Top The Loop, IL, USA house rentals

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Great room w/wood burning fireplace off kitchen / dining area

Urban Luxury Home In Downtown Chicago!

Sleeps 14 · 3 bedrooms · 3 bathrooms

Premier Host

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Sleeps 22 · 5 bedrooms · 3+ bathrooms

Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking!

Sleeps 10 · 3 bedrooms · 2 bathrooms

Feel at home with a large comfortable couch.

Premier Host

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Sleeps 18 · 4 bedrooms · 4 bathrooms

Top rated house rentals - The Loop

Premier Host

Excellent property for a large group.

We had a group of 30 stay across the two houses. They were very clean, adequately equipped and incredibly spacious for our group. Would definitely recommend Inna's property for any group large or small.

Mark W.

Stayed July 2022

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Enjoy full kitchens, laundry, pools, gardens and more
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Frequently asked questions

How much does it cost to stay in a holiday home house in The Loop?

Whether you're searching for an inexpensive getaway or a high-end retreat, Stayz has a range of holiday home homes in The Loop to choose from. Use our filter tools to compare prices and find the perfect stay to start your next adventure.

When is the best time to rent a holiday house in The Loop?

You'll have a great time whenever you decide to travel to The Loop. If you're hoping to experience this destination at its busiest, March is when most guests stay in a holiday home home here.

Where can I rent a The Loop holiday house with great views?

When looking for your holiday home home in The Loop, take advantage of our "Location" filter. This will help you narrow down the sorts of areas you prefer to stay in, whether that's near nature or somewhere more central.

Does The Loop have any weekend house homes?

Explore our weekend homes and get packing for an action-packed few days away. Our tips for booking the right house in The Loop? Stay flexible when searching and change your travel dates until you find the holiday home home that fits your needs.

Are there any pet-friendly house homes in The Loop?

If you'd like to explore The Loop with your faithful friend at your side, use our handy filter tool to browse pet-friendly houses. Select the "Pets allowed" box to find a holiday home home with perks like fenced-in yards, toys and treats. After all, when the family goes on holiday, the pets should share in the adventure!

What are the top things to do in The Loop?

Keep your crew busy by checking out Millennium Park, Art Institute of Chicago and Willis Tower. These are only some of the family-friendly attractions you'll find around The Loop. Whatever your idea of the perfect family adventure, our holiday home homes have the space you need to connect.