Stays for 8+ guests in Chicago, IL

Stays for 8+ guests in Chicago, IL, from $181 a night. Book direct on each manager's site, no OTA fee.

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Stays, best documented first

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $181 a night
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Premium 4 King Apartment w/ City Views
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $699 a night
- air conditioning
- bbq grill
- bed linens
- cable tv
Exact location
Book direct on Envitae
Bright 4BR Apartment Near Lincoln Park Zoo
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $193 a night
- air conditioning
- bbq grill
- bed linens
- blender
Exact location
Book direct on CielStay
Wrightwood Place | Lincoln Park 4BR Elegant Apartment
House · 4 bed · 3 bath · sleeps 12
Chicago, IL
From $367 a night
- body soap
- cleaning products
- conditioner
- hot water
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Douglass Atelier | 3BR Home & Private Garden
House · 3 bed · 2 bath · sleeps 10
Chicago, IL
From $499 a night
- conditioner
- hair dryer
- bed linens
- dryer
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Midcentury Artist Loft w/ King bed
House · 4 bed · 1 bath · sleeps 8
Chicago, IL
From $560 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
Location! Private Deck! Parking!
House · 4 bed · 3 bath · sleeps 14
Chicago, IL
From $983 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
Apartment Spacious 3Br Home Near Chicago Downtown, University Of Illinois Chicago & Medical District
Hotel · 1 bed · 2 bath · sleeps 8
Chicago, IL
From $294 a night
City-level location
Book direct on Chicago hotels & apartments, all accommodations in Chicago
The Pilsen House
House · 5 bed · 3.5 bath · sleeps 11
Chicago, IL
From $375 a night
City-level location
Book direct on Comfi-Stays
The Northside Club House | 2 Living Rooms | Sleeps 8
House · 4 bed · 2 bath · sleeps 8
Chicago, IL
From $713 a night
City-level location
Book direct on Luxury Vacation Rentals in Chicago
The Cubs Dugout | 2 Level Retreat
Apartment · 4 bed · 2 bath · sleeps 9
Chicago, IL
From $758 a night
City-level location
Book direct on Luxury Vacation Rentals in Chicago
Apartment Flexhome West Town - Spacious 2Br Duplex - Sleeps 8 Chicago
Hotel · sleeps 8
Chicago, IL
From $263 a night
City-level location
Book direct on Chicago hotels & apartments, all accommodations in Chicago
3BR Apartment Near Clybourn Corridor & Old Town
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
3BR Luxury Suite w/Gym and Balcony
House · 3 bed · 2.5 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
4BR City Retreat, Great for Business & Family
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bright 3BR Stylish Apartment Near North Ave Shops
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bright 4BR Apartment Near Lincoln Park Zoo
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bronzeville Gem: Balcony, Gym & Rooftop Deck
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Chic 4-Bedroom with Skyline Views, Firepit and Gym
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
ENVITAE Hotel / 4BR Luxury Modern Apartments
Apartment · 8 bed · 6 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- bbq grill
- bed linens
- carbon monoxide detector
Exact location
Book direct on Envitae
ENVITAE Hotel / 4BR Luxury Modern Apartments
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- bbq grill
- bed linens
- carbon monoxide detector
Exact location
Book direct on Envitae
Envitae Hotel, 4BR Modern Sleek Apartment
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Luxury Apartment w/City Views, Downtown Location
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Modern 3BR City Retreat - Near Old Town
House · 3 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
New 4 King Bed / Family Ready Apartment
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Premium Urban 4BR - Perfect Mix of Comfort & Location
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Sophisticated 4BR Suite - Walk to Shops, Dining & Transit
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
South Loop · 3 Kings · Steps from McCormick Place
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 4BR Central Apartment w/ Skyline Views
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 4BR Near Fulton Market & Riverwalk
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎
Condo · 3 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- hair dryer
Exact location
Book direct on CielStay
Maison Blanc Noir
House · 5 bed · 3.5 bath · sleeps 15
Chicago, IL
No nightly rate published
- air conditioning
- airport transfer
- free wi-fi
- laundry
City-level location
Book direct on Wieser Host
Spacious 3-Bedroom Ukrainian Village Home
House · 3 bed · 3 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- washer and dryer
- free wifi
- kitchen
City-level location
Book direct on Spacious 3-Bedroom Ukrainian Village Home with Private Deck
Stunning Designer Duplex in Fulton Market
Loft · 3 bed · 2.5 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- dishes and silverware
- hair dryer
- dedicated workspace
Exact location
Book direct on Updated Designer Duplex In Fulton Market W/parking
The En Bronze
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- free wi-fi
- full kitchen
- fireplace
City-level location
Book direct on Wieser Host
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- hair dryer
Exact location
Book direct on Wrigleyville Vacation Rentals
Villa Noir
Villa · 4 bed · 2.5 bath · sleeps 9
Chicago, IL
No nightly rate published
- air conditioning
- airport transfer
- free wi-fi
- laundry
City-level location
Book direct on Wieser Host
Gold Coast Estate | Luxury 6BR Home with Private Patio
House · 6 bed · 6.5 bath · sleeps 12
Chicago, IL
No nightly rate published
- hot water
- shampoo
- shower gel
- hair dryer
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Wrigley 4BR Home, Sleeps 10
Apartment · 4 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
- no pets
- no smoking
- no events or parties
Exact location
Book direct on Boutique Chicago Apartments
Gather, relax, enjoy— in chic contemporary home
House · 4 bed · 3.5 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- baking sheet
- barbecue utensils
- bbq grill
City-level location
Book direct on hospitablehosts.rentals
Apartment Near Clybourn Corridor & Old Town
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Bright Apartment Near Lincoln Park Zoo
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
City Retreat, Great for Business & Family
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Premium Urban - Perfect Mix of Comfort & Location
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Sophisticated Suite - Walk to Shops, Dining & Transit
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
South Loop 3 Bedroom Apt
Apartment · 3 bed · 1 bath · sleeps 8
Chicago, IL
No nightly rate published
Exact location
Book direct on CielStay
Bright Stylish Apartment Near North Ave Shops
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Chic with Skyline Views, Firepit and Gym
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Chicago Skyline View Pilsen Apt + Parking Spot
House · 3 bed · 1 bath · sleeps 12
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
ENVITAE Hotel, Luxury Modern Apartments
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Envitae Hotel, Modern Sleek Apartment
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Luxury Suite w/Gym and Balcony
House · 3 bed · 2.5 bath · sleeps 8
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Modern City Retreat - Near Old Town
House · 3 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Spacious Central Apartment w/ Skyline Views
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Spacious Near Fulton Market & Riverwalk
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark
2 bed · 1 bath · sleeps 8
Chicago, IL
No nightly rate published
Exact location
Book direct on TIBO Ventures

How prices are computed

Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.

Updated 2026-10-30 07:37 UTC. Prices and facts are whatever the manager published on their own site.