Book Holiday Rentals for Spring in Chicago Loop

We selected the 34 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Chicago Loop

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-to-ceiling windows.

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Jazz about town from this charming apartment in Chicago’s South Loop – a music hub filled with live venues, restaurants and bars. Grab a morning pick-me-up at the in-building gourmet coffee shop before heading out for a day of adventures.


We selected the top 3% holiday homes in Chicago Loop Vacation Rentals for Spring

Explore the 34 most perfect homes in our collection

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Most popular homes in Chicago Loop

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

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Check upcoming rates & availability for Chicago Loop Vacation Rentals for Spring


Frequently asked questions

There's no time for average stays, so rent one of the finest Vacation Rentals for Spring in Chicago Loop. Each home in our range must pass 3 rounds of meticulous tests, so you can be certain that your high standards will be met. Only the top 3% of homes become Plum Award winners, and every single property in our selection comes fully furnished - expect a well-equipped kitchen, essential bathroom toiletries, and all linen to be included. Book a stay in a luxury Spring Holiday Rental in Chicago Loop today, and make the most of the season. Reach out to our friendly experts too, who enjoy nothing more than helping you in the hunt for your ideal holiday home.

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