Behind The Cast: The “Great” American Road Trip Day 7

I realized that tomorrow, we hit our destination. It’s been a week. A full week in various cities and trapped in Beryl with two of my best friends and we still don’t hate each other. Last night I feel like we were all going through it a little, but like Steve said to me last night, it’s just so understandable for us to be absolutely exhausted at this point. You spend all day on the road, and then end up in a new city and feel the need to make the most of every minute, to do something as much as possible every second, and then you hit a wall and wonder why you’re such a crabby pants.

We did manage to have a hell of a lot of fun last night though. First stop in the Chicago scene in Lakeview was the ever popular Roscoe’s. Fantastic sprawling bar that felt like a cross of someone’s apartment and a modern saloon, the design of the place was fantastic from room to room, including a back dance floor and countless bars. The staff was phenomenal, and as I’m finding more and more with Chicago, the people are just effortlessly friendly.

Next we indulged Steve a little on his endless quest to find a cowboy, and found, that, yes indeed, the now infamous Charlie’s that we frequented two night in a row in Denver actually has a few locations in a few cities, and Chicago was one of those. So off trolling for his bronco to find him a cowpoke we did. Unfortunately the bar was rather empty, but he did meet a barkeep named Duggan (you heard correctly, that’s a real sentence), and he left with a stupid grin on his face, and a bounce in his step.

Yet again, around the corner, we ended up at Sidetrack, which completely blew my mind. Once again, a sprawling bar, a load of good looking guys, a room for every genre, and a plethora of friendly Chicagoans. We were a ton of a lot of tired though, called it a night early, cabbed back to Club Quarters, and slept the sleep of princes.

Today was a phenomenal brunch at Rockit where I can recommend one of the best Bagel and Lox platters I’ve ever had. We left feeling fresh, took a jaunt down to Millennium Park where I finally got to see Cloud Gate, which I’ve always wanted to check out (I flicked the giant metal bean), and then to the Navy Pier where we had Margaritas at Jimmy Buffets Margaritaville and checked out the view. We circled back to the Hancock Building, where (here’s a tip for everyone wanting a view of Chicago), you can sit and have a drink and look at the gorgeous lake and city for free, unlike the Sears building that you have to pay for. After a bottle of bubbly (complete with complimentary martini glass of chilled strawberries), we left feeling very successful.

I adore this city. We’ve lucked out on weather too. I was told last night this was the warmest weekend this year in Chicago. The sun is shining on the river outside my window, our last night before our destination lays ahead of us, these to assholes are snoring tiny snores, Bruce is purring, and my beer is cold. I’m a happy camper.

  • brian

    omg. I was just in chicago last weekend (for the first time) and did soo many of things you just did on your trip! The bean, the 95th floor for drinks..looks like you had a great time

  • meh

    I’m going to go to Chicago in June. Thanks for the mini preview of what I should expect. Road trips are amazing, especially with friends that you can get along with.