Theme Park Hotels - Vacation Rentals in The Loop

52nd Floor MagMile Penthouse Views Fireplace Pool From US $324
         

10.0 (408 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 (1112 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
51st Floor MagMile Penthouse Views Balcony Pool From US $305
         

10.0 (227 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
55th Floor Penthouse with Award-Winning Views From US $941
         

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
2-Story Penthouse Views, Fireplace, Pool, Gym From US $615
         

10.0 (212 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in The Loop

Over 1090+ Luxury Places to Stay in or Near The Loop
Iconic Downtown Penthouses Getaway + City Views From US $3,603
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool From US $2,359
         

Downtown Mich Ave - 6 Penthouses, Sleep 25 From US $2,281
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Luxury High-Floor Retreats + Lake Views From US $2,058
         

Top-Rated Vacation Rentals with a Pool in The Loop

Over 430+ 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 $446
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
53-54 Floor Penthouse From US $574
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Historic Charm + Modern Comfort for Tourists From US $564
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
50th Floor Mag Mile Views, Balcony, Pool, Gym From US $263
         

Luxury Penthouse: Iconic Views + Exclusive Comfort From US $1,606
         

Luxury 2BR near Millennium Park + 5-Star Reviews From US $664
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • 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

Pet-Friendly Vacation Rentals in The Loop

Over 527+ 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 (394 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $417
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown 3bd Penthouse| Lake Mich VIEWS +gym From US $313
         

10.0 (3 Reviews)
Apartment
  • 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
Sleep 25 - Huge Downtown Vintage Lofts From US $1,420
         

10.0 (1 Review)
Apartment
  • 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 71+ Large Vacation Homes & Villas in or Near The Loop
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow From US $368
         

10.0 (18 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
Front Row to the Lake & Skyline: Epic 60th Flr 3BR From US $1,238
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Modern 2BR in The Loop + Panoramic City Views From US $617
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
43rd-Floor Luxury Escape + Lake Views From US $924
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
60th Flr Lake Views, A Stay Above It All, Sleeps 5 From US $749
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in The Loop

Over 780+ Wheelchair Accessible Vacation Homes in or Near The Loop
West Loop 2BR with Skyline Views + Prime Location From US $430
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
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
The Langham, Chicago From US $480
         

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9.8 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Downtown 3bd #7 near Park+Museums From US $256
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Sky-High 3BR Penthouse in West Loop From US $874
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
River North Private Deck With In and Out Parking From US $721
         

West Loop PH: Unmatched Views & Private Deck From US $668
         

The Loop Varoom and Airbnb Places to Stay Under $200

Over 488+ The Loop Varoom and Airbnb Places to Stay Under $200
Downtown 2bd #6 +Gym near Park, Lake, Museums From US $191
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
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 $116
         

7.0 (101 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Downtown 2bd #4 - Near Grant Park, Museums, Lake From US $184
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Cozy 1-Bedroom Apartment From US $159
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Trendy & Comfy Studio Unit From US $155
         

9.6 (4 Reviews)
Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
Downtown Mich Ave #10 | gym+rooftop From US $180
         

9.4 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in The Loop

Over 689+ Instantly Bookable Vacation Homes in or Near The Loop
Boho Chic 2BR Condo, Queen Bed With Free Parking From US $260
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift From US $224
         

PH w/Bean & Lake Views, An Elite Stay From US $1,608
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
49th Fl Luxury Retreat + Stunning Lake Views From US $1,003
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

About The Loop Vacation Rentals

With more than 1099 The Loop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Themeparkhotels 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 Themeparkhotels 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 594.7 ft² on average, with prices averaging $334 a night.

Themeparkhotels 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 654
Hotels with Suites 268
Vacation Homes 116
Resorts 24
Hostels 2
B&B 1
Cabin Rentals 1

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

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