The Loop vacation rentals

We found 1,233 vacation rentals — enter your dates for availability

Discover a selection of 327 apartments, 31 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 Skyscrapers: Marvel at Chicago's stunning skyline filled with architectural masterpieces.
  • Urban Parks: Relax in beautiful parks like Grant Park and Millennium Park, perfect for family outings.
  • Cultural Experiences: Immerse yourself in the rich history and vibrant arts scene of The Loop.
  • Family-Friendly Attractions: Enjoy engaging activities suitable for all ages, from museums to theaters.
  • Diverse Accommodations: Choose from chic apartments and stylish condos that enhance your city experience.

Popular types of accommodation around The Loop

Planning a getaway to The Loop? You're in for an exciting experience. Discover a variety of accommodations, including chic Chicago Loop apartments, houses, and stylish condos. Whether you’re searching for luxury apartments or the perfect Linea apartments, we’ve got you covered. Enjoy the convenience, comfort, and unique charm that The Loop has to offer as you explore this vibrant area.

  • Apartments: The top choice for visitors in The Loop, offering modern living spaces ideal for short or extended stays.
  • Houses: A great option for families or groups, providing the comfort and privacy of a home away from home.
  • Condos: These stylish units combine convenience and luxury, perfect for enjoying city life in The Loop.
  • Cottages: Quaint and charming, cottages offer a cozy escape within the bustling city atmosphere.
  • Villas: For those seeking a touch of elegance, villas provide spacious accommodations with upscale amenities.**

Top attractions near The Loop

The Loop in Chicago is perfect for family vacations and outdoor adventures, offering a vibrant urban atmosphere. Visitors can explore iconic skyscrapers, relaxing urban parks, and historic buildings. This area caters to travelers seeking cultural experiences while enjoying the city's rich history and family-friendly attractions. You'll find plenty of activities that will make your visit memorable and engaging.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is famous for its shopping, dining, and vibrant urban atmosphere, just 0.6 miles from The Loop.
  • Navy Pier: A popular destination 2 miles from The Loop, Navy Pier offers stunning lake views, entertainment options, and a friendly community vibe, making it perfect for a fun day out.
  • Millennium Park: Located only 0.3 miles from The Loop, this urban park features beautiful landscapes, public art installations, and family-friendly activities, ideal for outdoor enjoyment.

Things to do recommended for couples

Ready for a romantic getaway in The Loop? Enjoy live music at House of Blues, indulge in a cozy dinner at the Historic Michael Jordan Restaurant, or catch a show at the Aragon Ballroom. Each experience promises unforgettable memories for you and your partner.

Things to do recommended for families

Families can catch a game at Wrigley Field, just 5 miles from The Loop, or unwind at the tranquil Northerly Island Natural Area, located 2 miles away. For fitness enthusiasts, The East Bank Club, only 0.7 miles from The Loop, offers a great spot for recreation and relaxation.

Things to do recommended for groups

Experience the vibrant culture of Chicago with a visit to the iconic Chicago Theatre, just 0.2 miles away, or enjoy a night of laughter at Second City, 2 miles from The Loop. For shopping enthusiasts, Chicago Place Mall is only 0.8 miles away, offering a variety of family-friendly options.

*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, or pets, or if you're seeking longer stays, it's important to prioritize your search effectively. Here are some helpful Vrbo booking tips to consider.

  • Traveling to The Loop with a group: Think about how many bedrooms you'll require, as well as any amenities you might want, like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to The Loop with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with finding age-appropriate 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 The Loop: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like food bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting The Loop: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right 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 as well.

Where to stay near The Loop

The Loop in Chicago is an exciting urban hub perfect for family vacations and outdoor adventures. Explore the vibrant downtown area, where you can enjoy lively neighborhoods like the South Loop. Experience the friendly atmosphere and stunning scenery that make this city a fantastic destination. With a mix of business and leisure, The Loop offers a unique blend of attractions that cater to all types of travelers looking to immerse themselves in the heart of Chicago.

  • Chicago: Chicago, a vibrant metropolis, is the backdrop for The Loop, the city's bustling downtown area. Known for its family-friendly atmosphere and outdoor activities, travelers can immerse themselves in a rich urban experience. Explore the iconic shopping areas, catch a game at a local sports facility, or take a leisurely stroll through the tourist precinct. With landmarks such as the stadium and various entertainment venues, Chicago offers an unforgettable blend of culture and excitement for all ages.
  • Downtown Chicago: Located a mere 0.5 miles from The Loop, Downtown Chicago is a thriving neighborhood filled with energy and charm. It attracts families and outdoor enthusiasts alike, offering an array of shopping destinations and entertainment options. Enjoy a night out at the theater or visit the sports facilities nearby. The area's notable landmarks, including the tourist precinct and stadium, make Downtown Chicago a perfect spot for those seeking a vibrant city experience.
  • Magnificent Mile: Just 0.8 miles from The Loop, the Magnificent Mile is a premier shopping district renowned for its upscale retail and dining options. Families visiting this area can enjoy a blend of outdoor experiences and city-themed attractions. With its proximity to educational venues and lively entertainment, the Magnificent Mile features local landmarks like the stadium and sports facilities, ensuring a fun-filled outing for visitors looking to explore Chicago's finest offerings.

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 a breeze

Are you eager to save money on your upcoming trip? Being flexible with your travel dates can be a great strategy, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its rewards. When you join our travel rewards program, One Key, you can immediately access member discounts and earn or redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy way to plan your travel. You can create new trips, continue from where you last stopped, or view and organize your travel plans all in one place. Your saved or booked properties will be neatly organized under 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 The Loop?
In The Loop, apartments are the most popular type of vacation rental, with about 12 available in this vibrant area. These apartments are typically located in the heart of the city, providing easy access to iconic landmarks such as Millennium Park and the Art Institute of Chicago. Most rooms come equipped with modern amenities including fully equipped kitchens, stylish living spaces, and often features like rooftop access or city views.

For those seeking more room, several vacation houses are also available. These properties generally offer multiple bedrooms, private outdoor spaces, and amenities for larger groups, making them suitable for families or gatherings.
Are there any beach house rentals in The Loop?
In The Loop, Illinois, vacation rentals primarily consist of apartments and condos, with several options available. These accommodations are typically found in vibrant urban neighborhoods, close to attractions like Millennium Park, the Art Institute of Chicago, and the Chicago Riverwalk. Most rooms feature modern amenities such as fully equipped kitchens, spacious living areas, and access to building facilities like fitness centers and rooftop decks, providing a comfortable city experience.
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, popular vacation rental amenities include fully equipped kitchens, fitness facilities, and stunning water views. Many rentals also feature access to pools, providing a refreshing escape after a day of exploring the bustling downtown area. Additionally, accommodations often cater to travelers with service animals, ensuring a welcoming environment for all guests.
Are there any family house rentals in The Loop?
In The Loop, Illinois, there are numerous family-friendly house rentals, with around 19 options available. This vibrant area offers easy access to a variety of attractions, making it an ideal spot for families. Many of these properties come equipped with spacious living areas, full kitchens for preparing meals together, and convenient amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.

Visitors will appreciate the proximity to local highlights like Millennium Park, where children can enjoy the interactive Crown Fountain and the nearby Art Institute of Chicago, offering enriching experiences for all ages. Additionally, the Loop's bustling atmosphere is dotted with family-friendly restaurants and parks, ensuring there's plenty to explore.
Can I rent a vacation home with a pool or hot tub in The Loop?
In The Loop, Illinois, travelers can find several vacation homes available for rent that feature pools and hot tubs. This vibrant urban area offers a mix of modern apartments and stylish condos, ideal for those seeking a central location with easy access to the city's attractions. Many of these properties come equipped with amenities such as private pools, hot tubs, and rooftop terraces, providing a superb setting for relaxation after a day of exploring.
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.
Are there pet-friendly vacation rentals in The Loop?
In The Loop, there are several pet-friendly vacation rentals available, offering a range of amenities that cater to both travelers and their furry companions. Many of these rentals feature modern designs with fully equipped kitchens, high-speed internet, and spacious living areas, making them comfortable for extended stays. The Loop is an urban area, so pet owners will find plenty of nearby parks and green spaces for walks, such as Grant Park, which provides expansive lawns and pathways superb for enjoying time outdoors with pets. Additionally, the vibrant atmosphere of The Loop includes various pet-friendly cafes and restaurants, enhancing the overall experience for those traveling with pets.
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 peak season for visiting The Loop in Illinois is from May to July, with July standing out as the most popular month among travelers. This vibrant period invites a flurry of activity, with visitors flocking to enjoy the warm weather, outdoor festivals, and a plethora of dining options. The city's energy is palpable, and the streets come alive with events, making it an ideal time for those who thrive in lively environments.

During these months, temperatures typically range from the mid-70s to low 90s Fahrenheit, offering comfortable conditions for sightseeing and exploring attractions such as Millennium Park or the iconic Art Institute of Chicago. The bustling atmosphere is great for those eager to explore urban parks, indulge in al fresco dining, or take in the stunning architecture of The Loop.

If you're looking for a more budget-friendly experience, consider planning your trip in December. While this month may be less popular, it brings its own charm with festive decorations and holiday markets. Visitors can enjoy the beauty of the city during a quieter time, great for leisurely strolls and exploring local shops without the summer crowds.

Ultimately, the best time to book a vacation rental in The Loop hinges on your preferences for bustling summer adventures or a more relaxed winter getaway.
Are there any remote work vacation rentals in The Loop?
In The Loop, Illinois, there are plenty of remote work vacation rentals available, with around 21 options to choose from. This vibrant area, known for its bustling atmosphere and proximity to iconic attractions like Millennium Park and the Art Institute of Chicago, offers a range of accommodations that cater to remote workers. Many properties feature dedicated office spaces, desks, and ergonomic chairs to ensure a comfortable working environment.

Travelers can also expect modern amenities such as high-speed Wi-Fi, making it easy to stay connected while enjoying the city's cultural offerings. 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?
In The Loop, travelers can experience firsthand a vibrant urban atmosphere filled with iconic attractions. The Art Institute of Chicago stands out with its vast collection of artworks and is located near Grant Park, which offers expansive green spaces ideal for leisurely strolls. Just a few blocks away, visitors can marvel at the stunning architecture along the Chicago Riverwalk, including the famous Willis Tower, which features an observation deck with breathtaking views of the city skyline.

Millennium Park is another highlight, where guests can take photos with the famous Cloud Gate sculpture, often referred to as "The Bean," and enjoy various outdoor concerts and events. The Loop is also home to historic theaters like the Chicago Theatre, which frequently hosts live performances and shows. For shopping enthusiasts, State Street features a mix of well-known retailers and local boutiques, providing plenty of options 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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