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Chicago >
Holiday homes

Vacation Rentals Chicago, Holiday Rentals

Sorting by

The Avondale Guesthouse

2973 North Elston Avenue, Hotel in Chicago, United States

Excellent
131 reviews

480 US$

min. price/night

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

2713 West Balmoral Avenue, Hotel in Chicago, United States

Excellent
43 reviews

270 US$

min. price/night

Lincoln Park Living - Suite 1

West Diversey Parkway, Hotel in Chicago, United States

713 US$

min. price/night

Lincoln Park Living - 3 Queen Beds - Sleeps 6

1147 West Diversey Parkway, Hotel in Chicago, United States

139 US$

min. price/night

Stunning Condo #2 - Downtown River North

811 N Sedgwick St, Hotel in Chicago, United States

39 US$

min. price/night

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

329 West Schiller Street Back, Hotel in Chicago, United States

Excellent
29 reviews

579 US$

min. price/night

The Black And White Suite

611 East 41St Street, Hotel in Chicago, United States

313 US$

min. price/night

Suite 2 On Southport 4 Queen Beds

2501 North Southport Avenue, Hotel in Chicago, United States

614 US$

min. price/night

Spacious Row Home Next Transit Near Downtown W Parking

3133 West Fulton Street, Hotel in Chicago, United States

Excellent
15 reviews

452 US$

min. price/night

Spacious 5-Br House Near Transit W Parking

1868 South Millard Avenue, Hotel in Chicago, United States

Excellent
14 reviews

517 US$

min. price/night

Chic Green L Near Downtown & Il Medical District

602 South Western Avenue, Hotel in Chicago, United States

118 US$

min. price/night

Chicago Home With Spacious Yard 14 Mi To Dtwn

Chicago, United States

112 US$

min. price/night

Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Hotel in Chicago, United States

329 US$

min. price/night

Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

3742 N. Keeler Avenue, Chicago,, Hotel in Chicago, United States

Excellent
8 reviews

Beautifully Renovated House 10 Mins From Downtown

4244 South Prairie Avenue, Hotel in Chicago, United States

Excellent
7 reviews

306 US$

min. price/night

Beautiful Remodeled Penthouse Unit In Old Town

1556 North La Salle Street, Hotel in Chicago, United States

139 US$

min. price/night

Beautifully Remodeled Flat Downtown #3N

858 North Orleans Street #3N, Hotel in Chicago, United States

239 US$

min. price/night

Immaculate Brand New Penthouse Chicago

1630 West Warren Boulevard, Hotel in Chicago, United States

799 US$

min. price/night

The Logandale: Huge Mid-Century Home, Sleeps 15

2920 North Gresham Avenue, Hotel in Chicago, United States

Excellent
5 reviews

698 US$

min. price/night

5 Mi To Millennium Park Apartment With Fireplaces

3461 W Adams St, Hotel in Chicago, United States

162 US$

min. price/night

Cozy 4Bd House Fireplace And Pond

8813 South Euclid Avenue, Hotel in Chicago, United States

535 US$

min. price/night

Chicago Treasure 4 Bed Getaway

712 North Willard Court, Hotel in Chicago, United States

Excellent
6 reviews

231 US$

min. price/night

Charming Home In Portage Park

4109 North Narragansett Avenue, Hotel in Chicago, United States

107 US$

min. price/night

Logan Square Oasis

2508 N Spaulding Ave, Hotel in Chicago, United States

142 US$

min. price/night

Goose Island Central Downtown Prime Location With Access To Patio Chi - 1

West Augusta Boulevard 1220, Hotel in Chicago, United States

179 US$

min. price/night

Chicago New 2Br Home W 3 Beds And Highspeed Internet

West Potomac Avenue 1731, Hotel in Chicago, United States

139 US$

min. price/night

Zen Escape-Chicago'S Urban Oasis

841 North Mozart Street, Hotel in Chicago, United States

79 US$

min. price/night

Romantic 3 Bed Home In The Heart Of The Park

5923 South Indiana Avenue, Hotel in Chicago, United States

393 US$

min. price/night

No. 1 Rated Lincoln Park House - Golf Simulator

210 W St Paul Ave, Chicago, Il 60614, Usa, Hotel in Chicago, United States

42 US$

min. price/night

River North Hideaway With Amazing Views And Parking

1 E Huron St, Hotel in Chicago, United States

264 US$

min. price/night

Chicago Home Near Navy Pier And Shedd Aquarium!

Chicago, United States

159 US$

min. price/night

Chic 4-Bedroom Haven: Designer'S Dream Home

2655 West Huron Street, Hotel in Chicago, United States

1155 US$

min. price/night

Spacious Luxury Retreat 8 Bed Oasis With 6 Baths

2630 South Throop Street, Hotel in Chicago, United States

1636 US$

min. price/night

Personal Gym Luxury Balcony Condo

5105 N East River Rd Unit 3F, Chicago, Il 60656, Usa, Hotel in Chicago, United States

Excellent
1 review

233 US$

min. price/night

Perfect Location Across From Park & Train Station

244 North Hamlin Avenue, Hotel in Chicago, United States

Excellent
3 reviews

612 US$

min. price/night

New Modern 3Br, Gym, Workspace, Quiet Location

3656 N Osage Ave Unit 3, Chicago, Il 60634, Usa, Hotel in Chicago, United States

Excellent
3 reviews

147 US$

min. price/night

Old Town 3Bd 3Ba Coach House, Garage Parking Incl

1435 N Mohawk Ch, Hotel in Chicago, United States

Excellent
1 review

Boutique Garden House Chicago 3-Story Sleeps 12

7131 South Michigan Avenue, Hotel in Chicago, United States

Excellent
4 reviews

494 US$

min. price/night

Roscoe Village Family Hideaway

1811 West Eddy Street, Hotel in Chicago, United States

Excellent
1 review

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

329 West Schiller Street, Hotel in Chicago, United States

Excellent
5 reviews

841 US$

min. price/night

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

1426 North North Park Avenue, Hotel in Chicago, United States

Excellent
3 reviews

767 US$

min. price/night

Stylish Chicago Retreat Walk To Loyola University

6242 N Kenmore Ave Unit D, Hotel in Chicago, United States

Excellent
1 review

Woodlawn Oasis

6433 South Minerva Avenue, Hotel in Chicago, United States

Good
3 reviews

364 US$

min. price/night

Amazing Penthouse Skyline Views!

1549 North Milwaukee Avenue Unit 4S, Hotel in Chicago, United States

Excellent
1 review

842 US$

min. price/night

The Village Inn By Dakota Gal Digs

2111 North Kenmore Avenue Unit 1, Hotel in Chicago, United States

Excellent
2 reviews

372 US$

min. price/night

Magnificent New Home W/8 Beds & Free Parking

2019 North Bingham Street, Hotel in Chicago, United States

Excellent
8 reviews

301 US$

min. price/night

Gorgeous 5 Bedroom Gem With Games

7928 South Ada Street, Hotel in Chicago, United States

Excellent
1 review

370 US$

min. price/night

Historic Luxury Townhouse In Downtown Chicago

71 East Bellevue Place The Townhouse, Hotel in Chicago, United States

1891 US$

min. price/night

Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

67 East Cedar Street, Hotel in Chicago, United States

Good
1 review

999 US$

min. price/night

8Br Kids Room, Game Room, Gym Andtheater

4038 N Central Ave, Chicago, Il 60634, Usa, Hotel in Chicago, United States

Other Places to Stay in Chicago

Types of Accomodations in Chicago

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Resort

Hotels near Popular Places to visit in Chicago

City Centre Midway International Chicago O'Hare International Wrigley Field

Navy Pier

Michigan Avenue

United Center Chicago Union Station

Chicago Theater

Millennium Park

Loyola University Chicago

Chicago Riverwalk

CIBC Theatre

House of Blues Chicago

Art Institute of Chicago

Willis Tower

Northwestern Memorial Hospital

Water Tower Place

Cloud Gate

Museum of Science and Industry Guaranteed Rate Field University of Chicago Union Park Lincoln Park Zoo Aragon Ballroom DePaul University - Lincoln Park Campus

Cadillac Palace Theatre

Rush University Medical Center Arie Crown Theater Credit Union 1 Arena Oak Street Beach Briar Street Theatre Second City Old Water Tower Chicago Skydeck Chicago 360 Chicago Ogilvie Transportation Center Illinois Institute of Technology Columbia College-Science/math Chicago History Museum Hubbard Street Dance Chicago Rush University LaSalle Street Station Civic Opera House Harold Washington Library Center Foster Avenue Beach University of Illinois College of Medicine Peggy Notebaert Nature Museum Steppenwolf Theatre Company Chicago Board of Trade Building Wicker Park
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