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Guesthouses in Chicago You’ll Love (Page 2)

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)

Ruby Room in Chicago, USA

Ruby Room

Inn in Chicago, Illinois , 1745 W Divison St
Located in Chicago, 2 miles from United Center, Ruby Room has air-conditioned accommodations and a garden.

Fabulous 58 Reviews 8.6

from $186.82 Show details »

Chicago Avenue Inn in Chicago, USA

Chicago Avenue Inn

Inn in Chicago, Illinois , 3305 West Chicago Avenue
Chicago Avenue Inn has free WiFi throughout the property and rooms with air conditioning in Chicago.
  • Family rooms

Pleasant 82 Reviews 6.6

from $53.37 Show details »

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Accommodation data and pictures provided by Booking.com