West Loop vacation rentals

We found 1,258 vacation rentals — enter your dates for availability

Discover a selection of 6 condos and other vacation rentals in West Loop that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

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Find out more about West Loop

Why visit West Loop

  • Trendy dining scene: West Loop features an array of stylish restaurants and eateries, perfect for food enthusiasts.
  • Urban parks: Enjoy relaxing moments in beautiful parks that provide a green oasis amidst the bustling cityscape.
  • Historic architecture: Explore stunning historic buildings that reflect the rich culture and history of the area.
  • Vibrant nightlife: Experience an exciting nightlife with lively bars and entertainment options throughout the neighborhood.
  • Family-friendly atmosphere: The welcoming vibe makes West Loop ideal for families seeking fun activities and outings.

Popular types of accommodation around West Loop

Planning a getaway to West Loop? You're in for a treat. This vibrant neighborhood offers a range of accommodations, from stylish apartments and houses to modern condos. Whether you’re looking for a cozy studio in West Loop or a spacious Chicago apartment, you’ll find the perfect spot to unwind. Discover the charm of West Loop and make your stay unforgettable with our diverse rental options.

  • Apartments: The top choice for visitors in West Loop, offering modern amenities and a home-like feel for a comfortable stay.
  • Houses: A popular option for groups or families, providing spacious and personalized accommodations for a home-away-from-home experience.
  • Condos: Ideal for those seeking a blend of luxury and convenience, with many featuring great city views and shared facilities.
  • Cottages: A cozy retreat that offers a charming and intimate atmosphere, perfect for a relaxing getaway.
  • Villas: The fifth choice, offering upscale living with ample space and often luxurious amenities for an indulgent stay.**

Top attractions near West Loop

West Loop, Chicago, is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can explore stunning skyscrapers, relaxing urban parks, and historic buildings that showcase the area's rich culture. Whether traveling with family or seeking a vibrant city experience, West Loop offers a variety of attractions that cater to diverse interests and create unforgettable memories.

  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street filled with high-end shops, vibrant restaurants, and stunning architecture, offering a quintessential Chicago city vibe.
  • Millennium Park: This urban oasis features beautiful gardens, iconic art installations like Cloud Gate, and a family-friendly atmosphere, making it perfect for outdoor activities and relaxation.
  • Chicago Riverwalk: A scenic walkway along the Chicago River, the Riverwalk is ideal for leisurely strolls, dining, and family outings, showcasing the city's vibrant waterfront culture.

Things to do recommended for couples

For a romantic getaway in West Loop, enjoy live music at House of Blues, just a mile away, or savor a cozy dinner at the historic Michael Jordan Restaurant, two miles away. Don’t miss the lively ambiance of Aragon Ballroom, located six miles from your stay.

Things to do recommended for families

Families visiting West Loop can enjoy a game at Wrigley Field, just 5 miles away, or explore the serene Northerly Island Natural Area, 3 miles away. For wellness and relaxation, The East Bank Club is conveniently located only 0.8 miles from West Loop.

Things to do recommended for groups

Experience the vibrant culture of Chicago by catching a show at the Chicago Theatre, just 1 mile from West Loop. Enjoy laughs at the Second City comedy venue, 2 miles away, or shop till you drop at the Chicago Place Mall, also 2 miles from your location.

*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 you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to West Loop with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and much more on Vrbo.
  • Traveling to West Loop with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private 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 vacation wouldn't feel whole without their furry companion by their side. If you can relate, explore Vrbo properties that welcome pets. Most 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 searching for vacation rentals that offer great deals for stays of a month or longer, 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 options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near West Loop

West Loop, a vibrant Chicago neighborhood, offers a perfect blend of urban charm and family-friendly vibes. Explore its trendy restaurants and lively nightlife options while enjoying stunning city views. The area's friendly atmosphere makes it ideal for outdoor activities and leisurely strolls. Nearby neighborhoods enhance the experience with their own unique flavors, ensuring travelers can soak in the best of Chicago's rich culture and scenic beauty during their vacation.

  • Chicago: Chicago is a vibrant city known for its rich history, diverse culture, and stunning architecture. Nestled along the shores of Lake Michigan, it offers an exciting blend of urban experiences and outdoor activities. Visitors can explore renowned attractions like the Art Institute of Chicago, Millennium Park, and the iconic Navy Pier. With a plethora of shopping areas and entertainment venues, including theaters and sports facilities, Chicago is a family-friendly destination that caters to all interests. Whether you're enjoying a deep-dish pizza or taking a stroll along the waterfront, Chicago promises an unforgettable experience.
  • Downtown Chicago: Located a mere 2 miles from West Loop, Downtown Chicago is the bustling heart of the city. This vibrant neighborhood is a hub for shopping, dining, and entertainment, featuring the famous Magnificent Mile, where you can find luxury retailers alongside popular brands. Downtown is also home to stunning architectural marvels and cultural landmarks, including the Willis Tower and the Chicago Riverwalk. Visitors can enjoy a range of activities from catching a show at a theater to attending a sporting event at one of the nearby arenas, making it an ideal destination for families and city explorers alike.
  • The Loop: Just 1 mile from West Loop, The Loop is Chicago's central business district and a cultural epicenter. This neighborhood is characterized by its iconic skyline and is home to many of the city's most famous attractions, including Grant Park and the Chicago Cultural Center. The Loop offers a vibrant mix of shopping, dining, and entertainment options, with easy access to theaters and sports venues. Whether you're exploring the art installations in the parks or taking in a Broadway-style show, The Loop provides a dynamic urban experience that captures the essence of 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.

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 trying to save on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, if you book a longer stay, you often can enjoy significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the trip planner has its perks. Sign up for our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Join us today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last left off, or manage your existing travel arrangements. You can easily access your saved or booked properties, organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in West Loop?
In West Loop, apartments are the most popular vacation rental option, with several available throughout the area. These apartments are typically located in vibrant neighborhoods close to local eateries, art galleries, and parks. Travelers can expect amenities such as fully equipped kitchens, modern living spaces, and often access to fitness centers or rooftop terraces that offer stunning views of the Chicago skyline.
How much does it cost to rent a vacation home in West Loop?
Prices for vacation 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 vacation 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.
What are popular rental amenities in West Loop?
In West Loop, popular vacation rental amenities include balconies that offer great views of the city, making it easy to enjoy the vibrant setting from the comfort of your own space. Many rentals also feature kitchen facilities, allowing guests to prepare their own meals, which is especially convenient for those who prefer a home-cooked option. Additionally, you'll find amenities such as coffee and tea makers for a cozy start to your day and desks for those who may need to work during their stay. For entertainment, many properties are located near casinos, providing easy access to nightlife and gaming options.

*Please play responsibly. You must be at least 21 years old to participate in any form of gambling in the United States. If you believe you have a gambling problem, seek help from professional organizations such as the National Council on Problem Gambling at www.ncpgambling.org or call their helpline at 1-800-522-4700.
Can I find family house rentals in West Loop?
In the West Loop neighborhood of Chicago, there are several family-friendly house rentals available, making it an excellent choice for travelers with children. This vibrant area is known for its trendy atmosphere, featuring a variety of dining options and local attractions. Many homes in this locale come equipped with spacious living rooms for family gatherings, fully stocked kitchens for preparing meals, and outdoor spaces where kids can enjoy the fresh air.

Visitors will appreciate the proximity to parks like Skinner Park, which offers playgrounds and open spaces for recreational activities. Additionally, the West Loop's close-knit community feel, combined with access to cultural hotspots, ensures a memorable stay for families.
Are there any West Loop vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in West Loop with parking available—perfect for families or travelers 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 vacation rentals in West Loop?
A long-stay vacation rental in West Loop is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit West Loop for a vacation rental?
July is the most popular time to visit West Loop, Illinois, making it an ideal month for those seeking vibrant city life and a variety of activities. During this peak season, which runs from July to September, travelers flock to the area to enjoy the warm summer weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit. This climate is superb for outdoor dining, exploring local parks, and attending the numerous street festivals that showcase the neighborhood's dynamic culture.

The bustling atmosphere in July is complemented by a rich array of culinary experiences, as West Loop is known for its renowned restaurants and trendy eateries. Visitors can indulge in the vibrant food scene while also exploring nearby attractions like the Chicago Riverwalk or the iconic Art Institute of Chicago, all easily accessible and superb for a day of sightseeing.

For those looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it offers a unique charm with festive holiday decorations, cozy cafes, and a chance to experience the city's winter wonderland. The quieter streets mean you can enjoy a more relaxed pace, with the possibility of discovering hidden gems without the summer crowds.

Ultimately, the best time to book a vacation rental in West Loop depends on whether you're eager to immerse yourself in the lively summer scene or prefer the tranquil, festive atmosphere of winter.
Are there any remote work vacation rentals in West Loop?
In the West Loop area of Chicago, there are several vacation rentals that cater specifically to remote workers. These accommodations typically include essential amenities such as high-speed internet, dedicated desks, and office spaces to ensure productivity during your stay. Many properties also feature comfortable living areas and fully equipped kitchens, allowing for a pleasant work-life balance.

The West Loop is known for its vibrant setting, with numerous dining options and cultural attractions nearby. Travelers can enjoy easy access to local parks and the bustling restaurant scene, making it an ideal location for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a West Loop vacation rental?
Book your West Loop vacation 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 vacation 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, visitors can explore a dynamic mix of attractions that highlight the neighborhood's culinary and cultural scene. The area is renowned for its vibrant food scene, with numerous acclaimed restaurants and trendy eateries, particularly along Randolph Street, often referred to as "Restaurant Row." Guests can enjoy a variety of cuisines, from upscale dining to casual bites, making it a culinary hotspot.

Art enthusiasts can visit the nearby Chicago Arts District, which features galleries and studios showcasing local artists. Additionally, the West Loop is home to the historic Union Park, a great spot for outdoor activities, concerts, and community events. The neighborhood is also conveniently located near the iconic Willis Tower, where visitors can experience breathtaking views of the city from the Skydeck.
Can I change or cancel my West Loop home rental booking on Vrbo?
To find West Loop vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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