
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.

NEW! 3BR/2.5B Duplex in Noble Sq
Welcome to our stunning 3 bedroom, 2.5 bath duplexed condo with free parking and ample outdoor space in the heart of the vibrant Noble Square neighborhood. This open, bright and spacious unit is a true urban oasis that will make you feel right at home in the epicenter of Chicago. Our condo is close to some of the city's best restaurants, cafes, and bars, as well as several beautiful parks. With its unbeatable location, modern design, luxurious amenities, and SuperHost service - look no further!
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Great Location & Bright 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!
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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.
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Modern River West 2 Bed 2 Bath-Steps to Blue Line
Enjoy Urban Living in my 2 bed 2 bath River West apartment. Located in a beautiful and secure new building, relax in a tranquil modern space with all of the conveniences of home. You'll be steps from the Grand blue line station and a quick walk to award-winning restaurants in trendy Fulton Market and Randolph Street. Downtown Chicago is just a short drive or train ride away. You won't run out of accessible Chicago charm here - and the proximity to the Loop really can't be beat. Book today!
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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.
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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.
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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.
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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!
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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.
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Luxury 2BR Apartment in Downtown Chicago
Experience downtown Chicago living at its finest in this stunning 2-bedroom apartment in the heart of the Loop. Wake up to breathtaking city views and step out to world-class attractions just minutes from your door. Enjoy in-unit laundry, gigabit Wi-Fi, free parking, and luxe building amenities, including a rooftop lounge, and gym. Perfect for business or leisure!
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Level One Bedroom Suite | Fulton Market
One Bedroom Suites offer approximately 650 sqft of living space and boast fully equipped kitchens, living room with sofa bed, spa-inspired bathroom, and separate bedroom with king bed and open-air balcony. All suites feature in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, and complimentary Wi-Fi.
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Fantastic West Loop 2 bedroom
Beautifully renovated apartment in Chicago’s best neighborhood for fun and food in Landmark building next to public transportation. Two bedrooms with two bathrooms and a chef’s kitchen. Everything you and your friends or family need for an awesome weekend in one of the best cities in the world.
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Popular amenities for West Loop holiday rentals
Other great holiday rentals in West Loop

Freshly Minted 2BR - Elegance & Comfort in Central
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Gym, Garage Parking, Balcony, Sleeps 4
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1BR Gem | Modern & Furnished
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1BR Modern Luxe Apt with In-Unit Laundry
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West Loop Living – Bright 1BR
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Sunlit 1BR Apartment | Warm & Welcoming Space
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Warwick Allerton Hotel Chicago, Selected by hotel
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Deluxe double
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Destinations to explore
- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park





