - fantastic restaurants, concentration of breweries, good cocktail bars, and a few bars that will offer a good night out for younger groups. Estereo and Welcome Back get pretty damn crowded at night, and I'd imagine Logan gets even more crowded once Federales opens their second Chicago location there (should be open by the time you visit).

Whether or not the Cubs are in town, Wrigley tends to be a wild place. Overrun by recent college grads on weekend nights, but can't go wrong with day drinking on a Cubs game day, either. Think you'd be totally fine making this your Saturday play, and you can just hit the Red Line to Addison or take Brown Line (Red, too) to Belmont and walk. If you take the Brown, can also get off at Diversey or Wellington and hit a few bars on your walk to Wrigley - Kirkwood and Will's have great patios. Kirkwood is definitely on the younger side, but a lot of fun on a warm day. It's an Indiana bar, but I don't hold it against them As you move closer to Wrigley, make a quick stop at Sheffield's for a beer. Again, nice patio and very solid beer selection. They throw a great Bourbon County release party on Black Wednesday (night before Thanksgiving).

There are other neighborhoods worth checking out, too, but since you're here for a bachelor party, just giving you some options for going out and getting drunk

I sort of kept Nebraska out of it since Kirkwood is more known as the big Indiana bar, but you are correct - Nebraska bar, too.

Will's gets sloppy for Wisconsin games. Definitely the younger side of Wisconsin alums in the city will be there. Friends and I just hit our early 30s, so I think we've graduated from Wills Now, mostly go to Ranalli's and Lottie's for Wisconsin games.

Good call on a CFB Saturday for both bars, but could be a fun way for a bachelor party to get drunk before/after Cubs game?

These responses have been tremendously helpful. Appreciate it much!

One other question:
Is Wrigleyville still a good Saturday for a Cubs game that late in the season?

Going to Chicago a couple of days before the LSU game at Lambeau Field was awesome. Went to a couple of Cubs games, hit the bars with a ton of LSU fans, started a huge GEAUX TIGERS cheer in a Wrigley Field bathroom during the Cubs game on Friday afternoon.

And you can smoke cigs inside

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Grab a hotel in River North, The Loop, or along Magnificent Miles. Greatest concentration of hotels, across all price ranges, in the city. There are some hotels in West Loop (i.e. The Hoxton and Nobu) and the neighborhoods (i.e. The Robey + Hyatt Place in Wicker, Hotel Zachary in Wrigley, etc.), but you won't find the cheapest prices.

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The LondonHouse is my favorite near that area. Rooftop is cool even if you are just standing there without a drink