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Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Hotel Perks - Private Bedroom | Private Bathroom
Hotel room · 2 guests · 1 bed · 1 private bath
Hotel Perks - Private Bedroom | Private BathroomFreehand Hotel is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe designed by Roman & Williams in River North Chicago, just two blocks from the Magnificent Mile. Walking distance to public transportation, Navy Pier, and more. $10 nightly resort fee plus tax paid at the property For long-term stays, guests must move rooms about every 30 days.
2R Location! Steps from South Loop 2bed/2bath Apt.
SUPERHOST
Entire rental unit · 6 guests · 2 beds · 2 baths
2R Location! Steps from South Loop 2bed/2bath Apt.Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 28th Place & Canal St to map transit options Newly remodeled 2bed/2bath apt with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago & steps from all that trendy Bridgeport has to offer. Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays
Restoring Chicago Speakeasy from 1920's Room 1A
SUPERHOST
Private room · 2 guests · 2 beds · 1 private bath
Restoring Chicago Speakeasy from 1920's Room 1ANote : Check in is at noon but you can come as early as you need pick up the keys and drop off your things. Welcome to an Authentic Chicago Speakeasy from the 1920s. Your room is numbered 1A and your keys will be marked 1A. We are currently restoring this original Speakeasy from the 1920s to its former glory. There is an additional $50 fee per person for the third and fourth guests staying in the room. PLEASE NOTE:::: We are cleaning painting and doing light construction during the day here in the common areas. Please be advised. Please read the complete summary before you book. It is not fair for anyone to be given a bad review because someone didn't read the summary of what they were booking. Thank you for understanding this. Your bedroom is completely restored. and the main bath is totally adequate for your needs. Some work will be going on during the daytime in the common areas. No work is done after 6:00 in the evening. Feel free to walk throughout the two floors and observe the restoration process. I am an artist for over 40 years and will be opening M gallery on the second floor. It will be an art gallery and event space hosting art exhibits and concerts. We are loving this grand space and the process of restoring it. Come join us. michaelmccafrey.com

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Popular amenities for Downtown Chicago vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Downtown Chicago

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Sonder at Grant Park | Spacious One-Bedroom Apartment w/ Lake View
ﺩ.ﺇ652 per night
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Fresh in River North!
ﺩ.ﺇ331 per night
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SHARED Artist Loft . Very Unique
ﺩ.ﺇ364 per night
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FOUND Hotel Chicago - Queen + Twin Room
ﺩ.ﺇ353 per night
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Spectacular Downtown High Rise Extraordinary view
ﺩ.ﺇ236 per night
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Grand Studio in the Heart of Lakeview!
ﺩ.ﺇ235 per night
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DOWNTOWN STUDIO BY RUSH STREET -GOLD COAST CENTER
ﺩ.ﺇ314 per night
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Cute Designer Touch Minimal Loft,Blue Line
ﺩ.ﺇ241 per night
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Beautifully Renovated, Walking distance to Lake!
ﺩ.ﺇ318 per night
SUPERHOST
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1bed/1bath !Location! Steps to South Loop Apt
ﺩ.ﺇ246 per night
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New Spot in West Town pt.2!
ﺩ.ﺇ368 per night
SUPERHOST
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★ DOWNTOWN CHICAGO ★.
ﺩ.ﺇ214 per night