FlyerTalk Forums - 72hrs in Chicago

Just wanted to share a recent trip report I wrote up:

<<<<<>>>>>

I’m already looking for a reason to go back to Chicago.

Last weekend, I traveled to the Windy City for a small college reunion with old friends and former roommates. The weekend began around 10AM Friday when I hopped off the El Train in Chicago’s downtown loop. It was a beautiful day (70s, sunny, light breeze), so I walked the mile or so to the hotel, strolling past skyscrapers and taking a detour through impressive Millennium Park on the shore of Lake Michigan. I arrived at the hotel, The W Hotel Lakeshore, around 11AM, but they were able to immediately accommodate me with early check-in. Our rooms were great, with uninhibited views of Lake Michigan and a full aerial view of Navy Pier out of our 29th floor windows. After a nap, I walked down the Magnificent Mile to grab an afternoon snack while waiting for the rest of my friends to arrive.

After some online research in the hotel lobby early that evening (wi-fi was free in the lobby, but cost quite a bit in the rooms), we decided to party in Wicker Park that night. The scene turned out to be excellent. The bars/lounges/clubs had a unique feel, and reminded me of a cross between the East Village and Williamsburg in NYC. Each place had it’s own character, such as Loft Six Ten where we enjoyed specialty burgers and good beer. Everywhere we went, drinks were about 1/2 of what I was used to paying on the East Coast, with many bars offering a $5 PBR/Whiskey shot special (yes, there were a lot of hipsters out). At Nick’s Beergarden, we listened to a great electro-funk band, later transitioning to the Debonair Social Club and Empire Liquors for more drinking and dancing.

Saturday felt like a different city. In addition to feeling like I was out the entire night before (hey, I was asleep by 5AM!), the weather took a turn for the worse. 70 and sunny was replaced with 35 with rain/sleet falling sideways thanks to a freezing 30mph wind blowing in from the lake. We only made it out of the hotel for brief stints, first visiting Giordanos for Chicago deep dish pizza, then going out later that afternoon to the Goose Island Brewpub in Wrigleyville. Throughout the day we enjoyed a few of the hotel amenities, including a free shuttle in a new Acura SUV that we could schedule to drop us off anywhere in a four mile radius, as well as a nice pool area and gym. After much needed naps, we began researching again where to go out, finally selecting the area around Rush and Division.

The neighborhood reminded me of DC’s Adams Morgan, but wasn’t as ghetto or trashy (though we did catch a fight towards the end of the night). For bars, we went to a few different places (none worth remembering by name) that all offered cheap drinks such as $1 Miller Light taps — they were died green from St. Patty’s day, but we were more than happy to help consume the dated inventory — as well as free shots with every drink at another bar. Eventually, we met a friend at a place called the Hannge Uppe, which turned out to be a lot of fun even though it felt like a bad frat party at times. Enthusiastic dance floors on two different levels, a pretty good variety of music (not my favorite stuff, but it did get people dancing), cheap drinks, etc., etc. Still, we tired of the place after a few hours and opted for late night eats at Jimmy John’s before heading back to the hotel, again around 5am…

Sunday turned out to be a relaxing day. We were checked out of the hotel by 11:30AM, then walked a mile or so to find brunch around the Chicago Museum of Contemporary Art. After eating, we stopped in the museum. Most of the exhibits were, ahem, “too contemporary” for me, but I did enjoy the work on display by Alfredo Jaar, including a cool installation piece called Geography = War that was really powerful and unique. After the museum, I returned to Wicker Park for some shopping and to check out the street art, taking the El back to the airport around 4:30PM for my 6:30PM return flight. As they say, all good things must come to an end…