Holiday houses in West Loop

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Quick stats about holiday rentals in West Loop

  • Total holiday rentals

    Explore 540 holiday rentals in West Loop

  • Nightly prices starting at

    West Loop holiday rentals start at $57 AUD per night before taxes and fees

  • Verified guest reviews

    Over 21,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 300 rentals that welcome pets

  • Holiday rentals with a pool

    290 properties feature pools

  • Rentals with dedicated workspaces

    320 properties have a dedicated workspace

  • Wi-Fi availability

    540 of West Loop holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across West Loop rentals

  • 4.8 Average rating

    West Loop stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in West Loop

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright living area features a spacious sectional sofa, accent chairs, and a round coffee table. Large windows allow natural light to fill the space. A colorful wall art piece adds a vibrant touch, while decorative plants enhance the inviting atmosphere.
Apartment in West Loop
4.94 out of 5 average rating, 143 reviews

Clean & Best Location 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

Top Guest favourite
Apartment in West Loop
4.95 out of 5 average rating, 113 reviews

Fulton House #1 (2bd/ 1ba)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago
4.81 out of 5 average rating, 1021 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Top Guest favourite
A spacious living room features a decorative fireplace and large bay windows that allow natural light to fill the space. Comfortable seating options include a light-colored armchair and couch, complemented by a glass coffee table and a colorful area rug.
Home in West Loop
4.98 out of 5 average rating, 376 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Top Guest favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.96 out of 5 average rating, 298 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite
A cozy bedroom features a spacious bed with hotel-grade bedding, complemented by warm tones on the walls. A green accent wall, potted plant, and stylish lamp create a calming atmosphere. Nightstands are placed on either side, enhancing the room's functionality.
Apartment in West Loop
4.95 out of 5 average rating, 76 reviews

Gym | Garage Parking | Balcony | Sleeps 6

Stunning 2 bedroom West Loop apartment with Private Balcony, Gym, 1 Garage Parking with 1 king bed and 2 full beds. Perfect for groups & families up to 6. You are a 5 min walk to Fulton Market, and a 12 min drive away from restaurants in downtown, Millennium Park, and 15 mins drive away from Navy Pier! This is the perfect place for tourists to immerse themselves in the central vibe of Chicago, and enjoy all the activities that West Loop has to offer.

Guest favourite
A spacious living area features a light-colored sectional sofa facing a mounted TV above a decorative fireplace. The open-plan design connects to a modern kitchen with bar seating. Natural light enters through large windows adorned with light curtains, creating a relaxed atmosphere.
Apartment in West Loop
4.92 out of 5 average rating, 161 reviews

Spacious Downtown 3BR with Free Parking

A beautiful, modern, three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'll have the whole space to yourself with easy access to some of the best restaurants in the city, a free parking space on premise, and nearby access to public transportation to quickly get around the city. The interior is recently renovated with new furnishings, and provides a beautiful space to relax and recharge between outings.

Top Guest favourite
Apartment in West Town
5.0 out of 5 average rating, 17 reviews

Bright & Spacious Boho Oasis: A Warm Retreat

Discover a sun-drenched sanctuary that feels like a hidden gem. This isn't just a place to stay; it’s an airy, open-concept retreat designed for those who want to settle right in. With high ceilings and a "Modern Boho" aesthetic, the space is flooded with natural light and a warm, inviting ambiance. Nestled in a quiet, residential pocket of West Town, you’ll enjoy peaceful surroundings with the professional service of a 5-star host.

Guest favourite
An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.
Home in West Loop
4.87 out of 5 average rating, 495 reviews

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea!

Superhost
Apartment in West Loop
4.84 out of 5 average rating, 149 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Superhost
A modern kitchen with an expansive island features sleek countertops and stainless steel appliances. Large windows fill the open living area with natural light, showcasing city views. A comfortable seating area and dining table create an inviting space for relaxation and meals.
Apartment in West Loop
4.86 out of 5 average rating, 42 reviews

Level Two Bedroom Suite | Fulton Market

Our Two Bedroom Suites are spacious and sophisticated boasting up to approximately 1,150 sqft of modern living space. Make a home-cooked meal in your fully equipped kitchen, host friends in your open concept living and dining area, and take in the city views on your open-air balcony. All suites also feature in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, and complimentary Wi-Fi.

Top Guest favourite
An open kitchen and dining area features exposed brick walls and a large wooden dining table surrounded by black metal chairs. Bright light streams in from skylights above, highlighting the warm wood flooring and a woven pendant light hanging above the table.
Apartment in West Loop
4.99 out of 5 average rating, 287 reviews

Beautiful and spacious West Loop apartment.

This sunny & spacious 2bd / 2ba is the perfect getaway in the epicenter of the bustling Fulton Market neighborhood. Find Chicago’s most eclectic restaurant scene steps from your apartment. Explore the many coffee houses, shops, and galleries the West Loop has to offer. Downtown and Millennium Park are a short "El" ride away. Complimentary assorted coffee, fluffy towels and a beautiful deck await!

Popular amenities for West Loop holiday rentals