Vacation rentals with breakfast in South Side
Find and book unique breakfast rentals on Airbnb
Top-rated breakfast rentals in South Side
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side breakfast rentals
House rentals with breakfast
Home in Winfield
4.98 out of 5 average rating, 132 reviewsCozy, Clean & Well-Stocked Home!
Mar 24 – 31
Home in Chicago
4.87 out of 5 average rating, 115 reviewsSoak Up Mid-Century Style in Wrigleyville and Boystown
Sep 13 – 20
Home in Des Plaines
4.83 out of 5 average rating, 167 reviewsExotic House - Few minutes from O'Hare and Chicago
Mar 2 – 9
Home in Gary
4.98 out of 5 average rating, 40 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Jun 1 – 8
Home in Westchester
4.98 out of 5 average rating, 55 reviewsJacuzzi, King Beds, Easy Access to DT Chicago!
Jul 23 – 30
Home in Forest Park
5.0 out of 5 average rating, 66 reviewsNEW Gather in spacious 3 bedroom 2 bath home
Jul 9 – 16
Home in Matteson
4.93 out of 5 average rating, 15 reviewsSoulful 5-Bedroom Home with Indoor Fireplace
Mar 6 – 13
Home in Chicago
4.98 out of 5 average rating, 59 reviewsLuxe SFH Bucktown Retreat with Garage Parking
Feb 18 – 25
Apartment rentals with breakfast
Apartment in Chicago
4.97 out of 5 average rating, 149 reviewsDecompress on a Sophisticated Chaise at a Glamorous Hideaway
Nov 14 – 21
Apartment in Chicago
4.95 out of 5 average rating, 360 reviewsA Vintage Pink House in the Heart of Chicago
Aug 29 – Sep 5
Apartment in Chicago
4.97 out of 5 average rating, 244 reviewsThe Garden on Wayne
Dec 18 – 25
Apartment in Chicago
4.81 out of 5 average rating, 192 reviewsIn artistic Pilsen~Continental Breakfast~Near DWTN
Jul 9 – 16
Apartment in Chicago
4.94 out of 5 average rating, 215 reviewsUrban Chic Apartment by the Magnificent Mile
Nov 9 – 16
Apartment in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
Apr 26 – May 3
Apartment in Evanston
4.89 out of 5 average rating, 265 reviewsAshland Ice Cream House
Jul 24 – 31
Apartment in Chicago
4.8 out of 5 average rating, 132 reviewsHeart of Wicker Park! Location. Walk to Everything
Jun 27 – Jul 4
Bed and breakfast rentals with breakfast
Room in Chicago
4.99 out of 5 average rating, 102 reviewsLovely UofC Prof mansion great on campus location
Feb 22 – Mar 1
Room in Elmhurst
5.0 out of 5 average rating, 113 reviewsCozy room with private bathroom.
May 26 – Jun 2
Room in Evanston
4.95 out of 5 average rating, 425 reviewsClassy and Cozy 2nd. Room
Oct 4 – 11
Room in Chicago
4.95 out of 5 average rating, 148 reviewsWrigleyville Private Twin Bedroom w/ Private Bath
Jun 7 – 14
Room in Wilmette
4.95 out of 5 average rating, 214 reviews(BR#1) Welcoming, warm & comfortable, 3 guests
Nov 6 – 13
Room in Chicago
5.0 out of 5 average rating, 85 reviewsUrban Oasis Pilsen - guest room in townhouse
Sep 8 – 15
Hotel room in Chicago
4.91 out of 5 average rating, 43 reviewsKing Room in Boutique Wicker Park B&B
Dec 11 – 18
Room in Chicago
4.84 out of 5 average rating, 359 reviewsBright Room with a Garden View
Jan 21 – 28
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