West Loop holiday homes

We found 1,210 holiday rentals — enter your dates for availability
Discover a selection of 183 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:18 Dec - 25 Dec

Room
Interior
Exterior
Living area
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
NZ$43,880
for 7 nights, 1 home
NZ$6,269 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Dining
Our downtown Townhouse is in an amazing location
Room
Interior
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$13,068
for 7 nights, 1 home
NZ$1,867 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Bedroom 1 (King Size) + 55Inch TV
Living Room
Front Yard View
Patio Deck 2
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

7% off
NZ$11,101
for 7 nights, 1 home
NZ$1,586 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Upstairs queen bedroom 2
Downstairs living area
Downstairs living room
Kitchen (upstairs)
Exceptional
(99 reviews)

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

Chicago

7% off
NZ$15,737
for 7 nights, 1 apartment
NZ$2,248 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Exterior detail
Living area
Private kitchen
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11

Chicago

7% off
NZ$3,133
for 7 nights, 1 apartment
NZ$448 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11
Exterior
Room
Private kitchen
Living area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
NZ$4,287
for 7 nights, 1 apartment
NZ$612 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

Why visit West Loop

  • Vibrant urban charm: Experience the lively atmosphere of West Loop, filled with bustling streets and friendly locals.
  • Cultural insights: Discover historic buildings that showcase Chicago's rich history and architectural beauty.
  • Family-friendly attractions: Enjoy a variety of activities perfect for families, ensuring fun for all ages.
  • Scenic urban parks: Unwind in green spaces that provide a refreshing escape amid the skyscrapers.
  • Diverse dining scene: Savor an eclectic mix of culinary delights from renowned eateries and trendy restaurants.

Top attractions near West Loop

West Loop, Chicago, is a vibrant neighbourhood perfect for families and outdoor enthusiasts. Explore stunning skyscrapers, unwind in urban parks, and discover historic buildings that reflect the city's rich culture. This area offers a variety of attractions and experiences that cater to those seeking a city-themed holiday filled with family-friendly activities and cultural insights. Enjoy the bustling atmosphere and unique charm that West Loop has to offer during your visit.

  • Grant Park: This expansive urban park offers a vibrant green space ideal for family outings and outdoor activities. With its stunning gardens and walking paths, it provides a refreshing retreat from the city's hustle and bustle.
  • 875 North Michigan Avenue: A striking skyscraper that showcases the impressive skyline of Chicago. Visitors can enjoy breathtaking city views from its observation deck, making it a must-see landmark.
  • Buckingham Fountain: A historic fountain that exemplifies Chicago's rich culture, featuring stunning water displays. It's a beautiful spot for photographs and to learn about the city's history.

Things to do recommended for couples

Searching for a romantic getaway in West Loop? Indulge in a candlelit dinner at a trendy restaurant, stroll through the vibrant art scene, or enjoy a couple's spa day. Don’t forget to explore the local breweries for a unique taste of Chicago together.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Chicago Children's Museum, visiting the animals at the Lincoln Park Zoo, and enjoying a fun-filled day at Maggie Daley Park's playground and ice skating ribbon, all within a short distance from West Loop.

Things to do recommended for groups

Groups visiting West Loop can savour delicious food at the renowned restaurant district, explore the vibrant street art scene, and join a guided brewery tour to taste local craft beers. Don't miss the lively atmosphere at the local markets for a true Chicago experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around West Loop

When planning your trip, whether you’re travelling with a group, family, or pets, or seeking extended stays, it’s important to apply the right filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to West Loop with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to West Loop with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to West Loop: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting West Loop: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near West Loop

Discover the vibrant urban charm of West Loop, Chicago, a neighbourhood full of family-friendly attractions and scenic urban vistas. Wander through its bustling streets, admire iconic landmarks, and experience the friendly local atmosphere. Enjoy a blend of business energy and relaxed city vibes in this dynamic part of Chicago, perfect for those seeking an engaging and diverse holiday experience.

  • Chicago: As one of the largest cities in the United States, Chicago is a vibrant urban hub offering a rich tapestry of experiences. Located in the heart of the Midwest, the city is renowned for its stunning skyline and diverse cultural attractions. Visitors can enjoy a dynamic blend of family-friendly activities, outdoor spaces, and a thriving arts scene. Key highlights include shopping districts, bustling entertainment venues, and renowned theatres. Don't miss the chance to explore iconic landmarks such as sports stadiums and urban parks that are perfect for a leisurely stroll or a picnic.
  • Downtown Chicago: Just 3km from West Loop, Downtown Chicago is the city's energetic core. This bustling neighbourhood is a magnet for families and tourists alike, offering a plethora of outdoor and city-themed experiences. With an array of shopping options, lively arena entertainment, and captivating theatres, there’s something for everyone. The area is home to major attractions, including vibrant tourist precincts and green urban parks, providing a refreshing contrast to the city's urban landscape.
  • The Loop: Located a mere mile from West Loop, The Loop is Chicago's historic downtown area and is known for its impressive architecture and cultural institutions. It offers a fantastic mix of family-oriented activities, outdoor recreation, and an urban atmosphere. Visitors can explore shopping areas, catch a show in one of its renowned theatres, or enjoy sports events at nearby stadiums. The Loop's proximity to urban parks and tourist precincts makes it an ideal spot for both relaxation and exploration.

Best time to go to West Loop

If you're planning a trip to West Loop, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverage
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudyAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly High
October54.9°F (12.7°C)Light RainMostly SunnySlightly Low
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

Looking to save on your next adventure? Being flexible with your travel dates can work in your favour, as prices often fluctuate. You might also find considerable savings by opting for a longer stay. To discover a Vrbo property that suits both your budget and preferences, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your next adventures. Here, you can start new trips, continue from where you last stopped, or neatly arrange your travel plans. You’ll discover your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find West Loop holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in West Loop to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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