Travel Party of 5 | Points & Miles for Family Travel

1 Day in Chicago (On Points!)

• Raya & Duane

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We spent 24 hours in Chicago before flying to Paris using points and miles, staying at the Intercontinental Magnificent Mile and exploring the city with our three kids. This strategic positioning flight saved us points while giving us an exciting mini-vacation in Chicago with deep dish pizza, the Bean, and activities like the Ice Cream Museum.

• Booked Chicago to Paris for 85,000 Flying Blue points for all five family members
• Used Southwest credits and gift cards for the positioning flight from Phoenix
• Stayed at the Intercontinental Magnificent Mile using a free night certificate
• Received a room upgrade thanks to IHG Platinum Elite status
• Kids enjoyed the hotel's indoor pool movie night with popcorn and lemonade
• Visited Chicago highlights: Lou Malnati's deep dish pizza, the Bean, and Starbucks Reserve
• Ice Cream Museum was expensive but memorable for the children
• Ed Debevic's restaurant with intentionally rude servers was entertaining
• Positioning flights can be cost-effective when traveling as a family
• Using hotel night certificates makes layovers more comfortable and fun

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Speaker 1:

Last month on our way to Europe, we spent 24 hours in Chicago before we flew to Paris, and in today's episode we are sharing all of the details, including the hotel, the activities that we did and more. So listen in. 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. We will also share how we use points and miles to travel as affordably as possible and sometimes even completely free. 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. So welcome to our podcast, where we hope you learn a thing or two to get you closer to your next trip. Hey guys, welcome back to Travel Party of Five podcast.

Speaker 1:

My name is Rhea, I am your host, I am solo today. Dwayne is running around picking up kids from playdates and birthday parties, and it's been a very busy weekend. So it is just me today and I realized that we never shared really any details around our 24 hours that we spent in Chicago before we flew to Europe, and I've got a couple of really good tips and tricks on like how we did that positioning flight and where we stayed and all that, and so I definitely thought it was worthy of a podcast episode. But before we get into all the details of that, I wanted to just go through a couple of quick updates around card applications that we have done and status of those future applications that I plan to make in the next week or so, and a quick reminder also about the Chase Sapphire Preferred 100,000 point offer. I believe that is set to end May 12th and so you've still got about two weeks if you have not applied for that card yet and you don't currently have it, that is by far the biggest signup bonus that card has ever seen. The Chase Sapphire Preferred is absolutely the number one most recommended card for beginners getting into points and miles. And, as a reminder, if you have never had this card or it's been more than 48 months since you last earned the signup bonus on the card, you are eligible to apply again. I wish that I was eligible but sadly we are not, so I will put our referral link in the show notes. If you are planning to apply for that card, I would first absolutely recommend it and second would love it if you would use our referral link. However, if you have a spouse or a friend or whatever who already has the card, get a referral link from them. That would be the best course of action. If you don't, then yes, please use our link. Again, I will put it in the show notes.

Speaker 1:

As far as card updates, so there's also currently elevated offers on the Hilton cards, so the Hilton Surpass and I forget the name of the other one, but they have elevated offers where you can get the welcome offer plus a free night certificate, and these cards don't normally come with free night certificates. And that offer is actually going to end, I think, april 29, which will literally be one day after this podcast airs. So if you're listening to this on Monday, april 28, and you are in the market for a new Amex or Hilton card, I would absolutely recommend getting those, or one of them at least. I have been trying to get that for myself and I am in Amex pop up. Jail Dwayne already has the Hilton Aspire card, which does come with a free night every single year, but I want to apply him for the Hilton Surpass because then he'll have a second free night that we could use, plus some points. However, it's a personal card and it will count towards his 524. And I also need to apply him for a Chase Inc card and I would like to do that also on the 29th of April, which is, as I mentioned, when the Hilton offers end. So I know this is a little bit rambly, but I think my plan is going to be to apply him for the ink Hopefully he gets approved he hasn't had a new Chase ink in like since sometime last year and then also try him for the surpass with the elevated offer. We could definitely meet both minimum spends. We are in the process of remodeling our shower and one of our bathrooms and so we can definitely meet it both on both cards. I'm just not sure if he'll get approved or not, and when I try I keep getting the pop up. So I'm an Amex pop-up jail, which is frustrating because I've been there for a very long time. I don't think I've ever even had an Amex personal card and they do not want me to get one. So TBD on that. But that's kind of what's going on in our ecosystem over here.

Speaker 1:

Okay, so let's jump into our positioning flight that we took to Chicago before our Europe trip, so when I was booking our flights and I potentially touched on this piece in the Paris episode. But I booked it so far out that the Phoenix to Paris direct route actually hadn't even been opened yet. Like you couldn't book it using points yet and I got impatient and so I, you know, looked around like LAX, sfo, dallas, chicago, like Denver those are kind of all within a couple of hour flight from us where it would make sense to reposition, and they did have really good availability out of Chicago. So I was able to book us for 85,000 points on Air France from Chicago direct to Paris, and that's again the price for all five of us. Since I made that booking, air France has done it and Flying Blue has done a devaluation, so it will cost a little bit more, probably a little over 100,000 points now to do that same flight for five kids as long as they're all under the age of 12. But it was cheap enough that it made sense for us to reposition to Chicago.

Speaker 1:

So we did that using Southwest. We actually paid cash. We had a combination of Southwest credits that we had earned from a Southwest flight being delayed more than two hours, and I also had some gift cards that I had bought. Costco sometimes has Southwest gift cards where you it's like 450 and you get a $500 gift card. I didn't do that, but I did buy a Southwest gift card once or twice when AMX was having like the sale where you you can use one membership reward and it gives you like a $30 or $50 credit, and so I bought a Southwest gift card with that. So all in all, I think out of pocket, we spent three or $400 and the rest were credits and I felt like that was not bad for a positioning flight. The cost of the flights themselves was astronomical in my opinion I think it was close to $1,000. But because we had all those credits and the gift card, it brought my out of pocket down pretty significantly and I was okay with paying like the three or 400 that it ended up costing.

Speaker 1:

We flew from Phoenix to Midway on a direct flight it's about three hours from Phoenix and we stayed overnight at the Intercontinental Magnificent Mile. So let's talk about this hotel for a second. The Intercontinental is under the IHG umbrella and it was Chicago in March, so definitely not peak tourist time at all. In fact, it snowed the day that we were there, which my kids thought was incredible. They loved it so much the day that we were there, which my kids thought was incredible. They loved it so much.

Speaker 1:

But we used the free night certificate that comes with my IHG Premier Rewards card to book that one night. And again, I booked for four people. Obviously we have five. It worked out fine. To get from the airport to the hotel, we took a taxi Actually, no, not a taxi, we took a Lyft. My five year old used the ride safer vest in lieu of a car seat and that worked out really well.

Speaker 1:

We checked into the hotel and they gave us you know I had booked a standard room and they gave us the room. We went up to the room and it was very small, like I am talking the size of a shoebox, two double beds, really no room for anything else. And the reality is it would have been completely fine for one night, even for all five of us, like we absolutely could have fit. It would have been fine. But about five minutes after we got into the room, I got a text from like the I don't know someone in the hotel, basically just saying you know, welcome and is everything up to your standards and is there anything we can do? And I have IHG platinum status with the premier rewards card, and so that is their second highest status level. So it's not highest. Highest would be diamond elite. So I'm sorry, it's not platinum, it's platinum elite, okay. And then highest is diamond elite, and so it's not the highest, but it's not the lowest. And I sent a simple text back saying thank you so much. Everything is great, but would it be possible to get a larger room? Due to my status? And they were pretty like within 20 minutes we were in a bigger room, and so I was super impressed with that.

Speaker 1:

Now the bigger room definitely still had the same like two double beds kind of vibe, but there was a ton more room. There was a little chair, and then we also asked them to bring up a pack and play. They ended up bringing up a crib, which I mean my five year old was like I'm not a baby, I'm not going to sleep in that, and she didn't actually. But we made it work. So one of my kids slept on the floor For the record. That was completely their choice, like they were excited to do it. And then there were actually two chairs in the room, and so we pushed the chairs together to kind of form, a little bed for my other kid, and then my daughter slept in the bed with one of us my youngest because she's the smallest and when I woke up in the morning my kid, who had wanted to sleep on the ground, was sleeping in that chair bed with their brother. So my two boys ended up sleeping in that chair, which was pretty funny because it was not very big, like it was probably the same size as the crib for the most part. But they made it work and they seemed fine about it. So no one complained, it worked great and it was definitely nice to have a smidge more space, even if it was just for that one night.

Speaker 1:

The other reason that I chose this hotel beyond the fact that I could use my free night certificate, which was expiring literally in April, and so I we used it in March, so just in the nick of time was they had an indoor pool. We used it in March, so just in the nick of time was they had an indoor pool, and that was important because I really wanted the kids to be able to get some energy out before we got on this long, you know, nine hour red eye flight, and so we did use the pool. It was great. This hotel also has like movie night. I think I don't know if it's every Friday or Saturday. We were there on a Friday so I'm not sure if they do it other nights, but definitely on Fridays they do like a movie by the pool where they set up like lemonade and popcorn and they put on a kid's movie and you can just go take your kids there and they can swim, and it was really nice. So we did that.

Speaker 1:

All the kids went in and I went in the water. The only thing I will say is this pool is not going to be great for young kids because the distance between the wall like the top of the pool, where you would get out, and the water is like a good two feet. So you have to use the ladder and if you're like wanting to hang on to the wall like it's, it's a little challenging. So, um, I went in with our five-year-old and it was fine, but I wouldn't have been comfortable with her being in there without one of us. It was also. It was also pretty deep. So two things to keep in mind. But if you've got, if your kids have floaties or they're greatimmers like my boys, then absolutely, and so they were playing. I think the movie was one of the more newer trolls movies and so it was great.

Speaker 1:

We went swimming, we had popcorn, we had lemonade and the kids got to swim and it was. It was a really fun thing to be able to do when it was literally snowing outside, so I would absolutely recommend this hotel. It was also very close and walkable to a lot of the touristy things, like the Starbucks Reserve. We probably could have walked to the Bean, but it was a little over a mile, so we took a taxi. We walked to the Ice Cream Museum and I'll get into details about that here in a moment. But all in all, we were pretty happy with with the hotel and the property would 100% stay again, and the service was very good, like the doorman was. The doorman was super helpful. We spoke to him and got his advice several times and he was great with the kids, and so we really enjoyed it and would definitely recommend it.

Speaker 1:

As far as activities, so we had about 24 hours in Chicago and so we wanted to make the most of it, so we did go and have some deep dish pizza at I forget the name, but one of the famous places. It'll come to me and the kids liked that. We also had wings. Um, my 11 year old loves chicken wings, so that was a win for him. And then we went to the ice cream museum and these ice cream museums are popping up in different like big cities, like I know they have one in New York City and a few others, and so we thought, okay, it'll be fun, we'll go check it out. I am going to be honest, I would not do that again. We didn't. The kids loved it. I as an adult, we didn't love it that much.

Speaker 1:

The ice cream is pretty basic, like it's. It's probably like Walmart brand ice cream. It wasn't anything special. The rooms are very like Instagrammy, so if you're, if you want to go take some cute photos for Instagram, you could definitely do that. It was cool for the kids.

Speaker 1:

Again, they enjoyed it. They did have like a hot dog ice cream that we tried. That was not good as a side note, but it was a fun you know, fun thing to try. We all laughed about it and at the end they have like a. It looks like a giant sprinkle pit. So imagine a ball pit but instead of the balls it's like multicolored rainbow sprinkles and that was fun too. I'm sure it's full of germs, but again, kids had a great time. They had some slides you could go down into it. It was maybe like a foot, a foot and a half deep. It wasn't super deep, but they had fun. I thought it was very expensive for what you got out of it. So again, I wouldn't personally pay for it again, but the kids the kids really enjoyed it and they still talk about it, so I guess that is worth something.

Speaker 1:

The other thing that we did was we woke up in the morning and went to the Starbucks reserve. We didn't end up getting anything here because the lines were very long, but we went up to each floor and just kind of scoped it out. It was cool. Not really like a kid vibe, though, and Dwayne loves shoes and all things Nike, so we also went in this Nike store that had like four levels to it. I don't know. It's again not my thing, but he was into it.

Speaker 1:

So we went, and then we met my brother in law who lives in Chicago. He lives about an hour outside of Chicago, actually. We met him for lunch at Ed DeBevix, which was walking distance from the hotel. Ed DeBevix is one of those restaurants where the servers are known for being rude to you. So instead of like being like, oh hi, welcome in Nice to meet you, they're like, what do you want? Like, get out of my face, like, and it's funny. And so we went there.

Speaker 1:

We ate. It's basic, like diner food. The kids enjoyed it. My 11 year old was working on his comebacks like to the server, like for like 10 minutes and then she would come back and he would use it and she was totally unfazed and it was hilarious because he was like getting kind of annoyed and I thought it was just the best. They do like some singing and dancing at one point and it's, it's funny, it's cute. I would totally go there again, but again, the food is basic diner food. So just keep that in mind, but that you don't go for the food, you go for the atmosphere, right?

Speaker 1:

Also, going back to the pizza, it was Lou Malnati's that we went to and had the deep dish pizza. So I mean that's a Chicago staple. I've had it before, but my kids, my kids had never been to Chicago, so this was like a quick introduction to Chicago for them. So this was like a quick introduction to Chicago for them. We looked at the river. We were actually there about a week before St Patrick's Day, so I was telling them that the river is going to be green in about a week, you know, in honor of St Patrick's Day. And so then we had a whole conversation about how that would work and the truth is I have no idea. And the other thing is we went to the bean, so we did, we took a taxi to the bean just kind of to see it. I know it was closed for a while. It is open now. Um, you know the kids I don't know if they really cared about the bean, but again, they still talk about the ice cream museum. So if you want to spend 200 plus dollars to give your kids a good memory, you can do that. Let's see what else.

Speaker 1:

Using the free night certificate from this credit card for a positioning flight is a fantastic use of it and the the. So the way that the IHG free night certificates work is you can get a free night in a hotel up to 40,000 points If it. If the room that night costs more than 40,000 points, then you have to pay that balance of points. So, like you know, if you don't have any, then you could maybe buy some, or you just can't use the certificate for that night. For the night that we stayed when I booked it it was around 37,000 points a night. So with the free night certificate it was completely free and I basically was very close to the $40,000 or, I'm sorry, the 40,000 point value, so I felt really good about that. Again, we stayed for free, so I don't know what more I could really ask for for free, so I don't know what more I could really ask for.

Speaker 1:

Cards like this that have this benefit, I think, make positioning flights much more doable. And we definitely didn't want to fly up on the same day, just in case there were any delays or anything like that, and because we were flying into one airport and out of another. So that would have just been way too stressful to do all in one day, especially when you have really no control over whether or not your plane is on time. And so we flew into Midway, we went into the city for you know, about 24 hours, and then we took a taxi back from the hotel to O'Hare and we flew direct out of O'Hare into Paris, and obviously we have a whole Paris episode and several other episodes about our Europe trip. If you are new and haven't heard those yet, I definitely think they're worth a listen because we had a great time. We had a great trip.

Speaker 1:

But I think positioning flights in general can be super, super helpful when you're trying to fly. A lot of people like we are, and this allowed us to save a ton of points and have a really fun experience as well. So now my kids have been to Chicago. It's almost like getting two trips for the price of one in a way. So I hope this episode was helpful.

Speaker 1:

If you've been considering a positioning flight, next week's episode is actually going to go into much more detail about how they work and maybe some tips and tricks that I've learned along the way, because we have several more positioning flights coming up this year and next. So definitely listen into that. If you would like more information and if you get any value out of this podcast whatsoever, I would be so, so grateful if you would take two seconds to go to wherever you listen to this podcast and leave us a rating or review. That really helps more people find our podcast, and that is my goal is to grow the podcast. So thank you very much for listening. We appreciate you. Come say hi to me on Instagram at travel party of five. I've been having some really good conversations over there in my DMS and I am super happy every time you message me. Okay, have a great week and I will catch you on the next episode. Bye.