Travel Party of 5 | Points & Miles for Family Travel

Chicago Athletic Association: A Hotel Review (And how we Manage Work Travel)

• Raya & Duane

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The Suite I stayed in (Founder's Suite)

In this episode of Travel Party of Five, hosts Raya and Duane dive into a review of the historic Chicago Athletic Association Hotel and share personal experiences and travel tips. Located in downtown Chicago, the Chicago Athletic Association Hotel is a beautifully restored property, originally built in 1893 as an exclusive athletic and social club. Now part of Hyatt's Unbound Collection, it offers unique features that make it a memorable choice for travelers.

Raya provides a detailed account of her stay, including her room upgrade to the spacious Founder’s Suite, which featured two fireplaces, a dining area, and views of Millennium Park. She also touches on the hotel’s blend of classic and modern amenities, from the Game Room, where guests can enjoy shuffleboard and pool, to the historic Milk Room, once a Prohibition-era speakeasy, now serving breakfast and coffee. The hotel’s Shake Shack in the lobby and the rooftop bar with city views add to its charm, making the Chicago Athletic Association Hotel a unique stay in the heart of the city.

The episode also includes practical advice for families managing work travel. Raya and Duane discuss the challenges of leaving family behind and share tips for keeping things running smoothly at home. They highlight the importance of meal planning, family support, and sticking to routines, which help make travel easier on both the traveling parent and the family at home.

While the Chicago Athletic Association offers plenty of character and charm, the hosts note that it may be best suited for adults rather than young families due to its historical decor and lack of child-friendly amenities like a pool. Overall, Raya and Duane agree that the Chicago Athletic Association Hotel is perfect for solo travelers, couples, or groups looking to explore the city with a touch of history.

Whether you’re interested in the architecture of the Chicago Athletic Association Hotel or seeking practical tips for balancing work travel and family, this episode offers insight and advice from experienced family travelers.












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Raya:

Today's episode is a review of the Chicago Athletic Association Hotel in obviously, chicago, as well as a discussion on work travel and a few tips on how to manage at home when your partner is traveling for work. Hi, I'm Raya. And I'm Dwayne, and we are your hosts of the Travel Party of Five podcast, where we share how we travel as a family of five around the world.

Duane:

We will also share how we use points and miles to travel as affordably as possible and sometimes even completely free.

Raya:

So if you're wanting to travel more with your family but you're not sure how, we'd love for you to listen in.

Duane:

So welcome to our podcast, where we hope you learn a thing or two to get you closer to your next trip.

Raya:

Hello friends, Welcome back to Travel Party of Five podcast. Welcome back. If Dwayne seems distracted, he's watching the Bears game on TV.

Duane:

I just thought you all should know he was a little salty that we had to record these episodes at this time during the day.

Raya:

I mean a little salty, but I wait all week for this and we have birthday parties and stuff to go to later and then it's dinner and bath and bed.

Duane:

So it was either and the bears aren't doing very well this year, so I'm a little frustrating, but I'm used to it well, it could be worse.

Raya:

You could be a Giants fan like me. Okay, today's episode is going to be I'm going to talk about the hotel I stayed at in Chicago. I was there for work a couple of weeks ago and stayed at a really nice property, so I'm going to talk about that. But before we get into the details of the hotel, I thought we could maybe have a chat about what it's like to be the parent left behind when your spouse or partner or whatever, is traveling for work. Because of the two of us, I'm the only one who travels for work.

Raya:

As of now and it's new like only within the last year or so have I been traveling yes, you've taken a few kid-free trips oh, I have taken a few kid-free trips also, in addition to work travel, that's true, yeah and I've taken one to go to a high school reunion. But okay, so tell the people. Inquiring minds would like to know when I go on a work trip or a kid-free trip, I guess, depending I have. I did both. This year I traveled what? Three times, for work, I think, and then I went to Europe with my mom and sister.

Duane:

Yeah, I mean really there's no, I mean, the only tip I can give is you just have to be prepared. I work full time, typically, not on a set schedule.

Raya:

You work more than full time. You work like, depending on the season, 50 to 60 hours a week.

Duane:

Yeah, but I mean, like I said, the only tip I have is have a game plan, be prepared. It also helps when you have grandparents around, like I do. I mean, I have my mom and dad and your mom and dad, so that's very helpful. Shout out to the single parents that do it. I don't know how you do it, but I have nothing but respect for you, because it's hard. I mean, to say the least, it's difficult, especially when you work full time and you know.

Raya:

Yeah.

Duane:

But yeah, you always got to have a game plan, you know dinner plans. We talk about dinner before I go yeah, who's picking up who from school? Like, yeah, I mean it's, it's tough, it's.

Raya:

I do all the food ordering, so like groceries and stuff, and so I'll say, like, what do you want to make for? And I do most of the cooking too. So, but Dwayne has a few things that he can cook and I like to grill. Yeah, I do bake chicken.

Duane:

Make some fire tacos as the kids would say Nachos, I mean nachos.

Raya:

Good nachos. Yeah, so you know, usually I'm only gone for a few days for the most part, and it's you know. You'll either make the things you make.

Duane:

Or I'll have my parents pick up the kids and tell them that we're eating dinner there, yeah, which the kids and I love, actually.

Raya:

So when I was telling Dwayne I wanted to talk about this. I was like what is your biggest tip for you know, like when you're left behind, when your partner's traveling? And he said have a grandparent.

Duane:

I, it's true, and, like I said, I mean I can't stress it enough if you're a single parent, I mean hats off to you. I know it's tough even with two parents.

Raya:

Yeah, when I called you and showed you my room, that they gave me like true or false were you jealous.

Duane:

I mean, yeah, it was like a suite. I mean it was a suite. It was a suite yeah, it was probably a 1,200-square-foot room if I had to guess I mean yeah, yes.

Raya:

So when I checked in okay, let me back up here. First of all, I booked at this hotel Again. This is the Chicago Athletic Association Hotel in Chicago, which is a Hyatt. It is a Hyatt hotel, which is why I booked it and it's part of their Unbound collection. I did not use points because it's a work trip, so my job is reimbursing me for the cost, but you can use points to book if you want to. The hotel has a ton of character, super cute. Very much reminded me of the Beakman on the inside which we stayed at in New York City last year, I think.

Duane:

Yeah, last August.

Raya:

So it's very moody, kind of like 1920s vibes. The building was built in 1893. It was originally an exclusive athletic and social club on michigan avenue and it was one of the country's most elite clubs at the time. The design of it was inspired by a palace from venice and the club was open until 2007. So it closed in 2007. The building was restored and it joined Hyatt in 2019. They have a Shake Shack in the lobby, which was important to me, as I arrived around four after a very long flight and Uber ride from the airport, and I inhaled some cheese fries immediately upon arriving, before I even checked in, because I didn't have dinner until like seven and I was so hungry.

Duane:

So shout out to Shake.

Raya:

Shack. I also had read on Reddit that regular rooms are small in this hotel, so I booked the Junior King suite. But the only reason I did that is when I was looking at the prices. It was the same price for the Junior King suite as it was for a regular room. So of course I'm going to book the suite and otherwise I obviously would not have done that.

Duane:

First of all, this room was so big. When she got there she FaceTimed me and I was like there's an Echo, and I didn't know she had that room. She was like well, let me show you why there's an Echo.

Raya:

Yeah. So when I got there to check in, they were like we upgraded you to the Founders Suite. And I was like, oh my God, that's incredible, like that's amazing. Like I didn't even ask, you know. I was like, wow, this is what happens when you book on cash versus points. I guess, yeah. So I'm like, okay, that's awesome, you know. And they kept telling me like this is a very nice suite, like it's like it's like, you know. They were telling me like at check in, like it's really great, and I was like, okay, so I'm so excited, so I go up.

Raya:

I was on the third floor. My room was, the lobby is on the second floor, so Shake Shack and the street is the first floor. You go up one store to the lobby, which is where you check in, that's where the bar is. And then I was one more floor up and I did like being low enough that I could take the stairs because the elevators were slow. I will tell you that. So if you're in a rush because the elevators were slow, I will tell you that. So if you're in a rush, I would take the stairs. But I go into this suite and I was shocked at how big it was Okay. It had two fireplaces.

Duane:

Two.

Raya:

Two A giant king bed, huge bathrooms with a separate tub and a shower and like a whole dining room table area. It was. There was like a dining room table area, a seating area, the bed. It was there was like a dining room table area, a seating area, the bed area.

Duane:

It was massive I mean the dining room table could sit like eight, I think uh, no, I think it was four, but it was big.

Raya:

It looked big. Yeah, it was big. Um, I mean it probably could have seated more, but there were four chairs. Um, I had a view of Millennium Park, but again, I was on the third floor. So the downside of that is you can hear more road noise and I would bring earplugs if that matters to you. The only thing like to, one thing made me a little nervous, I'll say as a solo female traveler. In this instance. There was no little latch you can flip to prevent the door from being open from the outside, so I put a chair in front of the it wasn't a chair.

Raya:

You put the ironing board, the first day I put the ironing board, but then housekeeping moved it, so then I put a chair. The second day I put a chair or an ironing board in front of the door, so I would wake up immediately if someone did try to enter, because I would hear, obviously, the chair being pushed across the floor. The hotel has some really cool features that I wanted to briefly talk about, some of which I visited, some of which I didn't. I was only there for two nights and it was a jam packed trip. So we're talking work dinner the first night. I arrived, the first full day, all-day work, followed by a second work dinner, and then the third day, all-day work, followed by a flight at like 7 pm. So no room for fun.

Raya:

So I don't have any touristy tips for you on Chicago, but this hotel has a rooftop terrace slash restaurant bar. They have a game room where you can play like pool, bocce ball, shuffleboard. They have a what's called the milk room, which is this is kind of cool. This was a former speakeasy club that members use during prohibition and now it's where they serve breakfast and coffee. I already mentioned the Shake Shack, but what I didn't know is you can get Shake Shack via room service. Apparently, I was not aware of that. That would have been fun. They have fairgrounds, which is like a little coffee shop, pastry market type place, and then they have a Topgolf Swing Suite, which is the first of its kind in Chicago, and it includes two indoor golf and interactive gaming simulator bays. You can book a four hour session for up to eight people and I thought that was pretty neat.

Raya:

The only thing I ate at the hotel besides Shake Shack was breakfast one day room service. It was waffles and eggs. It was good. I thought the service was really good. I had two small issues and both of them were resolved like super quick. One was really random. There was like an infestation of ladybugs outside the windows and I thought, wow, that's so lucky. You know, ladybugs are a sign of good luck. I thought, wow, I'm the luckiest. But I did have to ask housekeeping to come in and like vacuum them up, because there was probably about 20 that snuck through the window and were inside the hotel room so and the windows are right next to the bed, so I just didn't want to wake up with like a ladybug in my mouth, you know.

Duane:

That's super good luck.

Raya:

I mean I guess. And the other issue I had was the TV just stopped working on my last night there and it was like maybe 930. But I called and someone came in and fixed it within 15 minutes Like super easy.

Duane:

So what do they do? Plug it in.

Raya:

I don't know, he messed with the back of it and I don't know which. I had already tried to do but didn't fix it. So my only other complaint was I couldn't figure out how to work the fireplaces. There were switches and stuff and I'm pretty sure they do work, but I couldn't figure them out, couldn't figure it out. But also, to be fair, it was 75 degrees when I was there, even though it was the end of october, um, and so maybe they just don't allow you to turn it on until it's like below a certain temperature?

Duane:

I don't know I don't think that's the case. Should I ask the guy that came in? I mean, I probably should have.

Raya:

But by then I was like I'm gonna check out in the morning. So my cozy factor, my cozy factor, my cozy window of time has passed. Um, when we called, when I called the kids, the kids always love to see the hotel rooms like, especially our little one.

Raya:

Yeah, especially our daughter. She's like show me the hotel, show me the hotel. The kids were like Whoa, like that's the biggest room I've ever seen. Like why didn't you bring us with you on this trip? And I'm like, well, listen, I would have loved to, but it would not have been enjoyable for you at all.

Duane:

So what do you think this hotel is good for, Like I mean, if the kids wouldn't have had a good time? Are you just saying that because it was a work trip, or Well, yeah, I mean mainly because it was a work trip.

Raya:

Could you imagine our kids sitting still during all-day meetings? No, no, no, no, of course not. But also, I don't think this hotel is good for families. First of all, there's no pool, which I mean maybe matters, maybe doesn't, but it matters to me when my kids are with me. Excuse me, I'd also be worried they'd break stuff, because my room, like the suite, was filled with these old trains and cars and books inside shelves all around the whole suite and, like the, the doors to these shelves were not locked so you could easily open it up and take something out and they would have. They would have opened something For sure.

Raya:

I do think it would be good for a couple's trip or a girl's trip or a boy's weekend. I think that would be especially probably a boy's weekend. It would be really fun because they have the game room and all that. That seems more boyish to me. Yeah, you would have been more into that than I was. Ish to me. Yeah, like you would have been more into that than I was. Um, so I do think that that would be what I would go back there for. I do.

Raya:

I have a friend who, um, is familiar with Chicago, and she said that that hotel was like on her bucket list to stay at for a weekend and I mean I could see that, like it was, it was nice for sure, the service was great. I'm going to put a link in the show notes to the suite that they booked me in if you want to see it. It is unless they have more than one suite that looks the same. This is the exact suite that I stayed in. It's called the founder suite and I'll put a link to that in the show notes.

Raya:

You have any other like tips or anything about what it's like when I am traveling? And, as a as a side note, our seven-year-old, when I had told him that I was going away on this trip, he was just like threw a little bit of a fit and was like, oh, why is it always you, why is it never daddy? I was like I'm sorry, bud, but I'll be bad. I'm only going for two nights, and so I was, yeah, chuckling at that I'm tabloider over here oh, that's not true.

Raya:

They just feel more comfort from their mom. I feel like that's normal. Dads are the fun parent you know yeah do you think that you guys have more fun when I'm gone?

Duane:

oh, I mean, there's definitely more freedom for them, for sure like what kind of stuff do you?

Raya:

let them do that I? Don't let them do stay up later.

Duane:

Um, it's pretty much it. They, oh. And they also sleep in the bed with me, which I have no problem with. But Raya's perfect example was just last night. Two kids came and slept in the bed and she went and slept in our daughter's bed.

Raya:

Yeah, but if I leave then there's room for all three of you, but if I'm there there's not room.

Duane:

I mean to be honest, I didn't even know you left until I got up and I thought, man, I could have. I was sandwiched between two kids and there was a whole half a bed that was open anything else that's different when I'm not here um, no, I mean, that's it. I mean we eat food that the kids want to eat, because sometimes ray makes food that the kids want to eat, because sometimes Ray makes food that the kids are like, but other than that, Listen, my food is good.

Duane:

I mean, I'm not saying it's bad, but it's just not.

Raya:

I don't make all kid-friendly food. I believe in exposing them to a lot of different types of food, and that means that sometimes they don't like most of the dinner that I made.

Duane:

Yeah, and they know when you're gone and I make dinner, it's going to be something that they like. Or that grandma makes you know.

Raya:

Oh yes, they do. I mean your mom will. If our kids wanted three different dinners, duane's mom would make three different dinners.

Duane:

She definitely has done that many times.

Raya:

I am not that kind of mom. Maybe I'll be that kind of grandma, but I'm not that kind of mom. So I make what I make and they can eat it or not, but you can't deny that our kids are not picky eaters and they they eat a lot of stuff and they try a lot of stuff.

Raya:

Yeah, they do so I think I'm on to something here, but anyways, at this point we're just rambling. So overall, would totally recommend the Chicago Athletic Association. I think it's a fantastic hotel, just probably not a great fit for families, unless your kids are super well behaved or older. Um, ours are not, so hope this was helpful. Yep, if you have questions, send us a message on instagram at travel party five. That's the best way to find us. If you enjoy our podcast, we would so greatly appreciate a review or a rating. Wherever you listen, it really helps the show get found by more people and pop up in search results when people are searching for different topics yes, thanks for tuning in.

Duane:

We appreciate it.

Raya:

We appreciate you so much um have a good one yes, I was gonna say we're gonna take the week of thanksgiving off as a heads up, so if you don't see a podcast episode that week, that is why. But we will be back in december with a few more episodes to close out the rest of the year. Thank you so much. We'll catch you soon. Bye.