HomeToGo Top Picks
Last Minute Deals in Chicago

Does a last-minute getaway to Chicago sound good to you? We have compared 10,039 available vacation rental properties found on 18 partner websites and selected the very best. Have fun exploring!

3000 ft² House 10 guests 3 bedrooms
West Town, Chicago, Illinois, United States
5.0
(1 rating)
from $276
Vrbo
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1260 ft² Apartment 4 guests 2 bedrooms
Near North, Chicago, Illinois, United States
5.0
(16 ratings)
from $260
Vrbo
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4000 ft² Apartment 10 guests 5 bedrooms
Near North, Chicago, Illinois, United States
5.0
(50 ratings)
from $901
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2000 ft² Apartment 6 guests 2 bedrooms
South Loop, Chicago, Illinois, United States
4.6
(19 ratings)
from $274
Vacasa
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4000 ft² House 10 guests 4 bedrooms
Lake View, Chicago, Illinois, United States
5.0
(4 ratings)
from $761
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Apartment 2 guests 1 bedroom
Near North, Chicago, Illinois, United States
4.3
(50 ratings)
from $344
Booking.com
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1500 ft² Apartment 8 guests 3 bedrooms
North Kenwood, Chicago, Illinois, United States
 
from $144
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1800 ft² Apartment 7 guests 3 bedrooms
Streeterville, Chicago, Illinois, United States
 
from $282
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2500 ft² House 4 guests 2 bedrooms
Logan Square, Chicago, Illinois, United States
4.8
(41 ratings)
from $98
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1500 ft² Apartment 4 guests 2 bedrooms
Lincoln Park, Chicago, Illinois, United States
4.6
(9 ratings)
from $142
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