The Loop vacation rentals

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

Select from 57 houses, 250 apartments, and other vacation rentals to find the perfect place for your stay in The Loop. 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.

Vacation rentals with weekly discounts - The Loop

Showing deals for:Aug 8 - Aug 15
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Find out more about The Loop

Find out more about The Loop

Why visit The Loop

  1. Diverse attractions: The Loop features a mix of urban parks, beaches, and cultural experiences ideal for family outings.
  2. Vibrant neighborhoods: Explore the lively South Loop, known for its friendly locals and romantic spots.
  3. Exciting nightlife: Enjoy a variety of entertainment districts and nightlife options for a fun evening out.
  4. Stylish accommodations: Choose from luxurious apartments, convenient apart hotels, and cozy vacation homes for a comfortable stay.
  5. Artistic flair: Experience the dynamic art scene that showcases Chicago's cultural richness.

Popular types of accommodation around The Loop

Planning a getaway to The Loop? The excitement begins with selecting your perfect accommodation! Discover a variety of options, including chic apart hotels, stylish apartments, and spacious houses. Whether you're searching for luxury apartments or a cozy spot to relax, Chicago Loop vacation rentals offer something for everyone. Get ready to experience the vibrant heart of Chicago with comfort and convenience at your fingertips!

  • Apartments: The top choice for visitors in The Loop, offering a variety of styles and amenities for a comfortable stay.
  • Houses: A popular option for families or groups seeking more space and a home-like atmosphere during their visit.
  • Condos: A favored accommodation that combines luxury and convenience, ideal for those wanting a modern living experience.
  • Cottages: A charming and cozy option, perfect for those looking for a quaint retreat in the heart of the city.
  • Caravan Parks: A unique option for adventurous travelers, offering a more communal and outdoor experience near The Loop.**

Top attractions around The Loop

The Loop in Chicago is perfect for family outings, outdoor adventures, and city vacations. Explore urban parks, nearby beaches, and modern universities while enjoying a vibrant cultural scene. This area offers exciting entertainment districts and nightlife options, making it ideal for travelers seeking a mix of adventure and relaxation. Don't miss the chance to experience the diverse attractions that The Loop has to offer!

  1. Michigan Avenue: A bustling street known for its vibrant city atmosphere, Michigan Avenue offers a mix of shopping, dining, and iconic architecture, making it a perfect spot for urban exploration.
  2. Navy Pier: Stretching along Lake Michigan, Navy Pier features stunning waterfront views, artistic installations, and a friendly community vibe, ideal for leisurely strolls and cultural experiences.
  3. Millennium Park: A family-friendly urban park showcasing impressive art, beautiful gardens, and outdoor activities, Millennium Park is a perfect place to unwind amidst the city's energy.

Things to do recommended for couples

For a romantic getaway in The Loop, enjoy live music at the House of Blues Chicago, just 0.3 miles away, or savor a meal at the Historic Michael Jordan Restaurant, 0.6 miles away. For a thrilling night, head to the Aragon Ballroom, only 6 miles from The Loop.

Things to do recommended for families

Families can enjoy the excitement of Soldier Field, just 2 miles from The Loop, or unwind at the serene Northerly Island Natural Area, also 2 miles away. For fitness enthusiasts, The East Bank Club offers wellness activities and is conveniently located only 0.7 miles from The Loop.

Things to do recommended for groups

Experience the vibrant arts scene at the Chicago Theatre, just 0.2 miles from The Loop. Enjoy shopping at 900 North Michigan Shops, 1 mile away, or share laughs at Second City, located 2 miles from The Loop. Perfect for creating unforgettable memories with your group!

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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to prioritize your needs in the search process. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to The Loop with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to The Loop with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your distance to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to The Loop: For many families, a vacation wouldn't be the same without their furry companions. If you relate to this, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting The Loop: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay around The Loop

The Loop in Chicago offers an exhilarating blend of urban energy and artistic flair, perfect for family vacations or outdoor adventures. Explore the vibrant South Loop, a hot neighborhood brimming with friendly locals and romantic spots. Whether wandering through iconic parks or enjoying the bustling city atmosphere, you'll find plenty of family-friendly activities and cultural experiences that showcase the best of this dynamic area. Dive into the heart of Chicago and uncover its unique neighborhoods!

  • Downtown Chicago: Located a mere 0.5 miles from The Loop, Downtown Chicago is the bustling epicenter of the city, offering a vibrant mix of family-friendly activities and urban excitement. Here, you can indulge in shopping at renowned retail stores, catch a game at the arena entertainment facilities, or enjoy a night out at one of the many theaters. Notable attractions include the iconic tourist precinct and sports facilities like the United Center, making Downtown a must-visit for anyone looking to soak in the city's energy.
  • Magnificent Mile: Just 0.8 miles from The Loop, the Magnificent Mile is a shopper's paradise, renowned for its upscale boutiques and flagship stores. Families and outdoor enthusiasts alike flock here to experience its lively atmosphere and beautiful architecture. You can explore educational venues and enjoy arena entertainment, all while surrounded by stunning city views. The area is home to notable landmarks, including the historic Water Tower and various sports facilities, ensuring that there’s something for everyone to enjoy.
  • River North: Situated 0.7 miles from The Loop, River North is a vibrant neighborhood known for its artistic flair and culinary delights. This area is perfect for families looking for outdoor experiences and cultural enrichment. You can shop at trendy boutiques, enjoy performances at theaters, or visit popular arena entertainment venues. River North is also home to unique local landmarks, including the picturesque esplanade and various art galleries, making it a fantastic spot to explore Chicago's creative side.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 HighAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageSlightly High
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowSlightly Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to lower prices. Also, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your trips, allowing you to start new ones, continue from where you left off, or easily view and arrange your travel plans. You'll discover your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental accommodation in The Loop?
The most desirable types of vacation rentals in The Loop are apartments. Prefer something different? Vrbo has plenty of options to match our guests’ needs, so you’ll see properties in lots of sizes and shapes. The ideal home away from home is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in The Loop?
Season, length of stay and property type are some things that can determine the price of a vacation home. Simply click on your dates of travel to find your ideal match. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in The Loop?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside escape. Enter your The Loop travel dates to see all your options on Vrbo. Did someone just say “hot tub”? Use the filters to pick the amenities and features you need.
Are there pet-friendly vacation rentals in The Loop?
Yes. You can choose from 228 vacation rentals that allow pets in The Loop. Some of our pet-friendly vacation rentals have an outdoor space for your furry friend to play around in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in The Loop?
Add a whole new level of fun to your vacation by booking one of the 107 houses with a private pool in The Loop. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days playing and splashing in a swimming pool that’s just for you.
What are popular rental amenities in The Loop?
A water view, a nearby waterfront and a firepit rank as the most popular rental amenities in The Loop. Whether you’re taking a trip solo, with your other half or a group of friends, Vrbo will help you find a vacation home that fits your style with a load of extras you’ll love.
Are there large group vacation rentals in The Loop?
The Loop has five vacation properties that can cater to 10 or more people. These stays come with plenty of space to enjoy good times with family and friends.
Are there vacation rentals in The Loop that welcome kids?
The Loop has 227 family-friendly vacation homes to choose from. And securing a stay that welcomes children is a cinch with our “Properties good for families” filter. Besides having the whole place to yourselves, you’ll have access to amenities and perks such as bunk beds, kitchens and private pools.
Are there one-bedroom vacation rentals in The Loop?
The Loop has 113 one-bedroom rentals available. Typically situated in popular areas due to their compact size, a one-bedroom vacation rental is great if you’re getting away with a pal or your partner. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you’ll be able to chill out while sightseeing around this incredible destination.
Can I find two-bedroom vacation rentals in The Loop?
Gather your besties and relax in total privacy and comfort in one of the 41 two-bedroom vacation rentals The Loop has to offer.
Are there vacation rentals with WiFi in The Loop?
The Loop has 31 vacation rentals with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to writing and sending emails, these Vrbo homes make it easy to get online.
How can I find vacation rentals with air conditioning in The Loop?
Pick from 216 vacation rentals with air conditioning in The Loop offering that cool, cool breeze and extra level of comfort. Simply enter your preferred dates of travel and then take advantage of our filter tool to help you book properties with air conditioning.
How old do you have to be to rent a vacation rental in The Loop?
The minimum age requirements can differ across properties on Vrbo, so check the rules of the vacation rental in The Loop you’re interested in. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in The Loop for?
It’s down to the Loop property. To look over a list of options offering extended stays, simply enter your travel dates and number of people into Vrbo’s search page. Look forward to having the property to yourself, along with comforts such as a kitchen, air conditioning and an outdoor space where the kids can run around and play. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in The Loop?
On Vrbo, we’ve got some incredible discounts and deals for The Loop. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a mini getaway or an extended stay, Vrbo offers options for every style and budget.

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