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Trip Report Quick Trip to Chicago- Fun in the Rain!

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Life tends to get in the way of fun, and so it was with our planned long weekend in Chicago… my mother fell ill in Boston and I needed to rush there earlier in the week, which at first made unlikely that I could join my husband, and his son and fiancée for the trip. However, my mother’s condition improved enough that I could salvage part of the trip, so I joined the group a day later than planned.

With the quickly mounting costs of changing my tickets, again, I decided to stick with my original leg of flying into Milwaukee on Saturday. The group drove up to meet me, so we had lunch in the city at a lovely bistro called The Knick, in the Knickerbocker Hotel. The rain and fog was unrelenting, so our driving tour of the lakefront and city was pretty pointless, and we did not linger.

We easily made our way down Interstate 94 in about 90 minutes to the Loop. We stayed at The Inn of Chicago on Ohio St., two blocks from Michigan Avenue, about four blocks from the lake. Great, great location and the hotel was quite a value since DH’s son got a discounted rate via a Canadian website (about $85/night!) Our room was spacious enough and clean, bathroom small, but functional. My husband said the walls were paper thin on the first night, but luckily we had no neighbors for the remaining two nights of our stay. There was free wireless internet access in the lobby, and a coffee maker in the room, in addition to the coffee shop adjoining the lobby, not to mention the Dunkin’ Donuts and 7-11 right across the street. Every manner of restaurant, bar, pizza joint and retail store can be found within a five minute walk of this hotel, so no complaints that it’s in the middle of nowhere!

On Saturday night, we had reservations at my husband’s favorite Chicago throwback steakhouse, Gene & Georgetti’s. It was about a ten-minute cab ride from the hotel and very crowded when we arrived at 8:00. It is a classic restaurant from the 40s-50s, with dark paneling, Frank Sinatra and Dean Martin music playing, an all-male waitstaff and the walls covered with photos of the stars of the era. We had a drink at the bar and were seated upstairs in about a half hour… nothing moves quickly here. The menu is red meat and Italian dishes. Bring an appetite, the portions are enormous. The “small” filet looked to be about 12 ounces, and my husband’s t-bone flopped over the edges of his large oval plate. Most of the sides are a la carte and enough for four. You’d better like your meat black on the outside and bloody on the inside because no matter how you order it, that’s how it’s going to come out! Luckily, that’s my preferred order anyway. The prices aren’t quite as high as Morton’s (nor is the meat quite as tender), but dinner for four with a couple cocktails and a bottle of wine topped $300. We left happy and certainly not hungry!

We had wanted to take in some kind of show, preferably comedy, but nothing at Second City appealed to us. My online research revealed a small theatre with a production called “Cougars: The Musical.” I couldn’t resist that! We already reserved tickets online ($14 apiece) and headed over to the Greenhouse Theatre near Lincoln Park. It was tiny, all right, maybe 150 seats. The production was somewhat amateurish without any fancy props, but the performers were good, particularly a few of the singers. My one complaint was that the keyboard accompaniment sometimes drown out the lyrics, which were the key thing. What lyrics I could make out, however, were bawdy to say the least. The audience was very enthusiastic and everyone had a good time. We easily caught a taxi back to the hotel despite the downpour and fell into our rooms.

On Sunday morning, I had wanted to find a place for brunch in an interesting neighborhood where we could stroll around. I decided on Big Jones in Andersonville and made reservations for noontime on Open Table (a good thing I did because there was quite the wait for those without rez). What a great find – well worth the trip to this part of town. The food was fantastic, all Cajun/Creole inspired dishes. Everything we all ordered was declared fantastic. I had a ham and cheese omelet with the most succulent ham or “tasso” I’ve ever had. Grits, which I’m not a fan of, were smooth and delicious. French toast, crab cakes and eggs and andouille sausage all looked phenomenal. And a plate of beignets covered with sugar were served straight away… I could have munched on those all day! This is perfect brunch spot; actually any meal must be great. Do not miss it! Unfortunately, our planned stroll around the ‘hood was rained out and we headed back to the Loop to see what we could salvage from the afternoon.

I had so been looking forward to a tour of the city especially with my stepson and fiancée as guides since they’re both recent graduates of architecture school and they love Chicago. Despite the inclement conditions, we bundled up as much as possible and headed to the lake. The wind was fierce and cold, so we took a break inside by popping into an open house in a condo loft going for a reduced price of $1.2 million! The bored realtor really couldn’t have cared that a bunch of people obviously not seriously in the market stopped by and it was really cool to see what they had done to the place, with a rooftop deck and Tiffany stained glass hiding the horrible view from the windows on one side!

We trudged on to the Navy Pier, took a quick look and said, “bleh.” Nice for kids on a summer day, not for us. We got some good pictures on the lakefront with the waves crashing high on the seawall. We made it down to Millennium Park and I finally saw what “The Bean” is all about. I really liked it and we had a lot of fun taking photos of the reflections. Such public spaces in Chicago, I was so impressed! The whole lakefront area, of which I only saw a fraction, is just one of the treasures of the U.S.! We continued our walk into the downtown area, getting some interesting pointers from our architects, such as the tallest brick building in the U.S., the gothic-inspired design of the McGraw Hill building, which was a contest during the depression, as well as the new building near it which has arches which mirror it. Fascinating, really! We were cold and tired when we got back to the hotel, but definitely glad we made the effort to see the sights that Chicago does so well.

Dinner that night was a disappointment at Pizzeria Uno. The kids love Chicago pizza and I thought I’d like it too… sorry, but I guess I’m an east coast girl too much because the deep dish does not do it for me at all. I hate the crust. Sue me. Early to bed was not a problem.

Monday morning surprised us all by bringing out the full sun, despite the gloomy forecast! I had really wanted to do an architectural cruise, not having had enough of the Chicago skyline. We headed to where I thought the cruise departed… I’m normally a human GPS, but this time I totally failed to figure out which way was north. We missed the boat. However, a trip to the top of the Hancock Tower was very appealing on such a clear day. We decided to spend our money on a drink at the Signature Room instead of the entry fee to Observation Deck (about the same amount). Good idea – much more relaxing and the view couldn’t have been better. The lake is so blue on a day like this, almost like the Caribbean! It’s fun spotting all the landmarks and getting a better feel for how the city is laid out.

Our flight left Midway in the mid-afternoon, so we easily hopped the L to get there. We struggled a bit with refilling an existing fare card and the attendant came out of the booth and helped us get the money in and the right buttons pressed… this is service the likes of which I would never see in Boston or New York! The train is very easy to use and the station at Midway is not that long a walk from the terminal, all inside.

Oh, there was so much more I know I missed in Chicago, and twice as much that I still don’t know about. Just a small taste of goodness. We’ll be back, I will insist on it!

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