4 tips to traveling with an “other” – Chicago

This post is specifically regarding Chitown, but these tips can be applied to any trip that you happen to be taking with a friend, family member, boyfriend / girlfriend, etc.

I’m just going to be open and honest, I’ve never really wanted to go to Chicago. If I’m going to go to a big city that gets cold as early as October, it’s going to be the city of all cities – New York. However, a friend of mine decided to celebrate her birthday in Chicago and so T and I decided to do a romantic getaway weekend as well. LOTS of people to consider.

Normally I’m not a huge planner, but this trip required some beforehand thinking.

When was the birthday dinner, what was the plan after, who all was on our list of “people to see” while we were in Chicago, what sites did we want to see, where are all of these places, etc. Overwhelming right?

My first tip when taking on a feat like this: Be open and honest about what you want to get out of the trip.

For example, my trip goal was to see my friend S, and celebrate L’s bday with her. If I didn’t do those things, I would’ve been disappointed in the trip.

T had friends that he wanted to see, so he checked their availability. I checked with my friends to see what their weekend looked like, etc.

Next tip: Make a list of everyone’s availability.

Also: Make a list of everything you want to see and do.

T and I made a list of the top 3 attractions that we wanted to see in Chicago. For a long weekend, this was the perfect amount.

Although the priority order was different, 2 of the 3 items on our lists overlapped. Perfect!

We scheduled out times for the people that we were going to see, dinner with friends for L’s birthday, breakfast with S, lunch with M & M, etc.

After that was done, we examined our “free time.”

What times should we do the top 2 items on our lists and then what else could we squeeze in?

Because of our strategic planning and flexibility. Not only were we able to get done 2 of 3 items on both of our lists, but also squeeze in going to the Sky Deck and got to the Field Museum almost in time to see Sue. Next time, Sue!

Chicago, Sky Deck, skyline

Field museum Chicago

The Field Museum was closing as we arrived. We didn’t get to see Sue, but we got to see this view! (Call me Busta Rhymes…)

So, what were the two overlapping things that we wanted to see, you ask? 

bean, millenium park, chicago

The Cloud Gate, aka “The Bean”, was inspired by liquid mercury, weighs 110 tons, and was created to reflect the Chicago skyline and the clouds above. Mischief managed! 

Navy Pier, Chicago

Navy Pier, Chicago

Last tip: BE FLEXIBLE. When you’re traveling, things won’t work the exact way that you want them too. If you are flexible, you can make the most of your time away from home and with your loved ones regardless of how things fall into place.

One of my favorite memories of the Chicago trip was the night we took the train into downtown from the airport. We were staying in a gorgeous boutique hotel in the financial district, and not much stays open on the weekends in this area. Wandering around, T and I were able to find ourselves a delicious dinner and had a blast doing it! I think we ate at Trattoria No. 10, but I just can’t be sure.

Shout out to the hotel we stayed in and the place we went to dinner for L’s birthday.

Hotel Allegro was fabulous. I would recommend staying there to anyone asking. They have free bike rentals and a happy hour, great service and clean comfortable rooms. Thanks Hotel Allegro!

Dinner for L’s birthday was at Sepia. A one Michelin star restaurant in Chicago’s Fulton River District, we received superb service and the food was “melt in your mouth” good.

I’m sure there are hundreds of great places to eat in Chicago, but if you need someone’s approval before you decide to stop in somewhere new, here’s my stamp of approval for Sepia.

Navy Pier Chicago

Need some help planning a trip? Let me know!

Thanks for reading! Until next time, adios, ciao, sayonara, good-bye!

Published January 2015.

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