The Loop vacation rentals

We found 1,142 vacation rentals — enter your dates for availability

Discover a selection of 296 apartments, 20 condos, and other vacation rentals in The Loop that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about The Loop

Why visit The Loop

  • Iconic Architecture: Marvel at Chicago's stunning skyscrapers that define the city's skyline.
  • Chicago Riverwalk: Enjoy scenic walks along the beautiful Chicago Riverwalk, perfect for relaxation and sightseeing.
  • Cultural Attractions: Immerse yourself in diverse cultural experiences with museums, theaters, and galleries.
  • Vibrant Neighborhoods: Explore nearby neighborhoods filled with unique dining options and friendly atmospheres.
  • Variety of Accommodations: Choose from chic apartments to luxury condos for a comfortable stay in the heart of the city.

Popular types of accommodation around The Loop

The Loop vacation rentals offer a variety of accommodations to suit your needs, whether you're traveling solo or with family. Popular options include chic Chicago Loop apartments, spacious houses, and stylish luxury condos. From cozy studio apartments to well-appointed bedroom apartments, you'll find the perfect spot for your getaway. Discover the ideal blend of comfort and convenience in the vibrant heart of Chicago with our diverse rental choices.

  • Apartments: The top choice for vacation rentals in The Loop, offering a range of sizes and styles to suit your needs.
  • Houses: A popular option for families or groups seeking a home-like atmosphere during their stay.
  • Condos: A favored accommodation type, providing modern amenities and often stunning city views.
  • Cottages: A charming option, perfect for those looking for a cozy retreat within the city.
  • Villas: Ideal for travelers seeking a luxurious experience with ample space and upscale features.**

Top attractions near The Loop

The Loop in Chicago is perfect for family-friendly, outdoor, and urban-themed vacations. You'll find attractions like the iconic skyscrapers and the scenic Chicago Riverwalk, offering a rich cultural experience. Explore the vibrant streets and consider renting accommodations by neighborhood for a more local feel. Whether you're traveling solo or with loved ones, The Loop promises a memorable adventure filled with city charm.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street offers a vibrant mix of high-end shopping, dining, and iconic architecture, making it a must-see for any visitor.
  • Navy Pier: This lively waterfront destination features stunning views of Lake Michigan, a variety of attractions, restaurants, and friendly people, perfect for a day of exploration and enjoyment.
  • Millennium Park: A family-friendly urban park, it showcases beautiful gardens, public art installations like Cloud Gate, and hosts concerts and events, providing a perfect outdoor escape in the heart of the city.

Things to do recommended for couples

Discover romance in The Loop, Chicago. Enjoy a cozy dinner at a rooftop restaurant with stunning skyline views, take a leisurely walk by the iconic Millennium Park, or share a quiet moment at the picturesque Chicago Riverwalk. Don't forget to catch a show at the historic Chicago Theatre.

Things to do recommended for families

Families visiting The Loop in Chicago can explore the fascinating Shedd Aquarium, enjoy hands-on fun at the Museum of Science and Industry, and take a scenic boat tour on the Chicago River, all while discovering the city's rich history and vibrant culture.

Things to do recommended for groups

Explore the Art Institute of Chicago's stunning collection, take a stroll along the Riverwalk, and enjoy a deep-dish pizza at a local favorite. End your day with a breathtaking view from the Willis Tower Skydeck, perfect for group photos and unforgettable memories.

*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 The Loop

When traveling with a group, family, pets, or planning an extended stay, it's important to use the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to The Loop with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group activities. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to The Loop with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to The Loop: For many, a family vacation isn’t truly fulfilling without their furry companion along for the journey. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that your whole family feels comfortable and at home.
  • Planning for a long term stay visiting The Loop: If you're in search of vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near The Loop

The Loop in Chicago offers an exciting vacation experience, perfect for families and outdoor enthusiasts alike. Nestled in the heart of downtown, this vibrant neighborhood boasts iconic architecture, bustling business districts, and scenic parks. Exploring nearby neighborhoods, you'll find a friendly atmosphere filled with diverse dining options and cultural attractions. Whether you're soaking in the urban vibes or enjoying family-friendly activities, The Loop is the ideal base for your Chicago adventure.

  • Chicago: Chicago is a vibrant metropolis known for its remarkable skyline and rich cultural scene. The Loop, the city's central business district, serves as a hub for family-friendly attractions and urban adventures. Visitors can enjoy a variety of activities, from shopping at local boutiques to catching a show at the renowned Chicago Theatre. Key landmarks include iconic sports facilities like Wrigley Field and Millennium Park, where you can relax in green spaces or attend outdoor events. With its blend of entertainment, dining, and cultural experiences, Chicago promises an unforgettable travel experience.
  • Downtown Chicago: Just a short half-mile from The Loop, Downtown Chicago offers an exciting urban experience. This bustling neighborhood is perfect for families and outdoor enthusiasts alike, featuring an array of shopping options and entertainment venues. Visitors can explore the historic Chicago Riverwalk, enjoy a game at the United Center, or take in breathtaking views from the Willis Tower Skydeck. With its proximity to major attractions, Downtown Chicago is a vibrant area that seamlessly combines city life with recreational opportunities.
  • Magnificent Mile: Located 0.8 miles from The Loop, Magnificent Mile is Chicago's premier shopping destination, attracting visitors with its high-end retailers and diverse dining options. This iconic stretch offers an engaging experience for families, featuring educational attractions and cultural landmarks. Don't miss a visit to the Art Institute of Chicago or a leisurely stroll through the nearby urban parks. With its stunning architecture and lively atmosphere, Magnificent Mile is a must-visit for anyone looking to soak in the essence of Chicago.

Best time to go to The Loop

If you're planning a trip to The Loop, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudySlightly HighSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly 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 SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
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

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a helpful platform for planning your travel. You can easily create new trips, continue from where you last stopped, or organize and review your existing plans. Your saved or booked properties will be neatly arranged under categories like Potential, Upcoming, or Current Trips. To get started with 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 The Loop?
In The Loop, apartments are the predominant type of vacation rental, with several options available throughout this vibrant area. These apartments typically feature modern amenities such as fully equipped kitchens, spacious living areas, and in-unit laundry facilities. Many units also offer stunning views of the city skyline or nearby parks, allowing guests to enjoy the dynamic atmosphere of downtown Chicago.
Are there any beach house rentals in The Loop?
In The Loop, Illinois, there are several beach house rentals available, primarily situated along the waterfront. These properties often include amenities such as fully equipped kitchens, spacious living areas, and outdoor patios or balconies that provide stunning views of the lake.
How much does it cost to rent a vacation home in The Loop?
Prices for vacation rentals in The 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 The 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 The Loop vacation house rentals?
You can find great discounts on house rentals in The 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 The Loop?
In The Loop, Illinois, popular vacation rental amenities cater to both leisure and business travelers. Many rentals come equipped with fully functional kitchens, allowing guests to prepare their own meals. A coffee and tea maker is also commonly found, superb for starting the day with a warm beverage. Fitness facilities are available for those looking to maintain their workout routines while away from home. Additionally, many properties offer office spaces, making it convenient for business travelers to catch up on work. For families, some rentals provide travel cribs, ensuring that young children are accommodated comfortably.
Can I find family house rentals in The Loop?
In The Loop, Illinois, there are several family-friendly house rentals available, making it a great choice for group getaways. This vibrant neighborhood is filled with easy access to attractions that appeal to visitors of all ages. Many properties feature spacious living areas and fully equipped kitchens, great for preparing family meals after a day of exploring the city.

Families can enjoy amenities such as Wi-Fi, air conditioning, and sometimes even outdoor spaces to relax in. Additionally, nearby points of interest include Millennium Park, where children can play and families can enjoy concerts and events, and the Art Institute of Chicago, offering educational experiences for all ages.
Can I rent a vacation home with a pool or hot tub in The Loop?
In The Loop, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This vibrant area in downtown Chicago is known for its stunning skyline, cultural attractions, and proximity to Lake Michigan. Travelers can expect a range of amenities in these rentals, including private pools, hot tubs, and outdoor spaces for relaxation, all complemented by modern interiors and fully equipped kitchens, ideal for both comfort and convenience.
Are there any The Loop vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in The 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 book pet-friendly vacation rentals in The Loop?
In The Loop, travelers can find several pet-friendly vacation rentals that provide a comfortable stay in the heart of Chicago. Many of these accommodations come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and high-speed internet, suiting both short and extended stays.

The area is vibrant and full of attractions, including parks that are accessible for pet owners. While The Loop itself has limited green spaces, nearby Grant Park offers expansive lawns and walking paths where you can enjoy leisurely strolls with your furry friend. See all pet-friendly rentals in The Loop.
Can I find long-stay vacation rentals in The Loop?
A long-stay vacation rental in The 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 The Loop for a vacation rental?
The best time to visit The Loop for a vacation rental is during the peak season from May to July. This vibrant period draws visitors eager to experience the lively option of Chicago, with its bustling streets, outdoor festivals, and a wide array of cultural activities. The warm weather, with temperatures typically ranging from the mid-70s to mid-80s Fahrenheit, is superb for exploring the city's iconic landmarks, such as Millennium Park and the Art Institute of Chicago.

July, in particular, stands out as the most popular month for travelers. Expect a lively ambiance filled with events and activities, from concerts to street fairs, allowing you to immerse yourself in the local culture. The longer days and vibrant nightlife make it an ideal time for outdoor dining and enjoying the city's impressive skyline.

For those seeking a more budget-friendly option, December offers a unique charm with festive holiday decorations and events. The Loop transforms into a winter wonderland, providing opportunities to enjoy ice skating at Millennium Park or visiting the Christkindlmarket. While this month may be quieter in terms of tourist activity, it presents a cozy atmosphere superb for exploring at a leisurely pace.

Ultimately, your choice of when to visit The Loop should reflect whether you prefer the energetic summer vibe or the magical ambiance of the winter season.
Are there any remote work vacation rentals in The Loop?
In The Loop, Illinois, there are several vacation rentals that cater to remote work needs. Travelers can find properties equipped with high-speed internet and dedicated office spaces to ensure a productive work environment. Many rentals also offer amenities like comfortable workstations and easy access to local coffee shops or coworking spaces, enhancing the remote work experience. Additionally, the vibrant urban setting provides opportunities to explore cultural attractions, parks, and dining options during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a The Loop vacation rental?
Book your The 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 The Loop, Illinois, United States of America?
In The Loop, visitors can explore a variety of attractions that showcase the vibrant culture and architecture of Chicago. The Art Institute of Chicago, located here, is a must-see for art enthusiasts, housing an extensive collection of Impressionist and Post-Impressionist masterpieces. Just a short walk away, Millennium Park features the iconic Cloud Gate sculpture, also known as "The Bean," along with beautiful green spaces and seasonal events.

For those interested in architecture, the Chicago Architecture Foundation offers walking tours that highlight the city's stunning skyline and historical buildings. The Loop is also home to the historic Chicago Theatre, known for its marquee and diverse performances.

Shopping enthusiasts can visit State Street, which hosts a mix of department stores and unique boutiques. Additionally, the area is rich in dining options, from upscale restaurants to casual eateries, making it a great place for food lovers to explore.
Can I change or cancel my The Loop home rental booking on Vrbo?
To find The 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 The 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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