Chicago is a world-class city on the shores of Lake Michigan, celebrated for its iconic architecture, deep-dish pizza, world-class museums, and a thriving arts and music scene. Independent vacation homes and apartments offer a neighborhood experience in one of America's most walkable cities — from loft-style spaces in the West Loop to lakefront retreats in Lincoln Park. Chicago is a compelling year-round destination with something for every type of traveler.
CielStay lists 120 homes for rent in Chicago, run by independent hosts and property managers. All of them can be booked on the host's or manager's own website, across 9 booking sites. Some are also listed on Airbnb; each listing shows every place it can be booked.
The most common size is three bedrooms (42 homes). 61 homes sleep 10 or more.
Chicago rentals at a glance
Counted from what hosts list. Check the listing before you book.
| Studio or 1 bedroom | 3 |
| 2 bedrooms | 36 |
| 3 bedrooms | 42 |
| 4 bedrooms | 18 |
| 5 or more bedrooms | 21 |
| Sleeps 10 or more | 61 |
| Air conditioning | 50 |
| Pets allowed | 33 |
| Fireplace | 11 |
| Pool | 6 |
Homes in Chicago
Homes with the host's own booking site first. Prices can change and may not be exact; the asterisk shows what each one includes.
All 120 homes in Chicago
- Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectural Digest · 6 bd · sleeps 24
- Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Digest · 2 bd · sleeps 12
- 53 Floor MagMile Penthouse Views, Balcony, Pool · 2 bd · sleeps 6
- Chic Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- 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
- Luxury Penthouse Loft - Heart of Fulton Market · 5 bd · sleeps 16
- Chic River North 2BD Condo with Parking & Balcony · 2 bd · sleeps 4
- Chicago 2BD 2BA Apartment Perfect for Families · 2 bd · sleeps 6
- Luxury Designer Penthouse Loft 502 | River North · 3 bd · sleeps 10
- Luxury Loft Collection 901 - Terrace - River North · 3 bd · sleeps 10
- Luxury Loft Collection 01 - Terrace - River North · 3 bd · sleeps 12
- Luxury Designer Penthouse Combo |North| Gold Coast · 6 bd · sleeps 20
- Luxury Designer Penthouse Combo |South| Gold Coast · 6 bd · sleeps 20
- Luxurious River North 3BR/2BA- Free Onsite Parking · 3 bd · sleeps 10
- Luxury Loft Collection COMBO 01/03 | Terrace · 6 bd · sleeps 22
- Designer Loft 3W | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Luxury Penthouse COMBO 07/02 Terrace | River North · 5 bd · sleeps 16
- Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest · 3 bd · sleeps 12
- 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
- Rooftop, West Loop Chicago · 3 bd · sleeps 10
- Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural Digest · 5 bd · sleeps 24
- Cubs Apt, Near Wrigley! · 1 bd · sleeps 6
- 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
- Downtown Vintage Chicago APT · 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
- Gold Coast, Downtown Chicago, Sleeps 20 · 5 bd · sleeps 20
- Historic luxury townhouse on Chicago's Gold Coast · 4 bd · sleeps 10
- Stunning 3BR Penthouse in the Loop | Roof Deck · 3 bd · sleeps 8
- 2-Story Penthouse -Views, Fireplace, Pool, Gym · 2 bd · sleeps 7
- Wicker Park 4BD Home: Parking, Theater, & Rooftop · 4 bd · sleeps 16
- Pilsen Hub: Spacious Group Retreat · 4 bd · sleeps 20
- 55th-Floor 3BR Duplex Penthouse Lake & City Views · 3 bd · sleeps 8
- Spacious 3BR Home by United Center w/ Deck & Yard · 3 bd · sleeps 6
- 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
- Runway Retreat: 3 Levels, 3Bdrm, 1.5BA · 3 bd · sleeps 6
- Edgewater Glen 3BD Cozy Retreat Sleeps 6 · 3 bd · sleeps 6
- Streeterville Penthouse 2BR | Lake Views & Rooftop · 2 bd · sleeps 6
- Streeterville Corner 3BR | Lake Views & Rooftop · 3 bd · sleeps 6
- 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
- Chic Ukrainian Village Home: 4 Bedrooms 2 Bath · 4 bd · sleeps 10
- Urban Retreat by UC! 3BD 2BA w/ Parking & Balcony · 3 bd · sleeps 8
- Designer Loft 2E | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Cozy 2BD Apartment near United Center with Parking · 2 bd · sleeps 4
- Two Bedroom West Loop · 2 bd · sleeps 7
- 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 w/Terrace 507 | River North · 2 bd · sleeps 8
- Downtown South Loop Apt Close to Soldier Field · 4 bd · sleeps 9
- Luxury Designer Penthouse|Private Deck|Gold Coast · 3 bd · sleeps 8
- Luxury Loft Collection COMBO 01/02 | Terrace · 6 bd · sleeps 22
- Lakeview 3BD 2BA Penthouse near Wrigley Field! · 3 bd · sleeps 6
- Welcome to our Charming 2BD 2BA Pilsen Apartment · 2 bd · sleeps 4
- Luxury Two-Level Townhouse | Patio | Lincoln Park · 6 bd · sleeps 16
- Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- Pilsen Retreat: 4BR 3BA near Downtown Chicago · 4 bd · sleeps 8
- Luxury Designer Penthouse 3801 | Pool | Gold Coast · 3 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
- Luxury Penthouse Loft w/Terrace 504 | River North · 2 bd · sleeps 8
- Renovated 3 Bedroom Chicago Downtown Pilsen · 3 bd · sleeps 10
- Unique Luxury Fulton Market Penthouse - Sleeps 32 · 9 bd · sleeps 32
- Spectacular Corner 3BR in the Loop | City Views · 3 bd · sleeps 6
- Luxury 2BR Apartment in Downtown Chicago · 2 bd · sleeps 4
- Luxury Designer Penthouse Loft | Sleeps 20 · 4 bd · sleeps 20
- Luxury Designer Loft 402 | River North · 3 bd · sleeps 8
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views · 2 bd · sleeps 6
- Modern 3BR Penthouse in the Loop | Roof Deck · 3 bd · sleeps 8
- United Center 3BD Apt with Parking and Balcony · 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
- Welcome to our 2BR River West Retreat! · 2 bd · sleeps 4
- Luxury Designer Apartment 1202|Gold Coast/Old Town · 2 bd · sleeps 8
- Luxury Designer Loft 202 | River North · 3 bd · sleeps 8
- Beautiful Corner 2 Bedroom in the Loop | Roof Deck · 2 bd · sleeps 6
- 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
- Designer Loft 2W | Heart of Gold Coast/River North · 3 bd · sleeps 12
- Luxury Designer Apartment 803| Gold Coast/Old Town · 2 bd · sleeps 8
- 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
- Luxury Designer Loft 302 | River North · 3 bd · sleeps 8
- Chicago Chic: 2 BR - 1 BA & Garage · 2 bd · sleeps 7
- Luxury Designer Penthouse 3802 | Pool | Gold Coast · 3 bd · sleeps 10
- Luxury Designer Penthouse Combo | NW | Gold Coast · 6 bd · sleeps 20
- Splendid Corner 3BR in the Loop | City Views · 3 bd · sleeps 6
- 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
- Luxury Penthouse COMBO 04/02 Terrace | River North · 5 bd · sleeps 14
- Luxury Loft Collection COMBO 902/903 Terrace · 6 bd · sleeps 20
- Luxury Designer Penthouse | Gold Coast/Old Town · 2 bd · sleeps 8
- Luxury Designer Penthouse 3804 | Pool | Gold Coast · 3 bd · sleeps 10
- Luxury Loft Collection 02 - Terrace - River North · 3 bd · sleeps 12
- Luxury Designer Penthouse 3803 | Pool | Gold Coast · 3 bd · sleeps 10
- Luxury Loft Collection COMBO 02/03 | Terrace · 6 bd · sleeps 22
- Luxury Loft Collection 1, 2, 3 · 9 bd · sleeps 42
- Artsy Chicago: 1 bd/1 bth - Fun Modern Space · 1 bd · sleeps 4
- Luxury Loft Collection 03 - Terrace - River North · 3 bd · sleeps 12
- City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎ · 3 bd · sleeps 10
- Luxury Designer Penthouse Combo West | Gold Coast · 6 bd · sleeps 20
- Luxury Fulton Market Penthouse Amazing City Views · 4 bd · sleeps 16
Questions about renting in Chicago
How many vacation rentals are there in Chicago?
CielStay lists 120 homes in Chicago, counted from the homes live today with an exact map location.
Can I book a vacation rental in Chicago 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.
Are there pet-friendly rentals in Chicago?
33 homes list pets as allowed. Pet fees and limits vary by host, so check the house rules on the listing.
Are there rentals in Chicago for large groups?
61 homes sleep 10 or more, and 21 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.