West Loop holiday rentals

We found 1,205 holiday rentals — enter your dates for availability
Discover a selection of 185 apartments and other holiday rentals in West Loop that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – West Loop

Showing deals for:4 Dec - 11 Dec

Living area
Terrace/patio
Interior
Private kitchen
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$7,999
for 7 nights, 1 apartment
AU$1,143 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
The building
River North Luxury Living
Interior
Outdoors at night
Exceptional
(105 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$4,519
for 7 nights, 1 apartment
AU$646 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Patio Deck 2
Living Room
Bedroom 1 (King Size) + 55Inch TV
Front Yard View
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$6,659
for 7 nights, 1 home
AU$951 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Room
Interior
Private kitchen
Property grounds
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

7% off
AU$3,325
for 7 nights, 1 home
AU$475 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Kitchen (upstairs)
Downstairs living area
Fun Mirror Wall Upstairs
Upstairs queen bedroom 2
Exceptional
(98 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,201
for 7 nights, 1 apartment
AU$1,743 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Exterior detail
Living area
Private kitchen
Exceptional
(69 reviews)

Wicker Park near Downtown and the Salt Shed Special 149.00 Sept 7-12

Chicago

7% off
AU$2,391
for 7 nights, 1 apartment
AU$342 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 149.00 Sept 7-12
Room
Private kitchen
Exterior
Living area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
AU$3,243
for 7 nights, 1 apartment
AU$463 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit West Loop for a holiday rental?
July is the most popular month to visit the West Loop, Illinois, known for its vibrant setting and culinary delights. During the peak season from July to September, the area buzzes with activity as tourists flock to enjoy the bustling restaurants, trendy shops, and lively street festivals that define this urban neighbourhood.With average temperatures ranging from 20 to 30 degrees Celsius, July offers warm and pleasant weather, great for exploring outdoor spaces and enjoying al fresco dining. Visitors can stroll through the historic streets, take in the art installations, and immerse themselves in the local culture.For those seeking a more budget-friendly option, consider visiting in December. This month, while quieter, provides a unique charm with holiday decorations and festive events that showcase the city's winter spirit. You may also find more attractive rental prices during this time.Ultimately, the best time to book a holiday rental in the West Loop depends on your interests. If you thrive in lively environments filled with events and social gatherings, then the summer months will suit you perfectly. However, if you prefer a more relaxed experience with a touch of seasonal magic, December could be your ideal choice.
What are the top attractions in West Loop, Illinois, United States of America?
In the West Loop neighbourhood of Chicago, visitors will find a vibrant mix of attractions that cater to diverse interests. One of the standout features is the Fulton Market District, known for its trendy restaurants, art galleries, and boutique shops, all housed in former industrial buildings. This area is superb for food lovers, with many acclaimed eateries and food halls offering a variety of culinary experiences.Nearby, the iconic Chicago Union Station provides a glimpse into the city's rich architectural history, while the nearby Chicago Riverwalk offers picturesque views and a lovely spot for a leisurely stroll. For those interested in culture, the West Loop is close to the historic Greektown, where visitors can enjoy Greek cuisine and explore its unique shops.The neighbourhood is also home to several art installations and galleries, making it a great place for art enthusiasts.
Are all fees included in the West Loop holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any West Loop holiday homes with parking?
Stayz offers a wide selection of holiday homes in West Loop with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for West Loop holiday homes?
You can find great discounts on holiday homes in West Loop on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my West Loop holiday home booking on Stayz?
To find West Loop holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in West Loop?
A long-stay holiday home in West Loop is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a West Loop holiday home?
Book your West Loop holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in West Loop?
Prices for holiday homes in West Loop vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in West Loop to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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