As of November 2026, CielStay lists 440 homes for rent in Illinois, run by independent hosts and property managers. All of them can be booked on the host's or manager's own website, across 35 booking sites.
They include 150 houses, 244 condos and 13 resort suites. The most common size is three bedrooms (124 homes). 165 homes sleep 10 or more.
Illinois rentals at a glance
Counted from what hosts list. Check the listing before you book.
| Studio or 1 bedroom | 39 |
| 2 bedrooms | 113 |
| 3 bedrooms | 124 |
| 4 bedrooms | 85 |
| 5 or more bedrooms | 66 |
| Sleeps 10 or more | 165 |
| Air conditioning | 369 |
| Pets allowed | 161 |
| Pool | 103 |
| Hot tub | 77 |
| Fireplace | 47 |
| EV charger | 28 |
Homes in Illinois for 6 or more
8 of the 326. Search them with your dates →
Homes in Illinois with a pool
8 of the 103. Search them with your dates →
Homes in Illinois
Homes with the host's own booking site first. Prices can change and may not be exact; the asterisk shows what each one includes.
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
📍 Chicago, IL
$310 / night
Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectural Digest
📍 Chicago, IL
$705 / night
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
📍 Chicago, IL
$348 / night
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Digest
📍 Chicago, IL
$322 / night
400 of the 440 homes in Illinois
- Farm Stay Cabin Shawnee Wine Trail & Natl Forest · 1 bd · sleeps 3
- Tiny Cabin Near 2 Vineyards&Shawnee Pet Friendly · 1 bd · sleeps 3
- Go Boat-Lake Shore Cottage · studio · sleeps 2
- Lake Shore Cottage · 3 bd · sleeps 8
- Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest · 3 bd · sleeps 12
- The Ridge · 2 bd · sleeps 7
- Wooded Cabin near Blue Sky & Shawnee Pet-Friendly · 1 bd · sleeps 2
- Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectural Digest · 6 bd · sleeps 24
- Cedar Hills Retreat · 1 bd · sleeps 4
- Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Digest · 3 bd · sleeps 12
- 2 Rooftops, 2 Car Garage, 4 Stories · 3 bd · sleeps 14
- Wicker Park: Cozy Fireplace, Grand Piano · 4 bd · sleeps 10
- Bucktown Home - Rooftop Deck, Game Rm, & Garage · 4 bd · sleeps 16
- Glamping W/Hotub, pool, & lake · 1 bd · sleeps 6
- Majestic Meadows: 25 acres w/ hot tub · 5 bd · sleeps 16
- Hidden Grove · 2 bd · sleeps 6
- Wooded, Private Lake, Pool & Spa · 1 bd · sleeps 6
- Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Digest · 2 bd · sleeps 12
- Camp in quiet w/ Spa Lake Pool · 1 bd · sleeps 6
- Rooftop, West Loop Chicago · 3 bd · sleeps 12
- West Loop 2BR with Skyline Views + Prime Location · 2 bd · sleeps 6
- Panoramic City Views + Prime West Loop Location · 2 bd · sleeps 5
- 33rd-Floor Penthouse with Breathtaking Views · 3 bd · sleeps 7
- Luxury Penthouse: Iconic Views + Exclusive Comfort · 4 bd · sleeps 9
- Ideal for Groups: Spacious 2BR in The Loop · 6 bd · sleeps 12
- High-End 3BR Retreat + Steps to Millennium Park · 3 bd · sleeps 6
- Luxury 2BR on Michigan Ave with Private Balcony · 2 bd · sleeps 7
- Gold Coast Luxury: 2BR with Sweeping City Vistas · 2 bd · sleeps 5
- Sky-High 2BR w/ Gym & City Views · 2 bd · sleeps 5
- Fabulous 3 Bedroom in the Heart of North Center · 3 bd · sleeps 6
- Prime 2BR Apartments: Perfect Group Comfort · 4 bd · sleeps 14
- LIVN Millennium Park Downtown Chicago 2BR · 2 bd · sleeps 4
- Fulton House #3 (3bd/ 2ba) · 3 bd · sleeps 4
- Spacious West Loop Retreat for Business Groups · 6 bd · sleeps 15
- Spacious 3BR 2BA Haven City Views Steps to MagMile · 3 bd · sleeps 7
- River West 3BR Penthouse Duo: Skyline Comfort · 6 bd · sleeps 14
- PH w/ Bean & Lake Views, An Elite Stay · 3 bd · sleeps 7
- Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural Digest · 5 bd · sleeps 24
- 3 Stylish 2BRs Steps from Magnificent Mile · 6 bd · sleeps 15
- Stylish 2BR Retreat in Fulton Market for Getaways · 2 bd · sleeps 5
- 4BR Apt Same Floor Combo Group Stays Top Amenities · 4 bd · sleeps 10
- Front Row to the Lake & Skyline: Epic 60th Flr 3BR · 3 bd · sleeps 7
- Chic Fulton Market Oasis + Curated Comfort & Style · 2 bd · sleeps 5
- Luxury PH: Panoramic Views + Prime Location · 4 bd · sleeps 9
- Dual Penthouse Retreat: Perfect for Groups · 6 bd · sleeps 14
- Pentice Fulton Market · 2BR w/ Pool & Hot Tub · 2 bd · sleeps 5
- Luxury Meets Fun: Downtown PH w/ Private Game Room · 3 bd · sleeps 8
- High-end Luxury Units + Iconic Views for Groups · 5 bd · sleeps 15
- Fulton House #1 (2bd/ 1ba) · 2 bd · sleeps 4
- 5-Star Gold Coast Experience in a Luxe 2BR Retreat · 2 bd · sleeps 5
- Iconic Downtown Penthouses Getaway + City Views · 7 bd · sleeps 15
- Cubs Apt, Near Wrigley! · 1 bd · sleeps 6
- LIVN Millennium Park Downtown Chicago Superior 1BR · 1 bd · sleeps 2
- OakPk/PublicTran/2bd/sleep6/WiFi/Chgo/Lndry/Garage · 2 bd · sleeps 6
- Skyline - Military / Family Friendly · 3 bd · sleeps 7
- Luxury 5BD Home: Sauna, Hot Tub, Rooftop, Game Rm · 5 bd · sleeps 17
- United Center Compound w/Rooftop, Hot Tub, Sauna · 4 bd · sleeps 18
- The PanAm Flat - 2BR/2BA - Hospital/ScottAFB · 2 bd · sleeps 6
- Unique 7BR Dual-Apt Retreat · 7 bd · sleeps 16
- Steps to Shops, Restaurants, Trains; 5BR, 14 Guests, Parking · 5 bd · sleeps 14
- The McGann House built in the early 1900s · 4 bd · sleeps 8
- West Loop PH: Unmatched Views & Private Deck · 3 bd · sleeps 8
- Daisy Lane · 2 bd · sleeps 7
- South Loop 3 Bedroom Apt · 3 bd · sleeps 8
- Designer Oasis - Sauna, Hot Tub, Patios, Game room · 5 bd · sleeps 16
- Central 2-Story Apt, Walk to 'El', Downtown · 2 bd · sleeps 13
- Panoramic 2BR Penthouse in the Sky | Roof Deck · 2 bd · sleeps 6
- Family 7BD Home with Game Rm, Hot Tub, and Sauna · 7 bd · sleeps 16
- Designer 3BR Luxury Penthouse in Heart of Fulton Market | Featured In Architectural Digest · 3 bd · sleeps 12
- Edgewater Chic Apt: Near Beach & Eats · 4 bd · sleeps 16
- Spectacular Corner 2BR Penthouse in the Loop | Roof Deck · 2 bd · sleeps 6
- Designer Combo Loft 2E & 2W|Gold Coast/River North · 6 bd · sleeps 20
- Cozy Bee Hive · 2 bd · sleeps 4
- Private Balcony Oasis · West Loop 2BR Sleeps 5 · 2 bd · sleeps 5
- Great Location & Bright 2BR+2BA | Mapletree Suites · 2 bd · sleeps 5
- No stairs/Workers/Family/Parkng/GameRoom&Yard · 3 bd · sleeps 8
- 1,622SqFt Penthouse | 69th Flr Views | Sleeps 5 · 2 bd · sleeps 5
- Designer Furnished + Game Room | LCP Collection · 3 bd · sleeps 6
- Sky-High 3BR Penthouse in West Loop · 3 bd · sleeps 8
- Blossom Breeze Estate - Farmhouse Retreat · 5 bd · sleeps 15
- Gold Coast Gem: A 2BR Sanctuary w/ Stunning Views · 2 bd · sleeps 5
- Brand-New West Loop 3BR + City Views for Families · 3 bd · sleeps 7
- 43rd-Floor Luxury Escape + Lake Views · 2 bd · sleeps 5
- Private 3BR/2BA Home in the Trees | Stonecrest · 3 bd · sleeps 6
- Studio 604 · studio · sleeps 4
- Gold Coast, Downtown Chicago, Sleeps 20 · 5 bd · sleeps 20
- Group Weekend in River West · 3 Queens · Sleeps 7 · 3 bd · sleeps 7
- Zen in La Grange Park · 2 bd · sleeps 7
- Quiet Top-Floor Balcony · West Loop Sleeps 5 · 2 bd · sleeps 5
- Lincoln Park Getaway: Skyline Views & Luxury · 2 bd · sleeps 4
- 2BR Retreat in Downtown + City Skyline Views · 2 bd · sleeps 5
- Escape w/ Game Room near Sports Complex · 3 bd · sleeps 8
- Historic luxury townhouse on Chicago's Gold Coast · 4 bd · sleeps 10
- Cozy Old Chicago Style Retreat in Evanston · 3 bd · sleeps 6
- Stunning 3BR Penthouse in the Loop | Roof Deck · 3 bd · sleeps 8
- Something About Sara: 4BR, 2.5BA Gameroom, Dock · 4 bd · sleeps 10
- The Horizon | 3BR PH, 63rd Fl, Top Sky Deck · 3 bd · sleeps 6
- 49th Fl Luxury Retreat + Stunning Lake Views · 2 bd · sleeps 5
- Moxie - w/ Game Room- 4 Kings, Sleeps 15 · 5 bd · sleeps 15
- LIVN Millennium Park Downtown Chicago Prem Studio · 1 bd · sleeps 2
- Fun 5BR 4.5BA, Pool, Hot Tub, Game Rm, Near O’Hare · 5 bd · sleeps 15
- 2-Story Penthouse -Views, Fireplace, Pool, Gym · 2 bd · sleeps 7
- 51st Floor MagMile Penthouse Views Balcony Pool · 1 bd · sleeps 4
- 50th Floor Mag Mile Views, Balcony, Pool, Gym · sleeps 2
- Luxury 3BR Penthouses + Group Comfort Awaits · 6 bd · sleeps 14
- Fulton House #2 (2bd/ 1ba) · 2 bd · sleeps 4
- Modern 2BR Retreat Near Old Town & Lincoln Park · 2 bd · sleeps 6
- 53 Floor MagMile Penthouse Views, Balcony, Pool · 2 bd · sleeps 6
- Normal Escape Near ISU | Game Room, Hot Tub, Swing · 4 bd · sleeps 16
- Wicker Park 4BD Home: Parking, Theater, & Rooftop · 4 bd · sleeps 16
- 2-Story Penthouse Views, Fireplace, Pool, Gym · 2 bd · sleeps 8
- 50th Floor Mag Mile Views, Balcony, Pool, Gym · 1 bd · sleeps 2
- 52nd Floor Penthouse with Skyline Views and Pool · 1 bd · sleeps 4
- Two-Story Penthouse, City Views, Pool, Gym · 2 bd · sleeps 8
- Highwood Haven/Indoor Pool/Hot Tub/Arcade · 5 bd · sleeps 12
- LIVN West Loop Chicago King Studio · 1 bd · sleeps 2
- 55th-Floor 3BR Duplex Penthouse Lake & City Views · 3 bd · sleeps 8
- 52nd Floor MagMile Penthouse Views Fireplace Pool · 1 bd · sleeps 4
- 52nd Floor MagMile Penthouse Views Fireplace Pool · 1 bd · sleeps 4
- Cerro Vista Estate/Indoor Pool/Hot Tub/Game Room · 6 bd · sleeps 16
- West Loop Scenic Views + Private Balcony Retreat · 2 bd · sleeps 5
- Hinsdale Hideaway, Pet Friendly · 3 bd · sleeps 6
- Humble: 5 bd/4ba · 5 bd · sleeps 12
- Spacious 3BR Home by United Center w/ Deck & Yard · 3 bd · sleeps 6
- Enamored in Elmhurst · 4 bd · sleeps 12
- River West 4BD Home Near Fulton Market · 4 bd · sleeps 10
- Historic 4-Bedroom Edgewater Retreat Sleeps 10 · 4 bd · sleeps 10
- Luxury Penthouse COMBO 07/04 Terrace | River North · 4 bd · sleeps 16
- Nobu: 4BR - 3BA with Shuffleboard · 4 bd · sleeps 14
- Exuberant - Elmhurst Home! · 4 bd · sleeps 10
- Spacious Home in Chicago Suburbs - Holiday Home · 3 bd · sleeps 10
- Glamorous: Sauna & Bar · 3 bd · sleeps 8
- Oakley: 3BR - 2.5BT Home w/ main level B+B · 3 bd · sleeps 8
- Runway Retreat: 3 Levels, 3Bdrm, 1.5BA · 3 bd · sleeps 6
- Horizon - 4 BRs, 2 BA Game Room & Gym · 4 bd · sleeps 11
- Schaumburg Sunrise - 4 BRs & Outdoor Firepit · 4 bd · sleeps 10
- Magnolia: 4 BR - 2.5 BA Shuffleboard Table! · 4 bd · sleeps 12
- Edgewater Glen 3BD Cozy Retreat Sleeps 6 · 3 bd · sleeps 6
- Cali Coast ☀ Cozy Little 1bd/1ba home · 1 bd · sleeps 3
- Boho Heights Hideaway! - 4BR/2BA · 4 bd · sleeps 11
- Bougie Brookfield - 4BR - 2BTH Spacious Home + Bar · 4 bd · sleeps 12
- Streeterville Penthouse 2BR | Lake Views & Rooftop · 2 bd · sleeps 6
- Streeterville Corner 3BR | Lake Views & Rooftop · 3 bd · sleeps 6
- Comfy Cove: 3BR-2BT *NEW* w/ 2 Living Rooms · 3 bd · sleeps 8
- Love: Screened Porch, One Level · 3 bd · sleeps 10
- Happy at the Heights: 3+BRs/3BA · 4 bd · sleeps 12
- Family, Friends and Fun, Chicago Getaway · 3 bd · sleeps 11
- Historic 5BR Berwyn Home with Modern Comforts · 5 bd · sleeps 10
- Your Unique Stay by the Tracks | LCP Collection · 3 bd · sleeps 6
- The Brookfield Breakaway w/ Game Room · 4 bd · sleeps 11
- Lucky #7 · 3 bd · sleeps 10
- 3BR + Near Mall + Fast WiFi | LCP Collection · 3 bd · sleeps 6
- Kaleidoscope: 4 BR, 2BA · 4 bd · sleeps 12
- The Den: 2BR-1BT w/ 2 Living Rooms · 2 bd · sleeps 8
- Cozy Home by Midway Airport · 4 bd · sleeps 7
- Fulton House #2 - Studio Only (Monthly) · 1 bd · sleeps 2
- Family-Friendly Escape | Near Train & Dining · 3 bd · sleeps 6
- Mt. Prospect 4BR Haven Awaits · 4 bd · sleeps 8
- 4 King Beds w 4.5 Baths + Pool Table Arcade Sleeps 10! · 4 bd · sleeps 10
- Penthouse 3BR at Mag Mile | Lake Views & Rooftop · 3 bd · sleeps 6
- Stay near Wrigley Field! Spacious 3BD Penthouse! · 3 bd · sleeps 6
- Stylish Corner 2BR in the Loop | City & Lake Views · 2 bd · sleeps 6
- Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck · 2 bd · sleeps 6
- Monthly Stay! Stylish 2BD Apt with Parking & Gym · 2 bd · sleeps 4
- Chic Ukrainian Village Home: 4 Bedrooms 2 Bath · 4 bd · sleeps 10
- Pristine - 3 Beds, 1.5 Ba! · 3 bd · sleeps 8
- Urban Retreat by UC! 3BD 2BA w/ Parking & Balcony · 3 bd · sleeps 8
- Comfy Condo - Gym, Free Parking & Modern Amenities · 2 bd · sleeps 4
- Designer Loft 2E | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Welcoming Wheaton: 5BR, Pool Table · 5 bd · sleeps 12
- Chic Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- Edgewater Gem by the Lake! 2BR with Parking & Gym · 2 bd · sleeps 4
- Cozy 2BD Apartment near United Center with Parking · 2 bd · sleeps 4
- Two Bedroom West Loop · 2 bd · sleeps 7
- 5-BR Home: 1.5-Acre Yard & Fire Pit · 5 bd · sleeps 14
- Luxury SOHO Styled Two-Level Townhouse - Old Town · 3 bd · sleeps 14
- Fabulous Corner 2 Bedroom in the Loop | Roof Deck · 2 bd · sleeps 6
- Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking · 2 bd · sleeps 4
- Luxury Wicker Park Condo: 2BR 2BA with Parking · 2 bd · sleeps 6
- River North 2BD 2BA Retreat with Balcony & Parking · 2 bd · sleeps 5
- Luxury Penthouse Loft - Heart of Fulton Market · 5 bd · sleeps 16
- Luxury Penthouse Loft w/Terrace 507 | River North · 2 bd · sleeps 8
- Park Views on Walnut St. · 1 bd · sleeps 2
- Luxury Designer Penthouse|Private Deck|Gold Coast · 3 bd · sleeps 8
- Luxury Loft Collection COMBO 01/02 | Terrace · 6 bd · sleeps 22
- Stylish 2-Bedroom Retreat in Chicago with Parking · 2 bd · sleeps 4
- Spacious Chicago Getaway with Balcony and Parking · 2 bd · sleeps 4
- Comfy One-Bedroom Apt with Parking & Desk · 1 bd · sleeps 2
- Lakeview 3BD 2BA Penthouse near Wrigley Field! · 3 bd · sleeps 6
- Welcome to our Charming 2BD 2BA Pilsen Apartment · 2 bd · sleeps 4
- Chic River North 2BD Condo with Parking & Balcony · 2 bd · sleeps 4
- Luxury Two-Level Townhouse | Patio | Lincoln Park · 6 bd · sleeps 16
- Chicago 2BD 2BA Apartment Perfect for Families · 2 bd · sleeps 6
- Inviting & Serene | A Book Lover’s Haven · 3 bd · sleeps 8
- Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- City Living! Modern 2BD 2BA Condo in Tri Taylor · 2 bd · sleeps 4
- Oak Park 5bd 2bth sleeps 10 with 3 private parking · 4 bd · sleeps 8
- Top of River West: Luxe Penthouse for Groups · 3 bd · sleeps 7
- Downtown Luxury + Unmatched Comfort · 2 bd · sleeps 5
- Skyline View Duo for Groups: Unmatched Luxury Stay · 6 bd · sleeps 14
- Grand 6BR, 4.5BA Game Rm Near O’Hare, & Down Town · 6 bd · sleeps 15
- Prime Downtown 2BR with Resort Amenities · 2 bd · sleeps 5
- Townhome in Galena Territory w/ Pools, Lake, Gym · 3 bd · sleeps 8
- Balcony Loft · West Loop 2BR Sleeps 5 · 2 bd · sleeps 5
- Gold Coast Group Retreat + Breathtaking Views · 4 bd · sleeps 10
- Luxe 1BR: Unmatched Views & Location · 1 bd · sleeps 3
- LIVN West Loop Chicago Queen Superior Studio · 1 bd · sleeps 2
- Stylish Near West Stay Close to IMD & United Center · 3 bd · sleeps 6
- Prime West Loop 2BR Duo + Enjoy Unique Gatherings · 4 bd · sleeps 10
- Big 5BR 3.5BA Game Rm Prime Location minutes to DT · 5 bd · sleeps 11
- High-Floor 2BRs with City & Lake Views · 4 bd · sleeps 10
- City Views + Walk to Dining, Ideal for All · 2 bd · sleeps 5
- Perfect Spot & Spacious 2BR+2BA | Mapletree Suites · 2 bd · sleeps 4
- Penthouse Escape + Vibrant West Loop Access · 3 bd · sleeps 7
- Halloween family retreat! Firepit-hot tub-games · 6 bd · sleeps 14
- Two 2BRs Near Millennium Park, Ideal for Groups · 4 bd · sleeps 10
- LIVN Millennium Park Downtown Chicago Superior 2 BR · 2 bd · sleeps 4
- Top Floor Views + Central Comfort · 2 bd · sleeps 6
- Modern 3BR Home w/ Huge Backyard | LCP Collection · 3 bd · sleeps 6
- Explore Fulton Market + Retreat in Modern Comfort · 2 bd · sleeps 5
- Premium 2BR with City Views + Easy Access · 2 bd · sleeps 5
- Deluxe River West PH for Unforgettable Memories · 3 bd · sleeps 7
- King Bed, Game Room & Fire Pit | LCP Collection · 3 bd · sleeps 6
- Modern Near United Center | UIC & Medical District · 3 bd · sleeps 6
- Designer 3BR with Resort Amenities and Balcony · 3 bd · sleeps 8
- LIVN West Loop Chicago 1 BR · 1 bd · sleeps 2
- Elegant 2BR with Resort Amenities & City Views · 2 bd · sleeps 7
- Spacious 2BR in The Loop Downtown Resort Amenities · 2 bd · sleeps 5
- Near Casino | Downtown Joliet | Family-Ready · 4 bd · sleeps 8
- Prime West Loop 2BR Apts + Event Convenience · 6 bd · sleeps 15
- Downtown 2BR Oasis: Skyline Views + Prime Location · 2 bd · sleeps 5
- Skyline Views in 3BR Apartment w/ Top Amenities · 3 bd · sleeps 7
- Premium 2BR Apartments in Lincoln Park · 4 bd · sleeps 8
- Exclusive Group Getaway in Vibrant West Loop · 9 bd · sleeps 22
- Scenic 3BR PH for Tourism + Prime Location · 3 bd · sleeps 7
- Open Living Balcony · West Loop 2BR Sleeps 5 · 2 bd · sleeps 5
- 3 Penthouses, 1 Floor, Group Stay, Sleeps 21 · 9 bd · sleeps 21
- Two 2BR Apts for Business & Leisure Groups · 4 bd · sleeps 10
- Prime 2BR Retreat: Urban Vibes + Views Await · 2 bd · sleeps 4
- Historic Charm + Modern Comfort for Tourists · 2 bd · sleeps 5
- 4BR Family Home - Prime Location | LCP Collection · 4 bd · sleeps 8
- 3 Prime 2BR Units + Ideal Business Retreat · 6 bd · sleeps 15
- High-End 2BR Apartments in West Loop · 8 bd · sleeps 20
- 4 br/3ba, Great for Large Groups, Garage Parking · 4 bd · sleeps 10
- West Loop Balconied 2BR for Upscale Tours · 2 bd · sleeps 5
- Modern 3BR Urban Retreat | Near Med District & UIC · 3 bd · sleeps 6
- Prime Lincoln Park Views + Modern Amenities Await · 2 bd · sleeps 4
- 2BR near Riverwalk + downtown access · 2 bd · sleeps 7
- Spacious Penthouse Trio + Skyline Views for Groups · 9 bd · sleeps 22
- Prime 4BR Penthouse w/ Skyline Views for Families · 4 bd · sleeps 8
- LIVN West Loop Chicago 2 BR City View · 2 bd · sleeps 4
- 2,109 Sq Ft Sky Suite | 62nd Fl | Lake Views · 3 bd · sleeps 6
- Spacious Family Getaway | LCP Collection · 5 bd · sleeps 10
- Bluebird: 3 bd, 2ba & 1/2 acre yard · 3 bd · sleeps 8
- Marvel - 4BRs, 2 BA & Game Rm · 4 bd · sleeps 10
- Chic Hinsdale Home: Ranch Home · 3 bd · sleeps 6
- LIVN West Loop Chicago Classic Queen Studio · 1 bd · sleeps 2
- Modern Luxury · 3 bd · sleeps 10
- Skyway w/ Shuffleboard · 4 bd · sleeps 12
- Luma: 5BR - 2BT Spacious Retreat · 5 bd · sleeps 10
- Bright 4BR Apartment Near Lincoln Park Zoo · 4 bd · sleeps 10
- Edgewater Apt with Free Parking, Gym, City Living · 2 bd · sleeps 4
- Pilsen Retreat: 4BR 3BA near Downtown Chicago · 4 bd · sleeps 8
- Luxury Designer Penthouse 3801 | Pool | Gold Coast · 3 bd · sleeps 10
- Chic 4-Bedroom with Skyline Views, Firepit and Gym · 4 bd · sleeps 10
- South Loop 3BD 2BA Condo with Balcony and Parking · 3 bd · sleeps 6
- Studio flat in the heart of Chicago's Gold Coast · 1 bd · sleeps 4
- Modern 3BR City Retreat - Near Old Town · 3 bd · sleeps 10
- Premium Urban 4BR - Perfect Mix of Comfort & Location · 4 bd · sleeps 10
- Luxury Penthouse Loft w/Terrace 504 | River North · 2 bd · sleeps 8
- The Jetsetter ✈ 1BD/1BA Apartment - ScottAFB 6min · 1 bd · sleeps 3
- Unique Luxury Fulton Market Penthouse - Sleeps 32 · 9 bd · sleeps 32
- Spectacular Corner 3BR in the Loop | City Views · 3 bd · sleeps 6
- The Lamp Post Manor, 5BR Historic Gem in Danville · 5 bd · sleeps 10
- Luxury 2BR Apartment in Downtown Chicago · 2 bd · sleeps 4
- Sophisticated 4BR Suite - Walk to Shops, Dining & Transit · 4 bd · sleeps 10
- Luxury Designer Penthouse Loft | Sleeps 20 · 4 bd · sleeps 20
- Cozy Studio Suite, Steps from River North & Shops · sleeps 4
- Newly Remodeled 2BR 2BA Home Close to Barrington · 2 bd · sleeps 6
- Bright 3BR Stylish Apartment Near North Ave Shops · 3 bd · sleeps 8
- Luxury Designer Loft 402 | River North · 3 bd · sleeps 8
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- Modern Edgewater Apartment: 2BD 2BA with Parking! · 2 bd · sleeps 4
- Modern Lux Escape: 3BR & Gameroom · 3 bd · sleeps 8
- Modern 3BR Penthouse in the Loop | Roof Deck · 3 bd · sleeps 8
- United Center 3BD Apt with Parking and Balcony · 3 bd · sleeps 6
- Luxury Designer Penthouse Loft 502 | River North · 3 bd · sleeps 10
- Naperville Escape: 3BR -1.5 BT · 3 bd · sleeps 6
- Edgewater Apt: Walk to Beach & "El" Train! · 4 bd · sleeps 16
- Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop · 2 bd · sleeps 4
- Designer Loft 3W | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Quiet area/Petfriendly/Wi-fi/5 beds/1.5 bath · 2 bd · sleeps 6
- Serene One BD in Forest Park w/ Parking & Balcony · 1 bd · sleeps 2
- Welcome to our 2BR River West Retreat! · 2 bd · sleeps 4
- Divine - 3 King Beds! · 3 bd · sleeps 8
- Hope 4 BR, 2BA Fully Fenced · 4 bd · sleeps 10
- Sassy Skokie Stay: Fenced Yard · 3 bd · sleeps 8
- Darien Delight -Single Level Ranch · 3 bd · sleeps 10
- Mint: 4BR, 2BA~King Beds~Fully Fenced Yard · 4 bd · sleeps 11
- Downtown Brookfield Getaway! · 3 bd · sleeps 6
- Rejuvenate: 4BR, fenced yard · 4 bd · sleeps 10
- The Hangar ✈ Healthcare/Military Friendly! 🛩 · studio · sleeps 2
- Luxury Designer Apartment 1202|Gold Coast/Old Town · 2 bd · sleeps 8
- Luxury Designer Loft 202 | River North · 3 bd · sleeps 8
- Luxury Penthouse COMBO 07/02 Terrace | River North · 5 bd · sleeps 16
- A List Heights: Modern Home · 3 bd · sleeps 8
- True: *NEW* Spacious 5BR-2BT! Fully Fenced Yard! · 5 bd · sleeps 12
- Beautiful Corner 2 Bedroom in the Loop | Roof Deck · 2 bd · sleeps 6
- Cozy 4-Bedroom Apartment in Evanston · 4 bd · sleeps 12
- Stunning Corner 2BR in the Loop | City & Lake Views · 2 bd · sleeps 6
- Luxury Designer Apartment 802| Gold Coast/Old Town · 2 bd · sleeps 8
- Angel: Spacious Modern Home! · 4 bd · sleeps 12
- Designer Loft 2W | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Champagne & Co. 3BR - 2.5BA *NEW* · 3 bd · sleeps 9
- Compatible: 3BR Ranch w/ Finished Basement · 3 bd · sleeps 8
- Chic 2BR Apartment in Edgewater: Gym & Parking · 2 bd · sleeps 4
- House 3BR 1.5 BATH/Sleeps8/ GameRm/DogFrdly/BBQ · 3 bd · sleeps 8
- Luxury Designer Apartment 803| Gold Coast/Old Town · 2 bd · sleeps 8
- Modern Chicago Getaway · 3 bd · sleeps 10
- Amazing Penthouse: Views, Hot Tub, Cold Plunge! · 3 bd · sleeps 14
- Pilsen 2BA Condo Minutes from Chicago Attractions · 2 bd · sleeps 6
- River North 2BD Condo: Parking, Balcony, Laundry · 2 bd · sleeps 5
- Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck · 4 bd · sleeps 12
- Crisp: 4000 sq feet · 6 bd · sleeps 14
- Classic: 5BR, 3BA w/ bar · 5 bd · sleeps 12
- Enjoy our 2BD 2BD Condo with Parking in Tri Taylor · 2 bd · sleeps 4
- Bliss in Brookfield- 5BR, 3BA, Fenced Yard · 5 bd · sleeps 11
- Luxury Designer Loft 302 | River North · 3 bd · sleeps 8
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Schaumburg Sanctuary - New! · 3 bd · sleeps 5
- PLR Block · 9 bd · sleeps 32
- Chicago Chic: 2 BR - 1 BA & Garage · 2 bd · sleeps 7
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Wish - 3 King Beds! · 3 bd · sleeps 8
- Wonderful Willowbrook Escape: Hinsdale Schools · 3 bd · sleeps 8
- Fantastic: 3BR / 2 BTH - Modern & Stylish Home! · 3 bd · sleeps 8
- Luxury Designer Penthouse 3802 | Pool | Gold Coast · 3 bd · sleeps 10
- Charming & Cozy Getaway - A Heroic Stay Awaits! · 2 bd · sleeps 6
- Radiance - Single Level Home · 5 bd · sleeps 9
- LUX - 3 King Beds- Full Luxury · 3 bd · sleeps 8
- Luxury Designer Penthouse Combo | NW | Gold Coast · 6 bd · sleeps 20
- 3BR Apartment Near Clybourn Corridor & Old Town · 3 bd · sleeps 8
- Suburban Fab Part Deux · 3 bd · sleeps 6
- Splendid Corner 3BR in the Loop | City Views · 3 bd · sleeps 6
- Golden: Sleeps 8, 2.5 baths! · 3 bd · sleeps 8
- Chic Corner 2BR in the Loop | City & Lake Views · 2 bd · sleeps 6
- Luxury 4BD Gold Coast Penthouse with Deck & Views · 4 bd · sleeps 10
- Terrific Naper Townhouse 3beds/2.5 baths · 3 bd · sleeps 8
- The Ridge Retreat · 2 bd · sleeps 6
- Luxury Penthouse COMBO 04/02 Terrace | River North · 5 bd · sleeps 14
- 3BR w/ Large Yard + Near Mall | LCP Collection · 3 bd · sleeps 6
- Confidence: 4BR - 2 BT Beautiful Cozy Home · 4 bd · sleeps 10
- Casa 22 Luxury & Modern 3BD 2BA Home in Skokie · 3 bd · sleeps 6
- Pool Table and Fireplace by LCP Collection · 4 bd · sleeps 8
- 4BR Home | Ideal for Long Stays · 4 bd · sleeps 8
- Luxury Loft Collection COMBO 902/903 Terrace · 6 bd · sleeps 20
- Luxury Designer Penthouse | Gold Coast/Old Town · 2 bd · sleeps 8
- Family Stay in River West · 3BR/3BA · Sleeps 7 · 3 bd · sleeps 7
- Dash: 4 Bdrms, 2.5 BA · 4 bd · sleeps 10
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Tranquility - 4+BR, 2BA · 5 bd · sleeps 5
- Luxury Designer Penthouse 3804 | Pool | Gold Coast · 3 bd · sleeps 10
- Modern Comfort in Homewood · 3 bd · sleeps 6
- Modern 2BR in The Loop + Panoramic City Views · 2 bd · sleeps 4
- Mokena Spacious Stay - 3BR/2BA · 3 bd · sleeps 10
- Dazzling Des Plaines: 3 BR, Single Level Home · 3 bd · sleeps 8
- Elegance: 4BR - 2 BT Spacious Ranch w/ Basement · 4 bd · sleeps 8
- Grateful: 3BR - 1BT Modern Getaway · 3 bd · sleeps 8
- Elevation, 5+Beds, Open Concept, Huge Bsmt · 4 bd · sleeps 11
- Stokes Stay: Stunning 4BR/2.5BT · 4 bd · sleeps 10
- Daydream: Spacious 5BR-2BA-Newly Remodeled! · 5 bd · sleeps 12
- Luxury 4BR,3BA, GameRm Near O’Hare DT Free Parking · 4 bd · sleeps 15
- Renovated Mid-Century, 4 bed/2.1 bath townhome · 4 bd · sleeps 10
- Clean & Best Location 2BR+2BA | Mapletree Suites · 2 bd · sleeps 5
- Dream- 4 King Beds, Fully Fenced · 3 bd · sleeps 8
- Relax & Play - 4BR Home with Game Room for Family · 4 bd · sleeps 8
- Suburban Haven: Cozy Escape with a Touch of Luxury · 1 bd · sleeps 16
- Cloud 9: 4BR-2.5BT- Fully Fenced, 2 Story · 4 bd · sleeps 12
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Luxury Loft Collection 901 - Terrace - River North · 3 bd · sleeps 10
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Rose: NEW 4BR - 2 BT Ranch House · 4 bd · sleeps 10
- Rein - Rolling Meadows Home! · 4 bd · sleeps 10
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
- Believe: Fully Updated · 4 bd · sleeps 10
- Stylish 2-Bedroom Retreat with Parking and Balcony · 2 bd · sleeps 4
- Suburban Fab · 3 bd · sleeps 6
- Beautifully remodeled, Perfect for large groups · 4 bd · sleeps 10
- Basement Lounge & Games | LCP Collection · 4 bd · sleeps 8
- A+: 4BR-3BTH Spacious Home w/ 2 Living Rooms · 4 bd · sleeps 12
- Great Value 3BR 2.5BA Game Rm Free Park, Safe Area · 3 bd · sleeps 8
- Huge 4BR w/ Yard | Sleeps 8 | LCP Collection · 4 bd · sleeps 8
- Prime Loop Apts + Convenience for Groups · 8 bd · sleeps 20
- Relaxing Lake Zurich 3BR + Patio | LCP Collection · 3 bd · sleeps 6
- Family Haven Retreat, Sleep 14 guests · 6 bd · sleeps 15
- Evanston fresh and fabulous! · 2 bd · sleeps 5
- LIVN Millennium Park Downtown Chicago 1 BR · 1 bd · sleeps 2
- Sleeps 2/Aurora/Ext stay discounts/Wi-fi & Parkng · 1 bd · sleeps 2
- Tranquil Retreat: Cozy Studio @ Wyndham Galena · sleeps 2
Questions about renting in Illinois
How many vacation rentals are there in Illinois?
CielStay lists 440 homes in Illinois, counted from the homes live today. By type: 150 houses, 244 condos and 13 resort suites.
Can I book a vacation rental in Illinois directly with the host?
Yes. Every home here can be booked on the host's or manager's own website. Each listing links to it, along with any other place the home is listed.
How do I book a Illinois vacation rental directly with the owner?
Open a home and choose Book direct: it takes you to the host's or manager's own booking site, where you see their price and terms. You can also message the host first. CielStay doesn't take the booking or the payment. Booking direct often costs less, because no platform fee or commission is added; compare the final totals before you pay.
Where can I rent a house in Illinois for 6 people?
326 homes here sleep 6 or more; 140 are houses, the rest condos or resort suites. Add your dates and group size in the search to see which are free.
Are there vacation rentals in Illinois with a pool?
103 homes list a pool, and 77 homes a hot tub. Some pools are shared, in a resort or community, so check the listing if you want a private one.
Are there pet-friendly rentals in Illinois?
161 homes list pets as allowed. Pet fees and limits vary by host, so check the house rules on the listing.
Are there rentals in Illinois for large groups?
165 homes sleep 10 or more, and 66 homes have five or more bedrooms.
How are prices shown?
Each home shows one price with a note on what it includes; the asterisk explains how we work it out. Prices can change and may not be exact. If a host hasn't shared a fee with us, we can't include it. The host's site or booking channel has the final total; taxes are extra.