Free $50 gift card with a $250+ gift card purchase

Chicago Bed and Breakfasts

Sort by:

Inn of the Month: Villa D' Citta

Chicago, IL

Be A Guest Of Chicago's Most Unique
Experience. Call 800-228-6070

from $129

4.9 (820)
Accepts:

Visit Website

Inn of the Month

Villa D' Citta

Villa D' Citta

from $129

Chicago, IL

4.9 (820)

Visit Website

Harvey House Bed and Breakfast

Oak Park, IL

On Chicago Tribune's Best Hotel List and Chicago Magazine's Best Neighborhood Inns! Chicago's Mo...

from $175

4.7 (90)
Accepts:

Visit Website

Harvey House Bed and Breakfast

Harvey House Bed and Breakfast

from $175

Oak Park, IL

4.7 (90)

Visit Website

Roscoe Village Guesthouse

Chicago, IL

Roscoe Village Guesthouse 6 new contempory, tastefully decorated apartments with full kitchen

from $169

4.2 (91)
Accepts:

Check Dates

Welcome Inn Manor

Chicago, IL

Book our All Inclusive Budget Package: breakfast, transportation and dinner!

from $139

4.7 (145)
Accepts:

Visit Website

Welcome Inn Manor

Welcome Inn Manor

from $139

Chicago, IL

4.7 (145)

Visit Website

The Wicker Park Inn

Chicago, IL

The Wicker Park Inn offers high quality yet affordable accommodations in Chicago's "trendy" Wicke...

from $139

4.2 (309)

Check Dates

The Wicker Park Inn

The Wicker Park Inn

from $139

Chicago, IL

4.2 (309)

Visit Website »

Check Dates

Old Chicago Inn

Chicago, IL

We are located walking distance to world famous Wrigley Field, home of the Chicago Cubs!

from $110

3.9 (114)
Accepts:

Check Dates

Old Chicago Inn

Old Chicago Inn

from $110

Chicago, IL

3.9 (114)

Visit Website »

Check Dates

Lang House Bed and Breakfast on Sheridan

Chicago, IL

Welcome to Lang House, Chicago's impressive North side bed & breakfast . Whether you're in to...

from $149

5 (1)
Accepts:

Visit Website

Villa Toscana Guest House

Chicago, IL

Our Victorian-style B&B is located in the heart of Chicago's Lakeview area, also known as "Boysto...

from $99

4.0 (157)

Check Dates

Ruby Room Inn & Spa

Chicago, IL

Chicago's Urban Sanctuary Hotel & Spa

from $125

4.1 (58)
Accepts:

Check Dates

Ruby Room Inn & Spa

Ruby Room Inn & Spa

from $125

Chicago, IL

4.1 (58)

Visit Website »

Check Dates

Bishops Hall

Oak Park, IL

Bishops Hall provides a rare opportunity to stay in a well-appointed historic home only minutes f

from $175

5 (4)

Check Dates

Bishops Hall

Bishops Hall

from $175

Oak Park, IL

5 (4)

Visit Website »

Check Dates

Free $50 gift card with a $250+ gift card purchase

Ray's Bucktown Bed and Breakfast

Chicago, IL

Unique Bed and Breakfast in Chicago's Bucktown neighborhood!

from $119

4.5 (33)

Visit Website

Ray's Bucktown Bed and Breakfast

Ray's Bucktown Bed and Breakfast

from $119

Chicago, IL

4.5 (33)

Visit Website

Barrington House Bed and Breakfast

Barrington, IL

Barrington House Bed and Breakfast is the finest lodging in Barrington and we're better than a hotel

from $159

4.9 (124)
Accepts:

Check Dates

Benedictine Bed and Breakfast

Chicago, IL

Benedictine B&B offers two comfortable, completely private apartment suites [one is 6 room, the o...

from $180

4.6 (9)
Accepts:

Visit Website

Benedictine Bed and Breakfast

Benedictine Bed and Breakfast

from $180

Chicago, IL

4.6 (9)

Visit Website

The Bucktown House

Chicago, IL

Beautiful 4 bedroom coach house in Chicago's culturally rich neighborhood, Bucktown!

from $240

Visit Website

The Bucktown House

The Bucktown House

from $240

Chicago, IL

Visit Website

Margarita European Inn

Evanston, IL

Evanston, Chicago, newly remodeled Boutique Hotel Member of the Ascend Hotel Collection.

from $134

4.2 (151)

Check Dates

Margarita European Inn

Margarita European Inn

from $134

Evanston, IL

4.2 (151)

Visit Website »

Check Dates

Flemish House of Chicago

Chicago, IL

LAST MINUTE SPECIALS - Contact us for discounted rates for the coming week (based on availability).

from $200

4.3 (88)
Accepts:

Visit Website

Flemish House of Chicago

Flemish House of Chicago

from $200

Chicago, IL

4.3 (88)

Visit Website

Magnolia Studios

Chicago, IL

from $120

5 (3)

Visit Website

Magnolia Studios

Magnolia Studios

from $120

Chicago, IL

5 (3)

Visit Website

Thyme for Bed

Lowell, IN

from $115

4.8 (70)
Accepts:

Check Dates

Thyme for Bed

Thyme for Bed

from $115

Lowell, IN

4.8 (70)

Visit Website »

Check Dates

from $99

4.4 (69)

Visit Website

Ashland Arms Guest House

Ashland Arms Guest House

from $99

Chicago, IL

4.4 (69)

Visit Website

from $149

4.6 (10)

Check Dates

'Suite' Home South Loop

'Suite' Home South Loop

from $149

Chicago, IL

4.6 (10)

Check Dates

House of Two Urns

Chicago, IL

from $99

4.5 (122)

House of Two Urns

House of Two Urns

from $99

Chicago, IL

4.5 (122)

The Aster House

Chicago, IL

4.3 (36)

The Aster House

Chicago, IL

4.3 (36)

from $125

4.5 (2)

City Scene Bed & Breakfast

City Scene Bed & Breakfast

from $125

Chicago, IL

4.5 (2)

No results were found.

Your search was a little too specific.We suggest reducing the filters or searching for a different city.

Sponsored Links

Book a getaway today

Best Price Guarantee

We offer the Best Price Guarantee! Learn more

Recent reviews

Villa D' Citta

$129 - $399

4.8 (820)

"An aesthetic paradise in a vibrant city. A pinnacle of luxury, warmth, and welcome. ..."

Read more...


Villa D' Citta

$129 - $399

4.8 (820)

"After a long day of sightseeing, Villa D' Citta was an amazing, restful reprieve ..."

Read more...


Villa D' Citta

$129 - $399

4.8 (820)

"Outstanding B&B. Luxury, awesome food--love the place!!..."

Read more...


View More Reviews

Chicago B&B reviews

Overall rating:

The Chicago B&B review score is based on feedback from travelers from around the world. See property page for full, detailed reviews by real travelers.

Top