Chicago Vacation Rentals

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Luxury Chicago TH 10 Mins To DWTWN RSV Now!
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Luxury Chicago TH 10 Mins To DWTWN RSV Now!

3 Bedrooms
2 Bathrooms
3 Guides
4.79IconIconIconIconIcon
29 reviews
$200 / night (excl. fees & taxes)
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2 Bedroom + Office - Honeycomb Workspace
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2 Bedroom + Office - Honeycomb Workspace

2 Bedrooms
1 Bathroom
3 Guides
5IconIconIconIconIcon
5 reviews
$125 / night (excl. fees & taxes)
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Hyde Park 2BR UChicago Medical Museums 20% OFF
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20% OFF Hyde Park 2BR UChicago Medical Museums

2 Bedrooms
1 Bathroom
3 Guides
$46 - $251 / night (excl. fees & taxes)
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Large Cozy 3BR near UChicago Medical Midway Museum
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Large Cozy 3BR near UChicago Medical Midway Museum

3 Bedrooms
1 Bathroom
3 Guides
$72 - $349 / night (excl. fees & taxes)
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Chicago 2BR Condo- King Sleep Number
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Luxury King Sleep Number - Historic Safe Location

2 Bedrooms
1 Bathroom
3 Guides
4.63IconIconIconIconIcon
8 reviews
$99 - $647 / night (excl. fees & taxes)
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Chicago  2Br Condo -Nature Themed Downtown Access
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Safe Modern 2BrCondo City Access

2 Bedrooms
1 Bathroom
3 Guides
5IconIconIconIconIcon
2 reviews
$92 - $1000 / night (excl. fees & taxes)
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Chicago  2Br 90s Condo - Very Kid Friendly
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90s Condo- Safe Family Friendly- Arcade Game!

2 Bedrooms
1 Bathroom
3 Guides
4.5IconIconIconIconIcon
4 reviews
$102 - $1000 / night (excl. fees & taxes)
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Chicago  2Br Condo - Downtown Access
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Luxury Artistic Condo Safe Historic Location

2 Bedrooms
1 Bathroom
3 Guides
5IconIconIconIconIcon
3 reviews
$90 - $1000 / night (excl. fees & taxes)
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1500Main EVANSTON
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Visiting the Evanston area for 3 days + ? Check us out.

2 Bedrooms
1½ Bathrooms
3 Guides
5IconIconIconIconIcon
113 reviews
$249 / night (excl. fees & taxes)
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Luxurious Condo in Top Rated Neighborhood
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Luxurious Condo in Top Rated Neighborhood

1 Bedroom
1 Bathroom
3 Guides
4.46IconIconIconIconIcon
28 reviews
$85 - $444 / night (excl. fees & taxes)
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Cosy 4 Bedroom House & Backyard
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Cosy 4 Bedroom House & Backyard

4 Bedrooms
2 Bathrooms
3 Guides
$179 / night (excl. fees & taxes)
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Middle Level of the House with Working Space
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Middle Level of the House with Working Space

2 Bedrooms
1 Bathroom
3 Guides
4.73IconIconIconIconIcon
44 reviews
$93 / night (excl. fees & taxes)
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Luxury Estate: Heated Pool, Spa & Fire Pit
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Luxury Home w/ Heated Saltwater Pool, Spa, Fire Pit, on 1+ acres

6 Bedrooms
3 Bathrooms
3 Guides
5IconIconIconIconIcon
44 reviews
$1095 / night (excl. fees & taxes)
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Staycation Retreat
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Staycation Retreat

2 Bedrooms
1 Bathroom
3 Guides
$150 / night (excl. fees & taxes)
    1 – 14 Rentals