Bed and Breakfast in Chicago, IL

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Chicago, IL bed and breakfast
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528 Bed and Breakfasts in Chicago, IL

Best Chicago, IL bed and breakfasts with breakfast included

Dorothy's - Chicago, IL
8.6 130 reviews
Chicago, IL
10/07 – 11/07
NZ$487/nightfor 1 night

Dorothy's

1 1
B&B , Chicago
This Lakeview guesthouse is conveniently located less than 1.3km from Lake Michigan, a short walk from Wrigley Field and Briar Street Theatre, and close to the Addison and Belmont Red Line stations.
Offering free continental breakfast, Wi-Fi, and shared kitchen facilities including a fridge, freezer and microwave, this pet-friendly Chicago B&B provides housekeeping services on request and boasts a smoke-free environment.
Villa D' Citta - Chicago, IL
9.3 192 reviews
Chicago, IL
14/11 – 05/12
NZ$584/nighttotal: NZ$12264 (21 )

Villa D' Citta

1 2
B&B , Chicago
This charming bed and breakfast is situated in the heart of Chicago's Lincoln Park, a short walk from the zoo and just a few miles from the Magnificent Mile. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The guest rooms are beautifully decorated with an Italian-inspired theme and offer views of the neighbourhood. Guests can enjoy a range of amenities including a private grotto and garden with BBQ facilities, a hot tub, a gourmet kitchen and daily continental breakfast, plus a hot breakfast on weekends.
Dorothy's - Chicago, IL
Chicago, IL
25/06 – 26/06
NZ$356/nightfor 1 night

Dorothy's

1 1
B&B , Chicago
Dorothy's B&B in Chicago is situated 8km from the city centre, near the Ivy League Baseball Club, Our Lady of Mount Carmel Church, and Temple Sholom.
This pet-friendly guesthouse offers free Wi-Fi, on-site parking, and laundry services, providing a peaceful retreat with one bathroom in a quiet residential area.
Dorothy's - Chicago, IL
Chicago, IL
23/10 – 25/10
NZ$350/nighttotal: NZ$700 (2 )

Dorothy's

1 2
B&B , Chicago
This Chicago guest house is located in a district known for its excellent services and high-end amenities, offering a memorable guest experience.
This 50 square meter bed and breakfast provides complimentary Wi-Fi, air conditioning in some rooms, a communal kitchen with a fridge, microwave, and dishwasher, and a daily complimentary breakfast.

Best Chicago, IL bed and breakfasts with a garden

Private Suite In Lincoln Square - Chicago, IL
9.9 468 reviews
Chicago, IL
03/08 – 05/08
NZ$266/nighttotal: NZ$532 (2 )

Private Suite In Lincoln Square

1 2
B&B , Chicago
This Chicago basement flat, conveniently located near a Brown Line CTA station providing easy access to the city centre, offers a private entrance and is close to local amenities.
The self-contained apartment sleeps four, boasting a queen-size bed, sofa bed, well-equipped kitchenette (including microwave and mini-oven), full bathroom, laundry facilities, backyard seating, and the use of two bicycles; note that two friendly Labrador dogs reside on the property.
Music Hot Spot’s Main Level - Chicago, IL
9.4 45 reviews
Chicago, IL
07/07 – 24/07
NZ$345/nighttotal: NZ$5865 (17 )

Music Hot Spot’s Main Level

1 3
B&B , Berwyn
This charming guesthouse sits on the border of Berwyn and Oak Park, just a short walk from popular music venues like Fitzgerald's and Friendly Tap, and within easy reach of a variety of restaurants. The accommodation has consistently received excellent ratings from guests for its cleanliness, location and overall experience.
The guesthouse has one bathroom and can comfortably accommodate two guests. It features a fully equipped kitchen, a private garden, a swimming pool, a fitness centre and a patio with a Tiki bar, making it perfect for relaxing and enjoying the outdoors.
The Lyons' Den - Chicago, IL
9.6 14 reviews
Chicago, IL
22/06 – 24/06
NZ$305/nighttotal: NZ$610 (2 )

The Lyons' Den

1 2
B&B , Chicago
The Lyons' Den, a bed and breakfast in Chicago, is situated 2.25 kilometres from Wrigley Field, 5.95 kilometres from Lincoln Park Zoo, and 6.76 kilometres from Loyola University Chicago.
This 15 square metre guesthouse offers accommodation for up to three guests in one bedroom and one bathroom, featuring air conditioning, a terrace, a fully equipped kitchen with a dishwasher and oven, and complimentary WiFi.
Spacious Room By Medical District & Uic - Chicago, IL
7.7 6 reviews
Chicago, IL
01/07 – 10/07
NZ$128/nighttotal: NZ$1152 (9 )

Spacious Room By Medical District & Uic

1 1
B&B , Chicago
This Chicago guesthouse is conveniently located near the city's Medical District, approximately 3.2km from the United Centre and within 5.5km of Union Station, offering easy access to hospitals, universities, and major attractions.
The 8-square-metre studio features a fully equipped kitchen, a shared bathroom, and accommodates one guest, providing free Wi-Fi, air conditioning, and access to a private patio and garden.

Frequently asked questions about bed and breakfast in Chicago, IL

  • What are the must-see sights for first-time visitors on a day trip to Chicago, IL?

    For a day trip, you'll want to hit the highlights. Start with the iconic Willis Tower, formerly known as the Sears Tower, for panoramic views of the city. Then head to Millennium Park, where you can see the Cloud Gate sculpture, affectionately known as 'The Bean', and enjoy the Crown Fountain. A stroll down Michigan Avenue, known as the Magnificent Mile, is a must for some window shopping and people watching.
  • What are the best bed and breakfasts in Chicago, IL?

  • In which districts of Chicago, IL should you consider booking a bed and breakfast?

    For a charming bed and breakfast experience, consider the Lincoln Park, Lakeview, or Wicker Park neighbourhoods. These areas offer a mix of residential streets, green spaces, and easy access to public transport, making them ideal for exploring the city.
  • What are the best bed and breakfasts with a pool in Chicago, IL?

  • What is the typical weather in Chicago, IL, and how does it affect outdoor plans?

    Chicago weather can be unpredictable, with hot, humid summers and cold, snowy winters. Spring and autumn are generally mild, but can have sudden changes. Pack layers and be prepared for anything! It's worth checking the forecast before planning outdoor activities.
  • What are the best bed and breakfasts with a jacuzzi in Chicago, IL?

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Chicago, IL?

    For solo travellers staying in a bed and breakfast, there are plenty of options. Check out the restaurants in the surrounding neighbourhood, such as the cozy cafes in Lincoln Park or the trendy eateries in Wicker Park. Many offer a relaxed atmosphere and are perfect for a solo meal.
  • What are the best bed and breakfasts for families and kids in Chicago, IL?

    The best B&Bs for families and kids in Chicago, IL are Artist Loft - Very Unique, The Greenleaf House and Luxe Stay - King Bedroom With Glass Fireplace.

  • What are the best cultural activities and events in and around Chicago, IL?

    Chicago is a cultural hub. The Art Institute of Chicago houses an impressive collection of art, including works by Monet and Van Gogh. The Field Museum is a must-see for its dinosaur exhibits. And for live music, check out the schedule at the Chicago Symphony Orchestra or the Lyric Opera of Chicago.
  • What are the best pet friendly bed and breakfasts in Chicago, IL?

  • Which hiking trails are recommended for exploring in and around Chicago, IL?

    While Chicago is known for its urban landscape, there are some great hiking spots nearby. The Palos Preserves, about 40 km southwest of the city, offer miles of trails through forests and prairies. Closer to the city, the Lakefront Trail along Lake Michigan provides a scenic route for walking or cycling.
  • What are the best bed and breakfasts with parking in Chicago, IL?

  • What amenities are commonly offered in bed and breakfasts in Chicago, IL?

    Bed and breakfasts in Chicago typically offer a range of amenities, including a hearty breakfast, comfortable rooms, and often a shared living space. Some may also have additional features like a garden, patio, or even a hot tub. It's always best to check the specific amenities offered by each bed and breakfast before booking.

Destinations nearby

Best Chicago, IL bed and breakfasts with parking

Chrissy Place - Chicago, IL
Chicago, IL
14/10 – 14/12
NZ$110/nighttotal: NZ$6710 (61 )

Chrissy Place

1 1
B&B , Chicago
Chrissy Place, a guest house in Chicago, is located 5.8 kilometres from the Museum of Science and Industry and 9.9 kilometres from Guaranteed Rate Field, with the Field Museum of Natural History and Adler Planetarium & Astronomy Museum both approximately 12.9 kilometres away.
This 100-square-metre B&B offers one bedroom and one bathroom for a maximum of one guest, featuring free Wi-Fi, provided towels and bed linen, and a strict no-parties policy, with a checkout time between 08:00 and 11:00.
Wicker Park Inn - Chicago, IL
9.3 526 reviews
Chicago, IL
01/07 – 06/07
NZ$701/nighttotal: NZ$3505 (5 )

Wicker Park Inn

1 2
B&B , Chicago
The Wicker Park Inn is situated in the trendy Wicker Park neighbourhood, just 2.5 kilometres from DePaul University and Lincoln Park Zoo, offering easy access to both attractions and the Blue Line station. The inn has received excellent ratings for its location, cleanliness and overall experience.
The Wicker Park Inn offers comfortable rooms with luxury bedding and amenities, including a shared kitchen with a fridge, freezer, microwave, and dishwasher. Guests can enjoy a free continental breakfast, a terrace or balcony, a garden, a spa, concierge service, room service, and parking, all within a charming neighbourhood with a diverse range of shops, restaurants, and art galleries.
Arlo Chicago - Chicago, IL
9.1 7794 reviews
Chicago, IL
10/07 – 11/07
NZ$654/nightfor 1 night

Arlo Chicago

1 1
hotel , Chicago
The Arlo Chicago hotel is in the Loop district, a short walk (less than 1 km) from Millennium Park and Cloud Gate, with easy access to the Art Institute of Chicago and the Shops at Northbridge.
This 4-star establishment offers 1-bedroom suites with amenities including a fitness centre, restaurant, and bar; a daily resort fee covers Wi-Fi and breakfast.
Prime Avondale - Chicago, IL
9.9 7 reviews
Chicago, IL
15/09 – 18/09
NZ$333/nighttotal: NZ$999 (3 )

Prime Avondale

1 2
B&B , Chicago
Prime Avondale, a guesthouse in Chicago's Avondale neighbourhood, is situated under 5km from Wrigley Field, Lincoln Park Zoo, and the United Centre.
This Chicago B&B offers one bedroom, one bathroom, sleeps seven guests, and includes free Wi-Fi, parking, and air conditioning.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL bed and breakfasts with air conditioning

The Chicago Hotel, Upscale Deluxe Double Queen - Chicago, IL
9.6 20 reviews
Chicago, IL
21/06 – 23/06
NZ$552/nighttotal: NZ$1104 (2 )

The Chicago Hotel, Upscale Deluxe Double Queen

1 2
B&B , Chicago
This Chicago guesthouse is situated on the Magnificent Mile, offering easy access to high-end shopping and attractions such as the Art Institute of Chicago and Millennium Park.
The one-bedroom, one-bathroom lodging sleeps up to four guests and includes free Wi-Fi, a 24/7 gym, business centre, and concierge services, plus pet-friendly options (dogs only, up to 2, maximum 65 lbs, £60 fee) and valet parking (£60 per night).
Relax And Unwind! 2 Spacious Units, Full Kitchen - Chicago, IL
8.9 9 reviews
Chicago, IL
22/07 – 23/07
NZ$1599/nightfor 1 night

Relax And Unwind! 2 Spacious Units, Full Kitchen

4 8
B&B , Chicago
This Chicago guesthouse enjoys a prime downtown location, within easy walking distance of the Magnificent Mile and Navy Pier.
Offering two spacious 950 sq ft (88 m²) two-bedroom suites, each with a fully equipped kitchen, this pet-friendly establishment sleeps up to 10 guests and includes a complimentary breakfast buffet, fitness centre, and business facilities.
Caesar's Lair - Chicago, IL
10 5 reviews
Chicago, IL
16/09 – 17/09
NZ$653/nightfor 1 night

Caesar's Lair

1 2
B&B , Chicago
Caesar's Lair B&B, a private first-floor suite within a larger villa in Chicago, offers a luxurious stay.
This Chicago guesthouse features a queen-size bed, wet bar, 50-inch flat-screen TV, Sub-Zero refrigerator stocked with Italian provisions, and 24-hour access to cannoli and Italian ice, accommodating two guests and including a panini maker and well-stocked pantry for light meals.
Stylish Studio In Historic Logan Square - Chicago, IL
10 327 reviews
Chicago, IL
09/08 – 13/08
NZ$314/nighttotal: NZ$1256 (4 )

Stylish Studio In Historic Logan Square

1 2
B&B , Chicago
This Logan Square apartment is located on Logan Boulevard, a short 0.32 km walk from the CTA Blue Line, offering easy access to Chicago's city centre and O'Hare International Airport.
The self-contained studio features a spa-inspired bathroom, heated floors, access to a shared garden courtyard and a rooftop deck with a gas grill; it sleeps two guests and includes a kitchenette with a mini-fridge, microwave, and coffee maker.
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