Holiday homes & B&B in Downtown Chicago
Choose the right place for you
FACILITIES
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Wi-Fi
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Non Smoking Only
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Pets Allowed
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
Holiday rental deals near Downtown Chicago
We have selected the best vacation rentals near Downtown Chicago. Save money with Bluepillow by comparing the best deals from major travel websites near Downtown Chicago
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Downtown Chicago - United States
State and Grand by BridgeStreet
- Hotel
9 Exceptional (129)With a stay at State and Grand by BridgeStreet, you'll be centrally located in Chicago, just a 4-minute walk from Michigan Avenue and 7 minutes by foot from Chicago Riverwalk. This upscale apartment is ... -
Downtown Chicago - United States
3 BDR Downtown Luxury Loft-spacious, Safe & Secure
- Hotel
Located in Chicago (Downtown Chicago), this apartment is within a 15-minute walk of Willis Tower and Michigan Avenue. This upscale apartment is 0.6 mi (1 km) from Chicago Riverwalk and 0.7 mi (1.1 km) ... -
Downtown Chicago - United States
Sonder The Opal | Studio Apartment
- 2 Guests 0Bedroom
10.5 Exceptional (34)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Navy Pier and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Spacious & Private 3 BDR Luxury Condo in Downtown
- Hotel
Located in Chicago (Downtown Chicago), this condo is within a 15-minute walk of Willis Tower and Michigan Avenue. This upscale condo is 0.6 mi (1 km) from Chicago Riverwalk and 0.7 mi (1.1 km) from Millennium ... -
Downtown Chicago - United States
Breathtaking 6 BDR Luxury Condo Downtown Chicago
- Hotel
Located in Chicago (Downtown Chicago), this condo is within a 15-minute walk of Willis Tower and Michigan Avenue. This upscale condo is 0.6 mi (1 km) from Chicago Riverwalk and 0.7 mi (1.1 km) from Millennium ... -
Downtown Chicago - United States
Luxury Apartment With Private Office & Terrace
- Hotel
5 Pleasant (2)A stay at Luxury Apartment With Private Office & Terrace places you in the heart of Chicago, within a 15-minute walk of Michigan Avenue and Chicago Riverwalk. This apartment is 1.7 mi (2.8 km) from Navy ... -
Downtown Chicago - United States
Sonder Jewelers Row | Two-Bedroom Apartment
- 4 Guests 2Bedrooms
8.1 Fabulous (16)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Bright Loop Studio w/ Gym & W/D, near L & Millennium Park, by Blueground
- 2 Guests 0Bedroom
This apartment is located in Downtown Chicago, a neighborhood in Chicago. Navy Pier and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
- 6 Guests 2Bedrooms
9.6 Exceptional (23)Located in Chicago, this apartment is in the city center. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty ... -
Downtown Chicago - United States
2BR Elegant Premium Suite With Balcony & Sweeping City Views
- 6 Guests 2Bedrooms
10 Exceptional (2)Set in Chicago, 2 km from Ohio Street Beach and 2.2 km from Oak Street Beach, 2BR Elegant Premium Suite With Balcony & Sweeping City Views offers spacious air-conditioned accommodation with a patio and ... -
Downtown Chicago - United States
Stunning 3BR Penthouse in the Loop | Roof Deck
- 8 Guests 3Bedrooms
10 Exceptional (16)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
- 6 Guests 2Bedrooms
9.4 Exceptional (16)Located in Chicago, this apartment is in the city center. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty ... -
Downtown Chicago - United States
The Guild #3 | Mag Mile, Gold Coast, Downtown 1bd/1ba
- 4 Guests 1Bedroom
10 Exceptional (4)Located on a lake, this condo is in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the ... -
Downtown Chicago - United States
Sonder Jewelers Row | Studio Apartment
- 2 Guests 0Bedroom
8.2 Fabulous (16)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Sonder Jewelers Row | Superior Two-Bedroom Apartment
- 4 Guests 2Bedrooms
7 Very Good (7)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Sonder Jewelers Row | Superior One-Bedroom Apartment
- 2 Guests 1Bedroom
6 Pleasant (1)This apartment is located in Downtown Chicago, a neighborhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Generous River North 3BR w/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI324)
- 6 Guests 3Bedrooms
This apartment is located in Downtown Chicago, a neighborhood in Chicago. Navy Pier and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's ... -
Downtown Chicago - United States
Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck
- 6 Guests 2Bedrooms
9.6 Exceptional (30)Located in Chicago, this apartment is in the city center. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty ... -
Downtown Chicago - United States
Luxury Corner 2 Bedroom in the Loop | Roof Deck
- 6 Guests 2Bedrooms
9.4 Exceptional (15)Located in Chicago, this apartment is in the city center. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty ... -
Downtown Chicago - United States
Luxe Loop Studio w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- 2 Guests 0Bedroom
This apartment is located in Downtown Chicago, a neighborhood in Chicago. Navy Pier and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's ...
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 Downtown Chicago]()
Farmstays near Downtown Chicago -
![Hotels near Downtown Chicago]()
Hotels near Downtown Chicago
Downtown Chicago and the best offers per the best accommodation
What is the best period with the best offers to stay in Downtown Chicago? If you are looking for accommodation in Downtown Chicago during the best period without the chaos of mass tourism, the low season month with the best tariffs is in the month of January. The week with the best prices for that month is the week from 1/15 to 1/22.
If instead you are looking for accommodation in Downtown Chicago during the high season, to enjoy the destination and it's capacities, the month of May is right for you. The most amount of accommodation available at the most convenient price is during the week that spans from from 5/21 to 5/28.
Downtown Chicago is a touristic destination where the accommodation has an average cost of 283 euros per night.
If you have limited time and you love last minute holidays, you can organize a weekend in Downtown Chicago and find holiday homes and apartments with great low cost offers particularly in the month of January. The best lowcost weekend is the one that stats from 1/14 to 1/16.
If instead you are planning a medium or long term holiday, the best low cost week is in the month of January from 1/15 to 1/22.
