The Beaches Estates - Vacation Rentals in The Loop

52nd Floor MagMile Penthouse VIEWS Fireplace Pool From US $293
         

10.0 (406 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
HI Chicago Hostel From US $73
         

9.0 (1077 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
51st Floor MagMile Penthouse Views Balcony Pool From US $300
         

10.0 (226 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
55-56 Mag Mile Penthouse From US $893
         

10.0 (300 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
53 Floor MagMile Penthouse Views, Balcony, Pool From US $313
         

10.0 (241 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool From US $625
         

10.0 (209 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in The Loop

Over 1080+ Luxury Places to Stay in or Near The Loop
The Ritz-Carlton Club, Lake Tahoe - 3 bdrm From US $3,806
         

New
Resort
  • Air Conditioner
  • Security/Safety
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Iconic Downtown Penthouses Getaway + City Views From US $3,151
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury High-Floor Retreats + Lake Views From US $2,081
         

Downtown Mich Ave - 6 Penthouses, Sleep 25 From US $2,036
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Top-Rated Vacation Rentals with a Pool in The Loop

Over 428+ Top-Rated Vacation Rentals with a Pool in or Near The Loop
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym From US $245
         

10.0 (32 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $538
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Charm + Modern Comfort for Tourists From US $406
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Luxury Penthouse: Iconic Views + Exclusive Comfort From US $1,572
         

Luxury 2BR near Millennium Park + 5-Star Reviews From US $389
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
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
Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $475
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in The Loop

Over 532+ Pet-Friendly Vacation Rentals in or Near The Loop
Tranquil Portage Park Stay From US $128
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
UrbanEden Loft Apartment From US $103
         

9.4 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Kasa South Loop Chicago From US $186
         

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9.4 (385 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown 3bd Penthouse| Lake Mich VIEWS +gym From US $393
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Downtown Penthouse Huge Patio with Great View From US $1,589
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Downtown Vintage Group Lofts - Sleep 25 From US $1,369
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
See More Pet-Friendly Vacation Rentals in The Loop on PetFriendly.io

Large Vacation Homes & Villas in The Loop

Over 65+ Large Vacation Homes & Villas in or Near The Loop
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow From US $378
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Perfect Location Across from Park & Train Station From US $734
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
DTown Penthouse - 4bd/4ba (+Parking + Gym + Pool) From US $1,126
         

9.8 (8 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious/New Home - 8BD/4BTH - Sleeps 16 + Garage! From US $692
         

8.6 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Downtown 9bd - Sleep 18 - (4 units, same floor) From US $1,537
         

New
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in The Loop

Over 763+ Wheelchair Accessible Vacation Homes in or Near The Loop
2B 2BA Luxury Suite with Balcony and Wi-Fi, PAID IN and OUT PARKING IN BLDG From US $135
         

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8.8 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Child Friendly
Downtown 3bd #7 near Park+Museums From US $407
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
The Langham, Chicago From US $536
         

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9.8 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Front Row to the Lake & Skyline: Epic 60th Flr 3BR From US $1,055
         

River North Private Deck With In and Out Parking From US $721
         

West Loop PH: Unmatched Views & Private Deck From US $667
         

Sky-High 3BR Penthouse in West Loop From US $659
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV

The Loop Varoom and Airbnb Places to Stay Under $200

Over 496+ The Loop Varoom and Airbnb Places to Stay Under $200
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views From US $180
         

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9.2 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
1 Mi to Blue Line: Pet-Friendly Unit in Chicago! From US $167
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Chicago Avenue Inn From US $120
         

7.0 (99 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Cozy 1-Bedroom Apartment From US $159
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Homey 2BR Apt w/Parking From US $188
         

9.8 (6 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Trendy & Comfy Studio Unit From US $155
         

9.6 (4 Reviews)
Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
Minutes from Downtown Gorgeous ,spacious 2BD/1BA w/Parking From US $199
         

9.4 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in The Loop

Over 675+ Instantly Bookable Vacation Homes in or Near The Loop
Casa 22 Luxury Modern House for 6 3 Bed, 2 Bath From US $451
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Downtown 2bd #6 +Gym near Park, Lake, Museums From US $304
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Boho Chic 2BR Condo, Queen Bed With Free Parking From US $260
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern 2BR in The Loop + Panoramic City Views From US $547
         

Downtown 2bd #6 +Gym near Park, Lake, Museums From US $243
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible

About The Loop Vacation Rentals

With more than 1089 The Loop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebeachestates 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 The Loop.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thebeachestates The Loop, 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 The Loop. Places to stay near The Loop are 594.76 ft² on average, with prices averaging $329 a night.

Thebeachestates makes it easy and safe to find and compare vacation rentals in The Loop 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 The Loop

Type Count
Holiday Apartments 636
Hotels with Suites 263
Vacation Homes 119
Resorts 25
Hostels 2
B&B 1
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in The Loop

Pro Tip: Thebeachestates makes it easy to compare the best listings on Thebeachestates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebeachestates 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 The Loop.

Weather in The Loop

View the weather forecast for The Loop before booking your The Loop 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