Rent The Cottages - Vacation Rentals in The Loop

52nd Floor MagMile Penthouse VIEWS Fireplace Pool From US $281
         

New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
51st Floor MagMile Penthouse Views Balcony Pool From US $265
         

55-56 Mag Mile Penthouse From US $846
         

10.0 (300 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
53 Floor MagMile Penthouse Views, Balcony, Pool From US $303
         

53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool From US $608
         

Luxury Places to Stay in The Loop

Over 1078+ 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
  • Bedding/Linens
Iconic Downtown Penthouses Getaway + City Views From US $2,661
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury High-Floor Retreats + Lake Views From US $2,070
         

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 429+ Top-Rated Vacation Rentals with a Pool in or Near The Loop
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym From US $242
         

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $522
         

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 $1,518
         

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 $1,261
         

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 63+ 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 $1,072
         

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 $1,415
         

New
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in The Loop

Over 764+ Wheelchair Accessible Vacation Homes in or Near The Loop
Downtown 3bd #7 near Park+Museums From US $382
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
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
HI Chicago Hostel From US $73
         

9.0 (1077 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Front Row to the Lake & Skyline: Epic 60th Flr 3BR From US $1,099
         

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
1 Mi to Blue Line: Pet-Friendly Unit in Chicago! From US $167
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
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
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 672+ Instantly Bookable Vacation Homes in or Near The Loop
Casa 22 Luxury Modern House for 6 3 Bed, 2 Bath From US $447
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
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
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift From US $226
         

About The Loop Vacation Rentals

With more than 1087 The Loop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rentthecottages 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 Rentthecottages 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 597.04 ft² on average, with prices averaging $328 a night.

Rentthecottages 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 118
Resorts 25
Hostels 2
Cabin Rentals 1

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

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