Guide to a Chicago Getaway

Chicago has always been one of my very favorite cities. There’s just such a great vibe that surrounds the stunning architecture of the skyline; even in a simple walk around it can start to feel like home. I visit as often as I can and have accumulated some of my absolute favorite “must-do’s” of the city as well as some travel tips!

  • Travel

Although it’s a very easy three hour drive from where I live, taking the train from Grand Rapids is extra fun. We travel on the Amtrak train departing from the downtown Grand Rapids Station located on Century Avenue straight through to Union Station in Chicago. The ticket prices were extremely reasonable and it all can be found on the Amtrak website, link above. Making a couple stops along the way, the total travel time is a little over four hours. It’s a unique experience to stare out the window at the quickly passing scenery, much different than riding in a car on the highway, but the best part is pulling into the city and catching the first glimpse of the skyline. The tracks bring you right to the heart of it all as you step off with your bags strait into the hustle and bustle of the city life. Even if you decide to not take the train, I would still suggest taking a peak inside Union Station, it’s incredibly beautiful!

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Union Station ground entrance.
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Union Station waiting area.
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Union Station street entrance.


  • Hotel

There are obviously hundreds of hotels to choose from to stay in while you visit, my personal favorite has been the Wyndham Grand Chicago Riverfront. It is located directly along the river across from the Trump Tower; truly an incredible location with even more incredible views!

Our room.
Day view from our window.
Night view from our window.
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Incredible view from the banquet room.
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My very favorite spot in the hotel: the Penthouse balcony.


  • Wendella’s Boat Tour and City Trolley Tour

Wendella’s– This is a fantastic boat tour that takes you through the Chicago River for an up close perspective of the iconic architecture then ventures out to Lake Michigan for a spectacular view of Chicago’s twenty six mile skyline. The full tour is about ninety minutes long, there are two docks where you can board (the Main Dock, 400 North Michigan Avenue and Trump dock 402 N Wabash Ave) where tickets can be purchased. Tickets can be purchased online as well on Wendella’s website, here you can also find directions and more information as needed. This has been one of my favorite experiences I’ve had in the city, the pictures don’t even do the views justice. A definite must do!

Riding on the top deck of the boat through the river.
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View from Lake Michigan.


Chicago Trolley & Double Decker Co.– Since we didn’t drive our car, the hop-on-hop-off style trolley was the perfect transportation for us! Tickets can be purchased for a 24, 48 or 72 hour period in which you can use the trolley for as much or as little as you’d like for that amount of time. On the downtown tour, you can hop on and off as much as you want at the city’s most popular and famous attractions. There are thirteen different stops along the way ranging from each end of the city. The trolley gets to each stop every twelve to fifteen minutes so not only did we use it to take a tour and learn about the city, we used it to get to where we needed to go regardless if it was an attraction on the tour, just to save us some walking. There is also a double decker bus option to use rather than the trolley if you wish. Each ticket purchased comes with a night ticket tour as well that you definitely won’t want to miss out on! Definitely a fun and unique way to enjoy Chicago that I’d highly recommend. (This company runs all year round.)

The super cute trolley come to pick us up.
The inside view.


  • Skydeck Chicago, The Ledge

For all who are not afraid of heights, spectacular views can be found 365 days a year on the 103rd floor of the Willis Tower. The Skydeck ledge experience is one like none other, standing 1,353 feet above the ground in a glass box will provide you with a view of Chicago you can’t get anywhere else. As the eighth-tallest building in the world and a Chicago icon, this is something you have to try. Tickets here.


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Amazing views from all around the 103rd floor.


  • NBC Studios, The Steve Harvey Show

Although tickets for the show cannot be purchased, if you know the dates you will be in Chicago you can request free tickets here. We were selected for the free tickets when we went but happened to have a very unique experience. We showed up to the studio all ready to go in our brightly colored clothes we were told to wear, just then to be informed Mr. Harvey was sick that morning and the show taping would be canceled. As a courtesy to those who had tickets we were given the option to come back to the Mother’s Day show taping, since I am in school my mom and I knew that we wouldn’t be coming back to Chicago and were bummed we would be missing the show. So, we stuck around seeing if there was something else we could experience that day. Luckily enough some very nice staff members offered to take us on a private tour of the studios which was incredible and in my opinion even better than the show would’ve been!

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Inside the studio with my mom.


  • The Signature Room

The Signature room is a very special dining experience. Located on the 95th floor of the John Hancock building, the views while you eat are completely breathtaking. The fine dining experience is the perfect place to celebrate a special occasion, for my mom and I, we were celebrating our birthday’s as they are in the same week. A place and memory I will surely never forget. Also, located above on the 96th floor is the Signature Lounge and bar as well as an area for private events. More information here.

My cute mom.



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  • Broadway Chicago

If you’re anything like me you would never go into a big city without seeing a Broadway musical. We were lucky enough to be in Chicago the same time the traveling Broadway tour of 42nd Street was playing at the Cadillac Palace Theater. Spending time in the theatre district you can find great theatre themed restaurants for a meal before the show, or even just walking around you can enjoy the lively energy. The best way to find out what shows are playing while you’re in town would be on Broadway in Chicago’s website.

The Cadillac Palace.



  • The Classic tourist locations (of course!)

While you’re in Chicago you’ll definitely want to see the iconic best known tourist locations such as The Bean (Cloud Gate), Millennium Park, the International Amphitheater, the Chicago Cultural Center (where the Tiffany Dome is located), the Art Institute of Chicago, Shedd Aquarium, and the Navy Pier just to name a few. There are honestly endless things to experience in this city you are sure to enjoy yourself while you visit. Just get out and explore, Chicago truly never disappoints!


Let me know what you enjoy most when in Chicago, I’d love to try some new things next time I visit!

Sincerely, Sienna

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