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

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We love Italian, but we'll eat anything

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Piccolo Sogno, Prosecco, Quartino, and Osteria Via Stato are near you (short cab or walk) - I really like Prosecco and Quartino...never been to the others.

Most of the super-trendy/cutting edge stuff is either in West Loop or Wicker Park. I like Avec and Blackbird in the West Loop.

Really, you could spend hours googling around for great restaurants. Chicago is neck-and-neck with San Francisco for second-best in America when it comes to food.

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Should I buy some sort of pass for the Red Line that will last a few days?

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Three days passes are $20 - you'll end up paying about $4.50 or $5.00 for a single round-trip if you take the train anywhere - not a bad idea to get a 3 day pass, especially since you can use the buses with that pass as well.

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Anything really, but I'm sure we'll be doing a lot of shopping

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Architecture tours on the river are pretty cool, and the skyline on the river is magnificent.

If you don't have any kids with you, you could just pick a patio in one of the near north or near west neighborhoods, sip on beverages all day, and enjoy yourself.

You definitely need to check out the bar at the top of the Lincoln Hotel, the J Parker. Awesome views and cool spot.

Edit to add: if you're doing a lot of shopping, hit up the stores near Armitage and Halsted - it's probably the best shopping district in the city outside the Mag Mile.

FYI there is a "what to do/where to go in Chicago" thread almost weekly. Do some searching.

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

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You're right on the river, do an architechture river cruise. If it's too cold (which it may be- temps tend to fluctuate that time of year), do one of CAF's walking tours. They are top notch. LINK

Grab a drink at the 96th floor Hancock Building- awesome views of the city.

Eataly, Purple Pig, Frontera Grill or Topolabompo (make a reservation sooner rather than later), Giordanos (deep dish!), mEAT, Havana, RL Bar & Restaurant.

Bottlefork has great craft cocktails

Field Museum, Chicago Art Institute, Buckingham Fountain, the Bean, Millennium Park. Avoid Navy Pier- touristy af.

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

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Some cool neighborhoods- Southport, Old Town, Gold Coast
Science and Industry Museum
The Dawson= good rooftop bar
Zebra Lounge

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

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walk
cta (subway)
uber
cab

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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've only been here a year, but went to a game last year. We bought out tickets ahead of time on seatgeek. Take the red line on the CTA to Addison. By far the easiest and most efficient way to get to Wrigleyville.

I've done this and stayed on the Gold Coast just a little north of the Mag Mile. On Gameday take The El to Wrigley, get there plenty early, it's a freaking party. Murphy's Behind the Bleachers is fun but could be impacted by the construction. The Cubby Bear across from the front of the stadium is fun too. There are plenty of bar options all around, I only gave you two. If you are sitting in the bleachers, weather dependant, go inside early to get good seats, there will be a bleacher full party going on if the weather is nice and the beer is the same price on the inside as it is outside.

As for the other stuff, we walked around alot. Did the Navy Pier thing, it was ok. Ate at Chicago Chop House and a few other places. Found a good, I'll say college style, bar district up on on, I believe, Division Street. Good times.

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FYI there is a "what to do/where to go in Chicago" thread almost weekly. Do some searching.

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I did and I saw. FWIW, I have questions that I did not see asked or answered in the other threads

ETA:

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I was there in November do I missed out on catching a game. Warmer weather would be nice for my next trip there.

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Pack your bags, man. We fly out April 16

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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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Take the el from downtown, Chicago Ave., I believe. Buy tickets in advance so you can see the location--and make sure you don't get stuck behind a girder in the stands. Otherwise, you'll be staring at steel for 9 innings. Bring your parka, too.

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April 16 is the perfect day for me to skip town

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Damn, forgot about that

For a Cubs game take the red line (subway) its three blocks away west of Michigan ave. Cabs are expensive but everything on the mile is walk able if your able to do so and weather permitting. Tickets stubhub or the cubs website do it before hand. For food purple pig, and au cheval for great burgers. The navy pier is a must if it's not cold. South side has some of the most cultural diverse areas so wear your flak jacket.