Palmer Square Holiday Rentals

Compare Villas, Resorts, & Rentals in Palmer Square, Chicago, Illinois, USA

New

Apartment

Newly renovated, Chic, Spacious & Bright 1-bedroom apt in Lincoln Park!

From GB £300 per night

10.0 (3 Reviews)

1 Bedroom 5 Guests

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Apartment

Wicker Park 1-BR Walk to Train & Grocery Easy Downtown Access

From GB £137 per night

10.0 (8 Reviews)

1 Bedroom 2 Guests

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House

Wrigleyville Inn

From GB £388 per night

10.0 (21 Reviews)

1 Bedroom 2 Guests

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New

Apartment

North Center Gem - 3BR, 2BA Near Brown Line & Restaurants - Decks & Comfort

From GB £312 per night

10.0 (2 Reviews)

3 Bedrooms 6 Guests

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House

The Logandale: HUGE Mid-Century Home, sleeps 15

From GB £353 per night

10.0 (4 Reviews)

4 Bedrooms 15 Guests

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Bed & Breakfast

Ray's Bucktown B&B

From GB £119 per night

9.8 (386 Reviews)

1 Bedroom 2 Guests

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New

House

Bohome Chicago | 4BR + Sauna + Chefs Kitchen

From GB £838 per night

New

4 Bedrooms 8 Guests

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Apartment

Stylish 2BR stunner in unbeatable location

From GB £141 per night

10.0 (3 Reviews)

2 Bedrooms 6 Guests

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Bed & Breakfast

Villa D' Citta

From GB £177 per night

9.4 (114 Reviews)

1 Bedroom 2 Guests

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New

House

Sleeps 22 Modern Multi-Unit Gym Workspaces

From GB £715 per night

New

6 Bedrooms 22 Guests

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House

Stunning 5BR Home in Heart of Chicago with 2 Rooftops

From GB £693 per night

10.0 (2 Reviews)

1 Bedroom 16 Guests

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New

Condo

Modern Four-Bedroom Townhouse in River West

From GB £596 per night

New

4 Bedrooms 10 Guests

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Apartment

The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10

From GB £623 per night

10.0 (2 Reviews)

5 Bedrooms 10 Guests

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New

Apartment

Charming 6BD Retreat - Steps Away from Wrigley

From GB £479 per night

New

6 Bedrooms 13 Guests

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House

The Village Inn by Dakota Gal Digs

From GB £519 per night

10.0 (2 Reviews)

3 Bedrooms 8 Guests

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New

House

Game Room Fire-pit Playground Gym Billiard

From GB £438 per night

New

4 Bedrooms 9 Guests

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Apartment

Comfy 2BR Apartment near Wrigley Field - Grace 3

From GB £365 per night

10.0 (2 Reviews)

2 Bedrooms 4 Guests

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New

House

Giant 5-Bedroom Home w/Pool Table, 15 Min to Wrigley & Downtown

From GB £430 per night

New

5 Bedrooms 14 Guests

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Apartment

Stylish & Bright Gem Overlooks Lovely Park with Great Amenities

From GB £182 per night

10.0 (2 Reviews)

3 Bedrooms 6 Guests

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New

Apartment

Shorter Walk To Wrigley Than A Home Run

From GB £346 per night

New

3 Bedrooms 6 Guests

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Apartment

North Center Chicago - Walkable - Transit Accessible - King & Queen Beds

From GB £299 per night

10.0 (2 Reviews)

2 Bedrooms 4 Guests

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New

Apartment

Bold 3BR West Town Sleeps 8 | Patio + Free Parking

From GB £326 per night

New

3 Bedrooms 8 Guests

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Apartment

The Roscoe Village Guesthouse

From GB £143 per night

10.0 (2 Reviews)

3 Bedrooms 6 Guests

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New

Apartment

Private Apartment in Fulton Market

From GB £254 per night

New

1 Bedroom 8 Guests

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Apartment

Casa Palmera Fast Wifi, Pool Table Fire Pit

From GB £828 per night

10.0 (1 Review)

7 Bedrooms 23 Guests

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New

Apartment

2BR Fitness Pad Private Gym Sleeps 7

From GB £251 per night

New

2 Bedrooms 7 Guests

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House

Perfect Location Across from Park & Train Station

From GB £537 per night

10.0 (1 Review)

5 Bedrooms 13 Guests

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New

Condo

Fabulous 3 Bedroom in the Heart of North Center

From GB £219 per night

New

3 Bedrooms 6 Guests

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Apartment

Luxury 2BD-2BA View-Gym-Rooftop

From GB £431 per night

10.0 (1 Review)

2 Bedrooms 4 Guests

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New

Apartment

Private Workspace Sleeps4 Modern Stylish Stay

From GB £199 per night

New

2 Bedrooms 4 Guests

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Apartment

NEW! Spacious Art Deco Modern 5 BD/3BA Condo

From GB £424 per night

10.0 (1 Review)

5 Bedrooms 14 Guests

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New

Apartment

3 Bedroom Apartment, 15 min drive to Wrigley Field

From GB £180 per night

New

3 Bedrooms 5 Guests

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Apartment

Desert Mirage Free Parking & Private Patio

From GB £261 per night

10.0 (1 Review)

2 Bedrooms 6 Guests

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New

Apartment

Sleeps 4 New Modern 1BR Private Workspace

From GB £168 per night

New

2 Bedrooms 4 Guests

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House

Heart Of Humboldt Park Near Downtown Chicago

From GB £201 per night

10.0 (1 Review)

3 Bedrooms 12 Guests

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New

Apartment

Stylish 3-Bedroom Family Retreat-Walk to Transit-Quiet Tree-Lined Street

From GB £161 per night

New

3 Bedrooms 5 Guests

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Apartment

Flexhome West Town 2BR Duplex Apt T2

From GB £160 per night

10.0 (1 Review)

2 Bedrooms 6 Guests

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New

Apartment

Flexhome Wicker Park 2BR DV3

From GB £154 per night

New

2 Bedrooms 5 Guests

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Apartment

Modern River West 2BR with W&D by Zencity

From GB £56 per night

10.0 (1 Review)

2 Bedrooms 3 Guests

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New

Apartment

Sleeps 7 Huge Projector Designated Workspace

From GB £149 per night

New

2 Bedrooms 7 Guests

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New

House

Escape to Springfield Serenity—a stylish two-bedroom retreat designed for relaxation and play. Enjoy a peaceful meditation corner, cozy living, and a nostalgic Pac-Man arcade for the perfect balance of calm and fun.

From GB £149 per night

New

2 Bedrooms 5 Guests

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New

Apartment

Blueground | Lincoln Park, fitness center, nr Oz Park

From GB £138 per night

New

1 Bedroom 2 Guests

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New

Apartment

Blueground | Lincoln Park, fitness, nr Lincoln Park

From GB £137 per night

New

1 Bedroom 2 Guests

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New

Condo

By Wrigley+Reserved Parking+95 Walkscore+Laundry!

From GB £132 per night

New

3 Bedrooms 4 Guests

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New

House

2-bedroom house in terrific Chicago neighborhood walking distance to everything

From GB £125 per night

New

2 Bedrooms 5 Guests

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Apartment

Quiet Oasis Only Minutes from Downtown - Friendly Neighborhood! by AllSet Turnover

From GB £212 per night

10.0 (24 Reviews)

2 Bedrooms 4 Guests

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Apartment

Designer Apt Billiards Private Patio 1 Parking

From GB £377 per night

10.0 (1 Review)

3 Bedrooms 10 Guests

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Bed & Breakfast

Wicker Park Inn

From GB £150 per night

9.0 (259 Reviews)

1 Bedroom 2 Guests

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Apartment

2BD/1 BA with summer patio in quiet Roscoe Village

From GB £109 per night

10.0 (20 Reviews)

2 Bedrooms 4 Guests

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Apartment

Tranquil Library 2brm 1bath private eclectic apt at Solar Lodge

From GB £292 per night

10.0 (1 Review)

1 Bedroom 4 Guests

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House

Chicago Avenue Inn

From GB £85 per night

7.0 (101 Reviews)

1 Bedroom 2 Guests

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Apartment

Spacious loft in the heart of West Town, Noble Square Chicago

From GB £116 per night

10.0 (13 Reviews)

1 Bedroom 4 Guests

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House

Amazing City Getaway. Perfect for Entertaining!

From GB £621 per night

10.0 (1 Review)

5 Bedrooms 12 Guests

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Hotel

ENVITAE Hotel

From GB £331 per night

10.0 (3 Reviews)

3 Bedrooms 8 Guests

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House

jane's house a boutique historical flat in chicago - close to everything!

From GB £192 per night

10.0 (12 Reviews)

2 Bedrooms 4 Guests

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Apartment

East Lincoln Park Gem Spacious 4 BR

From GB £372 per night

10.0 (1 Review)

4 Bedrooms 10 Guests

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Apartment

NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!

From GB £174 per night

10.0 (12 Reviews)

2 Bedrooms 6 Guests

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Apartment

Spacious and Modern 3BD 2BA Home- Garage Parking!

From GB £218 per night

10.0 (1 Review)

3 Bedrooms 8 Guests

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Condo

Spacious Downtown Chicago Condo with Spa Bath, King Bed, Patio, 3 Blocks to L

From GB £166 per night

10.0 (12 Reviews)

1 Bedroom 4 Guests

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Apartment

Designer Home in Ukrainian Village - Chicago

From GB £168 per night

10.0 (1 Review)

1 Bedroom 3 Guests

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Condo

Bucktown Condo Just Two Blocks from the L by AllSet Turnover

From GB £137 per night

10.0 (12 Reviews)

2 Bedrooms 4 Guests

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Apartment

Two Bedroom Garden Apartment

From GB £135 per night

10.0 (1 Review)

2 Bedrooms 4 Guests

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Apartment

Stylish 2BR Apt in Irving Park

From GB £122 per night

10.0 (10 Reviews)

2 Bedrooms 3 Guests

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House

Prime Avondale

From GB £113 per night

9.9 (7 Reviews)

1 Bedroom 4 Guests

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Apartment

2BR Apartment Beautifully Furnished

From GB £209 per night

10.0 (9 Reviews)

2 Bedrooms 6 Guests

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Apartment

Pulaski Point Properties

From GB £138 per night

9.8 (32 Reviews)

3 Bedrooms 6 Guests

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Apartment

Modern & Bright Chicago City Escape

From GB £156 per night

10.0 (9 Reviews)

2 Bedrooms 6 Guests

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Apartment

The Wrigleyville VIP-200 Steps from Wrigley Field

From GB £225 per night

9.8 (13 Reviews)

2 Bedrooms 6 Guests

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Apartment

REMODELED Splendid Flat in Bucktown +Back Porch, Ranked GUEST FAVORITE! Pets OK!

From GB £152 per night

10.0 (8 Reviews)

2 Bedrooms 6 Guests

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Apartment

Avenir West Loop Penthouses with Iconic City Views

From GB £871 per night

9.8 (6 Reviews)

10 Bedrooms 24 Guests

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Apartment

2 Mi to Logan Square: Pet-Friendly Urban Oasis!

From GB £132 per night

10.0 (7 Reviews)

2 Bedrooms 4 Guests

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Apartment

Entire Apt in Heart of Chicago

From GB £97 per night

9.8 (5 Reviews)

2 Bedrooms 6 Guests

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About Casai's Private Villas and Holiday Rentals in Palmer Square

Discover more than 1891 vacation rentals available in Palmer Square. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Palmer Square.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Palmer Square, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Palmer Square. On average, places to stay near Palmer Square offer 826.85 ft², with nightly prices averaging GB £310.

With Casai, finding and comparing holiday rentals in Palmer Square is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Frequently Asked Questions About Palmer Square?

What are the top holiday rentals in Palmer Square?

How many Casai.uk holiday rentals are available in Palmer Square?

As of 2026, Casai boasts over 1891 properties listed in the Palmer Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Palmer Square.