Holiday homes & B&B in Chicago Loop
Choose the right place for you
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
Vacation rental deals in Chicago Loop
We have selected the best vacation rentals in Chicago Loop. Save money with Bluepillow by comparing the best deals from major travel websites in Chicago Loop
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Chicago Loop - United States
Cozy room in a Charming Coach House
- 2 Guests 1Bedroom
10 Exceptional (93)This apartment is actually a small house that sits behind an apartment building. With high ceilings, modern appliances, & an open floor plan, this newly renovated space has a cozy and chic feeling, thoughtfully ...Check Availability -
Chicago Loop - United States
Master Suite and Bathroom in Wicker Park
- 3 Guests 1Bedroom
10 Exceptional (200)Enjoy your home away from home in this spacious 3 bedroom 2 bath condo at the crossroads of Bucktown and Wicker Park. Close to bars, restaurants, boutiques, cafes, and grocery stores, as well as public ...Check Availability -
Chicago Loop - United States
Cozy private room on Chicago's west side
- 2 Guests 1Bedroom
10 Exceptional (163)Come stay in a budding west side neighborhood! The place is close to the beautiful Humbolt Park and within walking distance of dozens of bars, cafes and restaurants like, Sportsman's Club, The California ...Check Availability -
Chicago Loop - United States
Vintage Logan Square Bedroom
- 2 Guests 1Bedroom
10 Exceptional (181)We are located in the heart of Logan Square, two blocks from the California Blue Line train station. This is the first of two rooms listed on airbnb at this property. Your humble hosts are an artist couple, ...Check Availability -
Chicago Loop - United States
Trendy. Safe. Convenient to CTA
- 1 Guest 1Bedroom
10 Exceptional (111)I'm lucky to live in a fantastic Lincoln Park location that is central to everything Chicago has to offer. Shopping, check. Dining, check. Nightlife, check. Bed, check. I live next door to the train. You ...Check Availability -
Chicago Loop - United States
In the heart of Pilsen's art community.
- 2 Guests 1Bedroom
10 Exceptional (81)My place is very close to downtown and the Lakefront. Uber and Lyft cab service arrives within 5 minutes, Divvy bikes 1 block away. My neighborhood is the new hot spot, A mix of artists Mexican's and hipsters, ...Check Availability
Save on Bed & Breakfast in Chicago Loop
Are you looking for an accommodation in Chicago Loop and do you want to save money? Choose from 58 Bed & Breakfasts in Chicago Loop
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Chicago Loop - United States
Chicago Getaway Hostel
- Hotel
7.8 Very Good (3875)This Chicago hostel is located in Lincoln Park and is a few blocks from the Fullerton subway station. Free Wi-Fi is available throughout this hostel. Guest rooms at the Chicago Getaway Hostel include ...Check Availability -
Chicago Loop - United States
Sonder — Armitage Suite
- Hotel
9.4 Exceptional (11)Three-Bedroom on W Armitage Avenue Apt B offers accommodation in Chicago, 0.9 miles from Lincoln Park Zoo and 2.5 miles from Wrigley Field. The accommodation is 2.5 miles from the 360 Chicago and features ...Check Availability -
Chicago Loop - United States
Holiday Jones
- Hotel
8.5 Fabulous (731)Located on Division Street in the heart of Chicago's Wicker Park neighborhood, this hostel offers rooms with free WiFi and an on-site lounge. Offering a true Chicago experience, the hostel is located near ...Check Availability -
Chicago Loop - United States
Private Queen Room in a Boutique Hotel
- Hotel
10 Exceptional (15)Sleeping one or two guests, this spacious room offers one Queen bed, free Wi-Fi, complimentary toiletries, cable TV, iron and ironing board, hairdryer, and in-room safe. ...Check Availability -
Chicago Loop - United States
Sonder — Barry Apartments
- Hotel
Three-Bedroom on W Barry Avenue Apt 2F offers accommodation in Chicago, a 15-minute walk from Wrigley Field and 1.9 miles from Lincoln Park Zoo. The accommodation has free WiFi. The apartment is composed ...Check Availability -
Chicago Loop - United States
Sonder — South State
- Hotel
7.9 Very Good (12)One of our bestsellers in Chicago! Sonder — South State is located in Chicago and offers a fitness centre. This property is a 13-minute walk from Field Museum of Natural History and has free WiFi. The ...Check Availability
Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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![Farmstays near Chicago Loop]()
Farmstays near Chicago Loop -
![Hotels near Chicago Loop]()
Hotels near Chicago Loop
The best places to stay in Chicago Loop
Book an apartment in Chicago Loop and choose the right accommodation for your needs
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Chicago Loop - United States
Private Apartment in Humboldt Park/Logan Square
- 4 Guests 1Bedroom
10 Exceptional (85)You’ll feel like you’re at home in this comfy in-law suite that’s perfect for couples, families, individuals or small groups. The space has a private entrance, free and easy street parking, and is equipped ...Check Availability -
Chicago Loop - United States
Heart of Chicago 2BD + Parking
- 5 Guests 2Bedrooms
10 Exceptional (115)Comfortably fits 4-5Two private bedrooms and a queen foldout couch in living room. Impecable bathroom with great lighting. State of the art stainless steel appliances for a quick meal at home before a ...Check Availability -
Chicago Loop - United States
Master Bedroom, Heart of Wicker Park
- 2 Guests 1Bedroom
10 Exceptional (171)Large 4 bedroom located on Milwaukee Ave., half a block from Wicker Park's Six Corners. Live music, art, night life, amazing food all outside your door. Blue line stop half a block away. Shared unit with ...Check Availability -
Chicago Loop - United States
Private Rm in Artist Apartment near Wicker Park
- 2 Guests 1Bedroom
10 Exceptional (108)Our place is a recently rehabbed, fully updated 2 bedroom flat in a 3 floor grey stone with secure entry. Nice new wood floors throughout unit, kitchen includes marble counter tops, a breakfast nook, and ...Check Availability -
Chicago Loop - United States
Historic Brownstone in Lincoln Park
- 6 Guests 2Bedrooms
10 Exceptional (130)Prime Location! Brownstone in North Lincoln Park / South Lakeview, 2nd floor unit with high ceilings and tons of sunlight. Two bedrooms with queen beds, living room with pull out couch/queen size with ...Check Availability -
Chicago Loop - United States
Private Studio in Bridgeport, Chicago
- 2 Guests 0Bedroom
10 Exceptional (84)A bright studio guesthouse, perfect for business travelers, a couples getaway, personal retreat, or a solo adventurer. Equipped with a kitchenette that includes cabinet space for your non-perishable ...Check Availability
