Parishotel Travel - Vacation Rentals in Downtown Chicago

50th Floor Mag Mile Views, Balcony, Pool, Gym From US $263
         

Sophisticated 4BR Suite - Modern and Luxurious From US $373
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Accessibility
  • Security/Safety
ENVITAE Hotel From US $453
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Premium 4 King Apartment w/City Views From US $1,449
         

10.0 (5 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Sophisticated 4BR Suite - Walk to Shops, Dining & Transit From US $270
         

10.0 (5 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Luxury Places to Stay in Downtown Chicago

Over 2660+ Luxury Places to Stay in or Near Downtown Chicago
Luxury Loft Collection 1, 2, 3 From US $3,699
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool From US $2,995
         

Downtown Mich Ave - 6 Penthouses, Sleep 25 From US $2,166
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
870 bldg - 3 Separate Suites in same building From US $2,123
         

6.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Downtown Chicago

Over 1021+ Top-Rated Vacation Rentals with a Pool in or Near Downtown Chicago
52nd Floor MagMile Penthouse Views Fireplace Pool From US $324
         

10.0 (408 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
55th Floor Penthouse with Award-Winning Views From US $1,139
         

10.0 (301 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
53 Floor MagMile Penthouse Views, Balcony, Pool From US $284
         

10.0 (244 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
51st Floor MagMile Penthouse Views Balcony Pool From US $305
         

10.0 (227 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
2-Story Penthouse Views, Fireplace, Pool, Gym From US $769
         

10.0 (212 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
52nd Floor Penthouse with Skyline Views & Pool From US $376
         

10.0 (64 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym From US $234
         

10.0 (32 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Downtown Chicago

Over 1303+ Pet-Friendly Vacation Rentals in or Near Downtown Chicago
Freshly Minted 2BR - Elegance & Comfort in Central Chicago From US $349
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Accessibility
Kasa River North Chicago From US $311
         

|
9.6 (183 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Luxury Loft Collection 703 - Terrace - River North From US $1,129
         

10.0 (23 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Loft Collection 02 - Terrace - River North From US $942
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool From US $524
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Designer Penthouse 3804 | Pool | Gold Coast From US $840
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Designer Penthouse|Private Deck|Gold Coast From US $791
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Downtown Chicago

Over 265+ Large Vacation Homes & Villas in or Near Downtown Chicago
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $913
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Lux Apts with Lake Views and Top Amenities From US $1,582
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,177
         

10.0 (106 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
City Center, River North Condo HUGE 3BR, Patio, Parking(2x) From US $728
         

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow From US $368
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern West Loop Gem-City Views & Prime Location 6 From US $411
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Wheelchair Accessible Vacation Homes in Downtown Chicago

Over 1949+ Wheelchair Accessible Vacation Homes in or Near Downtown Chicago
Downtown Guild #3 | Mag Mile Gold Coast The Lake! From US $283
         

10.0 (23 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
The Publishing House B&B From US $206
         

|
9.8 (195 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Two-Story Penthouse, City Views, Pool, Gym From US $658
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury Loft Collection 903 - Terrace - River North From US $1,086
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown 3bd #7 near Park+Museums From US $465
         

10.0 (6 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 4 From US $809
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 3 From US $707
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Downtown Chicago Varoom and Airbnb Places to Stay Under $200

Over 1113+ Downtown Chicago Varoom and Airbnb Places to Stay Under $200
West Loop Living – Bright 1BR From US $176
         

10.0 (7 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
West Loop - City Views With In & Out Parking 5 From US $151
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
HI Chicago Hostel From US $73
         

9.0 (1112 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Chic Studio in the Heart of the Gold Coast From US $163
         

10.0 (5 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Sun-Drenched 1BR Apartment From US $176
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile From US $143
         

Chicago Cityview Chic - Gold Coast/River North From US $199
         

Instantly Bookable Vacation Homes in Downtown Chicago

Over 1751+ Instantly Bookable Vacation Homes in or Near Downtown Chicago
Brilliant Downtown Chicago 3-Bedroom Condominium From US $485
         

10.0 (51 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 3BR River North Condo - Free Parking From US $856
         

10.0 (30 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Designer Loft in Fulton Market with Parking From US $1,002
         

10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $545
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Boho Chic 2BR Condo, Queen Bed With Free Parking From US $260
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxury Loft Collection COMBO 902/903 Terrace From US $1,959
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern, Luxe, House 20mins to Downtown, Private Rooftop, 2car Garage From US $762
         

About Downtown Chicago Vacation Rentals

With more than 596 Downtown Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Parishoteltravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Downtown Chicago.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Parishoteltravel Downtown Chicago, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Downtown Chicago. Places to stay near Downtown Chicago are 253.31 ft² on average, with prices averaging $332 a night.

Parishoteltravel makes it easy and safe to find and compare vacation rentals in Downtown Chicago with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Downtown Chicago

Type Count
Hotels with Suites 596

Use these Quick Filters to Find a Vacation Rental in Downtown Chicago

Pro Tip: Parishoteltravel makes it easy to compare the best listings on Parishoteltravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Parishoteltravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Downtown Chicago.

Weather in Downtown Chicago

View the weather forecast for Downtown Chicago before booking your Downtown Chicago Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F