Chicago for Cubs' game

Day Game for sure

Get there early and drink at Sluggers

Bleacher seats are great, don't do a roof top

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Is it worth it to carve out 3,4 hours of her day to go to a game? If so, are day games or night games better?

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In the summer, doesn't totally matter - all three in this homestand will be packed. If bar hopping Wrigleyville is part of the experience for your group, run with Saturday night. Otherwise, 1:20 is great because bars open early, you'll get drunk in the stands, and be out at a good hour for anything at night.

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What are the best places to sit?

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Just grab GA tickets for bleachers and give yourself some flexibility of arriving early for seats closer to the vines or chilling on the Budweiser Deck. Personally, I go with the Budweiser Deck and get the flexibility of easily grabbing beers and watching a few pitches if I want.

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Does Wrigley offer any good food / drink items or is it standard baseball fare?

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It's fine - there are stations to run your hot dog through the garden, which is a nice touch.

Home Run Inn also does a solid enough job with their pizza inside the stadium.

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Do they still offer the "Old Style" beer?

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It's actually not at many concessions but is around.

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Any good bars and restaurants around Wrigley

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Plenty. Crawl up Clark for some wilder bars (i.e. Sluggers, Moe's, Old Crow) and Murphy's is a classic and across Sheffield from bleachers entrance. For something in-between that and chill, aim for Will's -> Sheffield's. You could even go a way more chill route and do Southport Corridor for food/beer at Corridor, drinks at Toons and a patio drink at Tuco and Blondie.

Me and about 6 other guys went to the Cubs game the day before LSU played Wisconsin. Day game at Wrigley on a Friday at 1:20 and it was packed. We sat in the upper deck behind home plate in the shade and had a blast. If you sit upper deck, 1st base side, very top row, you can see the Chicago skyline. Great spot

Went to first Cubs game last summer after always having wanted to attend one. Saturday day game.

Definitely worth carving out time to do it, IMO.

I sat down the 3rd baseline where the equipment manager sits in the outfield to shag foul balls.

Came home with a baseball.

We stayed in an Airbnb just north of Wrigleyville. One block to a Redline stop. Very easy to access everything in the city and we weren't that worried about crime

I'd try to go into Sluggers. My wife was preggo when we went, so I didn't want to drag her in there

Been a few times, with a bunch of dudes, I have to say sit bleachers. Hit up Murphy's, The Cubby bear, Sluggers, tons of great bars in that area. Or, or you could do it big and do the Makers Mark bar inside of Wrigley. I have never done it, but I know some who have been, it would probably be a cool experience. Maybe something to look into.