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Guesthouses in Chicago You’ll Love

Top-Rated Chicago Guesthouses for Every Budget and Style!

Looking for a guesthouse in Chicago (Illinois)? Discover and compare a wide selection of cozy guesthouses, bed & breakfast and inns in Chicago – perfect for solo travelers, couples, or families. Whether you’re planning a weekend getaway or an extended stay, you’ll find charming, affordable options starting at just $21.17 per night. From centrally located guesthouses near downtown to peaceful retreats close to the beach, explore accommodations that match your style and budget.

Easily browse photos, read guest reviews, and book the ideal guesthouse in Chicago today.

We found 27 Guest-houses in Chicago and the surrounding area (within 30 miles)

HI Chicago Hostel in Chicago, USA

HI Chicago Hostel

Hostel in Chicago, Illinois , 24 E Ida B Wells Drive
Experience the excitement of Chicago from the center of all the action at this beautiful historic hostel, offering comfortable and contemporary accomm...
  • Street parking
  • Family rooms

Very good 9747 Reviews 8.5

from $30.52 Show details »

Chicago Getaway Hostel in Chicago, USA

Chicago Getaway Hostel

Hostel in Chicago, Illinois , 616 West Arlington Place
This Chicago hostel is located in Lincoln Park and is a few blocks from the Fullerton subway station.
  • Parking
  • Family rooms

Very good 4841 Reviews 8.3

from $51.66 Show details »

Wrigley Hostel - Chicago in Chicago, USA

Wrigley Hostel - Chicago

Hostel in Chicago, Illinois , 3514 North Sheffield Avenue
Wrigley Hostel is just steps away from Wrigley Field and only a 10-minute walk to the nearest public beach.
  • Parking

Very good 589 Reviews 8.2

from $29.35 Show details »

Stay 424 in Chicago, USA

Stay 424

Hostel in Chicago, Illinois , 1415 North Ashland Avenue #2
Stay 424 in Chicago provides adults only accommodations with a shared lounge, a terrace and a restaurant.
  • Parking
  • Restaurant

Good 262 Reviews 7.0

from $37.13 Show details »

Ohio House Motel in Chicago, USA

Ohio House Motel

Motel in Chicago, Illinois , 600 North La Salle Drive
Ohio House Motel is conveniently located in downtown Chicago, 1.5 miles from Navy Pier and 2.4 miles from Shedd Aquarium.
  • Parking

Very good 1752 Reviews 8.4

from $72.02 Show details »

Villa D' Citta in Chicago, USA

Villa D' Citta

B&B in Chicago, Illinois , 2230 North Halsted Street
Villa D' Citta enjoys a location in Chicago, 1.3 miles from Fullerton Beach and 1.4 miles from North Avenue Beach.
  • Parking
  • Family rooms
  • Breakfast in the room
  • Kid meals
  • Kid-friendly buffet

Superb 37 Reviews 9.2

from $248.36 Show details »

The Polo Inn Bridgeport U.S.A. in Chicago, USA

The Polo Inn Bridgeport U.S.A.

B&B in Chicago, Illinois , 3322 South Morgan Street
Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A.
  • Parking
  • Restaurant
  • Kid meals

Superb 49 Reviews 9.2

from $304.83 Show details »

Wicker Park Inn in Chicago, USA

Wicker Park Inn

B&B in Chicago, Illinois , 1329 North Wicker Park Avenue
Offering air-conditioned rooms in the Wicker Park district of Chicago, Wicker Park Inn is 2.4 miles from United Center.
  • Parking
  • Breakfast in the room
  • Allergy-free room

Fabulous 42 Reviews 8.9

from $214.75 Show details »

Rays Bucktown Bed and Breakfast in Chicago, USA

Rays Bucktown Bed and Breakfast

B&B in Chicago, Illinois , 2144 North Leavitt
Rays Bucktown Bed and Breakfast provides a sauna and spa facilities, as well as air-conditioned accommodations in Chicago, 2.5 miles from Lincoln Park...
  • Parking
  • Pets allowed
  • Sauna
  • Family rooms
  • Breakfast in the room

Exceptional 150 Reviews 9.5

from $153.31 Show details »

The Sono Chicago in Chicago, USA

The Sono Chicago

B&B in Chicago, Illinois , 1428 North Cleveland
The Sono Chicago is located in The Old Town neighborhood of Chicago.
  • Parking

Superb 343 Reviews 9.3

from $486.00 Show details »

The Publishing House Bed and Breakfast in Chicago, USA

The Publishing House Bed and Breakfast

B&B in Chicago, Illinois , 108 North May Street
Offering a bar and a shared lounge, The Publishing House Bed and Breakfast in Chicago is close to United Center and Union Station.
  • Parking
  • Restaurant
  • Bar

Superb 38 Reviews 9.4

from $198.75 Show details »

The Villa Toscana in Chicago, USA

The Villa Toscana

B&B in Chicago, Illinois , 3447 N Halsted
The Villa Toscana provides free Wifi and rooms with air conditioning in Chicago.
  • Parking
  • Pets allowed

Very good 240 Reviews 8.0

from $57.53 Show details »

Private room with full size bed in Lakeview - 3C in Chicago, USA

Private room with full size bed in Lakev...

B&B in Chicago, Illinois , North Sheffield Avenue 3222
Private room with full size bed in Lakeview - 3C offers accommodations in Chicago, 1.6 miles from Fullerton Beach and a 10-minute walk from Wrigley Fi...
  • Parking
  • Pets allowed

Pleasant 2 Reviews 6.0

from $50.00 Show details »

Private bedroom with shared bath in Chicago, USA

Private bedroom with shared bath

B&B in Chicago, Illinois , 3445 North Halsted Street
Private bedroom with shared bath is located in Chicago, just 2 miles from Lincoln Park Zoo and 3.7 miles from 360 Chicago.
  • Parking
  • Pets allowed

no reviews

from $116.01 Show details »

Four bedroom apartment in Chicago, USA

Four bedroom apartment

B&B in Chicago, Illinois , 3445 North Halsted Street
Four bedroom apartment is located in Chicago, just a 9-minute walk from Wrigley Field and 2 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed

Good 57 Reviews 7.6

from $81.02 Show details »

Private room with shared bathrooms in Chicago, USA

Private room with shared bathrooms

B&B in Chicago, Illinois , 3445 North Halsted Street
Private room with shared bathrooms is located in Chicago, just a 9-minute walk from Wrigley Field and 2 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed

no reviews

from $79.00 Show details »

Blue Room in Dorothys BNB in Chicago, USA

Blue Room in Dorothys BNB

B&B in Chicago, Illinois , 3445 North Halsted Street
Blue Room in Dorothys BNB is a recently renovated bed and breakfast in Chicago, near Wrigley Field.
  • Parking
  • Pets allowed

no reviews

from $128.93 Show details »

Green Room in Dorothys BNB in Chicago, USA

Green Room in Dorothys BNB

B&B in Chicago, Illinois , 3445 North Halsted Street
Green Room in Dorothys BNB is a recently renovated bed and breakfast in Chicago, near Wrigley Field.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $84.00 Show details »

McCormick Place Guest House in Chicago, USA

McCormick Place Guest House

Guesthouse in Chicago, Illinois , 3643 South Indiana Avenue
McCormick Place Guest House in Chicago provides accommodations with a garden and a shared lounge.
  • Parking
  • Family rooms

Good 181 Reviews 7.1

from $84.00 Show details »

Villa Dubois Guest House in Chicago, USA

Villa Dubois Guest House

Guesthouse in Chicago, Illinois , 3722 South Calumet Avenue
Villa Dubois Guest House offers accommodations in Chicago, 1.6 miles from Oakwood Beach and 1.2 miles from Guaranteed Rate Field.
  • Parking
  • Family rooms

Pleasant 238 Reviews 6.4

from $90.00 Show details »

Logan Square Coach House in Chicago, USA

Logan Square Coach House

Guesthouse in Chicago, Illinois , 2438 North Maplewood Avenue Coach House
Featuring a garden, Logan Square Coach House provides accommodations in Chicago.
  • Parking

Superb 29 Reviews 9.2

from $147.95 Show details »

Stylish Shared Condo Minutes from Downtown Chicago, 1Bedroom and Shared access in Chicago, USA

Stylish Shared Condo Minutes from Downto...

Guesthouse in Chicago, Illinois , W 15th St
Stylish Shared Condo Minutes from Downtown Chicago, 1Bedroom and Shared access offers accommodations in Chicago, 1.8 miles from United Center and 2.7 ...
  • Parking

Okay 5 Reviews 5.8

from $181.34 Show details »

Modern Shared Condo Near Downtown Chicago, Flexible Room Options and Shared Amenities in Chicago, USA

Modern Shared Condo Near Downtown Chicag...

Guesthouse in Chicago, Illinois , W 15th St
Modern Shared Condo Near Downtown Chicago, Flexible Room Options and Shared Amenities offers accommodations in Chicago, 1.8 miles from United Center a...
  • Parking

Pleasant 8 Reviews 6.8

from $154.43 Show details »

Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities in Chicago, USA

Spacious Shared Condo Near Downtown Chic...

Guesthouse in Chicago, Illinois , West 15th Street
Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities provides air-conditioned rooms in Chicago.
  • Parking

Passable 2 Reviews 5.0

from $181.34 Show details »

Charming Shared Condo in Prime Chicago Location, 1 Bedroom and 1 Bathroom in Chicago, USA

Charming Shared Condo in Prime Chicago L...

Guesthouse in Chicago, Illinois , West 15th Street
Charming Shared Condo in Prime Chicago Location, 1 Bedroom and 1 Bathroom provides air-conditioned rooms in Chicago.
  • Parking

No reviews yet 1 Reviews 1.0

from $181.34 Show details »

Number of Guesthouses in Chicago 27
Number of guest ratings 216,870
Average price per night $111.00
Lowest price per night $21,17
Highest price per night $520,32

Top 10 Most Popular Guest-houses in Chicago

Explore the Most Popular Guest-houses in Chicago – Ranked by Average Guest Ratings.

Top 10 Cheapest Guest-houses in Chicago

Discover the Cheapest Guest-houses in Chicago – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Guest-houses in Chicago

Check out the Most Booked Guest-houses in Chicago – Based on Guest Popularity.

Guesthouses in Chicago (Illinois), small and cozy

Guesthouses are small, cozy accommodations that offer a more personal and authentic experience than larger hotels. Often family-owned and operated, guesthouses provide a home-away-from-home atmosphere for travelers seeking a warm and welcoming environment. Typically located in residential areas or rural settings, guesthouses offer a peaceful and relaxing escape from the hustle and bustle of the city. With a focus on personalized service and attention to detail, guests can expect comfortable rooms, authentic food, and insider tips on local attractions and activities. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, guesthouses in Chicago offer a unique and memorable way to experience a new destination.

Find the best guesthouse in Chicago for your needs

When looking for the best guesthouse for your next stay in Chicago, there are a few key factors to consider. First and foremost, location is important - choose a guesthouse that is conveniently located to the attractions and activities that you want to experience. Next, read reviews from previous guests to get a sense of the guesthouse's quality, cleanliness, and hospitality. Look for guesthouses that have consistently positive reviews and a high rating. Additionally, consider the amenities offered, such as free Wi-Fi, breakfast, and on-site parking. Finally, don't forget to consider the price - guesthouses can vary widely in price, so be sure to choose one that fits within your budget. With these factors in mind, you can find the best guesthouse in Chicago for your next vacation and enjoy a memorable and comfortable stay.

Accommodation data and pictures provided by Booking.com