Top Guest Houses in Chicago in 2026

A river with a yellow boat, surrounded by tall buildings and a bridge.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Chicago guest houses

Chicago Avenue Inn

Humboldt Park

"Location worked very well for our needs. Location was a bit sketchy but we came across zero issues with the neighborhood. Room wasn’t perfect and could have been a little more clean as there was a dirty rag on the floor and the bed sheets/pillows had some questionable stains. Best New Subs across the street was delicious and worth stopping by. Keep in mind all amenities, bathrooms, kitchen, lounge areas are all shared spaces. Doors to the rooms could have been more secured with deadbolts."

Julian

฿5,798 total

includes taxes & fees

14 Jul - 15 Jul

Villa Dubois Guest House

Bronzeville

Stefano

฿5,290 total

includes taxes & fees

12 Jul - 13 Jul

The Plainfield Inn

Plainfield

Lucas

฿3,695 total

includes taxes & fees

21 Jul - 22 Jul

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Chicago Hotel Reviews

Hyatt Regency O'Hare Chicago

8/10 Good

"Dated but comfortable and had all amenities"

Hotel Riu Plaza Chicago

10/10 Excellent

"The staff were absolutely wonderful. Every encounter with a staff member was pleasant and friendly. The doormen were exceptional with their assistance to me and my husband by aiding me in loading my husband's mobility scooter that we rented and it was very heavy. They were kind, helpful, friendly and compassionate and I appreciate them very much. The breakfast was delicious and very abundant with selections of breakfast food from all over the world. The coffee was strong and yummy, and I never say that about brewed coffee unless it's brewed by myself plus I was a barista for 18 yrs. My husband was happy every morning with his filling selections and variety of items. The bacon was perfectly cooked and their chicken sausage is the best! The French toast was wonderful also. The view from our 25th floor room gave us many spectacular sites, from colorful lights, to bustling sidewalks and vibrant city life. The city skyline at night from the rooftop bar at something I am unable to adequately describe other than they were remarkable in way I am unable to remark on, other than beautiful and amazing. This trip meant a lot to my husband and I for a few reasons. One is it was our first time away together in over 17 years and two, he was diagnosed with terminal brain cancer in December on 2025 so we made memories on this trip we will treasure for years to come. The staff even assisted our cousins who met up with us by letting/helping them set up special surprises for us. Top notch."