Chicago Guesthouses and B&B

From dramatic views and rose-petal bubble baths to hostel bunks and homestays, you’ll find amenities at every level in Chicago. Finding something at a reasonable rate? That’s more difficult. Chicago is the Midwest’s biggest city and convention central, so demand is high year-round, and it gets near impossible to find value on summer weekends (June through August), when the festival season and tourism peak. If you’re willing to be flexible with your dates, you’ll have a better chance of finding a place to stay that won’t break the bank. Consolidators and online room bookers are another way to go if cost cutting is your primary objective.

More than 30,000 hotel rooms blanket the city, most in high-rise buildings. With so many choices, picking a place can be daunting. It helps to decide on a neighborhood first. If you’re going to tromp up and down the Mag Mile and binge on shopping, the Gold Coast or slightly more moderately priced Near North are the places to lay your head. If you’re interested in snoozing amid the architecture and museums of the Loop and South Loop, there are plenty of options in those central neighborhoods, almost all of which are located near El stations for easy transportation to anywhere in the city. These core areas have the greatest concentration of hotels, and generally speaking, the farther south you go, the lower the prices.

Less central, but more personal, are area bed-and-breakfasts. A few old townhomes – in Wicker Park, Lake View and Andersonville – have been turned into great places to stay. There are even a couple in the Gold Coast. Pluses such as free internet, quieter surrounds and some free parking give B&Bs more bang for the midrange buck. Check out Bed & Breakfast Chicago, which represents 18 local guesthouses. Most do have minimum stay requirements.

Vacation rentals in local apartments are also a good deal in Chicago, especially for traveling families.

Using search engines, you’re likely to find the most affordable chain options close to Chicago’s airports. Even though these are connected by reliable public transportation, it’s worth it to put down a little extra to spare the long commute.

from $186 per night

Inn

Ruby Room

Wicker Park, Bucktown & Ukrainian Village

Take an Anusara yoga class, go on a guided intuitive journey or ...

Chicago Guesthouses and B&B

Ruby Room

$15 Per Night, 15 Min To Loop Apartment

Villa Toscana

Old Chicago Inn

Wicker Park Inn