
Bed and breakfast vacation rentals in Chicago
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts in Chicago
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

Bright Room with a Garden View
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off. Shares bathroom with 2 rooms Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

(BR#1) Welcoming, warm & comfortable, 3 guests
Welcoming, warm & comfortable home, BR#1 for up to 3 guests. (LISTING #1 OF 3; see other listings for additional space.) A lovely and spacious bedroom in our home. Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Meaningful conversation (if you want it).

Private room with private entrance in Boystown
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Cute room in downtown Boystown
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Large private room w/ shared bathroom in Boystown!
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Cozy Garden Room in the middle of Boystown!
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

British Themed Room in the Middle of Boystown
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Queen Bed with Private Bath in Boystown
Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

House 5863 Bed and Breakfast Room 2
This room offers quiet comfort and value. We have discounted the price only because the bath, although private, is located across the hall from the guest room. The room is located at the center of the house and is very quiet. Features: Queen bed Private bath [Bath is located across the hall from guest room] Flat screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bath robes

Wrigleyville Suites Room 1
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe, just minutes away from local restaurants, downtown, public transit (both bus and train), Divvy Bike Stations, and Cubs Stadium. Room 1 is a private room with a queen bed and shared bathroom for up to 2 guests. It is one of our largest and brightest room.

Luxurious King Room in Boutique Wicker Park B&B
Bright and modern guest room located just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Hoyne King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood

Private bedroom with shared bath
Located in the heart of Boystown, this private room has a full sized bed, shares two bathrooms with three other rooms, shared kitchen, shared living room and dining room. Wifi throughout the property. Main thing to be aware of, is due to its centrality, it can be loud, especially at night on weekends. Weekly cleaning of all shared spaces included.
Popular amenities for Chicago bed and breakfasts
Family-friendly bed and breakfasts

Private room with private entrance in Boystown

Cute room in downtown Boystown

Bright Room with a Garden View

Private bedroom with shared bath

Large private room w/ shared bathroom in Boystown!

Cozy Garden Room in the middle of Boystown!

(BR#1) Welcoming, warm & comfortable, 3 guests

Caesar's Lair
Bed and breakfast rentals with breakfast

Romantic Queen Room in Boutique Wicker Park B&B

Queen Bed with Private Bathroom in Boystown

Sun-Filled King Room in Boutique Wicker Park B&B

Queen Room w/ Balcony in Boutique Wicker Park B&B

Romantic King Room in Boutique Wicker Park B&B

Peaceful King Room in Boutique Wicker Park B&B

Gorgeous King Room in Boutique Wicker Park B&B

King Room in Boutique Wicker Park B&B
Other bed and breakfast vacation rentals

Private room with private entrance in Boystown

Cute room in downtown Boystown

Bright Room with a Garden View

Private bedroom with shared bath

Large private room w/ shared bathroom in Boystown!

Luxurious King Room in Boutique Wicker Park B&B

Cozy Garden Room in the middle of Boystown!

(BR#1) Welcoming, warm & comfortable, 3 guests
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $167 CAD | $140 CAD | $196 CAD | $126 CAD | $150 CAD | $168 CAD | $165 CAD | $182 CAD | $158 CAD | $150 CAD | $149 CAD | $136 CAD |
| Avg. temp | -3 °C | -1 °C | 4 °C | 10 °C | 16 °C | 22 °C | 25 °C | 24 °C | 20 °C | 13 °C | 6 °C | 0 °C |
Quick stats about bed and breakfast rentals in Chicago

Total vacation rentals
Explore 70 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at $69 CAD per night before taxes and fees

Verified guest reviews
Over 5,250 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Chicago vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chicago rentals

4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chicago’s top spots, include Millennium Park, Wrigley Field, and Lincoln Park
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