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Trip Report It's My Kind of Town: Chicago! A trip report...

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The year of domestic travel continues for my husband and me. This time, it was a weekend in Chicago. I was there three years ago for a girls weekend of wine and theatre, but my husband had not been to Chicago since he was a teenager. Despite the bi-polar disorder that is Chicago weather in May, we had an awesome time!

Chicago has it all- the art! the architecture! the food! the baseball! In our four days, we covered a lot. However, there is always more to see and do in the ever-changing city and we can't wait to get back!

Who: My Husband (32) and Myself (31). It was just the two of us for the majority of the trip, but we did meet up with a friend who was visiting his girlfriend who is in grad school in Chicago.

When: May 12-15, 2011. What started out as 86 degrees, hot, humid, and no breeze, turned to 43degrees, rain, and 30mph winds within 36 hours! Oh, mother nature, you fooled us yet again! Not to worry, we soldiered on!

Transportation: American Airlines non-stop CLT to ORD. With taxes and fees included, tickets were about $300/each. I did have a $100 voucher from American Airlines as compensation from a disasterous trip to Denver, but that's a story for another time. So, about $500 total for the two of us. Not too shabby given the current hike in fares.

I never knew the L was so easy! Yet again, I find a hallmark of a great city is easy, accessible public transportation and Chicago Transit did not disappoint. After winding our way through the basements of O'Hare, we found the L. $14/each bought us a 3-day pass- a great investment. We hopped on the train at O'Hare and took it directly into the Loop. Hopping off at Clark/Lake, it was a short four blocks to our fabulous hotel...

The Hotel Monaco on the corner of Wabash and Whacker was home for three nights. We could not have been more pleased with the hotel, the location, and the staff. Full Disclosure: I'm a Kimpton Rewards Member, so I tend to like Monacos- they're funky and cool, but always impeccable. The best part of this Monaco- the very cool window seats (really, it's more like a bed elevated in the cubby next to the window with awesome views of the river and the street below). The free wine hour for guests isn't so shabby either. That, and the staff does everything they can to meet your requests. I'm pretty sure they sent someone out to buy a can of starch so my husband could iron the collar of his shirt. I can't say enough good things about our stay at the Monaco and would highly recommend it to others.

In light of my corporate discount, the room was $169.00 a night, plus another $25 or so in taxes and fees. Less than $200/night? River view? Steps from Michigan Ave? And steps from the L? SIGN ME UP.

Next Up: Cardinal Nation invades Chicago, the Culinary Pursuit of Happiness, and More Layers of Clothes...

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    Cardinal Nation invades Chicago:

    We had an EARLY flight in on Thursday morning so we could make it to Wrigley in plenty of time for the Cubs v. Cardinals game at 1:20pm.

    I had surprised my husband with tickets to the game earlier this spring. As he is an avid Cardinals fan, I knew he would be excited to see his Cards take on the Cubs at Wrigley. However, I was concerned that being decked in red from head to toe may draw some unwanted attention to us in the stadium. Thus, I forewent bleacher seats and opted for Field Box tickets. I figured it was worth paying a little more to ensure our safety and lack of heckling. At $70/each, I thought our seats should be decent (Secton 122, Row 3, seats 3-4). I didn't realize I had bought us seats 12 rows back, directly behind home plate, and really close to the beer stand that sold the good beer (read: not Old Style :-)).

    So, my worrying about heckling was more than a little unnecessary. It seemed half of St. Louis travels for the Cubs v. Cards series. The stadium was probably 1/3 Cards fans and our entire section was dressed in red.

    It was a sunshine filled afternoon of 9 glorious innings at one of the most storied parks in the country, Wrigley Field. We drank beer, we cheered on the Cards, and the Red Birds walked away with a victory. A great afternoon in a great place.

    Oh, I almost forgot one of the most important parts of our first day in Chicago! AL's #1 Italian Beef!!

    Forgive me for backtracking, but after we took the L from the airport and got checked in to the hotel, we set off to find lunch. Initially, my plan was to have lunch near the hotel and then hop on the Red Line to Addison and spend some quality time in Wrigleyville. However, my first option for lunch turned out to be closed (The Purple Pig- more about this later as we did go there for dinner). After discovering the Pig was not open for lunch, we continued on up Michigan Ave. As we approached Ontario, I realized that both Portillos and Al's were located on this street. (Thank goodness for over preparation! When prepared and well researched, you can turn a disappointment into a different, great experience.) We hung a left on Ontario and trecked several blocks down, passing steak houses, the Rock n' Roll McDonalds,and other places. I knew if we kept on going, we would hit the Mecca of Chicago lunch specialties.

    After passing Portillos and deciding it looked too gimicky from the outside, we found ourselves at Al's... from the outside, it looks like all of the best dive joints: slightly grungy, worn out, and busy with patrons. Inside we went, bellying up to the counter, ordering a 6" Italian Beef, wet, with Giardiniera. OMG, people. A cheap cut of meat, rubbed with cheap dried spices, roasted over a cheap buillion broth, served on cheap, glutinous bread. It goes against all culinary sense. But it is truly amazing. In fact, I'm still thinking about it now and wondering how I can get it in Charlotte for lunch today.

    After indulging in the greatness of Chicago Italian Beef, we walked off a few bites and headed back to the hotel. A quick stop at the hotel and we were off to the Red Line and Addison and to Wrigley Field.

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    Post Cardinals Game:

    After the game, we relaxed and washed up at the Hotel. We did not have dinner reservations for Thursday night and wanted to see where the evening would take us. In Chicago, it is probably best to always have a reservation- everywhere was slammed! However, we made do and everything turned out ok.

    As it was early in the evening, 6pm, I was hopeful we would be able to find a spot at the Purple Pig. I had read so much about it in Food and Wine and other magazines and wanted to experience it for myself. Even at 6pm, the inside was completely full, the outside was completely full, and there were people waiting up and down the alley way leading to the Purple Pig!

    Husband and I decided we would stop back by later on in the evening to see if it had cleared out. As I was getting pretty hungy, we ducked into a Brazilian Steakhouse we came across that was advertising happy hour prices at the bar. I am not usually a chain-restaurant type girl, for good reason. The Texas de Brazil steakhouse left A LOT to be desired. Service was less than mediocre. However, it was only a few dollars for some pretty tasty meat and $5 for a glass of wine- gotta love happy hour. It filled the gap and served it's purpose.

    Next, we headed up Michigan Ave to the John Hancock tower, window shopping as we went. The 96th Floor Lounge of the John Hancock tower has a reputation for over priced drinks, but everyone says the views are worth it. We found the drinks to be priced normally ($14 for a glass of Sauvignon Blanc and $12 for Bookers on the Rocks). And the views were more than worth the price of drinks.

    It was a clear evening and the sun was just starting to set. We giggled together, enjoying oneanother's company, marveling at the beautiful city and sunset, grateful for the shared experience.

    We finished our drinks and headed out to take in more of the city. Not before a quick stop in the restroom. I have never entered a bathroom and had my breath taken away. The women's bathroom has the best view in the entire bar! It has expansive views of the city and the lake. If it wouldn't have seemed odd, I would have spent more time in there! No trip to the 96th floor lounge is complete without a trip to the ladies' powder room.

    Unfortunately, the men are out of luck- no view for you! My husband was very disappointed when I showed him a picture I took from infront of the stall. I know it sounds odd and gross, but I needed to capture the view!

    By this time, it was getting close to 8:30p and I was hopeful the Purple Pig would have slowed down a bit. I was wrong. It was still jam packed, but fortune smiled on us and 2 seats at the bar opened when we walked through the door! A coppa, provolone, mustard, and hot pepper panini and one asparagus, hazelnut, arugula, and treviso salad later and we were very satisfied! (As a warning, it is crowded and loud and they don't serve liquor, but they have an amazing wine list and menu and it is well worth a visit.)

    After a long day and a great dinner, we fell into bed. Next: The Segway Tour and Mother Nature's Shenanigans.

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    The Segway Tour:

    Many thanks to @swalter518 for the tip that Living Social Chicago was offering half price segway tours! At $35/each, we snagged this deal as did our friend and his girlfriend. I was not willing to pay the $65 full price, but $35 was much more reasonable and worth it.

    Friday morning, Husband and I grabbed some fruit and coffee from the hotel and ventured south in the lovely 72 degree weather. The Segway tour was to start at 10:30a, but we were instructed to be there by 10:10a for helmet fitting and instructions.

    The planner in me wanted to make sure I knew exactly where we needed to be- as the general instructions said Randolph Street side of Millenium Park. So, we got to the park early and tried to find the tour. At the corner of Michigan and Randolph was a sign for the tour with an arrow pointing straight down the Michigan Ave side. Always one to follow signs and directions, off we went down the Michigan Ave side and into Millenium Park.

    It's a beautiful park- the amphitheatre and it's wonderful architecture, the "Bean" reflecting the beautiful blue skies, all the tulips in full bloom! We loved the happy tulips throughout Chicago. The park was really well done. That said, there was no Segway tour to be found. Consulting a map, I found the "Bike Center" to be the opposite direction from where we were- I guess someone put the sign up backwards. No matter, we looped around the lawn of the amphitheatre and found the bicycle center. Notably, there was another sign for the segway tour again pointing the wrong direction. Not to be fooled twice, we ignored the sign and entered the bicycle center to sign the waivers and prepare for the segway tour.

    Our tour ventured through Millenium Park, Grant Park, past the Art Institute, the Shedd Aquarium, the Planetarium, and down to Soldier Field... the tour guides were entertaining, but the tour wasn't quite as informative as I had hoped. Though the segways were so much fun! It was worth $35 to see the southside of the loop and to ride the segways! A word of advice, pack a sweater. Even though the tour started out sunny and warm, the temperature was dropping and when we went out to the jetty where the planetarium is located, I thought I was going to freeze!!

    2.5 hours later, we dismounted the segways. It felt strange to walk on the ground again! A brief stop at the hotel to add more layers, and we trudged up to Lou Malnati's at Wells and Illinois. As it was 1:30p, we thought getting a table for 4 wouldn't be a problem. Again, we were wrong! There was a 30-45 minute wait, so we put our name in and began going over the menu. They suggest you put your pizza order in while you wait b/c the deep dish pizza can take 40 mins to bake.

    Within 5 minutes of putting our name in, fortune smiled on us and 4 seats opened up at the small bar in the front of the restaurant. Never afraid of eating at the bar, we sat down, ordered some 312s two salads and waited for our pizza.

    Given that we ordered 2 salads, we ordered a medium "Lou"- spinach, mushrooms, fresh tomatoes. For the 4 of us, it was more than enough food- we even had leftovers!

    I have now eaten at Lou's and at Giordano's. In my very humble and mostly uneducated opinion, I prefer Lou's. The crust was buttery and a little crispy, the sauce was tangy, the toppings perfectly balanced. A culinary delight. I am more than willing to try out Giordano's or Gino's East again to challenge my preference :-)

    After lunch, we walked back towards the hotel, noticing that the temperature was continuing to drop. The day that started as 73 and sunny, was 50 and cloudy by lunch time. The rain was coming in and the temperature was continuing to fall.

    Before we left Charlotte, we discussed at length the weather and the clothes we would need to pack. The forecast on the morning we left said the overall low for the entire weekend was 60 and only a chance of rain on the Sunday we were leaving. WEATHERMAN GOT IT WRONG!

    In desperate need of more layers and clothes, Husband and I beat a path down Michigan Avenue in search of winter clothes in all the stores ladden with spring lines. A few sweaters, leggings, thermals and the like later, we were heading back to the hotel to rest and get ready for dinner.

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    Great great report so far. We absolutely love the City of Chicago, and our travel style is the same as yours (take it as it comes, be flexible, sit at the bar!). Looking forward to getting back and trying Al's!

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    Beef it's what's for Dinner:

    No trip to Chicago is complete without a visit to a steakhouse. My parents very generously gave us a gift card to Gibson's to ease the pain when the check came. However, no one told us it would be almost impossible 2.5 months out to get a reservation at Gibson's!

    Luckily, a wise soul here on Fodor's recommended Lux Bar. It's owned by the Gibson's people, serves Gibson's steaks, and we could get a reservation! Double plus that our gift card would work there as well.

    Initially, our reservation was for 2 people- me and hubby. That morning, we asked our friends if they would like to tag along and they said "sure!". One call to the hostess and our reservation was easily changed to 4 at 7:30p.

    After a quick, $10 cab ride from the hotel, Husband and I got to Lux a few minutes after 7. The bar was crowded, but we found one bar stool open. I sat, husband stood. A nice glass of Zin and a Bookers on the rocks and we were set. There were people wheeling and dealing, lots of dates, and some people grabbing after dinner drinks with colleagues. We noticed some children in the dining room, but on the whole, it was a trendy set. I am sure when the weather is pretty, the outside patio is full as well.

    When our friends got there a few minutes before 7:30p, we alerted the hostess and we were seated within 5 minutes. They pack the tables in, so there is not much room to maneuver in the dining room (we were seated downstairs). However, our actual table did not feel over crowded and it wasn't like people were bumping into us. Just not a quiet, romantic type setting. We were seated next to the fireplace, which has a large television broadcasting ESPN over it- the boys were happy with the TV and we were happy with the fire- great combo for us, but again, maybe not the right ambience for romance. Also, the food comes out pretty quickly- but again, not exactly rushed- so if you're wanting to linger while star gazing into each other's eyes, this is not the place.

    The food was stellar. Calamari, shrimp cocktail, Husband and I split a filet. The filet was melt in your mouth perfectly rare with a slight seasoning on the top. It is actually served with sides- sauteed spinach and mashed potatoes. I'm used to most steak houses serving things a la carte, so I thought $35 for a 10oz filet with sides was more than reasonable.

    All 4 of us were VERY HAPPY with Lux Bar. We'd highly recommend it and will definitely go back. Gibson's filet was one of the best steaks I've ever had and I've had a lot of steak.

    After dinner, we hopped in a cab and went up to Logan Park. Friend's GF lives in Logan Park and we wanted to get a feel for her neighborhood. First stop, Longman and Eagle. What a hipster little bar! Great bourbon selections and they make their whiskey sours with hand-whipped egg whites!

    We hopped down Milwaukee Ave for a few more hours and then poured ourselves in a cab to go home. It had been a long, but productive day, and I needed my beauty rest!

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    The Weather, It Puts a Damper on Things:

    Saturday morning we awake with slight headaches and parched mouths- it is the price you pay for so much fun the night before! We asked the front desk if there were any greasy spoons or diners around. They said there were no diners near the hotel, but the South Water Kitchen served a nice breakfast or there was a Einstein Bagel down the street.

    Not wanting a full on, sit down breakfast, to Einstein we went. I would have preferred to have a more authentic Chicago experience, but I was STARVING. Admittedly, the bagel thin sandwich with egg whites, turkey sausage, and salsa was pretty awesome for less than 300 calories. It was exactly what I needed at that point.

    After inhaling breakfast, Husband and I set off for the Sears tower and to take in some of the architecture in the loop. I don't know what we were thinking. It was 47 degrees and the fog had set in- you couldn't see the top of our 12 story hotel, let alone the top of any sky scraper. No matter, it wasn't really raining- think annoying cold mist- and we wanted to spend as much time as possible soaking (literally) in the city.

    We wandered around, reading from one of the architecture tours I had printed off, stopping for coffee here or there and enjoying our morning together. Slowly though, the temperature was dropping and the rain was increasing- at one point, I swear I saw snow or at least freezing rain. I was also getting hungry again. I really wanted to make it to the Custom House on S. Dearborn, as Food and Wine had voted it one of the best hamburgers in the country. Alas, it was not meant to be.

    Frustrated because we couldn't find the restaurant, starving, wet, and getting grumpy, we ducked into the L station. Come to find out it was the Blue Line at Jackson. As luck would have it, I knew the Blue line would take us right up to Wicker Park (again, preparation and research is key!).

    We live in a pretty funky area of Charlotte and love artsy/hipster/funky/good eating and drinking areas. Based on my reading, I thought Wicker Park may be an area we would really like. And like it, we did.

    Jumping off the Blue Line at Damen, walking around a bit to get our bearings, and back-tracking, we found Big Star- it was right next to the L stop. Call me a Food and Wine junky, but again, it had recommended Big Star (same people as Blackbird and Avec). Big Star is a beer drinking, honky tonk of a taco joint. However, they put a spin on tacos and the result is awesomeness. 2 beers, an order of guacamole, some fish tacos and some pork tacos, and we were set. Notably, it was crowded at 1:30p on a saturday with a mix of tatoo-bearing neighbors, a few children, and some yuppies who ventured out from other suburbs. A really cool vibe and a recommendation if you're looking for something a little different.

    After lunch we wanted to explore Wicker Park more, but the weather scared us off. It was really raining and really cold by that time. We went back to the hotel to take a hot shower, nap, and unwind.

    Dinner was at the South Water Kitchen in the bottom of our hotel. It was good- a great salad, green bean casserole, and a wild mushroom flat bread. We just ordered at random and it all was really good. We sat at the bar, had good service, good food and never had to leave our hotel. It was a little pricey, but not overly so. For the convenience, it couldn't be beat.

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    I Forgot One of My Favorite Things!

    After lunch in Wicker Park, we did head to the hotel for a bit, but I forgot that we ventured out one more time to see another part of the city.

    I had read about Old Town Oil in several places and really wanted to check it out. We decided we could brave the weather for a short L ride up to Clark and Division and walk a few blocks through Old Town.

    We loved Old Town! All the little shops, boutiques, and quaint restaurants. Very cute!

    Old Town Oil did not disappoint us either. The small shop has a room full of different olive oils and balsamics. Each imported from Italy and infused with different flavors. The well educated sales associate pairs the oils and the vinegars and let's you taste at will. We walked out with a bottle of Meyer Lemon Infused Extra Virgin Olive Oil, a Tuscan Herb Infused Extra Virgin Olive Oil, and a White Balsamic Infused with Lemon... Incredible!

    Since we've been home, I've already made a pasta with the Tuscan Herb and a vinagrette with the Meyer Lemon. If you're in the Lincoln Park Area, or Gold Coast, or anywhere near Old Town, stop in. I don't think you'll be disappointed.

    Ok, after that detour, it was back to the hotel for dinner at South Water Kitchen.

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    Last Day in Chicago:

    Sunday, we awoke to the same lovely weather we left behind on Saturday night- even colder, actually. We took one last walk up Michigan Ave, hit a few stores that opened at 10am for last minute shopping, and went back to the hotel to pack.

    Luckily, the Monaco has a 12pm Checkout time. No matter, we were out the door by 11:30a. We caught the L back to O'Hare and then sat in the security line for a good 45 minutes. Since we were flying out of G Terminal, the TSA/O'Hare Security lady at the big security check point told us that we couldn't go through security there, but would have to go all the way down to the far end security check point.

    One to follow orders, I obliged. BIG MISTAKE. There was only one baggage scanner open and one of the body scanners running. Tell me again, why it takes over 15 (and I counted) TSA agents to run one line of security???? Usually, I am a pretty patient traveler, but this just put me over the edge.

    Luckily, we made it through, grabbed a quick bite at Subway, and made it to our gate in time for boarding. Once at the gate, we found out our flight had been delayed and they had changed our gate. The joys of flying these days.

    Eventually, we did make it out of O'Hare and arrived in CLT one hour later than expected. Weather upon our arrival at CLT: 73, sunny, with a slight breeze. But, hey, Charlotte is no Chicago :-)

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    What a nice weekend. I always have fun in Chicago. We have a girls' weekend planned in June. We are hoping the weather improves.

    We are having the same rainy, freezing weather here in Akron, Ohio that they are having in Chicago. We are about to lose it--our pastor even prayed for sun at church last Sunday.

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    Loved your report. Taking notes on where to eat next trip to the city. And, hey, you should've drug your hubby into the women's room at the Hancock Building. We've snuck boys in there many times. Even if you get caught, the cleaning lady just gives you a stern look and shoos you out the door ;)

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    Sounds like a great trip. Chicago really is a great city and a lot of fun. I was there for a Red Sox @ White Sox game and Cardinals @ Cubs game as a Red Sox fan. That was a fun weekend. Wrigley is amazing. We got to Wrigley at 9am for a 3pm game to find the bars hopping already...And it was an even split among fans plus the 4 Red Sox fans....

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    Oh that Chicago lakefront weather! Yes, it can change so quickly! Glad for your report on a trip to the city of my birth. But having lived in St. Louis and that general area many years...always glad when the Cards win (wife does not agree). And touring via segways...how interesting indeed.

    You evidentally didn't have time or interest in the museums which are outstanding...and so accesible. Nor the theaters. But you surely did enjoy the dining. Longman and Eagle Bar...hmm Longman is my name and not that common.

    Bill in Boston

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    Hi Ozarksbill! My last trip, we did theatre and museums... this trip, we wanted to focus on more outdoor activities and food. However, the weather got in the way for some of our activities. We tried to persevere and just enjoy our time together.

    Thanks to everyone for reading my report! I know I can be long-winded, so I appreciate those who were committed to the read!

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    we too just returned from Chicago. Stayed at the Amalfi Hotel - great boutique hotel on Kinzie and State. Took in a game (SF vs Cubs) cold - very cold on Friday afternoon considering it was 91 when we landed on Thursday. Unfortunately our Sunday game got rained out - bummer. However, we took advantage and spent the day at the Art Institute, Also toured the Robie House (FLWright design) too cold and windy and rainy to do the Oak Park tour so will do on next trip. Monday was an walking tour with the CAF - interesting tour of the architecture - highly recommend. Cold, cold, but clear blue skies on monday. can't wait for another visit......

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    Thanks for the report. I'm heading to Chicago next month for work (staying at the Monaco--another thank you for the review!), and have added a couple of days to enjoy the city. Can't wait!

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