re: Any must do things in Chicago

Redhead Piano Bar. the casino. Navy Pier. Millennium Park

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Any must do things in Chicago

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Stay low.

There's a bar on top Hancock tower that has expensive drinks but they are top shelf and you get an amazing view of the skyline and Lake but restaurant is expensive as hell, the bar requires no reservations, Cubs and white Sox game, plenty of beer gardens near Wrigley, Luckys sandwich shop and weiner circle are also near Wrigley, millennium Park, science and industry museum, al's Italian beef on University of Illinois campus is phenomenal (get the sandwich fully dipped and dressed), night cruise on river, take a tour of goose Island brewery, the chop house is rated as one of the top 10 steakhouses in America but it is expensive and there is a dress code, the steak was amazing, Skywalk on top of sears tower, and finally Gino's East for the best deep dish pizza in the world

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Any must things to do in Chicago?

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+1 for 2nd City Comedy Club

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There's a bar on top Hancock tower that has expensive drinks but they are top shelf and you get an amazing view of the skyline and Lake but restaurant is expensive as hell,

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bottle service isn't it?

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bottle service isn't it?

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No, it's just regular old bar that anyone can go up to. Little frightening how lax security is to get up there. Anyone can just walk in and hop on the elevator to the lounge. No price of admission. Drinks are pricey though. But a $9 beer is worth the view of the Midwest.

Rent a boat on the lake from captain Chris. He's awesome and it was a great time. Also went to the art institute and planetarium.

Get a drink at Trump Tower then Chicago Chop House then Redhead piano bar.

Shaw's crab house right by the river is awesome. Ralph Lauren bar by the John Hancock has great drinks and people watching. Gibson's is also very good with great people watching at night.

Field Museum and the aquarium are both worth the time. I didn't care for the art museum.

Where are you staying?

Good Lord, stay away from North Avenue Beach unless you're a 25 year old bro with tribal tats and a bad case of herpes.

Restaurants:

Blackbird and Avec are both wonderful - owned by the same chef - he also is the driver behind The Publican which is also quite good
GT Fish & Oyster - solid and won't hit the wallet that hard
Longman & Eagle - one of the best bourbon selections I've ever seen and the menu is very solid
Santa Monica Summer House - new and interesting menu without being too off the wall - I really like this place
Alinea - incredible menu (but pricey)
Le Bouchon - my favorite French place in the city
Butcher & the Burger - my favorite burger in the city

There are hundreds of restaurants worth trying...might just be worth doing a bit of research beforehand.

I like Lou Malnati's more than Gino's East or Giordano's for Chicago-style pizza, but that tends to be up to one's taste. Stay away from places like Girl & the Goat that require reservations months in advance. You're only in town for a weekend or so...not worth your time or hassle.

Stay away from the tourist clap traps like Harry Caray's or Michael Jordan's or Ditka's or wherever. In fact, you're probably best off avoiding the Magnificent Mile altogether, at least in my opinion.

Find a cool patio or rooftop spot in one of the Northside (Old Town, Lincoln Park, Lakeview/Wrigleyville) or near west side (Wicker Park, Bucktown, Logan Square, Ukrainian Village) neighborhoods and just enjoy it. I like a lot of the Old Town bars during the day and the Lincoln Park and Wicker Park bars in the evening. I'd avoid River North unless you are into the club scene and bottle service and all that crap. The neighborhoods are more interesting in my opinion than downtown.

For entertainment, the Chicago architecture tour is actually really cool (and your wife will probably like it). The museums are definitely interesting as well - my favorite is the Field Museum. I am very fond of the Lincoln Park Zoo and surrounding park area...well worth a visit if you have time.

For the Cubs game I like the suggestion above of Sluggers, but be prepared...it is a zoo before and after games. The Cubby Bear is fine if cheesy and tourist trappy. I like Murphy's, and John Barleycorn and Houndstooth (an Alabama bar) will be fun sh*tshows if you're into that.

Actually not too terribly far from Wrigley (in between Wrigley and Lincoln Park proper) is Headquarter's Beercade. It's fantastic - pay a small cover and play NFL Blitz and Mortal Kombat and every other arcade game known to man for free and get blasted. That place is always really fun on the weekends.

Edit to add: catch a show at Second City if you can. Hang out on one of the patio bars in Old Town beforehand during the afternoon, have fun, and then walk to Second City.