West Loop holiday lettings

We found 1,432 holiday rentals — enter your dates for availability

Discover a selection of 8 homes 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:14 Nov - 21 Nov
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about West Loop

Find out more about West Loop

Why visit West Loop

  • Culinary delights: West Loop is renowned for its trendy eateries and fine dining, offering a delightful array of local and international cuisine.
  • Urban charm: Stroll through lively streets lined with impressive skyscrapers and historic buildings, showcasing Chicago's architectural beauty.
  • Family-friendly activities: Enjoy urban parks and cultural experiences that cater to families, making it perfect for outings with children.
  • Shopping hotspots: Explore unique boutiques and fashionable shops, ideal for picking up distinctive souvenirs.
  • Convenient accommodation: Choose from a variety of stylish apartments and condos, providing a comfortable base for your adventures.

Popular types of accommodation around West Loop

If you're pondering the ideal accommodation in West Loop, look no further. Our most sought-after options include charming apartments, spacious houses, and stylish condos. Whether you're searching for West Loop apartments, apartment rentals, or specific West Loop Chicago apartments for rent, we have a variety to suit your needs. Enjoy your stay with transparency and reassurance in this vibrant neighbourhood.

  • Apartments: The most sought-after accommodation in the West Loop, offering a comfortable and convenient stay for all types of travellers.
  • Houses: Ideal for families and groups, these homes provide a home-away-from-home experience with added privacy.
  • Condos: A popular choice for those seeking modern amenities and a community atmosphere during their visit.
  • Cottages: Quaint and charming, these rentals offer a unique and cosy retreat in the bustling city.
  • Villas: Luxurious options for visitors looking for spacious accommodations with upscale features.**

Top attractions near West Loop

West Loop in Chicago is ideal for family and city-themed holidays, featuring impressive skyscrapers, urban parks, and historic buildings. Visitors can immerse themselves in the local culture while exploring various points of interest, including notable landmarks. This vibrant area offers a delightful blend of experiences that cater to families and those seeking a taste of urban life.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street is a bustling hub of shopping, dining, and entertainment, showcasing the city's architectural grandeur and urban energy.
  • Millennium Park: A delightful urban park featuring iconic installations like Cloud Gate, this family-friendly space offers outdoor concerts, gardens, and art, ideal for leisurely strolls.
  • Chicago Riverwalk: A scenic pedestrian promenade along the Chicago River, perfect for families, offering picturesque views, dining options, and a chance to explore the city's waterfront.

Things to do recommended for couples

If you're seeking a romantic getaway in West Loop, Chicago, consider a night of live music at the House of Blues, just 1.6km away. Alternatively, indulge in a delightful meal at the historic Michael Jordan Restaurant, two miles from your location, for a perfect couples' evening.

Things to do recommended for families

During your family vacation in the West Loop, Chicago, explore the excitement of Wrigley Field, just 3.1km away, for a thrilling sports experience. Alternatively, unwind at the serene Northerly Island Natural Area, 1.9km away, or enjoy wellness activities at The East Bank Club, merely 497m from your location.

Things to do recommended for groups

Experience the vibrant culture of Chicago by visiting the Chicago Theatre for a lively performance, enjoying a night of laughter at Second City, and indulging in retail therapy at Chicago Place Mall. Each destination offers a unique atmosphere perfect for group travellers.

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

If you’re planning a trip with a group, family, or pets, or if you’re seeking extended stays, it’s important to set the right priorities in your search. Here are some helpful booking tips for using Vrbo.

  • Traveling to West Loop with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space 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 be quite demanding. 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 wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 with special offers for stays of a month or more, you've come to the perfect destination. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near West Loop

West Loop, a vibrant neighbourhood in Chicago, offers a delightful mix of urban charm and friendly atmosphere, perfect for family outings or city adventures. With its proximity to downtown, visitors can easily stroll through lively streets filled with trendy eateries and boutiques. Nearby areas add to the scenic experience, making it an ideal base for exploring the rich culture and bustling vibe of the Windy City.

  • Chicago: Situated merely 621m from West Loop, Chicago is a vibrant metropolis renowned for its family-friendly attractions and outdoor spaces. Visitors can indulge in a diverse shopping experience, enjoy high-energy arena events, and explore educational venues. Key landmarks include the iconic stadium and sports facilities, alongside a bustling tourist precinct that offers a taste of the city's rich culture and history. Chicago's blend of urban excitement and accessibility makes it a must-visit destination.
  • Downtown Chicago: Located 1.2km from West Loop, Downtown Chicago is a lively neighbourhood that perfectly encapsulates the city's energetic spirit. Ideal for families, this area boasts numerous shopping opportunities, arena entertainment, and a thriving theatre scene. Visitors will find themselves surrounded by notable landmarks such as tourist precincts and sports stadiums. The combination of urban parks and cultural attractions ensures that there is something for everyone to enjoy while exploring this dynamic part of the city.
  • The Loop: Just 621m away from West Loop, The Loop is a central neighbourhood that serves as Chicago's heartbeat. With its family-centric activities and outdoor offerings, The Loop is perfect for visitors seeking a quintessential city experience. Popular venues include shopping areas and theatres, with must-see landmarks such as urban parks and sports stadiums. This area is bustling with life and provides an ideal backdrop for those looking to immerse themselves in the vibrant culture and entertainment that Chicago has to offer.

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. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to make your next getaway more affordable? Being flexible with your travel dates can lead to better pricing, as fares often fluctuate. Additionally, opting for a longer stay can result in substantial savings. To discover a Vrbo property that suits your financial plan, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a convenient space to plan new adventures, pick up from where you last paused, or view and arrange your travel plans. You can easily access the properties you've previously saved or booked, now organised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in West Loop?
Apartments are the most popular type of holiday rental in West Loop, according to our data. Even if you have a different idea about what you want, Vrbo has holiday homes in all shapes and sizes. Look through our options to find your perfect match.
How much does it cost to rent a holiday rental in West Loop?
Different factors can affect how much you'll pay for a holiday rental in West Loop, such as the type of property, length of stay and season. However, all of our holiday homes have something in common — exceptional value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in West Loop?
The average price for a holiday home near the beach in West Loop depends on when you're going and the type and size of property you're searching for. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then use the filter tool to select the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
Are there pet-friendly holiday rentals in West Loop?
There certainly are. You'll find 99 holiday homes that allow pets in West Loop on Vrbo. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to find a perfect property where Fido can join in the fun.
Can I rent a house with a pool in West Loop?
Grab your swimwear and inflatable unicorn, because there are 46 houses with a private pool in West Loop. Base yourself at one of these superb holiday homes and every day can be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in West Loop?
When it comes to rental amenities that people prefer in West Loop, a fireplace, a nearby river and a firepit rank the highest. With Vrbo holiday rentals, you'll find options to suit your style and taste, whether you're going away with your partner, family members or even pets.
Are there large group holiday rentals in West Loop?
West Loop has nine holiday homes that can host 10 or more guests. These stays come with the space you need to share good times with your nearest and dearest.
Are there holiday rentals in West Loop that welcome kids?
With 99 family-friendly holiday homes to choose from in West Loop, now is a superb time to introduce the kids to the thrills of travel. Click on our "Properties good for families" filter to find stays loaded with amenities ideal for travelling families, such as full kitchens, backyards, entertainment areas and hot tubs.
What are the top attractions for families in West Loop?
Keep the kids occupied at these fantastic family-friendly attractions in West Loop:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday rentals in West Loop?
Take your pick from 46 one-bedroom rentals in West Loop. Whether you want a cosy cottage or a fancy condo, our one-bedroom properties are great if you don't require huge amounts of space. One of the major perks of having your own digs? You won't need to share your holiday with strangers.
Can I find two-bedroom holiday rentals in West Loop?
West Loop has 14 two-bedroom holiday properties to select from. Find a holiday home with all the privacy and space you need at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in West Loop?
West Loop has 10 holiday rentals with WiFi, so you can stay connected while on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to updating your social media, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in West Loop?
Pick your dates and then make use of the filters to look for holiday rentals with ac in West Loop on Vrbo. With 99 air-conditioned properties to choose from here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a holiday rental in West Loop?
The minimum age allowed can differ between properties on Vrbo, so be sure to check the rules of the holiday rental in West Loop you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in West Loop for?
The amount of time you can stay in a West Loop holiday rental for differs depending on the property. Simply enter your dates of travel to see options that offer extended stays. They feature the things you need to make your extended break more enjoyable and convenient, such as laundries and air conditioning. Some properties might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

More Holiday Rentals ideas

People also search for