Seaside Haven At Shoreline Journeys: Chicago Trip Recap
Happy Sunday! It’s hard to believe another week has passed. And crazy to think that we are back almost a week from our fun Chicago weekend! Trip #1 of the amazing Summer of travel is in the books, and I thought I would spend some time sharing a quick recap.
There is so much to see in this city that we could have probably used a few more days to slow down and take it all in. I don’t regret it though, as we had a blast. From spending time with friends, to all the good eats, to the excitement of experiencing Wrigley Field, it was a trip to remember.

Shoreline Journeys participates in affiliate marketing programs. I may receive a small commission from any purchases you make through links on this blog. Please see my full disclosure policy for more information.
We managed to cram so much stuff into a short amount of time, it’s hard to believe. I am going to share some of the highlights with you, and just know that I will write more in further detail in future blog posts. Wrigley Field deserves a post all of it’s own, and I will share that later in the Summer.
Where We Stayed In Chicago
You would think that being a travel agent, I could easily pick a hotel without thinking. Let me let you in on a little secret, it took me about a month to finally pick one. And I think it was the perfect spot for us! We stayed at the Residence Inn Chicago Downtown Magnificent Mile. It is a Marriott brand hotel, and it was at a great spot.
It was a really nice room and it worked very well for our needs. With the included breakfast buffet, and being in walking distance to a lot of the major spots we wanted to see, it was the right choice. Our friends stayed here as well, and they enjoyed it too!


The hotel staff were very friendly, and it served our needs well. I will post a full review of the hotel at a later time when I can. The two biggest surprises: a huge 4 story Starbucks and the Harry Potter Chicago store were only steps away. Our hotel is the tan building just behind it, so we were really close.

The Harry Potter shop was a half block down in the opposite direction from the Starbucks. They had a really cool queue to get in, and it went fairly quickly.

The hotel is also in walking distance of some terrific eating places. Let’s talk a little bit more about those. Eating on vacation is some of my favorite things to do!
Chicago Eats: So Many Good Things, So Little Time
When you think of Chicago, the first thing that usually comes to mind in pizza. Deep dish pizza. Ooey gooey delicious deep dish pizza. Lucky for us, it was a short walk to Giordano’s for some of the best pizza around.


They have an amazing system set up for getting your table and your pizza. And to be honest, it did not seem like it took the 40 minutes they were saying. I guess partly because we were having such a good time catching up with our friends and enjoying the scenery.

We couldn’t come to Chicago, and not try some Chicago hot dogs. We were in walking distance of Portillo’s and had to check it out. What a cool atmosphere and the food was pretty good as well!

Youngest ended up getting it Chicago style, but I can never say no to a good chili cheese dog!

We liked it so much, we had to go back a second time. We took the time to relax and grab a table and just take in the ambiance. If you get the chance, you definitely need to stop in.


And we had to try some sweet treats, so we took a moment and stopped at Stan’s Donuts during our city exploration. Such a cute atmosphere and the donuts were delicious too!


That’s just a short description of some of the food we ate. Let’s move on to the main reason why we came to Chicago: baseball!
The Magic Of Wrigley Field
In case you didn’t know, our family are HUGE Philadelphia sports fans. Normally we just see them at Citizens Bank Park because we are only 90 minutes away. In 2024, we saw the Phillies play the Marlins in Florida, and had a blast.
We decided that we wanted to see the Phillies at another stadium in the US, so we came up with the idea of Chicago and seeing them at Wrigley Field. It worked out that they were playing on a weekend, so we made a whole mini-vacation out of it!

Let me start out by saying that the staff at Wrigley Field were absolutely some of the nicest people out there. Even though we were there decked out in our Phillies gear, they were gracious and helpful. And we had so much fun.
It was such a nice experience seeing a game in a stadium you have ever only seen on TV. Being there is like being part of history, and I loved every minute of it. Don’t skip out on a hot dog from the stadium. We also had to get hot chocolate because it was chilly.

It was very easy to use the public transportation system to get to and from the stadium, and it made it so much easier. The place to get on the train was near the hotel and we got back from the game in less than 30 minutes from leaving the game, which was nice.

We had nice seats for the game, and the absolute best part was seeing the Phillies win both the games we were at. To be honest, I would have been happy with 1 win, so it was a great for the double victory. The second game was definitely a nail biter and went into extra innings.


After the first game, we headed down to Al’s Beef for some eats before heading back to the hotel. I had to laugh as one “tough guy” was attempting to heckle us when we were coming out of the game. Sorry dude, you don’t mess with Philly fans. We just laughed and moved on. I will admit there are some Philly fans that give the rest of us a bad name, but we are not like that. It didn’t ruin our fun at all, and gave us a good laugh while we were eating and a fun story to tell in the future.

We headed back to the hotel on the train, and ended up falling asleep really early. It was windy and cold (I actually went and bought blankets in the gift shop and so did a lot of other guests) at the game, so I am not totally surprised. Youngest ended up going out to meet a friend that lived nearby, so at least one of us checked out the nightlife.
Checking Out The Local Sights In Chicago
On the Sunday before the game, we had all day to wander around and see some of the sights. My boys wanted to see Millenium Park, so we strapped on our walking shoes and checked it out.
We first made a stop and got some good pictures at the river. It was such a lovely day that I wished we would have had time to take in a boat ride.



It was a short walk further to get to Millenium Park, and we had to get some pictures at the Bean. It was a nice place to walk around and the day was perfect for it.



We walked a little bit further and checked out Lake Michigan, too. I thought it was a fun thing to add to my bucket list since I have never been that close to the Great Lakes.


All in all, it was a fun day before we headed to our second game of the weekend.
We were up super early on departure day to head back to the airport. Our UBER driver was on time, and we made it to the airport in plenty of time, got through security quickly, had a quick breakfast and then relaxed at our gate. I ended up sleeping the entire flight home, and we were back at our house in the early afternoon.
Now I am scheming for next year for which famous ballpark we can visit next. Any suggestions?
Next Up On The Travel Agenda: Sandals Grenada
Now that this trip is over, the husband and I have our anniversary trip coming up to Sandals Grenada. I really can’t wait! We have never been to this resort, and I have heard nothing but great things about it. From the service to the food, and our room category is something I have been looking forward to for a long time!
I plan on having a whole blog series on Sandals Grenada in the month of September, so mark your calendar and come back. I can’t wait to share it with all of you!
So now it’s off to make packing lists and make sure my clients are ready to travel for their trips coming up. There will be no Seaside Haven posts for the next couple of weeks, but will return in June. Have a wonderful day, and happy early Mother’s Day to all the Mom figures out there!
Want To Have A Vacation? Let Me Help You Out!
Are you convinced? Ready to experience this for yourself? As a travel agent, I would love to help you plan your next vacation. Simply fill out this contact form or send me an email and I will be in touch with you shortly!
More Posts You Will Enjoy Reading!
- Why Working With A Travel Advisor Makes The Most Sense
- Stress Less, Travel More: Why You Should Use a Travel Agent for Your Next Getaway!
- Skip the Stress: Let a Certified Sandals Specialist Plan Your Ideal Sandals Resorts Vacation!
- Flying A Day Early To Your Destination Is A Smart Travel Idea
My Favorite Travel Essentials You Will Love
- K.Y.S.S. Locking Bag or Backpack
- Duncan & Stone Travel Journal
- Sun Bum Original SPF 70
- Portable Power Bank Large Capacity
- Luggage Packing Cubes Set of 5