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Search results; Over 1,000 places in Chicago

Boutique hotel in Chicago
Luxury Stay - Claridge House, Queen Room
1 queen bed
Apr 28 – May 3
4.43 out of 5 average rating, 689 reviews
Hotel room in Chicago
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Apr 20 – 25
4.48 out of 5 average rating, 3620 reviews
Superhost
Apartment in Chicago
Decorated 1BR Apt, Natural Light, Comfy King Beds
1 king bed
Apr 21 – 26
4.8 out of 5 average rating, 208 reviews
Superhost
Room in Chicago
Stay with Nala & OwenHosting for 6 years,
Fashionable Room w/ full bathroom - FREE PARKING!
Apr 20 – 25
4.77 out of 5 average rating, 188 reviews
Hotel in Chicago
Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe
1 king bed
Apr 24 – 29
4.54 out of 5 average rating, 1216 reviews
Apartment in Chicago
Standard King Bed Hotel Room at Magnificent Mile
1 king bed
Apr 28 – May 3
4.58 out of 5 average rating, 108 reviews
Guest favorite
Apartment in Chicago
Spacious, light-drenched studio-private entrance!
Apr 21 – 26
4.94 out of 5 average rating, 190 reviews
Guest favorite
Apartment in Chicago
Costa Lota near Wrigley
1 queen bed
Apr 21 – 26
4.91 out of 5 average rating, 54 reviews
Guest favorite
Tiny home in Burr Ridge
Less is more! Pet friendly Tiny Home near Chicago!
2 beds
Jun 2 – 7
4.92 out of 5 average rating, 238 reviews
Guest favorite
Apartment in Chicago
A Novel Situation at Wrigley
1 king bed
Apr 22 – 27
4.9 out of 5 average rating, 165 reviews
Guest favorite
Home in Chicago
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
Guest suite in Chicago
Luxe, Private Suite w/Own Entrance-2023 Renovated
1 queen bed
Apr 21 – 26
4.92 out of 5 average rating, 309 reviews
Guest favorite
Condo in Chicago
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
Apartment in Chicago
Newly Renovated 1BD near West Loop & Little Italy
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 26 reviews
Guest favorite
Guesthouse in Chicago
Quiet, Cozy 1-Bedroom Carriage House in Chicago
1 double bed
Apr 21 – 26
4.94 out of 5 average rating, 81 reviews
Guest favorite
Guest suite in Chicago
1 mile from Wrigley Field
2 beds
May 12 – 17
4.95 out of 5 average rating, 174 reviews
Guest favorite
Apartment in Chicago
Lincoln Square Oasis - Bright, clean studio
2 beds
Apr 21 – 26
4.95 out of 5 average rating, 22 reviews
Guest favorite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
2 beds
Sep 1 – 6
4.96 out of 5 average rating, 415 reviews