Trip Notes: A Father & Son Day Trip To Chicago For A Ballgame And A DO

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I’m a bit of a baseball nut. My parents can’t stand spectator sports, but both of my grandfathers are sports nuts, so apparently it managed to skip a generation.


Rafi, plane-spotting, from the Airspace Lounge CLE before our flight to Chicago on 9/7/15:



My maternal grandfather has taken me to hundreds of ballgames since my first, an Indians win over the Blue Jays at Cleveland’s old Municipal Stadium on 6/8/92. And I’ve cherished every one of them. Nowadays, my grandparents are snowbirds and spend their winters in Florida, but summertime means going to see our beloved Indians. In 2013 I even got to take a trip with my grandfather to all 3 sports hall of fames, capped off with seats on top of the Green Monster to see the Indians beat up the Red Sox. We were in 7th heaven.

My father-in-law would rather watch paint dry than go to a baseball game. But there’s something about baseball that’s magical for me. It’s carefree and every ballgame brings me back to my childhood. A sport with no clock or deadlines is a beautiful thing in a world where everything has a deadline. Just sitting out under the summer stars and shooting the breeze in between the action…it’s the stuff dreams are made of.

It helped that I was obsessed with math as a kid and baseball is as analytical as it gets. I was a studious kid, but after I finished my homework I’d study the Baseball Weekly and know the entire league’s stats by heart. Our class was featured several times in Baseball Weekly’s fantasy leaderboard.

And of course it helped that the Indians were amazing in the 90s.

So that feeling carried over into my adulthood. I’ve flown around the world in first class suites, but my coolest use of miles was for the opportunity to run out and steal second base during an Indians game.

So you can see why I was excited to bring Rafi to his first ballgame as a 2 year old. Since then I’ve brought Talia to her first game as well and then some.

While it’s always fun to root for the hometeam, it’s also great to see your team on the road. In 1995 as a 10 year old we stayed in Toronto’s Westin Harbour Castle when the Indians were there. Aside from getting tons of autographs we were even given free tickets to the Indians game by Manny Ramirez when we held the elevator for him.

Rafi has been on dozens and dozens of flights and is obsessed with aviation. He had been asking for a father son trip for years, even as a 2 year old he was asking to fly with me to Hawaii. So when he turned 4, it seemed like a great opportunity to bring him on a trip to see the Tribe on the road.

In July I asked on the DDF DO board if people were interested in seeing the Indians play the Cubs. That didn’t work out, but on September 3rd I asked if people wanted to have a Labor day DO and go to Milts, the Indians @ White Sox game, and Shallots for dinner.

I mean what could be better then getting to spend the day with my son sharing my passions for flying, talking miles, eating great food, and watching a ballgame?

Well it could, I asked my grandfather if he wanted to join us and he said that he would love to!

Meanwhile on DDF, there were several locals who also came for the DO and a longtime user even flew in from NYC for the day. Another DDFer couldn’t make it, but hooked us up with awesome comped tickets for the game!

So we got 4.5K BA Avios tickets and left bright and early to catch an 8:18am flight from Cleveland to Chicago.


Airspace Lounge CLE:




Thanks to the time zone difference, we got to Chicago before we left and had a solid few hours before Milt’s would open.

My father’s parents live in Northbrook in the summer, so we detoured there and Rafi got to spend some time watering plants with that set of great grandparents.

While driving from there to Milt’s we got stuck behind a train. I’m mumbling to myself about it getting late, but this was altogether fascinating for Rafi, he could not stop laughing at how long the train was and the situation we were in. Before the train finished going by though, Rafi had dozed off for a nap.

When we arrived at Milt’s he was still sleeping, but my Chicago based Aunt (4 years my senior), kindly volunteered to stay in the car with Rafi. She’s awesome like that!

Between other young DDF Jetsetters, my grandfather, a Roman Catholic postal worker, and myself, it was quite the eclectic DO. But those are the best kind of DOs. There is now a dedicated DO board on DDF where people get together to talk about miles, flights, or anything else under the sun.


Milt’s Brisket Chili Nachos are always great ($15, 8.5/10), especially since they listened to my review a couple years ago and got better chips:


There was no Fried Okra, but the Fried Green Tomatoes were unique and tasty as well ($7, 8/10):



Pretzel Bites were outstanding and addictive ($8, 9/10):




But the highlight is the Rib Sandwich ($18, 10/10). Spicy smoked rib meat in Milt’s excellent BBQ sauce with sauteed peppers and onions, it’s one of the best sandwiches around. The Milt’s Burger is an awesome sandwich as well thanks to the Brisket chili, “bacon”, and crispy onions on it, but the rib sandwich is just heavenly.

I’ve been kvetching for the rib sandwich to be on the menu for years and we had to special order this sandwich. Later in 2015 Milt’s finally added it as a permanent menu item!




In the meantime Rafi did wake up and came to join the DO where he was peppered by questions such as his favorite airplane type and airline. He’s quite the talkative one and was happy to oblige while eating a Milt’s Dog.

Despite some rain driving from Milt’s to Comiskey, it turned out to be a great day for baseball.

Rafi had a grand time at the ballpark. And he was thrilled with the parve dippin dots.



The Indians wound up taking down Chris Sale and the Sox 3-2.

But somebody wasn’t ready to leave when it was over…




What do you mean it’s over? C’mon guys, let’s play 2! Oh wait, that was the Cubs.




And of course a trip to Chicago wouldn’t be complete without a DO at Shallots.


Rice Crackers (9.5/10, $16) are always a highlight:




The Dynamite roll is excellent as well (9/10, $25)




Homemade Gnochetti was a very good dish (8/10, $15). Doesn’t compare to Mike’s Bistro’s version, though the portion is much more generous.



This garlic encrusted steak though stole the night, one of the best steaks I’ve ever had (10/10, $70). Unfortunately it was a special for the night, though you may be able to request to order it.


The strawberry shortcake dessert at Shallot’s is always good with their sugar biscuit interpretation of the dish. This time we got lucky though as the cookies were still in the oven. It took a little longer to receive, but it was pure bliss (10/10, $13). I told the authors of Secret Restaurant Recipes From the World’s Top Kosher Restaurants of a number of dishes to include in a 2nd volume of their book and they got the recipe for this dish and published it in Everyday Secret Restaurant Recipes: From Your Favorite Kosher Cafes, Takeouts & Restaurants




Rafi was up at 6am and didn’t get to sleep until past midnight. But he was amazing. Which is a good thing as he still talks about the trip and wants to know when we’re going on our next trip together. 🙂

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25 Comments On "Trip Notes: A Father & Son Day Trip To Chicago For A Ballgame And A DO"

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Bravo dan. I look forward to taking my 3 yr old to Chicago for a game and flight…maybe this summer!




Cool gutsy of u Dan to take ur little one to a Chris sale game most times that would end in a loss and some heartache


Make a DO of it 🙂

As a lifelong CLE sports fan, I’m quite used to heartache. It builds character 😉

But yes, the win was a very pleasant surprise.


I’m a jet fan so I can relate 😑


Nobody can relate to the suffering of CLE sports fans. My Uncle is 50 and has yet to see a CLE championship in his lifetime 🙁

Which explains why Clevelanders are just awesome 😉


Has anyone made the strawberry shortcake recipe from the cookbook? How does it compare?


@dan I beg to differ, as a Cubs fan and even as a bears fan recently


Great father son bonding. I’ve been doing this with my son and we’ve been to 15 ballparks so far. Thanks to avios! We also check out the kosher hot dog stands and Toronto has by far the best!! Grilled onions and largest assortment of condiments.


youve got quite the cooperative little guy! entertaining tr as usual!


As a lifelong CLE sports fan, I’m quite used to heartache. IT BUILDS CHARACTER. 😉


U win but barely 😉


Chicago sports teams have won at least 10 championships since the last Cleveland championship.
‘Nuff said.

Have you done Spring Training yet?
Cleveland used to have amazing grilled onions with their kosher hot dogs, but then they got cheap.

But we do have the best mustard in the world in Bertman’s ballpark mustard and their new beer mustard.




Thanks Dan for another great TR! Thoroughly enjoyable.


Your comment



Haven’t done spring training,were tying to get all 30 parks done in the next 4 years before my son goes to college. but we did do Cleveland and were happy to have the kosher dogs 2 years ago.


Did the Roman Catholic postal worker happened to be known as chaim?



Great report. You are blessed with many things, not the least of which is a wonderful and loving extended family!

DDFers might remember that my oldest and I are on a quest to see at game at every MLB park before he goes off to college. We have about 8 to go in the next 1-2 years. It would be great to make a DO out of one (or more) of them….


Ha! I didn’t see your post before I added mine. We’re on the same quest! Let’s connect on DDF.


That’s awesome, great bucket list and father-son time.

Hit up the DDF DO board 🙂

Uncle Em

Do you remember meeting an 11 year-old Prince on that trip to Toronto in the hotel lobby as well?
On our way out the Tigers were arriving with Cecil Fielder and his future All-Star son (who was huge even then).
Nice baseball TR on a cold and snowy day. Thanks.


Well said on your love of baseball and the beauty of the game, i feel the same way.


Get your priorities straight with your children. Food and Sports is not the passion you should be showing them. כי הם חיינו לאורך ימינו

"dan" likaf zecus...

@Judah: every person needs a bit gashmius in order to be going up in ruchnius, so the learning part shld be self understood, im assuming the rest of the 364 days a year he’s busy with his son learning and davening…it’s a few times a year he treats his son to an u said×›×™ הם חיינו לאורך ימינו and then those odd times Dan will show he treats his kid to some gashmiyus.