Illustration by David Galletly
Illustration: David Galletly

Hamilton Nights

Peninsula Chicago

108 E. Superior St.,

From:$2,250 for two (through March 2017)
Perfect for:The Hamilton obsessed
The package:Two tickets to the show and a stay in a deluxe suite, plus breakfast, parking, and a chocolate treat in the shape of the Hancock Center
How much you’re really saving:The suite and breakfast cost about $1,000. That means you’re paying around $600 each for seats in orchestra center (roughly what a broker charges). Face value? About $180.
Bottom line:No deal here. Just guaranteed seats to the show.

Guys’ Getaway

Acme Hotel Company

15 E. Ohio St.,

From:$650 for six
Perfect for:A mancation
The package:The whole crew can plop in a four-room block (one room will be set up for a card tournament, with snacks and drinks) before visiting three breweries. Counter the boozing with the Hair of the Dog add-on ($25), which includes Gatorade, aspirin, and a $25 gift card from M Burger.
How much you’re really saving:The block of rooms would typically cost about $440.
Bottom line:No big savings for a local men’s getaway—but you’d blow your mortgage payment for anything like it in Vegas.

Brunch and Recover

Thompson Chicago

21 E. Bellevue Pl.,

From:$479 for two
Perfect for:Holiday party animals
The package:Replenish your hung-over bod with a hydrating IV, oxygen therapy, and an in-room breakfast from Nico Osteria. (Plus a free chauffeured ride in the hotel’s Lexus if you absolutely must venture out.)
How much you’re really saving:The IV treatment alone, including house call, would normally set you back $750.
Bottom line:A pro-level hangover cure while you lie in bed might be the best money you ever spend.

Kids Kamping

Radisson Blu Aqua Hotel Chicago

221 N. Columbus Dr.,

From:$249 for four
Perfect for:Stir-crazy families
The package:An in-room tent, milk and cookies, a teddy bear for each child, and a s’mores kit for the fire pit on the hotel’s huge outdoor terrace? Talk about glamping.
How much you’re really saving:The package costs about $50 more than an ordinary night in the hotel—but that stay doesn’t come with a tent, toys, cookies, and s’mores.
Bottom line:It’s less about huge savings than a clever change of scenery for kids.