The Best Chicago Hotels For a Staycation

From art installations to skyscrapers to sports, from Magnificent Mile shopping and world-class theatre, to the beaches on Lake Michigan…Chicago has a lot going on. And what better way to see it than like a tourist. What? We’re talking about a stay-cation! Instead of flying somewhere else and booking a hotel, get out of your place for the weekend. Dress up, see a show, hit a nice restaurant, or just book a spa treatment and let someone else make the bed for a change. If you’ve never booked a stay-cation, give it a try. And as the weather’s getting colder, room prices are going down and it feels quite cozy in a nice hotel room!

This article will show you a few great options for a ‘stay-cation’ here in the CHI.

The Drake

Yes, we’re starting out with the absolute best. (Or at least, the most well-known.) If you don’t already know, the Drake is ‘the’ big luxury hotel in Chicago. It’s where presidents, kings and queens, and famous people from all walks of life stay. They were the first hotel in Chicago to have air conditioning. They still use elevator operators. It’s one of those kinds of places. Ever been inside? Slept on one of their beds? Why not? You might not book the ‘Princess Diana Suite’ (which exists) but going there on a random Tuesday for a spa treatment puts you into another world. Even if only for a little while. Expensive, but worth it.

Chicago Athletic Association Hotel

It was a glamorous private club for movers and shakers for over a hundred years. The Venetian Gothic exteriors and luxurious interiors have few equals in the world, much less the city. Here’s where you go for old-school cocktails, steaks, classic luxury. Speaking of old-school, if you book here don’t forget to check out the Milk Room. The name is a bit of a misnomer, as during Prohibition there was a secret eight-seat ‘microbar’ created so that the club’s often-notorious members could imbibe. It still exists, and the vibe does as well.

The Langham

As fancy as the first two are, neither might be as artistically cool as the Langham. It’s housed in a Mies van der Rohe skyscraper, and the interiors are similarly sleek. They have a decent art collection, and their restaurant Travelle is quite lovely. The Langham literally employs a team of butlers, so if you’re into getting true first-class treatment, they can solve almost any problem you might encounter. Hit the Chuan Spa or the pool if you’re in need of further relaxation.

The Peninsula

Some hotels are about opulence. This one is about softness and a bit of minimalism. It’s part of the Hong Kong and Shanghai Hotels Group and is in the middle of the Magnificent Mile. A rather luxurious stay-cay might involve a day of shopping, followed by room service then a nightcap at the fancy Z Bar, one of the coolest rooftop lounges in the city. How can you not feel like a Hollywood star after that? Pro tip- if you really like it here and you’re a Chicago resident, you can join the fitness center and spa on a membership basis and do this sort of thing regularly. 

The Abbey Resort

Okay, we cheated a bit here. If you go an hour and a half away from the city, is it really a stay-cation? But sometimes you wanna get away without really getting away! And The Abbey Resort is considered one of the top 100 spas in the USA. Obviously, this is more if you want peace and quiet instead of bright city nights. It’s a 30-acre property surrounded by the woods and water of Lake Geneva, and they have a full spa and fitness program as one might imagine. Though, if it was us…the Abbey might be a great place to book a room for a couple of days and do absolutely nothing. Maybe read a book! 

Thanks for reading this article, and hopefully it’s helped you think about a stay-cation of your own.


We are one of Chicago’s leading providers of comprehensive real estate services. We are home to an ever-growing team of savvy & reputable local realtors, seasoned property managers, and customer-service-oriented staff. Whether you’re looking to find a new home, sell your home, or have your property managed, let us be your trusted real estate advisors.


Leave a Reply