City Of My Heart

I left New Jersey in 1996 and didn’t look back. I have joked for decades that people “shouldn’t get married or have babies in the winter, because I won’t come!”. So…of course…Sweet Stevie moved to Chicago. He moved for love, and we are very happy and proud of him for making such a drastic move. He’s even getting married. 

Before he moved, we had never been to Chicago, but since his move we have visited several times, and I even went with students over the summer for FBLA National competition. It’s been an awesome way to get to know both the tourist and the local parts of this beautiful city, and one I absolutely think should be on your list for vacations. Our trips have varied from three days up to a week, and I’ve got some suggestions for how you spend your time there, no matter if it’s a quick stopover or a week-long event. 

Getting There

When Sweet Stevie moved, he drove across the country in his car. While it is free to park on the street near his apartment, parking fees within the city and tourist areas are quite steep. While street parking near the Navy Pier was only $15, parking at our latest hotel was $55 a night! So consider carefully how you travel to Chicago. 

Obviously, we fly there from Nevada. While we have used both Chicago Midway and O’hare airports for our trips, we don’t have a preference. Our preference is whichever airport Southwest has on sale when we want to go, because both are outside of the city and away from where Sweet Stevie has settled in the surrounding suburbs. 

Getting Around There

We usually don’t rent a car in Chicago. When we are visiting, Sweet Stevie will usually do the bulk of the driving and we will use street parking as much as possible. For this upcoming trip, we will be staying mostly in the suburbs, so we are renting a car, but we wouldn’t if the hotel didn’t have free parking. 

Chicago public transportation is excellent, and I strongly recommend that you use it. It is timely, reliable and quite inexpensive. Traveling with twenty teenagers last summer, we used the public bus, the train and a water taxi to find our way around. It was both exciting for the kids and convenient for us. Concierge at that hotel was a lifesaver, mapping out for us the most efficient ways to get from tourist location to location with minimal transfers.  

My Favorite FREE Things To Do

Loyal readers know I’m a big fan of free. A very big fan! My vacation dollars need to stretch as far as possible, because I’m certainly not going to cut down how many trips I take! So, every time we visit Chicago, we pick at least one thing to do that is absolutely free to take the monetary pressure off at least one day. Here are a few that are worth several hours of your day:

Lincoln Park Zoo

You read that right: The zoo is free. And it’s one hell of a zoo, too.

Located in a public park, Lincoln Park Zoo has a paid parking lot near one entrance, and that lot was about $15 for a few hours. We have also taken an Uber and taken public transit to get to the Zoo, and every method was efficient and easy. The Zoo also has several restaurants on property, so this is a great location for you to plan a morning with a nice lunch before you leave. 

Navy Pier

We took a water taxi last summer from one tourist destination to the Navy Pier, and it was a lovely way to get there with a fantastic view of the city from the water. The Navy Pier stretches out into the lake, and is a wonderful place for a nice walk, to get some shopping done, and have a nice meal. There are several rides on the pier itself for the kids in your party, and the Pier is the starting point for many of the water tours of the city, including one on a pirate ship! 

Magnificent Mile

This shopping mecca is a great place for a nice long walk. While I didn’t do any actual shopping, I’ve enjoyed a nice cafe style meal on the Magnificent Mile, and sampled some famous Chicago pizza. My favorite part, however, is the unbelievably beautiful architecture that you can see up close from the street. Buildings and especially churches are just stunning, and worth your time to explore. 

The Bean

This epic photo spot is definitely worth a quick visit. I was surprised, however, with what a short visit it ended up being. There isn’t much here except that photo spot, but it’s worth it for a short walk to see. 

Worth The Money Ideas For You

As a tourist in a major United States city, you’re going to spend some money. While I try to infuse as many free and culturally significant locations in my travels, the truth of the matter is, at some point, you’re going to have to open your wallet. My goal with this blog is to share my experiences and help you make informed choices. Here are a few places I’ve dropped some money that I would absolutely go back to:

Shedd Aquarium

What in the world is more fun than a stingray touch pool? I ask you—isn’t it a blast holding wriggly fish in your fingers waiting for the ray to come up and have a nibble??? That’s just one little exhibit in this beautiful aquarium. It is several levels large, and includes hourly shows. My favorite part of the hourly shows that take place in an amphitheater seating area are that they aren’t guaranteed—if the animals don’t want to perform at that time, they simply change the plan. I appreciate that level of respect for the animals. This location is definitely worth a full day of touring for you, in our opinion. 

Field Museum

Into natural history? Want to see the largest tyrannosaurus rex skeleton in the world (her name is Sue—seriously)? Then head next door to the aquarium to the Field Museum. Another full day event from our perspective, this extensive museum has so many different sections it’s hard to hit them all. Just relaxing in the lobby of this beautiful architectural piece was worth the price of admission, and we strongly suggest you make it a point to visit the Field when you are in Chicago.

Take a water taxi/city tour

The water taxi appears above when I was talking about using public transportation, but it is so much more. When we took the water taxi from the Shedd to the Navy Pier, we were treated to a fantastic view of the city from the water. If you are interested in seeing more of the city from this vantage point, consider taking a water tour of the city itself, or specifically the architecture. The Chicago River bisects the city, and floating on a boat is the very best way to take in the sights without putting the miles on your own feet. These tours are quite reasonable, and primarily leave from the Navy Pier. 

Where Are You From?

I’m from the New York metropolitan area, but consider myself a Nevadan. No matter where in this country you are from, you can’t escape professional athletics. So here is my last piece of advice for you, from a NON-FAN: Go to a professional athletic event! Chicago has a variety of sports represented with their professional organizations, and I recommend you take in a game while you are exploring this fantastic place.

Last summer, with the students, we went to Wrigley Field to see the Cubs take on…somebody… The tickets were quite reasonable for great seats, and coming up to Wrigley Field—a historical marvel—was awesome. It was very odd for me to see a huge baseball stadium RIGHT NEXT TO apartment buildings and stores! No matter what season you visit, there will likely be some professional sports going on, and I encourage everyone in your party to take advantage and see a game. I had an absolute blast at the Cubs game—even saw a grand slam!!!

Even In The Winter

Hopefully I’ve shown you a small sampling of what you can do in that beautiful city in Illinois we call Chicago. I’m very glad Sweet Stevie ended up there, because it wasn’t even on my travel radar before he moved. Now, I look forward to every trip and trying something new every time we go. 

Next month we will visit again, and will be sharing this trip with some of the people who we love the most in this world. Not only are all of my children going, but so are my two brothers, our closest friends, and my Bestie Boo. 

We will be there to celebrate Sweet Stevie’s wedding.

In the winter.

I can’t wait. 

THANK YOU FOR READING THIS FAR

Thank you for reading all about going to Chicago!!

Hey, since you’re here! You may as well check out some other tips, like taking a short cruise, here, or traveling for Halloween, here! Or, check out our other topics here! Either way, I appreciate you!

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