How to have the best time in Chicago

I have decided to continue my ‘how-to’ series following my “How to Survive a Mega Bus trip to Chicago” post last week. Minus the fact that it took every bit of patience to travel to and from Chicago for vacation, my week in the Windy City was nothing less than awesome. Put three old friends in a big city to take by storm and you create outrageously awesome memories to last a lifetime. Believe me, this equation has worked multiple times before. I would like to tell you how to have the best time in Chicago, just in case you are planning a trip. And if you are planning a trip, call me-I want to go back!

1.) Find some fun friends to travel with. I was fortunate enough to have a couple of friends from Northern Ireland want to experience the Midwest, thus decided to end their time in America in Chicago. I think the consensus was that Chicago was their favorite city among the others they had visited (Boston, Washington DC, Philly-just to name a few). I like to think that they loved Chicago because they got to spend their time with me. Either way-woot, woot Chicago!

2.) Make a list of everything that you want to see, do, and eat. This helped because having four people with different opinions can make for lots of ideas. We decided to see the big ‘tourist’ sights, such as the Willis Sears Tower, Wrigley Field, Millennium Park, Navy Pier, The Blue Man Group at Briar Theatre, Lincoln Park Zoo, shopping on Michigan Ave, Ed Debevics, and real Chicago-style pizza from Gino’s. After deciding what we wanted to see, do and eat, we scheduled each day. While weather is something that you’ll normally have to take into consideration, we did have to worry about it too much. The only time it stormed was right before the baseball game at Wrigley Field (go figure), but the game still went on-1.5 hours after the scheduled first pitch. I found, however, that if you sit down and have a really nice conversation with the weather before you go out for the day, he normally cooperates.

3.) While it’s good to plan, it’s also good to be flexible. I knew that I wanted to head out to the Hyde Park area to visit my cousin and her husband for an evening. This was something that my friends needed to be flexible with. We also wanted to student rush tickets for the Blue Man Group for the 2:30pm show. This was not possible because the 2:30pm show was sold out. This meant being flexible and willing to do the Sears Tower during the day instead of the proposed night-time. It is also good to understand the importance of downtime. We would just go grab a coffee and sit at Starbucks for an hour or two every once in a while and chat. This was good because it rejuvenated us in order to continue walking the city streets. Everything ended up working out amazingly. Maybe I need to take this advice for my own everyday life-not just my vacation life.

4.) Take silly pictures. Seriously, who cares if you make a fool out of yourself. Your friends won’t (well, shouldn’t) judge you and let’s get real-the people around you are people you will probably never see again. Here is just a sample of the silly photos that we took.

5.) On a more serious note: cherish the moments that you are spending with your friends experiencing new things. I have been blessed to have seen some of my beautiful friends from Northern Ireland all three years since I left studying abroad, but as always, I never know when I will be able to see them [in person] again. These are memories that will be with me until we can create more in the future.

I hope these tips are helpful ones when planning a trip to Chicago, or any other place for that matter. I can’t wait to enjoy more vacations with even more fun friends in the future!

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