Chicago Day 1

I can't decide the best way to describe our first day in Chicago. Considering the first post was rather long-winded, I thought of just doing a series of pictures or possibly a list of "Highs and Lows" of the day... Wait, yeah we'll go with that. Also, I did go to first grade and I do know that 2 comes after 1, but herein lies the post about Day 1 in Chicago... AFTER Day 2. It's weird, I know. Try to keep up. (Read: I don't know how to put this one first, I'm new here!!)

Bad (funny) news first. I can't even call them "Lows" so I'll call them "Typicals"...

Typicals:
The El Train. Although Day 2 proved otherwise, I really did study up on where to go, what to see, and how to get there, (promise!) and I felt I had a pretty good handle on how we should get from O'Hare to downtown Chicago. After landing at 10am, we hustled through the airport following signs for the train, got our tickets, and set on our way. Well, I did at least. I'm about to cross the last landing to get on the blue line, and um, Crawford...? While I was busy trying to blend in and act local, my travel companion was busy blowing my cover. He had some seriouuuuusss issues putting the little ticket into the slot and couldn't get through the gate. Turn it over! No, I mean flip it! No, the other way!! HILARIOUS.

Getting hustled. Jump off the train, bags in hand, and not a clue where to go, sore thumbs don't even begin to describe us. Well me, especially, in my STARK white sweater and my "transitional" outfit being 90% Spring, 10% Winter. (So much for looking local...) Anyway, we are heading in what we think is the right direction when Smiley McSmilerson stops us and says, "Ohhhh no, no, no! The James is THIIIIIS way." He points out all the buildings along the way, gives a one-liner about each and every one, and it's CLEAR he has taken us for fools. Well me, especially. We get to The James and he looks at us with puppy dog eyes and says "my 2 daughters" and "Cubs tickets" 187 times, and of course this sucker asks if he has change for a 20. Which of course he doesn't. So I give Crawford the same puppy dog eyes, he hands Smiley a 20, annnd then hands me a 20 minute earful. (Which I deserved 100%). I just hope Smiley actually went to the Cubs game with these 2 daughters and that's not code for a Mickey's and 2 needles. It totally is, I'm an idiot.

MOVING ON.

Thank goodness I left the white jeans at home.

Highs:
Chicago Art Institute. Unreal. Amazing. Everything and more. LOVED the Impressionist Exhibit- It's strange that a 27 year-old former Sorostitute would love Monet and Van Gogh... so unexpected, right?! The modern art prettyyy much freaked me out. Not modern art as in Jackson Pollack and... well... that's the only one I can remember- but "modern art" as in WHY are you making me watch a video of you, as I stand in a dark room, with freaky music, while you paint yourself in what can only be described as oil? FAVORITE (so the Highest High, if we're sticking with a theme here) were the miniature rooms!!! Exact replicas of homes in England and the US ranging from a formal dining room in London to a casual, open living area in California. The detail was impeccable. We're talking that if you crane your neck to see the furthest nook of a room, there is an intricately designed stairwell leading upstairs with the perfect amount of natural light highlighting its banister. UNREAL, I tell you!

The Gage. Our cute waitress from Terzo Piano*, where we ate lunch in the Art Institute (dangit, that's another high!), told us a nearby bar to checkout after perusing all the exhibits. It was right on Michigan Ave, had like 100 beers on deck, and the ambiance was just as a bar should be... Cubs fans tying yet another one on (Opening Day, hellooo) mingling with business men in fancy suits, dark wood accented with crisp shades of green, and a cool name: The Gage. (Sidenote: This reminds me of the college Drake that I ALWAYS pick in March Madness brackets, because I like the name... Relevant? Nope). After hours of wandering the Art Institute, our (my) feet hurt, and this was right on the money.

When you drink a Goose Island brew, you get these cool glasses. Goose Island is one of the very few

places in Chicago that brews and serves their own beers. Stayyyy tuned for more on GI!

The Violet Hour* Mayyybe the coolest part of the whole trip. A legit speakeasy in the eclectic, hipster neighborhood, Wicker Park. Even with the address, an iPhone, and a cab driver, finding the little gem was no easy task. I finally just opened a door that was painted into the graffiti on a wall (seriously, that obscure. and seriously, do I have death wish?) and we were in! High-backed leather chairs, lighting so dim we had to hold the candle to the menu to read it, and an all-around "we're not cool enough to be here" vibe that was intimate and awesome. Drinks were DELISH. I went with a vodka something or other... light and refreshing. So did Crawford. Until he remembered he was a guy and ordered an Old-Fashioned.

Pictured: Don and Betty Draper (I refuse to acknowledge Megan)

Pump Room at Public Hotel. After doing some seriouuuuus blog-stalking of any and every cute girl in Chicago that I could find, I happened upon Pump Room. Creepy? Probably. Resourceful? Definitely. This is the old hangout of Frank and the Rat Pack, and let me tell you, it exuded just that. The food was out of this world, and the only thing to match it was the atmosphere. Also, our waiter was so helpful! He wrote down the recipe for the roasted broccoli we were raving over, annnnnd he whole-heartedly supported our next move of the night- to the blues bar Kingston Mines**- so naturally I felt that we had a special bond over vegetables and shaking it. I distinctly remember him saying, "I'm from Chicago, and I still geek-out over Kingston Mines." Which brings me to...

Pump Room

Doesn't Crawford look like Michael Douglas here??? Oh wait, that's MD above him.

Kingston Mines** Two stages. Two dance floors. 2am closing? NOPE. 4am. In a nutshell, Mary Clay's heaven. The bands were INCREDIBLE. One band would play a full set on one stage, then they'd take a break, and the whole bar would get up and move to the other room of the bar with the other stage. The energy was HIGH, HIGH, HIGH, and we had an absolute blast. I truly couldn't think of a better way to end Day 1 in Chicago. (You can probably tell by this last tidbit why Day 2 started off so swimmingly :)

Happy.

*Thank you to Charlotte and John for these (and more) AMAZING recommendations!
**Thank you to Emily for the insightful article about Chi-town!

Chicago Day 2 (Day 1 Coming Soon...)

The rumors are true. Deep-dish pizza the size of a small planet, beer-guzzling Cubs fans more interested in the bottom of their cup than any double-play, the Magnificent Mile is just that- Magnificent, and if you don't know what you're doing... Just ask someone. Friendliest "big city folk" ever. Which brings me to the theme of Day 2 in CHI "If you don't know what you're doing..."

After a 3am bedtime, we knew a 9am arrival at the Willis Sky Deck was beyond ambitious. Rolling out of bed at 10:40 for our 11am brunch reservation, the day is already off to rough start. Charging down Rush St to make the 11am rez, (anyone who knows me knows I LOATHE being late) we be-bop into an EMPTY restaurant where I sheepishly admit to having a reservation. We sit down... it's lunch, not brunch. Our hungover hearts are set on eggs, so we decided to ditch the reservation.

OPH- too embarrassed to fully caption the name of the restaurant

BUT I'M STARVINNNNNNNNNNG...

Lark! Next door is a cute porch to a restaurant with a line out the door... but it seems to be moving quickly! Hey! I think we found a local hot-spot!! Things are lookin' up... Get in the door, read the menu of this so-called "Original Pancake House" and we sink yet again. Damn. DALLAS HAS ONE? No, actually Dallas has 3. UGH.  We then convince ourselves this HAS to at least be the "Original" Original, right? After we score a spot outside, waitress tells us the Original is actually in Portland. OK, we're over you OPH, but at least your food was decent, and we got a spot in the sun.

ONWARD! Cue the Seinfeld episode:

Soo should we check out the Willis Sky Deck? Hmm sure. Where is it? No idea. Wait- is that Rajan Rhondo?! CELEB sighting! (Apparently... I still have no idea who that is). Anywho, we look up to our left, very tall building. Hmm... is that the Willis Sky Deck? Embarrassed... We ask a man holding a Macy's bag if it is. (Because locals DEFINITELY shop at Macy's...). "Haha. Yeah, thaaas it." Laugh at what helpless tourists we are and walk over... Um, thanks buddy. This is the Hancock Building (in retrospect, we should've just gone up, but we were SET on the Willis). Deflated, yet again, something magical happens... WE SEE "CHICAGO VISITORS CENTER" AND AT 12:30PM ON DAY 2, MARY CLAY AND CRAWFORD GET A MAP.

From here you'd think we get it together... Nope. We do however find our way to the Willis Sky Deck. Never seen so many people in a line in my life. Ladies and Gentlemen, who knew that Good Friday at 1pm = TOURISTS EVERYWHERE??? More prepared tourists than we are (CLEARLY), but tourists nonetheless. Sooo, we scrap it. From here it just gets hazy with us deciding to do one thing, then scrapping it, deciding to do another, then scrapping it... All while wandering pretty much aimlessly. Sounds miserable? You would think! However, we see so much of the city on accident, get a LOT of exercise, and just enjoy each others' company. Especially when I say things like, "UGH. I don't knowwwwwwww! YOU figure it out." Then immediately question any judgment call made. Pout. Whine. Repeat. (You are so patient, thank you dear Crawford). We do get some incredible views of the Lake and a great picture of us with the skyline, all before I have my one good idea of the entire day. "Why don't we walk into that bike shop and ask them for a cool bar around here." 

Photo taken on the steps of the Field Museum... Chapter 17 in scrap, rinse, repeat.

Bike shop bro's pull through and lead us to the Wabash Tap, a charming dive of a joint with a delightful, Irish bar-keep named Mary (one name) showing the Masters on one TV and the Rangers v. White Sox on the other. Sierra Nevada is the beer of the day, and we are happy.

This is also where we meet _____, the nice man who gives us EVERY.DETAIL.EVER. about how to properly attend the Cubs game the following day. We're talking what time to wake up, breakfast spot on the way, trains & buses to take,  approximate temperature decline due to where are seats are, instructions to go buy long underwear, where to buy them... This guy is a straight up sage on Wrigley.  Whiiiiich is completely ironic because he is a huge White Sox fan. He also played baseball at Hahhhh-vard, has a keen sense of humor, and a strict 2 beer limit. So with his finale of advice to "drink beer" in order to fit in in Wrigleyville, I am instantly giddy for tomorrow.

Another long walk to the hotel to prepare for pre-dinner drinks with a view at Trump Terrace, a boozy shower, and a rushed cab ride to Trump... Sorry, the Terrace is closed. We do have a lovely bar area on our Mezzanine Level though! Nope. We want to SEE the cityyyyyyyy from up high, lady! Cab it to the Hancock. Think we've finally got it figured out... YET ANOTHER WINDING LINE. Give up. Go to a bar CMG's buddy suggests that is near our dinner reservation (Public House- very cool spot) and chalk it up as a loss in terms of "high-rise city views." Our RESERVATION (what a concept!) works out, the food at Hub 51* is delicious, and the drinks are even better. Of course I order GUACAMOLE in Chicago. It was superb though. Swear.

Hub 51

After finishing up, we look at each other and are spent. With our sights set on making our Saturday in Wrigleyville the BEST EVER, we end the funny, whirlwind of a day with peanut M&M's and a Peanut Butter Snickers bar. Annnnd scene.

*Thank you to Kristin and Bailey for this (and other!) great recommendation!