Bed and breakfast holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Room in Wilmette

4.95 out of 5 average rating, 214 reviews

(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.) 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. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).

14–21 Oct

$145 NZD per night

Guest favourite

Room in Chicago

4.99 out of 5 average rating, 102 reviews

Lovely UofC Prof mansion great on campus location

No closer accommodation to U of C anywhere. Large light filled bedrooms, private bathrooms, huge balcony in 4 story light filled home on sought after University of Chicago campus. Two blocks from the University, four blocks from Lab school. Short walk to train to downtown, beach, bike path, Science and Industry Museum and lakefront. A rare, privately owned home in the heart of campus. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

1–8 Mar

$423 NZD per night

Guest favourite

Room in Chicago

5.0 out of 5 average rating, 84 reviews

Urban Oasis Pilsen - guest room in townhouse

A walk-up in Chicago's coolest neighborhood - Pilsen! Your private bedroom has a queen-size bed and an en-suite bathroom with a tub/shower combo. There is a small desk, ample storage space, and a TV with streaming services. While your many triple-paned windows let in light, air, and sunshine, you will also hear the I-90/94 nearby. Please note that your room is on the third floor of the building (40 steps). On the second floor, you'll find (y)our kitchen, living rooms, TV den, and balcony.

6–13 Sep

$202 NZD per night

Guest favourite

Room in Chicago

4.95 out of 5 average rating, 213 reviews

Great Edgewater/Andersonville private suite

1904 Greystone 2-Flat gut rehabbed into Single Family Home: Loft style w/ exposed brick & duct work. Private guest suite (w/ separate entrance) that sleeps 2-4 persons, There is a King bed in the private bedroom & queen tempurpedic topped sofa sleeper in the private living area, wet bar w/ mini fridge, Keurig coffee maker, sink and microwave, 2 flat screens TVs, private bath, piano, and use of the backyard garden. Also, the main house Kitchen/Living Rm are available to use upon request

26 Nov – 3 Dec

$318 NZD per night

Guest favourite

Room in Chicago

4.89 out of 5 average rating, 75 reviews

Serene and and wholistic place with the garden.

I live in Albany Park, Chicago. It's quiet, family oriented, with lots of parks and treelined streets. The Chicago River Trail is within walking distance too. My home is a charming 2 flat building, built in 1909. It has lots of original, unique details. My home is a tranquil and peaceful place. My decor mainly consists of hand-made furniture, artwork, crystals, wind chimes, etc. I don't use any chemical cleaning supplies, I use only home-made products and essential oils.

20–27 Feb

$136 NZD per night

Room in Chicago

4.86 out of 5 average rating, 333 reviews

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

19–26 Jan

$301 NZD per night

Superhost

Room in Chicago

4.79 out of 5 average rating, 297 reviews

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules :-). Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Yoga, Gym, Movie Theater, Multiple Bars & Diverse Cuisine within 5-15 min walking

4–11 May

$94 NZD per night

Guest favourite

Room in Chicago

4.9 out of 5 average rating, 313 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access, use of entire level including bright spacious family room. Located minutes from bus, DIVVY bikes, and "el" (2 blocks), Wrigley Field (6 blocks) and 1.5 miles to Lake Michigan. Walk Approximately 20 minutes by train to the downtown area or central city "Loop."

2–9 Oct

$239 NZD per night

Guest favourite

Room in Chicago

4.93 out of 5 average rating, 103 reviews

Edgebrook Lg bdr by golf course

Beautiful private bedroom (1 of 2) in a ranch style home, you have full access to everything on the ground floor including living room, kitchen, and bathroom (shared if there is a tenant in the second bedroom). I live in the basement level and have my own space and will only share the kitchen with you. All guests are required to be vaccinated to maintain a safe environment for all.

7–14 Sep

$172 NZD per night

Home in Forest Park

4.78 out of 5 average rating, 40 reviews

Cozy and Convenient Forest Park Retreat

Enjoy a restful stay in our historic home in charming Forest Park—conveniently located to both the Blue and Green line trains for a short ride to downtown Chicago. Relax with everything you'll need during your stay in this spacious 1 bedroom with additional room on the sofa bed—all just a short walking distance away from the charming shops and dining of Forest Park.

19–26 Dec

$220 NZD per night

Guest favourite

Room in Evanston

4.95 out of 5 average rating, 424 reviews

Classy and Cozy 2nd. Room

2nd. Room available quiet suburban Evanston close to dowontown. Comfortable for two. Bathroom, full bed, closet, chests. street parking always available. Original art, books, Old World decor, wifi, personalized attention, delicious hearty breakfast. We are Covid-19 compliant and fully vaccinated.

23 Feb – 2 Mar

$166 NZD per night

Guest favourite

Room in Chicago

4.79 out of 5 average rating, 254 reviews

Cloudgate Room, minutes to O'Hare in Safest Area

My other listing can be found through my profile. This room is just next to the washroom. My place is only 1 mile/1.6km to USMLE Center; 10 minutes driving to O'Hare, 0.6 miles to CTA Blue Line station. Early check in is available for an additional fee. Prices are subject to change.

30 Aug – 6 Sep

$126 NZD per night