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Exploring Chicago

Exploring Chicago had been on my travel to-do list for quite some time. I’ve flown through both airports in Chicago on multiple occasions for layovers, and I’ve actually flown into Midway airport every year for the last four years as part of a trip I go on with the high school kids. But I’ve never been able to visit the city and explore it the way I wanted to, so when the details all game together for me to spend Labor Day weekend exploring Chicago AND cross both baseball stadiums off my list…I was thrilled!

Chicago Illinois

My first and last days were spent flying in and out plus a baseball game each day. I’ll outline both stadiums in separate posts. Sunday was the day I set aside entirely for sightseeing and was one of my favorite travel days I’ve had all year. I completely fell in love with Chicago. While I never want to live there (Chicago winters do not appeal to me) this city will always remain high on my list of favorite US cities.

I started my day off by heading to Millennium Park to see the famous “bean” that I’d been wanting to visit for so many years. I ended up taking entirely too many pictures there, but it’s definitely an essential picture to have if you visit Chicago. Wondering around the rest of the park is also something I would highly recommend to people.
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Can you find me? =D

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This one should make it a bit easier…

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I noticed that Chicago also has a bike share system and while I didn’t use it on this trip I do plan to next time I’m there. There are so many wonderful parks in Chicago that I never got a chance to explore, so next time I’ll grab a bike and explore some of them that way.

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I love a city with good mass transit, and Chicago’s “L” did not disappoint. Easy to navigate and got me everywhere I needed to go. My hotel was right off an L stop on the far end of the blue line, so I got to spend quite a bit of time riding the L.

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One of the other essential places to visit while in Chicago other than Millennium Park would be Navy Pier. I’ve been to Navy Pier once before in the winter and it was horrible. Everything was closed and looked lifeless. I didn’t have high hopes for Navy Pier on this trip because of my bad prior experience but I was so pleasantly surprised to find out that I love Navy Pier. It’s an entirely different being during the summer than it is in March. So full of life.

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And my #1 recommendation for someone visiting Chicago would be to go on a boat tour. I did one that took us out on the lake and then into the river (going through the city). I had no idea there were so many different architectural things going on in Chicago and loved the entire boat ride. I went with Seadog boat tours and had a great guide.

I had decided to save the boat tour for the evening because I thought it would be cool to float through the city at night when the buildings were all lit up. I ended up unintentionally booking a tour that happened right around when the sun was setting. So when we went out on the lake and got a wide look at the city the sun was just setting behind the buildings and it was stunning. And then as we were going into the rivers all the buildings were fully lit up and it was just a magical time of day to be taking the tour. If you have the opportunity, try to time your tour so that it starts right before sunset!

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Now, you might be wondering about the Sears/Willis tower or the John Hancock building and whether or not I did one of them. I did indeed do one of them and I didn’t think it was worth it so I won’t be recommending it to people.

I went with the John Hancock building (which is now called Chicago 360) because I heard the lines were often better there than at Willis Tower. Well, it turns out that Willis Tower was closed that day and so all the traffic they would have been receiving was coming to Chicago 360 instead. Eek! It was not a good situation. They actually shut down admission for a while in the afternoon because the line was so long, so I came back later that night since I figured the night time view would be pretty good too.

First off, while the view is cool, it’s not worth the money to me. Plus it’s really hard to actually get a good picture of yourself up there. Most of the ones you seen are the picture they take in front of a green screen and charge you way too much money for. And not only do you have to wait in line for quite a while to go up, you also end up waiting in line again just to leave and get back down. If you don’t buy your ticket online you have to wait in another long line just to buy a ticket before you can enter the admission line.

Two tips about that: first, just buy your ticket online. After waiting in line for awhile I pulled up the website on my phone to see if they sell same day tickets online (turns out all tickets are generic tickets) and bought one on my phone and got out of the long line. And secondly, if for some reason you really want to buy the ticket in person, have someone get in the main admission line and start waiting in that line while you get the tickets. They don’t check your admission tickets until right before you get in the elevators to go up.

Or maybe the best tip is to just not try to go on a day when Willis Tower is closed? =D

And last but not least, be sure to get some deep dish pizza while you’re there. Everyone seems to have strong opinions about which pizza is the best and which is not, so I’m going to avoid that debate all together and just make the general recommendation of getting some pizza.

Oh and of course go to Wrigley Field if you’re there when the Cubs are at home! Classic baseball at it’s finest with fun fans.

All in all, I loved my time in Chicago and it’s a city that I’m sure I’ll repeat visit in the future. But probably only in the summer!

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  • Love this! I’ve done a boat tour in Chicago with a friend before. It really was amazing! There is a lot more to that city than I thought. My husband and I are going to Chicago in November (we are braving the cold), and I am looking forward to taking him on a boat tour.

    • Hopefully you’ll get some really nice weather in November! Either way, definitely do a boat tour if you can, it’s totally worth it.
      And I want to see lots and lots of pictures on your blog afterward. =D

  • Sara Barnes

    Great post! I didn’t care for visiting the tower either when I was there. Love your pictures of the bean though! The group I went with refused to go there because it was too touristy (and yet they waited in line to take selfies at the hancock building…) I suppose I’ll make it my excuse to go back someday!

    Sara
    506miles

    • Sara, definitely make sure to get pictures with the bean next time you go! It can be kind of crazy with how many people are hanging around trying to get pictures, but it’s totally worth it. Plus the park is a gorgeous place to hang out in general.
      And it cracks me up that your friends didn’t think the Hancock building was touristy! Haha =D

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