Book a Bed and Breakfast in Southwest Side, IL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top B&B in Southwest Side

The Sono Chicago
1428 N Cleveland Ave Chicago IL
$206 nightly
The price is $242 total per night
$242 total
Sep 30 - Oct 1
Total with taxes and fees
A rooftop terrace, free self parking, and concierge services are featured at this bed & breakfast. WiFi in public areas is free. A terrace, a lobby fireplace, and luggage storage are also on offer.
Parking included
Free WiFi

The Villa Toscana
3447 N Halsted Chicago IL
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $116 total per night
$116 total
Sep 30 - Oct 1
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and luggage storage are also on offer.
Pet friendly
Parking included

House 5863 - Chicago Bed and Breakfast
5863 North Glenwood Avenue Chicago IL
$179 nightly
The price is $210 total per night
$210 total
Oct 4 - Oct 5
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the express check-out and free internet in public areas. A terrace, a garden, and a snack bar/deli are also on offer.
Breakfast included
Free WiFi

Dorothy's
3445 N Halsted St Chicago IL
$87 nightly
The price is $96 total per night
$96 total
Sep 30 - Oct 1
Total with taxes and fees
Free WiFi in public areas, a communal living room, and luggage storage are available at this bed & breakfast. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.
Breakfast included
Pet friendly

Ray's Bucktown B&B
2144 N. Leavitt St Chicago IL
$185 nightly
The price is $208 total per night
$208 total
Sep 29 - Sep 30
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a rooftop terrace on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Spa

Harvey House Bed & Breakfast
107 South Scoville Avenue Oak Park IL
$293 nightly
The price is $325 total per night
$325 total
Oct 5 - Oct 6
Total with taxes and fees
A hot tub, free self parking, and wedding services are featured at this bed & breakfast. Guests will appreciate free perks like daily breakfast and WiFi in public areas. A business center, a snack bar/deli, and a lobby fireplace are also on offer.
Hot Tub
Breakfast included

The Publishing House B&B
108 N May Street Chicago IL
$251 nightly
The price is $284 total per night
$284 total
Oct 25 - Oct 26
Total with taxes and fees
An attached winery and a restaurant are featured at this smoke-free bed & breakfast. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free full breakfast.
Breakfast included
Free WiFi

Villa D' Citta
2230 N Halsted Street Chicago IL
$252 nightly
The price is $296 total per night
$296 total
Oct 7 - Oct 8
Total with taxes and fees
This bed & breakfast features free WiFi in public areas, concierge services, and self parking. Enjoy the free cooked-to-order breakfast each morning. A terrace, limo/town car service, and a garden are also on offer.
Breakfast included
Free WiFi

Wicker Park Inn
1331 N Wicker Park Ave Chicago IL
$317 nightly
The price is $373 total per night
$373 total
Oct 4 - Oct 5
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. Self parking, a garden, and express check-out are also offered.
Breakfast included
Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top hotels in Southwest Side

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$157 nightly
The price is $187 total per night from Oct 26 to Oct 27
$187 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (10,269 reviews)
Bed and Breakfast in Southwest Side
Some travelers are just looking for a place to crash at night. Not you, wise wanderer. Where you stay is an integral part of the destination itself. For you, we recommend a beautiful bed & breakfast. Before images of creaky Victorian houses and floral wallpaper creep into your mind, know that today’s B&B scene is a completely different story.






