1031+ Vacation Rentals & Holiday Homes in The Loop |
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The Loop Accommodations - Hotels & Rentals

About The Loop Vacation Rentals

Discover More than 1031 Incredible Getaway Rentals Available in The Loop. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in The Loop.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in The Loop, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in The Loop. The Average Size of Places to Stay Near The Loop is 604.81 ft², with Prices Averaging US $373 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in The Loop. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in The Loop

Type Count
Holiday Apartments 608
Vacation Homes 111

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in The Loop with Online Reservations.

Weather in The Loop, IL

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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Chicago 7,265 Properties
333 West Wacker Drive 4,290 Properties
Civic Opera House 4,251 Properties
Cadillac Palace Theatre 4,224 Properties
Chicago City Hall 4,216 Properties
Monument with Standing Beast 4,207 Properties
Chicago 4,203 Properties
Printers Row 4,021 Properties
Central Chicago 1,799 Properties
Downtown Chicago 1,640 Properties
Lakeshore East 735 Properties
Near East Side 735 Properties

Frequently Asked Questions About The Loop?

What are the top hotels, lake houses & vacation rentals in The Loop?

We provide an array of great vacation destinations in The Loop. If you are looking to stay in or around the The Loop area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in The Loop:

How many Hotels & Vacation Rentals have private pools in The Loop?

We have 29 Hotels & Vacation Rentals featuring a private pool in and near The Loop. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in The Loop is best for families?

Searching for a family-friendly getaway in The Loop? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in The Loop?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 1031 in the The Loop area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in The Loop.

Nearby Neighborhood (10) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1640
Near North Side Vacation Rentals in Chicago, Illinois 691
South Loop Vacation Rentals in Chicago, Illinois 368
River North Vacation Rentals in Chicago, Illinois 356
West Loop Vacation Rentals in Chicago, Illinois 200
West Loop Gate Vacation Rentals in Chicago, Illinois 2257
Lakeshore East Vacation Rentals in Chicago, Illinois 735
Near East Side Vacation Rentals in Chicago, Illinois 735
Printers Row Vacation Rentals in Chicago, Illinois 4021
Chicago Museum Campus Vacation Rentals in Chicago, Illinois 3407

People Also Ask

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