Chicago hotel concierges routinely arrange horse rides, make plane reservations, or score last-minute seats to a popular musical, but some requests are a bit more demanding.

When a family from Arabia was staying at the Four Seasons Hotel Chicago, a family member asked concierge Edward Tobin if he could find out how much it would cost for 25 people to fly one way on a private jet from Chicago to Montreal. “I found a charter jet for $85,000,” says Tobin. “And they did book it.”

Planning the trip was all in a day’s work for Tobin. Hotel visitors ask Tobin and other hotel concierges for everything from nurse costumes to illegal drugs to help with perfecting a wedding proposal.

Tobin recalls a guest who gave a new car as a birthday present to his wife. “We had to find this really big bow” to put around the car, Tobin says. “And we only had two or three hours” to find a bow, which the hotel borrowed from a car dealership on Clark Street.

Another time a wealthy San Francisco woman brought her 16-year-old niece to town to shop before the girl’s school year began. “She thought that I was friendly and nice,” Tobin says, so the woman asked him to come along and offer input about the clothes that the girl tried on. They rode in a chauffeured car and shopped for a few hours at unique boutiques and vintage stores.

Andrea Behrstock, a concierge at the Doubletree Guest Suites, says, “Sometimes people want hair appointments for their dolls” at the American Girl Place.

She also recalls reserving a window table at Spiaggia for a couple that loves to row boats. A waiter brought to the woman an oar, which read, “Will you marry me?”

Another time the Doubletree lined a room with rose petals for a man planning to propose to his girlfriend. The man delivered one of his girlfriend’s fancy dresses and a pair of her shoes, along with a new fancy dress and pair of shoes. He requested that a note be left to his girlfriend saying to go to the hotel’s downstairs bar. When she reached the bar, he surprised her there. They had a drink, took a carriage ride to a restaurant, and he proposed. “He planned it so beautifully,” Behrstock recalls.

Dozzy Ibekwe, a concierge at the Amalfi Hotel, says, “If it’s within the law and ethical, we take care of it.”

As for the wedding proposals that he has helped with, Ibekwe says with a laugh, “We haven’t had a ‘No’ yet.”