Manage your B&B

B&B Sleepy Hollow

240 Bed and Breakfasts in Sleepy Hollow City district (Chicago, Illinois, United States)

Our top selectionPrice: Low → HighPrice: High → LowBest rated

Accommodation type

Apartment

Holiday home

Bed & breakfast

Pension

Review score

General amenities

Free Wifi

Electric vehicle charging station

Garden

Pets allowed

Free parking

Sauna

More

Room Amenities

Private bathroom

Private entrance

Air conditioning

Bath

Private terrace

Private kitchen

More

Accessibility

Wheelchair accessible

Entire unit located on ground floor

Upper floors accessible by elevator

Adults only

Accommodations just outside your destination

Near Sleepy Hollow

Art Downtown Fulton Market Entire 3 bedroom Home Sleep10 Private Garage Roof EV Tesla - B&B Chicago

Art Downtown Fulton Market Entire 3 bedroom Home Sleep10 Private Garage Roof EV Tesla - B&B Chicago

Art Downtown Fulton Market Entire 3 bedroom Home Sleep10 Private Garage Roof EV Tesla

Direct reservation

(10.6 km from Sleepy Hollow)

15 mins DT HumboldtPark Gem Sleeps 8 FreePark - B&B Chicago

15 mins DT HumboldtPark Gem Sleeps 8 FreePark - B&B Chicago

15 mins DT HumboldtPark Gem Sleeps 8 FreePark

Direct reservation

(10.6 km from Sleepy Hollow)

Trendy West Town Flat - 2 bed / 1.5 bath w parking - B&B Chicago

Trendy West Town Flat - 2 bed / 1.5 bath w parking - B&B Chicago

Trendy West Town Flat - 2 bed / 1.5 bath w parking

Direct reservation

(10.6 km from Sleepy Hollow)

Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place - B&B Chicago

Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place - B&B Chicago

Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place

Direct reservation

(10.6 km from Sleepy Hollow)

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail - B&B Chicago

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail - B&B Chicago

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

Direct reservation

(10.6 km from Sleepy Hollow)

McCormick Oasis with Balcony, Optional Parking, Patio and Gym Sleeps 6 Near McCormick Place, Grant Park, Soldier Field & Museum Campus - B&B Chicago

McCormick Oasis with Balcony, Optional Parking, Patio and Gym Sleeps 6 Near McCormick Place, Grant Park, Soldier Field & Museum Campus - B&B Chicago

McCormick Oasis with Balcony, Optional Parking, Patio and Gym Sleeps 6 Near McCormick Place, Grant Park, Soldier Field & Museum Campus

Direct reservation

(10.6 km from Sleepy Hollow)

South Loop 2BR Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College - B&B Chicago

South Loop 2BR Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College - B&B Chicago

South Loop 2BR Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College

Direct reservation

(10.6 km from Sleepy Hollow)

McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field - B&B Chicago

McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field - B&B Chicago

McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field

Direct reservation

(10.6 km from Sleepy Hollow)

Forrestville Ave Large Suite - B&B Chicago

Forrestville Ave Large Suite - B&B Chicago

Forrestville Ave Large Suite

Direct reservation

(10.6 km from Sleepy Hollow)

Spacious Oak Park Home, 11 Mi to Downtown Chicago! - B&B Oak Park

Spacious Oak Park Home, 11 Mi to Downtown Chicago! - B&B Oak Park

Spacious Oak Park Home, 11 Mi to Downtown Chicago!

Direct reservation

(10.7 km from Sleepy Hollow)

Oak Park Home w/ Grill - 5 Mi to Garfield Park! - B&B Oak Park

Oak Park Home w/ Grill - 5 Mi to Garfield Park! - B&B Oak Park

Oak Park Home w/ Grill - 5 Mi to Garfield Park!

Direct reservation

(10.7 km from Sleepy Hollow)

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop - B&B Chicago

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop - B&B Chicago

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop

Direct reservation

(10.7 km from Sleepy Hollow)

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions - B&B Chicago

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions - B&B Chicago

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions

Direct reservation

(10.7 km from Sleepy Hollow)

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park - B&B Chicago

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park - B&B Chicago

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park

Direct reservation

(10.7 km from Sleepy Hollow)

McCormick Place 2BR Stylish Suite with Optional Parking and Gym for up to 8 guests Near Soldier Field and Grant Park - B&B Chicago

McCormick Place 2BR Stylish Suite with Optional Parking and Gym for up to 8 guests Near Soldier Field and Grant Park - B&B Chicago

McCormick Place 2BR Stylish Suite with Optional Parking and Gym for up to 8 guests Near Soldier Field and Grant Park

Direct reservation

(10.7 km from Sleepy Hollow)

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park - B&B Chicago

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park - B&B Chicago

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park

Direct reservation

(10.7 km from Sleepy Hollow)

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown - B&B Chicago

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown - B&B Chicago

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown

Direct reservation

(10.7 km from Sleepy Hollow)

McCormick Place Beautiful 2BR Apartment with Optional Parking Sleeps up to 8 Near Soldier Field, Grant Park and Lakefront Trail - B&B Chicago

McCormick Place Beautiful 2BR Apartment with Optional Parking Sleeps up to 8 Near Soldier Field, Grant Park and Lakefront Trail - B&B Chicago

McCormick Place Beautiful 2BR Apartment with Optional Parking Sleeps up to 8 Near Soldier Field, Grant Park and Lakefront Trail

Direct reservation

(10.7 km from Sleepy Hollow)

Convenient Cozy 2BR Loft with Optional Parking for 8 guests Near McCormick Place, Soldier Field and Lakefront Trail - B&B Chicago

Convenient Cozy 2BR Loft with Optional Parking for 8 guests Near McCormick Place, Soldier Field and Lakefront Trail - B&B Chicago

Convenient Cozy 2BR Loft with Optional Parking for 8 guests Near McCormick Place, Soldier Field and Lakefront Trail

Direct reservation

(10.7 km from Sleepy Hollow)

Modern 2BR Loft with Amazing City Skyline View and Optional Parking for 8 Guests Near McCormick Place and Soldier Field - B&B Chicago

Modern 2BR Loft with Amazing City Skyline View and Optional Parking for 8 Guests Near McCormick Place and Soldier Field - B&B Chicago

Modern 2BR Loft with Amazing City Skyline View and Optional Parking for 8 Guests Near McCormick Place and Soldier Field

Direct reservation

(10.7 km from Sleepy Hollow)

Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field - B&B Chicago

Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field - B&B Chicago

Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field

Direct reservation

(10.7 km from Sleepy Hollow)

Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field - B&B Chicago

Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field - B&B Chicago

Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field

Direct reservation

(10.7 km from Sleepy Hollow)

Group-Friendly 2BR with Optional Parking and Gym Access Near McCormick Place and Soldier Field - B&B Chicago

Group-Friendly 2BR with Optional Parking and Gym Access Near McCormick Place and Soldier Field - B&B Chicago

Group-Friendly 2BR with Optional Parking and Gym Access Near McCormick Place and Soldier Field

Direct reservation

(10.7 km from Sleepy Hollow)

Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront - B&B Chicago

Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront - B&B Chicago

Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront

Direct reservation

(10.7 km from Sleepy Hollow)

Discover unique B&B destinations

Subscribe to our newsletter

United States
Illinois
Chicago
Sleepy Hollow

Bedandbreakfast.eu

Service & Contact
About us
Travel inspiration

B&B hosts

Manage your B&B
List your B&B
Starting a B&B
FAQ
Must reads for B&B Innkeepers

Popular Destinations

Bed & Breakfast Edinburgh
Bed & Breakfast Dublin
Bed & Breakfast London
Bed & Breakfast Paris

English

Deutsch Español Français Italiano Nederlands

© 2026 Bedandbreakfast.eu