Visiting Chicago

As the 3rd largest city in the US, Chicago has something for everyone, but where do you start? We discuss what to see and do when visiting Chicago.

Visiting Chicago

  • Why Chicago is called “The Windy City.”
  • Getting to Chicago (2 airports, train, car)
  • Getting Around (walk, Uber, elevated train)

In Chicago, You Can do Many Things in One Day

  • Sports (NBA, NFL, NHL, MLBx2, Pro Soccer, College)
  • Museums (Museum Campus, Museum of Science and Industry)
  • Institute of Art (Picasso Old Guitarists, Hopper Nighthawks, American Gothic, Wharlhal Liz Taylor)
  • Navy Pier
  • Shopping! (Miracle Mile, Water Tower Place)
  • Cloud Gate

Question: What would you like to do when visiting Chicago?

Please let us know in the All Things Travel Podcast Facebook group!

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Episode ??? Transcripts

Episodes are transcribed with artificial intelligence, so some highly amusing translations are likely!

Ryan: Hello and welcome to All Things Travel. Ah, the Windy City as the third largest city in the United States. Chicago has something for everyone today, Shayne and I discuss what to see and do your next time in Chicago.

Shayne. I absolutely love Chicago. It’s the closest big city to me. I used to go as a kid, I, I, we go as a family now it’s easy to get to for us. My grandfather actually drove the train between South Bend and Chicago for his job. I’ve got a lot of connection with it and I just think it’s a great place to.

Shayne: I’ve been twice. Once was just an overnight trip sorta, and then once I went training for work. It’s been several years, a lot of years, but I. Had so much fun there. It is a great city.

Ryan: Well we need to meet up there cuz there’s a lot to offer.

Shayne: Giddy up

Ryan: So I will give you a little tidbit of information, my friend. Chicago’s nickname is what?

Shayne: the windy city

Ryan: The Windy City. Why do you think that is?

Shayne: because of the nice, calm, cool air that comes across the, the lake at what, 20, 30 miles per hour.

Ryan: You are halfway right? So it, there is some convergences there with the, the Great Lakes you know, lake Michigan, which for those of you who have not been to Chicago, it pretty much looks like Chicago sitting on an ocean. You know? So if you’re not familiar with the Great Lakes, it’s very different than what you’re envisioning.

And there’s some rivers and there is kind of a confluence of weather. However, that’s not why Chicago’s named the windy.

Shayne: really.

Ryan: So in the late 18 hundreds, there was a newspaper reporter that talked about the politicians out of Chicago being windbags, and started to coin Chicago being the windy city because of the politicians there.

And that’s where the nickname actually comes from.

Shayne: Wow, interesting

Ryan: There you go.

you learned something today.

Shayne: Yeah, if you don’t get those kind of tidbits just anywhere, you only get that on All Things Travel

Ryan: There you go. That’s your, your All Things Travel educational moment for the episode. Well, hey, Chicago has tons to offer. I’m excited to talk about it. I want to get into talking about Chicago.

Most families are confused and overwhelmed when planning a vacation. We work with you to plan a trip perfect for your interests, saving you time, money, and stress.

Shayne: We would love to help you plan your next amazing vacation.

Ryan: You can reach out to me, R Y a N, at creating magic All right, Jane, so first of all, if you’re, if you’re coming from outside the Midwest and you’re thinking about coming to Chicago, there’s a couple different ways you can do it. There are two major airports in Chicago.

There’s O’Hare and there’s Midway. You’ve probably heard of both of them.

Shayne: Yeah. And how do you know which one to fly?

Ryan: So O’Hare is, is a larger airport, but it’s more outside the city, mid. Is more central in the city. And I would say also selfishly, we tend to fly in and of out of Midway because that’s a Southwest hub.

Shayne: Okay. Makes.

Ryan: I’ve only ever flown Southwest out of O’Hare once I’ve flown outta midway multiple times.

You can also obviously drive into Chicago. Chicago is centralized with a lot of major highway. Um, You know, and obviously centralized in the United States, and you can also take the train in whether it’s, it’s locally, like what we do from South Bend or using Amtrak or something else like that.

So multiple ways to get there.

Shayne: great way to try a new mode of transp.

Ryan: absolutely. Once you’re there, Chicago is a very walkable city. You know, when my last time we were there, my kids and I were doing most everything together. My wife was at a, at a meeting and you know, we would, it was very easy to walk to most places that we wanted to. Uber is very easy there. And they also have the l or the elevated train, which is their version of the subway, which is fun to.

Shayne: Yeah, that was how I got back and forth both times was using the EL elevated train.

Ryan: let’s talk about some of the reasons that Chicago is a great place to vacation and really it has a little something for everybody. And the first thing that has is it has tons of sports. every major league has at least one team, if not several, that have a home base in Chicago.

Shayne: Two baseball teams. That’s

Ryan: Two baseball teams. Absolutely. And also major colleges. You’ve got a Big 10 college there with Northwestern. You’ve got Notre Dame, which is not too far away. You’ve also got multiple colleges in Chicago and fun fact was sports one time when I was there. They were actually the city was a buzz because Manchester United was actually in Chicago and was gonna be playing at soldier.

Shayne: when I was there for training for work, that’s one of the things I made sure I did was I went to a Blackhawks game.

Ryan: Uh Huh

Shayne: That was a lot of fun.

Ryan: absolutely. Absolutely. It’s, it’s, they’ve got a good blue collar spirit around their sports, and I, I, I really like that. one thing that Chicago is very well known for, and we take advantage of this as a family all the time, is they have great museums. They have a wonderful museum campus with places like the field museum the aquarium.

The planetarium. They also have the Museum of Science and Industry, which I obviously not for you growing up in Texas, but for us, that was a requisite field trip when we were in sixth grade. they also Shayne, I don’t know if you knew this, but the Institute of Art in Chicago has some of the most famous.

Artworks in the United States. So for instance, you’ve got Picasso’s old guitarists, you’ve got Hoppers, Nighthawks, which is the painting of the people sitting in the cafe at at night.

Shayne: Okay,

Ryan: got American Gothic is there. You’ve also got Andy Warhol’s, Liz Taylor painting is there.

Shayne: Oh wow.

Ryan: There is tons of museums and art, both big and small in Chicago.

It’s a great place to go to soak up some. So I know you’ve been to this next place, Shayne. Talk to us about Navy Pier.

Shayne: Navy Pier, it’s up here. That extends out into Lake Michigan and it’s got an IMAX theater, a few amusement park rides, and a lot of restaurants. that was one of the places that a coworker and I visited. in the, in our time during Chicago, we saw a movie in the IMEX Theater and I remember hanging out, I don’t know if that bar is still open.

It has been several years, but a nice little Irish pup where we hung out before the movie. Lot of fun there.

Ryan: It, it’s very touristy, but a lot of. it’s got a giant Ferris wheel now. That’s enclosed. That’s a lot of fun. My kids enjoy doing that. We actually saw one time many years ago we saw a Cirque dele type show with acrobats and martial arts and everything. There. The, the Children’s Museum is actually right at the base of Navy Pier.

It’s a good place with lots of uh, restaurants, so it, it’s definitely worth your time.

Shayne: and I bet extending out into Lake Michigan. The views from that Ferris wheel are

Ryan: Yeah, it’s really cool. It, it, it’s a really neat really neat part of, of Chicago. So the next one, Shayne is shopping. Chicago is known for shopping. Most specifically, if you’re talking about downtown, you’re talking about the Miracle Mile along Michigan Avenue where you can find any type of shop you want to.

Shayne: Now, this next one, I don’t know if I’m familiar with, what is Cloud Gate?

Ryan: Cloud Gate is the Bean. So if you’ve taken, if you’ve seen people take pictures in the park there, the, first of all, it’s a, it’s in a beautiful park setting in downtown Chicago. And the Cloud Gate is the actual name for the Bean.

Shayne: Nice. Okay. I’ve seen your picture there and my older daughter has sent pictures from, from the Bean, so very

Ryan: Oh, and, and it’s, again, it’s one of those things that, it’s a, I think I even took a picture once and, and posted and said requisite. I’m in Chicago picture. But, you know, it’s just, it’s cool. It’s fun. Well, hey, before we talk about more things on this list, Shayne, I wanna know where in the world is All Things Travel.

Shayne: Well, I would like to go back to episode 1 34 when Chicago was our All Things Travel destination. That was our, that was our episode about Madrid, summer festivals. it would’ve been nice if those had lined up. But we’ve already mentioned Chicago as an All Things Travel location.

So today we are going to Ashland, Kentucky

Ryan: Ashland, Kentucky, Thank you for listening.

Shayne: and I do love getting outdoors and speaking of parks, Ashland has a really nice central park that I think would be lovely to go visit while we’re there.

Ryan: That sounds fun. Well, hey Ashlyn, do me a favor, reach out to me either on Facebook or on the email that I give during this show because I’ve got a nice little gift for you being featured on today’s show.

Shayne: and to make sure that you hear where in the world is All Things Travel next week, subscribe to the show or follow the show to make sure you never miss any of our travel ideas, travel tips, or travel stories.

Ryan: I’ve never done this next one. Shayne. I know it’s a big thing in Chicago, especially if you’re, you. Going there for the first couple times as a tourist. This is taking a architectural river cruise, so Chicago has these fantastic rivers running through the downtown area and it has a really nice. Riverfront canal kind of setting, if you will.

Much bigger than canals, but you know what I’m talking

Shayne: Yeah.

Ryan: And they do architectural tours because Chicago was one of the first cities in the United States to really embrace the The high rise, the skyscraper because there was a fire in Chicago and they were basically able to rebuild the city at that time.

That was the thing, and so really the skyscraper was born and they really talk about the different architecture and the rivers are a great way to see that. My wife and I were signed up to take one of these tours one time and actually, There was so much rain the day before that the rivers were too high, so they

Shayne: Oh wow. Oh.

Ryan: the tour.

Shayne: That does sound like a fun trip. You know? And speaking of the architecture, we also had an episode where we talked about visiting cities where your favorite books are set, or doing the opposite reading books set in your favorite city and one of My favorite books is a book called Devil in the White City, which was about the building among other things.

It was about building the Ferris wheel, which made its debut in the world’s fair. 1893 in Chicago. So if you are, if you wanna tie a book to your trip to just keep in mind though, that it’s also about a serial killer that was on a rampage during that time. But the stories about the World’s fair and the the surrounding area are pretty fascinating and there’s even a tie to Walt Disney in it, which I will leave for you to enjoy for yourself

Ryan: We are throwing down so much knowledge on today’s podcast.

Shayne: much inform.

Ryan: Well, hey, if you think of Chicago and the skyline, speaking of the architecture, you’re obviously gonna be thinking about the Sears Tower, which is now called the Willis Tower. It’s great to see from outside, but you can also go in it, go up to the top, and you can actually step out onto a glass four and look down from.

Shayne: I would imagine there’s some pretty nice views from there too.

Ryan: Yeah, I, I have not been up there since I was a kid. I don’t, my family went up there one time with, when I was not with them, and they really, well, my son did not care for the glass floor. But I would certainly do that if I was going to Chicago.

Shayne: I think I would try it, but I don’t know if I would care for it either.

Ryan: Well, I mentioned this a little bit earlier, but Chicago is on Lake Michigan, one of the Great Lakes, and because of that Shayne, they actually have a really cool beach culture. You know, it’s like you’re, you’re in, you’re in the midst of this major US city and two blocks away you can be on the beach.

Shayne: that’s insane. And

Ryan: It is. It is really, really,

Shayne: and it’s just like a coastal beach, right? Except it’s freshwater because it’s a lake.

Ryan: it is. It’s, it’s freshwater. In graduate school, my roommate was from Delaware and when he first moved to Michigan, his family who was helping him move in, they went to Lake Michigan for the day and he said it was the weirdest thing because he ran into this body of water that looked like the ocean and it was fresh water and that that.

Yeah, absolutely. So no, there you can, especially if you’re there during the summer, you know, taking a stroll along the beach, relaxing at the beach for a while. My family has done this where, you know, my kids and I will be at the planetarium and, you know, it’s about a half hour walk up back to where like the cloud gate is and then you’re getting into the city and and that’s a really nice way to kind of,

Shayne: Very cool.

Ryan: So this next one, to be quite honest, I have the least experience with, but if you talk to my friend Dan, who was one of my college roommates, he’s lived in Chicago for over 20 years, and I remember my, my kids and I had breakfast with him the last time we were there and we said, okay, we’re gonna be doing all this touristy stuff.

What else should we be doing? And he said, you gotta get into the neighborhoods of Chicago because there’s about 80 different distinct neighborhoods in the Chicago land area. And each one kind of has its own vibe, right? Certainly not as big as boroughs of New York City, but they’re all kind of, you know, kind of glommed together, if you will.

And. As I’ve been doing some research on visiting Chicago, I, I am realizing that I need to do that more and more, get out of the miracle mile area that I’m used to being in and really seeing the neighborhoods.

Shayne: Some of that deep trouble. I guess that’s where gonna be, where all the really good food and cultural thing that we enjoy is gonna be found.

Ryan: Yeah, good coffee shops, you know, it’s, it’s, it’s less congested, you know, more trees, you know, a slower pace. And you get to see, I, I always like to see people as they’re living, right?

Shayne: right? Yeah. That’s part of the fun.

Ryan: Yep. So speaking of food, that’s the last one on our list here and in Chicago. Oh man, food is a biggie. You’re talking about deep dish pizza.

You’re talking about Chicago beef, you’re talking about Chicago style hotdogs. But on top of that, Shayne Chicago is a foodie capital in and of itself. You got anything from great street food to fine dining in, in the city of.

Shayne: When I was there training for the, my job at the time, I went to Giordano’s twice

Ryan: which is one of the deep dish pizza.

Shayne: yes. And it was it. Absolutely incredible. This pizza was fantastic.

Ryan: Yeah, it’s got great food all around and like I said, it’s anything from food trucks, donut places all the way up to, you know, fine dining establishments. There’s really just about anything you want to have food wise, Chi Chicago can offer. And it, it, you know, just like any big city, it’s easy to. Order Uber Eats, it’s easy to make, you know, reservations on Yelp.

It’s a very manageable city to try a lot of things.

Shayne: You know, speaking of Uber Eats and pizza deliveries, back in that time, this would’ve been early nineties I had a friend who was from Chicago and worked for the airlines, so he would fly back and forth a lot, and there was a couple of times where we had him bring us back as year Donald’s pizza.

So we were wondering what the, the longest pizza delivery distance was.

Ryan: As we kind of wrap up here, you know, I would implore anybody, you know, o obviously Chicago is in my backyard ish, you know, it’s, it’s a, I, we can do it as a day trip or a nice long weekend, but I would implore everybody, it, it’s a great place for a vacation in and of itself. You could easily come here.

And, and spend even a week, you know, seeing different things, going to the, going to sports, going to the museums, going to the theater, you know, seeing the architecture. There’s a lot you can do here. So, Shayne, which on this list, what has you most excited about coming back to Chicago?

Shayne: The Architectural River cruise sounds.

Ryan: I tell you what my friend, you tell me when you wanna make that happen. I’ll drive up or I’ll meet you at the train station. We’ll head into the city. We’re gonna have a nice deep dish pizza. We’re gonna do an architectural river cruise. It’ll be a great day.

Shayne: Can we ride the Paris Wheel on Navy Pier also

Ryan: And we can ride the Ferris wheel and we will let everyone on Facebook, on the All Things Travel Facebook group, know that we’re riding the Ferris wheel.

Shayne: I’m sure they’ll love that. Well, we would love to help you plan your next amazing vacation.

Ryan: You can reach out to me at Ryan at Creating Magic Vacations. That’s R Y A N, at

Shayne: Most families are confused and overwhelmed when planning a vacation. We work with you to plan a trip that is perfect for your interests, saving you time, money, and stress.

Ryan: All

Shayne: really do not even see the recording button. There it is. Okay.

Ryan: He’s gone blind.

Shayne: different.