The interior of Rebar at Trump Tower

If buildings were sized like clothing, Chicago’s Trump Tower would fly an XXL flag over its front door. It’s not just tall; it’s all-around roomy. The lockers in the spa are so big I can barely reach the hooks. If I find myself walking down any of the hotel’s extra-wide hallways alone, I feel like Alice, post “shrink me,” and must resist the urge to skip from side to side in a zigzag pattern. And if I have visitors in from out of town, I always take them to the Trump for a cocktail—if only to overwhelm them with the gargantuan splendor.

Earlier this week, when my sister, Claire, and her friend Jenny were visiting from Kentucky, we headed to the Trump’s second-floor lounge, Rebar, with my teacher friend Tim in tow to cap off an exhausting day of eating and shopping with one final burst of consumption.

I wanted to give them a Trump experience—and a Trump experience they got.

“Table for four? Right this way,” said the hostess, ushering us toward a bank of windows overlooking the river. She laid cocktail menus on a round table that easily could have sat at least eight and smiled. “Your waiter will be right with you.”

We settled into the prearranged seating configuration and began hollering: “Hey, do you feel like we’re a little far away?” “Yes! You’re waaay over there!” “Can you pass me that drink list?” “Sorry, I can’t reach; let me walk it around!” “Maybe we should scooch in!” “But I can barely move this giant chair!”

We finally arranged ourselves in a line at the northwest quarter of the table—the side with the best views of the river, which, as always, was glitteringly spectacular. You should have joined us. There was plenty of room.

We ordered drinks (more on that in a sec), and Tim told a joke he’d learned from one of his first-graders that day:

Tim: Knock Knock.

Us: Who’s there?

Tim: The interrupting cow.

Us: Who’s the . . .

Tim (interrupting): MOO!

It was innocent conversational fare, but when the talk eventually took an R-rated turn, we again found our luxurious XXL table working against us. “He had a what? He wore it how? You saw it when?” we hissed, trying to keep it down while fielding raised eyebrows from a group of suits at the next table over.

The Chaser’s Trump Tip of the Day: If you’re a party of four, say you’ll you be two. If you’re a party of two, say you’ll be one—and share a chair.

And now, what to drink: 

1. After waffling between the Cassis and the Winter Magic (“Winter Magic sounds so good, and maybe a little dirty”), Tim went for the Cassis (black currant, St. Germain, and prosecco; $15). The verdict: “bountiful, bubbly, berrily boozy,” and perfect for the Indian summer day.

2. My encounter earlier in the day with a Sprinkles cupcake led me to order the Reveev ($15), which, with its organic Veev Açaí vodka, luscious Laurent Perrier Ultra Brut champagne, and fresh blackberries, seemed like the healthiest possible way to consume alcohol. It was smooth and sweet and went down fast.

3. Jenny went with a Kettle vodka martini, straight. “If it weren’t for those snacks on the table, I probably wouldn’t have remembered walking out,” she says.

4. Kentucky girl Claire ordered a Manhattan made with Booker’s bourbon, which is somewhere in the vicinity of 121 to 127 proof. Claire doesn’t mess around. This cocktail lasted an hour; one sip would do you for a full five minutes (I should know: We all took a turn).