City Escape! 4 Relaxing Units Near Skydeck Chicago
4 8
B&B , Chicago
This Chicago River North guesthouse offers four en-suite rooms, each measuring 17 square metres, a short distance from the Magnificent Mile, Navy Pier, and Washington Square Park. The establishment provides a 24-hour reception, fitness centre, business centre, and daily housekeeping, accommodating up to eight guests with the option of additional units for larger groups; pets are welcome at an extra cost.
9.6 44 reviews
Chicago, IL
09/07 – 13/07
NZ$381/nighttotal: NZ$1524 (4 )
2nd Floor In Law Suite With Separate Entrance.
1 2
B&B , Chicago
This Portage Park apartment, a short distance from the Jefferson Park Blue Line/Metra station and approximately 16km from O'Hare International Airport, offers convenient access to Chicago's attractions. The self-contained first-floor unit sleeps two guests, features a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews; nearby amenities include Walgreens, Starbucks, Dunkin', and a grocery store.
10 1 review
Chicago, IL
24/07 – 25/07
NZ$1336/nightfor 1 night
Suite 505 | Stay One Chicago
1 2
B&B , Chicago
Stay One Chicago offers a refined boutique hotel experience in a central Chicago district, with self check-in and dedicated workspaces. This establishment provides exclusive access to Lifetime fitness and wellness amenities, alongside three on-site restaurants for curated dining, and boasts one bedroom and one bathroom to accommodate up to two guests.
Chicago, IL
04/12 – 09/12
NZ$756/nighttotal: NZ$3780 (5 )
Wrigleyville Inn
1 2
B&B , Chicago
The Wrigleyville Inn is located in Chicago's Wrigleyville neighbourhood, just 8 kilometres from the city centre, close to the famous Wrigley Field and its lively atmosphere, especially during Cubs games. The inn offers a comfortable and affordable stay for up to two guests, and includes a kitchen with a microwave oven and dishwasher, a terrace or balcony, a garden, and free parking. Guests can enjoy free Wi-Fi, laundry services, and weekly housekeeping, as well as enhanced cleaning and safety measures.
9.8 519 reviews
Chicago, IL
23/10 – 25/10
NZ$236/nighttotal: NZ$472 (2 )
Cozy, Quiet, Garden Getaway!
1 2
B&B , Chicago
This peaceful garden flat is located in Chicago's North Center/Lincoln Square neighbourhood, a 1.6km walk from the 'L' train and Lincoln Square's amenities. The self-contained apartment, sleeping two guests in one bedroom and one bathroom, features a kitchen with a fridge and microwave, air conditioning, free on-street parking, and a private entrance.
Chicago, IL
10/07 – 11/07
NZ$1961/nightfor 1 night
Vacation At Its Finest! 3 Units, Pet-friendly!
3 5
B&B , Chicago
This Chicago guesthouse is ideally located in the downtown area, near the Chicago River, within easy walking distance of numerous bars and restaurants and a few kilometres from Soldier Field, Wrigley Field, and the United Center. Offering three king-size bedrooms, each with 450 square feet of space, this pet-friendly establishment sleeps six guests and boasts on-site dining at Hoyt's American Tavern, plus a fitness centre and 24/7 reception.
8.3 21 reviews
Chicago, IL
07/09 – 12/09
NZ$174/nighttotal: NZ$870 (5 )
Afrique Francaise De Woodlawn 1
1 2
B&B , Chicago
Afrique Francaise de Woodlawn 1, a guesthouse in Chicago's Woodlawn neighbourhood, is situated 4 km from the Museum of Science and Industry and 8.4 km from Guaranteed Rate Field, offering easy access to these attractions and a glimpse into the area's history. This 100 square metre self-catering property features one bedroom, one bathroom, sleeps two guests, and includes a private garden, terrace, parking, and a shared kitchen.
10 2 reviews
Chicago, IL
27/06 – 28/06
NZ$483/nightfor 1 night
Pet-friendly Hotel! Full Kitchen, Free Shuttle!
1 4
B&B , Schiller Park
This Franklin Park guesthouse is conveniently located near O'Hare International Airport, approximately 5km away, offering a complimentary airport shuttle and easy access to Oak Hill Park and Rosewood Park. The 753 sq ft (70 sq m) self-catering suite features a queen-size bed, sofa bed, full kitchen, and accommodates up to four guests, with wheelchair accessibility and on-site amenities including a fitness centre, business centre, and laundry facilities.
9.5 213 reviews
Chicago, IL
18/07 – 24/07
NZ$266/nighttotal: NZ$1596 (6 )
Alewyfe Farm Urban Garden Oasis- Free Parking!
1 2
B&B , Chicago
This Bohemian Garden Apartment is located in a bohemian neighbourhood in Chicago, two blocks from the Pink Line CTA, Lagunitas Brewery, and Cinespace Film Studios, offering a view of Douglas Park and just 5.6 kilometres from the Loop. The apartment, situated on the first floor of an 1880s brick cottage, features a private bathroom, private entrances, multiple fans, a small window AC for hot days, and a stocked pantry and coffee/tea bar, with a permaculture garden with chickens, a fire pit, and a BBQ available for guests to enjoy.
8.9 9 reviews
Chicago, IL
05/07 – 06/07
NZ$1132/nightfor 1 night
Relax And Unwind! 2 Spacious Units, Full Kitchen
4 3
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.
9.8 70 reviews
Chicago, IL
27/08 – 30/08
NZ$341/nighttotal: NZ$1023 (3 )
Live Local Private Sanctuary; 1 Br/wfh/pvt Entr.
1 2
B&B , Chicago
This charming bed and breakfast is located in Humboldt Park, a trendy neighbourhood just a short walk from the 606 Bloomingdale Trail and the park itself. The accommodation has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The guest suite offers a private bathroom and office, ideal for longer stays or those working remotely. Guests can enjoy complimentary morning coffee, snacks, and a mini fridge/freezer in their suite, along with a gated yard and street parking.
9.8 485 reviews
Chicago, IL
25/11 – 29/11
NZ$231/nighttotal: NZ$924 (4 )
Private Lincoln Square Garden Apt
1 2
B&B , Chicago
This charming garden apartment is situated in a lively neighbourhood close to Lincoln Square, just a short walk from the train station and the Old Town School of Folk Music. It has received excellent ratings for cleanliness, location and user experience. The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It offers a kitchenette with a microwave, coffee maker, toaster and mini-fridge, as well as a shared front yard with a bench and picnic table. The apartment also benefits from a portable air conditioner, shared laundry facilities, and a tree swing and treehouse for children.
Best Chicago, IL bed and breakfasts with breakfast included
9.1 7794 reviews
Chicago, IL
19/08 – 24/08
NZ$561/nighttotal: NZ$2805 (5 )
Arlo Chicago
1 2
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.
Chicago, IL
24/09 – 26/09
NZ$369/nighttotal: NZ$738 (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.
9.7 702 reviews
Chicago, IL
03/07 – 06/07
NZ$740/nighttotal: NZ$2220 (3 )
Ray's Bucktown Bed And Breakfast
1 4
B&B , Chicago
Ray's Bucktown Bed and Breakfast is located in the Bucktown neighbourhood of Chicago, just a short distance from the Congress Theater, DePaul University, Wrigley Field, and Lincoln Park Zoo. The B&B has excellent user, location, and cleanliness ratings. Each room in the guesthouse has hardwood floors and a flat-screen TV, while some rooms also have a spa bath. Guests can enjoy a delicious breakfast delivered to their room, relax in the communal areas, or unwind in the sauna after a day exploring the city.
Chicago, IL
24/07 – 28/07
NZ$432/nighttotal: NZ$1728 (4 )
Dorothy's
1 2
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.
Best Chicago, IL bed and breakfasts with a garden
10 153 reviews
Chicago, IL
09/09 – 14/09
NZ$722/nighttotal: NZ$3610 (5 )
Exemplary Wicker Park Manor Two Bed Guest Suite
1 3
B&B , Chicago
This Chicago guest house is situated in the Wicker Park/Bucktown historic district, conveniently located steps from the Damen Blue Line station offering easy access to the city. The property, a renovated Victorian mansion dating from 1894, features a spacious family-friendly layout with three private bedrooms, each with a TV and Apple TV, a full kitchen, laundry facilities, and a master suite with a private balcony; parking is available.
9.9 417 reviews
Chicago, IL
24/07 – 26/07
NZ$519/nighttotal: NZ$1038 (2 )
Luxe, Private Suite W/own Entrance-2023 Renovated
1 2
B&B , Chicago
This Bucktown studio apartment is ideally located in a quiet residential area, within easy walking distance of Damen Avenue's shops and restaurants, and approximately 3km from Wrigley Field and Lincoln Park. The self-contained unit, sleeping up to two guests, boasts a newly remodelled ensuite bathroom with underfloor heating, a private keyed courtyard, and free on-street parking – a rare find in Chicago's city centre.
9.7 112 reviews
Chicago, IL
25/08 – 30/08
NZ$368/nighttotal: NZ$1840 (5 )
Logan Square Chicago 2br Cottage, Close To It All!
1 2
B&B , Chicago
This charming two-bedroom flat is located in Logan Square, a lively neighbourhood with a mix of trendy restaurants, bars, and independent shops, just a short walk from the Logan Square Blue Line station, offering easy access to downtown Chicago. This property has received excellent ratings for its cleanliness, location, and overall user experience. The flat is a comfortable and well-equipped home away from home, suitable for up to four guests. It features a fully equipped kitchen with modern appliances, a private backyard space for enjoying the outdoors, and a convenient work-friendly setup with dedicated workspaces in each bedroom.
8.8 43 reviews
Chicago, IL
24/12 – 26/12
NZ$254/nighttotal: NZ$508 (2 )
A Hidden Gem, Approx 15 Mins To Downtown Chicago!
1 2
B&B , Chicago
This charming bed and breakfast is situated in Chicago, just 11 kilometres from the city centre and 11.4 kilometres from Shops at Northbridge and 360 Chicago. It has received very good ratings for location, cleanliness and overall experience. The property offers a single bedroom and bathroom, accommodating up to two guests. It features a fully equipped kitchen, a garden, a fitness centre, free parking and free Wi-Fi, providing everything you need for a comfortable and enjoyable stay.
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?
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
9.1 16 reviews
Chicago, IL
30/06 – 03/07
NZ$154/nighttotal: NZ$462 (3 )
Chateau De Woodlawn - Room I - La Tour Eiffel
1 2
B&B , Chicago
Chateau de Woodlawn, a family-friendly guesthouse in Chicago, is conveniently located approximately 5 kilometres from the Museum of Science and Industry and 8.5 kilometres from Guaranteed Rate Field. This Chicago B&B offers a 15-square-metre room with one bedroom, one bathroom, accommodating up to three guests, and features free Wi-Fi, private parking, a shared kitchen, terrace access, and concierge services.
9.4 1068 reviews
Chicago, IL
22/06 – 25/06
NZ$671/nighttotal: NZ$2013 (3 )
The Greenleaf House
4 7
B&B , Chicago
The Greenleaf House is situated in Chicago's Illinois region, close to Loyola University Chicago and within easy reach of attractions like Wrigley Field and Lincoln Park Zoo. This guest house consistently receives excellent ratings for cleanliness, location and overall experience. The Greenleaf House offers a range of amenities, including a garden, a tennis court and an indoor play area, making it ideal for families. Guests can enjoy free Wi-Fi, private parking, a kitchen with modern appliances and an outdoor fireplace.
10 3 reviews
Chicago, IL
03/07 – 05/07
NZ$786/nighttotal: NZ$1572 (2 )
Mccormick Suites By Slumber Stay | 2br
1 4
B&B , Chicago
This luxury 2-bedroom flat in Chicago's South Loop is situated a mere 800 metres from McCormick Place, offering convenient access to downtown attractions and the lakefront. This modern accommodation provides sleeping arrangements for up to six guests, featuring a fully equipped kitchen, WiFi, in-building laundry, and access to a fitness centre and communal patio with a fire pit and BBQ area, with optional secured garage parking available for £24 per day.
7.7 6 reviews
Chicago, IL
08/07 – 12/07
NZ$145/nighttotal: NZ$580 (4 )
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.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL bed and breakfasts with air conditioning
Chicago, IL
20/10 – 23/10
NZ$262/nighttotal: NZ$786 (3 )
Kid- And Dog-friendly 2-br Near Downtown Chicago
1 3
B&B , Chicago
This Chicago bed and breakfast is situated in a secure, peaceful area just 24 kilometres from the city centre, offering excellent public transport links with the Orange 'L' line and five bus routes a 2-minute walk away, providing easy access to Chinatown, Grant Park, and the United Center. This family-friendly guesthouse accommodates up to five guests, featuring two bedrooms, a living room, a workspace, a full kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a fitness centre, laundry facilities, and is pet-friendly for guests travelling with dogs, with a nearby park offering walking paths, a playground, and a swimming pool.
9.8 259 reviews
Chicago, IL
24/07 – 27/07
NZ$326/nighttotal: NZ$978 (3 )
Lincoln Square In-laws Suite: Private Entrance
1 2
B&B , Chicago
This Chicago garden apartment is located in Lincoln Square, a short distance from the train station providing easy access to the city centre. The self-contained unit, sleeping two guests, features a private ensuite bathroom, keyless entry, fast Wi-Fi, a workspace, laundry facilities and complimentary local beers; nearby attractions include Lincoln Park Zoo (a short train ride away).
10 1 review
Chicago, IL
08/10 – 09/10
NZ$2063/nightfor 1 night
Three Cozy Units Near Riverwalk! Indoor Pool!
3 1
B&B , Chicago
This Chicago guesthouse is centrally located less than 1.6km from Millennium Park, offering easy access to the Magnificent Mile, Art Institute of Chicago, Willis Tower, Navy Pier, and the Chicago Riverwalk. The property boasts three 34-square-metre deluxe rooms, sleeping up to 12 guests, and features a heated rooftop pool, fitness centre, and on-site restaurant and bar, alongside valet and off-site parking options.
8.7 51 reviews
Chicago, IL
23/07 – 27/07
NZ$453/nighttotal: NZ$1812 (4 )
River North Stay | 1 Unit | Near Chicago Loop
1 2
B&B , Chicago
This Bed and Breakfast is located near Chicago's River North, offering convenient access to the Magnificent Mile and Navy Pier, approximately 1 kilometre away. This accommodation provides a 355 sq ft room with a 50-inch TV, complimentary toiletries, air conditioning, internet access, daily cleaning, a fitness centre, and a shared indoor heated pool, with on-site paid parking for £39 per day and a guest capacity of two.
