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Catching a Train to Chicago

I love our apartment in Pittsburgh. I love the proximity to downtown, I love the view of the skyline, I love the distance to PNC Park, I love being able to watch the boaters on the Allegheny, I even love the sound of the trains rolling by from parts unknown across the nearby bridge and into the city.  The sound is constant though, a low rumble that has become white noise in effect to me, but watching the trains roll by inspired me to plan out a weekend trip from Pittsburgh (PGH) to Chicago.

I have been to Chicago once for a wedding, years ago in the age before the internet. Back in the day when we booked our rooms out of a telephone book (and had no idea that we booked a hotel in the south side and not the best part of town). We drove from Maryland and had never been. But, we survived and now with the age of the internet we can see the location and pictures of the hotels we book before we go. Ah, what an exciting age we live in.  I digress, so here are the details of my plan for a weekend trip in Chi-town in August to see the O’s play the Cubs at what might be the greatest ballpark ever, Wrigley Field.

Wrigley Field | Photographs in the Carol M. Highsmith Archive, Library of Congress, Prints and Photographs Division.

I would book an overnight train from Pittsburgh to Chicago leaving on Friday the 5th of August leaving at 11:59 am and arriving at 8:45 am on Saturday. The trip would take 9h 46min and we could travel two ways, the first option is an Upper Level Reserved Coach Class Seat offering wide seats and power outlets for the ride for $344 round trip for two.  The second option (and the one that is the most romantic and relaxing) is the Superliner Roomette a private room with two bunks, seats, climate control, outlets and bottled water for $598 Round Trip for two.  I think the roomette is the best deal. Think of it this way: if you had were flying 9 hours you’d kill for a bed and some private space. This is like that, but you don’t have to pay $2,600 plus per person for it.

So now that we’ve made our way overnight from Pittsburgh to Chicago and arrived rested we have some time to explore and see the sights.

You have time to take a stroll through Millennium Park, a 24 acre park filled with art and nature in the middle of downtown. You could visit Navy Pier along the lake, filled with shops and restaurants and the 15-story Ferris wheel, the same one they climb for a view of the city in the dystopian romance book and movie Divergent.  You might want to hit The Magnificent Mile for your breakfast, the dozen blocks hosts 56 hotels and 124 restaurants.

We’ll rest our sore feet (from our morning sightseeing) at the ballpark. Orioles vs Cubs starts at 1:20 pm  and is only a taxi or a 30-40 minute ride on the Chicago Red line away. We will already have our tickets – we can buy them for anywhere between $20-100.  I’ve been to Wrigley before and suggest paying a little extra to sit so you are facing the outfield; the skyline behind the low outfield wall is one of the best parts of the experience. If you’re visiting on a non-game day you can still take a tour of the park, visiting the press box, bleachers, visitors club house, cubs club house, visitors and Cubs’ dugout as well as the field. You’ll learn all about the history of the 100 year old venue.  The tickets are around $25 and the tour lasts for about 75-90 minutes.  You can take a tour on game day but it’s limited due to the team use of the facilities.

The game done, take a trip back to the downtown area and check in at your hotel. Grab a nap (or just rest) to refresh yourself before going to dinner.

I picked three hotels all within a 20 minute walk of Chicago’s Union Station. I was also willing to spend a little more because we would only be staying one night, so each of the hotels are 3-4 star and considered luxury.  The rooms are, of course, beautiful as well as the lounges.  I think the Club Quarters has the best of the gilded age extravagance and detail that makes you at least feel rich.

The Club Quarters $152

Palmer House Hilton $169

Fairmont Chicago for $212

For dinner you can visit one of the restaurants you saw earlier on The Magnificent Mile or take a short cab ride to Chicago’s Greektown, the home of some of the best Greek restaurants in the United States.

You can then retire in your well-appointed room and rest up for a morning in bed and an afternoon of sightseeing before boarding the overnight train home. I know that times and prices do create many variables and they may not be the same for you, but if we get the idea in your head to take a train trip then our job is done.


About No Kids, Will Travel

In the eyes of their friends and family, Amanda and Zeke are a young jet setting couple without any real responsibility. In real life, the stress of work and raising a kitten push them to flee reality at every opportunity. The "lack of obligation" gives them the chance to explore the world.

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