West Loop holiday lettings

We found 1,208 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:11 Dec - 18 Dec

Interior
River North Luxury Living
Outdoors at night
French Bistro and Wine Bar - right downstairs
Exceptional
(105 reviews)

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

Chicago

7% off
£2,516
for 7 nights, 1 apartment
£359 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Kitchen
Living Room
Patio Deck 2
Front Yard View
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

7% off
£2,910
for 7 nights, 1 home
£416 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Kitchen (upstairs)
Downstairs living area
Fun Mirror Wall Upstairs
Downstairs living room
Exceptional
(98 reviews)

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

Chicago

7% off
£6,791
for 7 nights, 1 apartment
£970 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Stop by say Hello to Dave our neighbor at his newest hipest Italian eatery
Polk Street
Room 2  Queen bed  black out curtains vintage snd Original art and a TV
Open Concept Living Room
Exceptional
(313 reviews)

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago

7% off
£1,643
for 7 nights, 1 apartment
£235 per night
includes taxes & fees
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Room
Exterior detail
Living area
Dining
Exceptional
(69 reviews)

Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 7-11

Chicago

6% off
£946
for 7 nights, 1 apartment
£135 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 7-11
Everything you need to make a meal
Tree lined Polk Street
Interior
Living Room 50” TV
Exceptional
(199 reviews)

1F Chicago's Little italy Graystone nearDowntown

Chicago

7% off
£1,808
for 7 nights, 1 apartment
£258 per night
includes taxes & fees
1F Chicago's Little italy Graystone nearDowntown
Exterior
Room
Living area
Interior
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

7% off
£1,348
for 7 nights, 1 apartment
£193 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit West Loop

  • Trendy dining scene: West Loop boasts an array of fashionable restaurants, offering diverse cuisines that cater to every palate.
  • Artistic flair: The neighbourhood is home to numerous art galleries and creative spaces, showcasing local talent and vibrant exhibitions.
  • Historic architecture: Visitors can admire beautifully restored buildings that reflect the rich history and culture of the area.
  • Urban parks: Enjoy green spaces perfect for relaxation and family outings amidst the bustling city.
  • Lively markets: Experience the vibrant atmosphere of local markets featuring fresh produce and unique artisanal goods.

Popular types of accommodation around West Loop

Welcome to West Loop, Chicago, a vibrant neighbourhood known for its dynamic blend of culture, cuisine, and creativity. Explore trendy restaurants, art galleries, and lively markets, all while enjoying the convenience of modern accommodations. Whether you prefer stylish apartments, houses, or luxurious condos, West Loop has a diverse range of options. Experience the charm of this bustling area, where every corner offers something unique for your holiday adventure.

  • Apartments: The most sought-after choice for a stay in West Loop, offering modern amenities and a vibrant atmosphere.
  • Houses: A popular option for those seeking a homely feel with more space and privacy during their visit.
  • Condos: Ideal for travellers looking for a blend of comfort and convenience, often in prime locations.
  • Villas: A luxurious choice, providing ample space and upscale amenities for an indulgent getaway.
  • Cottages: A charming alternative, perfect for those wanting a quaint and cosy retreat.**

Top attractions near West Loop

West Loop, Chicago, Illinois, is a vibrant neighbourhood perfect for family and outdoor vacations. Visitors can explore stunning skyscrapers, enjoy urban parks, and admire historic buildings that showcase the area’s rich culture. With a variety of attractions catering to families and those seeking urban experiences, West Loop offers a delightful blend of culture and city life, making it an ideal destination for travellers looking to immerse themselves in the essence of Chicago.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street offers a bustling atmosphere with an array of high-end shops, restaurants, and cultural landmarks, making it perfect for a day of shopping and exploration.
  • Millennium Park: A beautiful urban park that features stunning art installations, lush gardens, and family-friendly activities, it's a perfect spot for relaxation and enjoying outdoor events.
  • Chicago Riverwalk: A picturesque waterfront area ideal for leisurely strolls, dining, and enjoying scenic views of the city, offering a unique perspective on Chicago's architecture.

Things to do recommended for couples

Seeking a romantic getaway in West Loop? Enjoy a candlelit dinner at a chic restaurant, explore the vibrant art scene, or take a leisurely stroll through the local parks. Don't miss the chance to indulge in a wine tasting at a nearby vineyard for a perfect couple's experience.

Things to do recommended for families

Your family will delight in the interactive exhibits at the Chicago Children's Museum, just a short ride away, or explore the vibrant murals and parks in the West Loop. Don't miss the delicious offerings at local eateries, perfect for a family-friendly dining experience.

Things to do recommended for groups

Groups visiting West Loop, Chicago, can indulge in a culinary tour featuring renowned restaurants and vibrant food markets. They can also enjoy a lively evening at the local breweries or take a guided street art tour to discover the area's unique murals and urban culture.

*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

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, be sure to use filters that align with your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to West Loop with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all 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 ensuring access to 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 feel complete without their beloved four-legged companion. If this resonates with you, explore 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 right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near West Loop

West Loop, Chicago, Illinois, is a vibrant neighbourhood brimming with a unique blend of urban charm and scenic beauty. This area is known for its trendy eateries, art galleries, and bustling markets, providing a perfect backdrop for family outings or city-themed adventures. Visitors can immerse themselves in the friendly atmosphere, explore iconic landmarks, and enjoy the lively vibe that makes West Loop a delightful destination for all types of travellers.

  • Chicago: As a vibrant metropolis, Chicago is renowned for its rich cultural scene and architectural marvels. The West Loop, where you’ll be staying, is a prime example of the city's dynamic urban landscape, offering a plethora of restaurants and galleries. Here, you can enjoy family-friendly activities, explore expansive urban parks, and indulge in shopping at iconic areas. Don't miss the opportunity to catch a game at one of the city's sports facilities or experience the lively atmosphere at the theatre venues that dot the city.
  • Downtown Chicago: Located a mere 3km from West Loop, Downtown Chicago is the heart of the city, bustling with energy. This area is perfect for families and outdoor enthusiasts alike, featuring lush urban parks and a variety of shopping options. With its proximity to major attractions like theatres and arena entertainment facilities, Downtown Chicago promises an exciting experience. Be sure to visit the tourist precinct and take in the stunning skyline views from the park, making it an ideal spot for leisurely strolls and family outings.
  • The Loop: The Loop, situated just 2km from West Loop, is Chicago’s central business district, rich in history and culture. This neighbourhood is known for its impressive architecture and is home to numerous theatres, shopping areas, and sports facilities. Visitors can enjoy family-friendly experiences in the urban parks or take part in various outdoor activities. The Loop’s vibrant atmosphere, combined with its easy access to essential attractions, makes it a must-visit location during your stay in Chicago.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you hoping to save on your upcoming journey? We recommend being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in substantial savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume from where you last stopped, or organise your travel arrangements. You will find your saved or booked properties neatly arranged under Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in West Loop?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in West Loop to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for West Loop holiday house rentals?
You can find great discounts on house rentals in West Loop on Vrbo, 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.
Are there any West Loop holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in West Loop?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a West Loop holiday rental?
Book your West Loop holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my West Loop home rental booking on Vrbo?
To find West Loop holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the West Loop holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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