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Casual Hotels in Chicago

Photo of The Villa Toscana Guest House

The Villa Toscana Guest House

(42 Ratings)

Elegant & unique accommodations

In the heart of Boystown, Villa Toscana offers a charming Victorian-inspired B&B experience. Mere steps away lie the...

Northalsted · 3447 N Halsted St, Chicago

outdoor seating

family-friendly

bed & breakfast

mixed gay/straight

Map of Casual Hotels in Chicago

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These one-of-a-kind accommodations will make you feel like royalty

Best of GayCities

These one-of-a-kind accommodations will make you feel like royalty

This Chicago hotel is a legendary launch pad for downtown fun

Millennium Park merriment

This Chicago hotel is a legendary launch pad for downtown fun

Staying at this hotel will make you feel like you're in 'The Gilded Age'

spectacular stays

Staying at this hotel will make you feel like you're in 'The Gilded Age'

San Francisco boutique hotels within walking distance of happy hour

stay a while

San Francisco boutique hotels within walking distance of happy hour

Check out these stunning ice hotels around the world

chill out

Check out these stunning ice hotels around the world

This gay filmmaker’s private yacht on the Mediterranean is up for grabs

below deck

This gay filmmaker’s private yacht on the Mediterranean is up for grabs

History Articles