Hamilton Nights
Peninsula Chicago
108 E. Superior St., chicago.peninsula.com
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., acmehotelcompany.com
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., thompsonhotels.com
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., radissonblu.com More Top Picks Best Bose Speakers
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.