re: Going to Chicago mid-April for 4 days. Staying in Magnificent Mile area

That bean / ufo can be skipped. Lots of people looking at their reflection.
Subway is very easy to get around including cubs and sox games.

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1) What are some must-sees & restaurant suggestions in/around Magnificent Mile?

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Much has already been mentioned: Hancock Building bar, Rooftop bar at Hotel Lincoln in Lincoln Park is nice anytime of year, the Macy's in the Loop is stupid. As far as drinking, I highly recommend Three Dots & A Dash (One of World's 50 best bars of 2014) which is about a 3-4 block walk from Mag Mile, directly underneath Bub City (neat BBQ/modern country joint). You should def take in a show in the theatre district, Bank of America Theater and Chicago Theatre usually has some solid stuff. Harry Caray's has a nice sports museum, worth grabbing a drink and checking out.

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2) Anything outside of Magnificent Mile area that is a must-see?

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I'm a huge fan of the Lakeview area and comedy shows. The Laugh Factory has a great dirty show on Friday and Saturday nights (late), while The Second City is internationally known for putting out big time comedians. On Lincoln Avenue, The Red Lion is an outstanding British Pub, while Prost! has the best selection of German beer in the city IMO. A really bomb pizza joint (not Chicago style) called Homeslice just south of the Fullerton stop on the Red/Brown Line too. For Chicago style, do the $10 lunch at Giordano's, get a personal sausage deep dish, salad and drink.

Of course, there's Wrigleyville. On game days, expect to be price gouged. If I were you, I'd go on Groupon and see if I could find a deal in that area at one of the bars that would work while you are in the area. Also recommend buying the batting tokens Groupon for Sluggers. Nice place to take hacks at 90 mph fastballs in upstairs batting cages while plastered. Country bar called Old Crow has the HOTTEST bartenders, but they charge out the arse for Old Smokey Apple Pie moonshine. Blokes & Birds, Casey Moran's, Trader Todd's also some bars. Being a Tennessee fan, I highly recommend staying away from The Houndstooth unless you want to drink a 40. They also have Fireball on tap.

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3) Best way to get around city? Cab, public transportation, walk, etc?

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Have everyone in your party download Uber and use the $20 or $30 free ride codes. You can walk pretty much everywhere in the Mag Mile/Loop area. The CTA train is an experience, especially late night. You will see some trannys, drug deals, homeless folks, all walks of life on that thing.

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4) Planning on going to a weekday Cubs game. Best way to get to Wrigley Field area from Mag Mile? Should I buy tickets in advance or will they be available on the streets on gameday?

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I bought great upper deck seats on Stubhub for $12-under for eight games in August/September last season. Being early in the year, I'd keep an eye out on Craigslist, Stubhub and also scalpers. Even if you miss an inning or two, you can usually find some bottomed out prices on great seats. I'd check into a Rooftop deal on Groupon or LivingSocial, especially if it works out to be the weekday game you are attending. The roof is fun especially with all you can eat food and all you can drink draft beer.

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Knocksville

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Listen to this guy - except I think the CTA is fine, at least on the north side. The Red Line and Brown/Purple Lines don't have too much of that stuff.

For me, Howl at the Moon was an awesome experience. It's a dueling piano bar, and the players can play just about anything you request.

Purchase a 3-day train ticket when you get there. Will save you from having to pay for a pass every time you ride the train.

Restaurants in/ close to Mag Mile:

RL (Ralph Lauren's restaurant)

Gibson's for steaks or burgers

Purple Pig

Artisan Cellar at Merchandise Mart for lunch/ mid-day is something I highly recommend (cafe/ sandwich shop using authentic Spanish & Italian ingredients. Great selection if international wine and craft beer as well)

Cafecito (100% authentic Cuban sandwich shop)

Hannah's Bretzel for a quick lunch (organic sandwich shop with a great variety of ingredients. Serrano, salmon, sirloin, ect..)

Brandos Speakeasy for $6 manhattans and karaoke

Signature Lounge for overpriced drinks and amazing views of the city from the 96th floor of the Hancock Building


I'll suggest more as they come to me. I go to school nearby so I know the area pretty well.

There is also so much more to see than Mag Mile. It all depends on personal preferences

I haven't been for lunch, only at night to the lounge. How is the menu?

I recommend you eat at the Ed Debevic's which is a really cool restaurant and if I remember correctly there is 70's music and the waiters dance on tables.