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Search results; Over 1,000 places

Superhost
Apartment in Old Town
Oldtown Stylish cute studio
1 bed
Apr 25 – 30
New place to stay
Guest favorite
Home in Gold Coast
Designer Wicker Park Home for Spring
3 king beds
Apr 21 – 26
4.76 out of 5 average rating, 54 reviews
Superhost
Apartment in Old Town
Old Town/Gold Coast Masterpiece (+private rooftop)
4 beds
Apr 21 – 26
4.85 out of 5 average rating, 52 reviews
Guest favorite
Apartment in Lincoln Park
Historic Old Town Flat - Minutes from Downtown!
2 beds
Apr 21 – 26
4.87 out of 5 average rating, 269 reviews
Superhost
Townhouse in Magnificent Mile
Historic lux Townhouse on Chicago's Gold Coast
4 beds
May 12 – 17
4.8 out of 5 average rating, 152 reviews
Guest favorite
Condo in Lincoln Park
Lincoln Park Hideaway - 5 Min Walk to the Park!
3 beds
Apr 21 – 26
4.92 out of 5 average rating, 101 reviews
Guest favorite
Condo in Lincoln Park
Old Town Pied-à-Terre w/Pvt Terrace and Parking
3 beds
Apr 24 – 29
4.91 out of 5 average rating, 244 reviews
Guest favorite
Apartment in Magnificent Mile
Elegant Suite in Gold Coast
1 king bed
Jul 27 – Aug 1
4.98 out of 5 average rating, 83 reviews
Superhost
Apartment in Magnificent Mile
Gold Coast Pristine Paradise 3BR/2BA. Free Parking
3 beds
Apr 27 – May 2
5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Magnificent Mile
Urban Oasis in Vibrant Gold Coast
1 bed
Jul 6 – 11
4.96 out of 5 average rating, 24 reviews
Guest favorite
Apartment in Old Town
OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
3 beds
Jun 24 – 29
4.91 out of 5 average rating, 154 reviews
Guest favorite
Apartment in Old Town
OLD TOWN GARDEN GETAWAY
2 beds
May 20 – 25
4.92 out of 5 average rating, 76 reviews
Guest favorite
Apartment in Magnificent Mile
2BR Retreat with a Fireplace in Gold Coast
2 beds
May 18 – 23
4.94 out of 5 average rating, 89 reviews
Guest favorite
Home in Lincoln Park
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 beds
Apr 28 – May 3
5.0 out of 5 average rating, 44 reviews
Guest favorite
Apartment in Magnificent Mile
French design Luxurious Downtown 3br+2ba/sleeps 8
4 beds
Apr 21 – 26
4.95 out of 5 average rating, 56 reviews
Guest favorite
Apartment in Magnificent Mile
Luxury 3BR Duplex in Prime Location
4 beds
Jul 9 – 14
5.0 out of 5 average rating, 19 reviews
Apartment in Magnificent Mile
Modern 3b Apartment close to Michigan Lake
8 beds
Apr 20 – 25
New place to stay
Guest favorite
Home in Lincoln Park
Luxury SOHO Styled Two-Level Townhouse | Old Town
7 beds
Apr 21 – 26
4.95 out of 5 average rating, 58 reviews