Old Town Triangle vacation rentals

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Discover a selection of 5 homes and other vacation rentals in Old Town Triangle that are perfect for your trip. Vacation rentals provide the amenities you need and want for you and your friends, family, or even pets, such as air conditioning and a pool. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Find out more about Old Town Triangle

Find out more about Old Town Triangle

Why visit Old Town Triangle

  1. Historic Charm: Old Town Triangle offers a glimpse into Chicago's rich history with its well-preserved architecture and heritage sites.
  2. Outdoor Activities: Enjoy local parks like Peterson Park, perfect for picnics, sports, and family outings.
  3. Cultural Experiences: Explore art galleries and cultural events that showcase the vibrant local arts scene.
  4. Shopping and Dining: Stroll through unique boutiques and cozy cafes, offering delightful shopping and dining options.
  5. Family-Friendly Atmosphere: With a variety of attractions, Old Town Triangle caters to visitors of all ages, making it ideal for family vacations.

Popular types of accommodation around Old Town Triangle

If you're searching for the perfect getaway in Old Town Triangle, look no further! Our top accommodation options include Apart Hotels, cozy studio apartments, and spacious houses. Whether you're seeking a stylish studio or a charming town triangle apartment, we have a variety of choices to suit your needs. Discover the best apartments in Chicago and find your next ideal vacation rental with us!

  • Apartment Rentals: The top choice for visitors in Old Town Triangle, offering stylish and convenient living spaces for solo travelers or couples.
  • Houses: A great option for families or groups seeking comfort and privacy, with home-like amenities.
  • Condominiums: Ideal for those wanting a balance of luxury and location, with shared facilities and stunning views.
  • Cottages: Quaint and cozy, these rentals provide a charming escape for couples or small families.
  • Caravan Parks: A unique option for travelers looking for affordable and community-oriented stays.**

Top attractions around Old Town Triangle

Old Town Triangle in Chicago is perfect for family and city vacations, offering a mix of urban parks, modern universities, and nearby beaches. Visitors can enjoy cultural experiences, art galleries, and local shopping malls. Don't miss the chance to explore Peterson Park or request guided tours for a deeper dive into the area's charm. With a variety of attractions catering to all ages, there's something for everyone to enjoy in this vibrant neighborhood.

  1. Michigan Avenue: Known as the Magnificent Mile, this bustling street boasts upscale shopping, dining, and stunning architecture, embodying the vibrant spirit of Chicago.
  2. Navy Pier: A lively waterfront destination featuring gardens, restaurants, and entertainment, offering picturesque views of Lake Michigan and a vibrant arts scene, perfect for family fun.
  3. Millennium Park: A beautiful urban park that hosts art installations, concerts, and family-friendly activities, making it an ideal spot for relaxation and exploration in the heart of the city.

Things to do recommended for couples

For a romantic getaway in Old Town Triangle, enjoy a concert at the Aragon Ballroom, dine at the historic Michael Jordan Restaurant for an intimate meal, or relax in luxury at Sportsman's Country Club. Each experience offers a unique vibe perfect for couples!

Things to do recommended for families

Explore family-friendly fun at Wrigley Field, just 3 miles away, where sports excitement awaits. Enjoy nature at Northerly Island, 4 miles away, perfect for relaxation, or visit The East Bank Club, 2 miles away, for wellness activities and quality family time.

Things to do recommended for groups

Experience the vibrant culture at the Chicago Theatre, just 2 miles away, or enjoy a family-friendly comedy show at Second City, only 0.2 miles from Old Town Triangle. Don’t miss shopping at 900 North Michigan Shops, located 1 mile away, for a fun group outing!

What do I need to keep in mind when booking a vacation around Old Town Triangle

When planning your trip, whether you're traveling with a group, enjoying family time, bringing along your pets, or seeking extended stays, it's important to apply the right filters based on your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Old Town Triangle with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Town Triangle with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you may want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town Triangle: For many families, a vacation isn't truly fulfilling without their beloved pets. If this resonates with you, take a look at Vrbo listings that welcome furry companions. Many pet-friendly properties offer amenities like feeding bowls and pet beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Old Town Triangle: If you're in search of vacation rentals with special rates 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay around Old Town Triangle

Old Town Triangle offers a delightful blend of family-friendly activities, outdoor adventures, and urban charm. As you explore this historic neighborhood, you'll encounter vibrant boutiques, cozy cafes, and beautiful parks. Just a short distance away, the South Loop invites further exploration with its rich cultural scene. Discover the essence of Chicago's old town and immerse yourself in its welcoming atmosphere, perfect for family vacations or a romantic getaway.

  • Downtown Chicago: Downtown Chicago is the vibrant core of the city, located about 2 miles from Old Town Triangle. This bustling neighborhood offers a dynamic mix of family-friendly activities, outdoor spaces, and urban experiences. Visitors can enjoy shopping along State Street or exploring the iconic Millennium Park, home to the famous Cloud Gate sculpture. Entertainment options abound, with numerous theaters and the United Center nearby, where you can catch a Bulls or Blackhawks game. The area is also rich in dining choices, from casual eateries to upscale restaurants, making it a perfect stop for both tourists and locals alike.
  • Magnificent Mile: Also situated approximately 2 miles from Old Town Triangle, the Magnificent Mile is a premier shopping and dining destination. This iconic stretch along Michigan Avenue features luxury boutiques, department stores, and a diverse array of restaurants. Visitors can take in the stunning architecture while strolling past famous landmarks, including the historic Chicago Water Tower and the John Hancock Center. The area is lively and offers various entertainment options, from theaters to art galleries, ensuring a fulfilling city experience for families and individuals alike.
  • Lincoln Park: Just 0.6 miles away from Old Town Triangle, Lincoln Park is a charming neighborhood known for its lush green spaces and family-oriented attractions. The Lincoln Park Zoo, one of the oldest zoos in the U.S., provides a free and fun outing for visitors of all ages. The area also boasts lovely parks and scenic lakefront paths, perfect for outdoor activities. Shopping and theater options are plentiful, with quaint boutiques and vibrant local performances adding to the neighborhood's appeal. Lincoln Park's friendly atmosphere makes it a delightful place to explore.

Best time to go to Old Town Triangle

If you're planning a trip to Old Town Triangle, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to February and November 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 CloudyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyModerately HighSlightly High
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately 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 SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately 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 significant price differences. Also, opting for a longer stay can often result in even greater 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. We're here to help you find the best options for your travel needs!

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash™ on your entire reservation. Being the planner truly has its benefits! When you join our travel rewards program, OneKey, you'll gain access to exclusive discounts and earn OneKeyCash™ on qualifying bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, refine your existing plans, or manage your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the 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 in Old Town Triangle?
In Old Town Triangle, apartments are the most popular type of vacation rental, with about 13 available throughout the neighborhood. These apartments are typically situated in charming buildings, featuring amenities like fully equipped kitchens, cozy living areas, and some even have access to private balconies for enjoying the vibrant surroundings. Additionally, there are around 10 vacation houses that provide more space, ideal for families or larger groups. These homes often come with multiple bedrooms, outdoor areas, and amenities such as BBQ grills, making them great for gatherings.
Are there any beach house rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there are several beach house rentals available, primarily situated near the scenic shores of Lake Michigan. These properties typically feature charming architectural styles that reflect the historic nature of the neighborhood, offering a mix of modern amenities and classic details. Travelers can expect vacation homes with multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces for enjoying the beautiful lake views.
How much does it cost to rent a vacation home in Old Town Triangle?
Prices for vacation rentals in Old Town Triangle 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 Old Town Triangle 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 Old Town Triangle vacation house rentals?
You can find great discounts on house rentals in Old Town Triangle 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 Old Town Triangle?
In Old Town Triangle, travelers can expect a variety of vacation rental amenities that enhance their stay. Most rentals typically feature a fully equipped kitchen, superb for preparing meals during your visit. Many rooms also include a coffee and tea maker for a warm beverage in the morning, as well as a kitchen island that provides additional prep space and a casual dining area. Outdoor spaces are common, with patios available for enjoying the fresh air and city views. Additionally, many rentals come equipped with convenient appliances like blenders, making it easy to whip up smoothies or other blended beverages.
Are there any family house rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there is a great selection of family-friendly house rentals, with around 17 options available. This historic neighborhood is known for its charming architecture and vibrant atmosphere, making it an ideal spot for families to stay. Many of these homes come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces where children can enjoy themselves. Visitors can often find amenities like laundry facilities, Wi-Fi, and comfortable furnishings to make their stay even more enjoyable.

The locale is conveniently located near popular attractions such as the Lincoln Park Zoo and the beautiful Lincoln Park Conservatory, both of which are great for family outings. Additionally, families can explore nearby parks and playgrounds, ensuring plenty of opportunities for outdoor fun.
Can I rent a vacation home with a pool or hot tub in Old Town Triangle?
In Old Town Triangle, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This historic neighborhood is known for its charming architecture and vibrant atmosphere, making it an appealing destination for travelers. Properties in this area often include amenities such as private pools, hot tubs, outdoor seating areas, and well-equipped kitchens, great for relaxation and entertaining.
Are there any Old Town Triangle vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Town Triangle 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 Old Town Triangle?
Yes, you can book pet-friendly vacation rentals in Old Town Triangle, with around 17 options available. This charming neighborhood is known for its historic architecture and vibrant community atmosphere. Many of the vacation rentals here come equipped with modern amenities such as updated kitchens, spacious living areas, and outdoor spaces where your pets can enjoy some fresh air.

Old Town Triangle is close to several parks, including the picturesque Lincoln Park, which features walking trails, gardens, and even a zoo, making it an ideal spot for pet owners. The area is also dotted with pet-friendly cafes and boutiques, adding convenience and enjoyment for travelers with furry companions.
Can I find long-stay vacation rentals in Old Town Triangle?
A long-stay vacation rental in Old Town Triangle 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 Old Town Triangle for a vacation rental?
July is the most popular time to visit Old Town Triangle, where the vibrant energy of summer captivates travelers seeking a blend of culture and outdoor exploration. This peak season, which runs from May through July, attracts visitors eager to experience the area's charming streets, historic architecture, and bustling art scene. With average temperatures hovering in the mid-70s to low 80s Fahrenheit, the warm weather creates an inclusive setting for leisurely strolls and outdoor dining.

During this lively period, you'll find an abundance of events and activities, including street festivals and art fairs, making it an ideal time for those looking to immerse themselves in local culture. The proximity to beautiful parks and the scenic Lake Michigan shoreline also adds to the appeal, offering ample opportunities for sightseeing and outdoor adventures.

If you're seeking a more budget-friendly option, consider visiting in December. This month, while quieter, presents a unique charm as Old Town Triangle transforms into a winter wonderland, superb for cozy walks and enjoying the festive holiday lights.
Are there any remote work vacation rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there are numerous vacation rentals well-suited for remote work, with around 25 options available. This vibrant neighborhood is known for its historic charm, featuring beautiful architecture and tree-lined streets, making it a pleasant environment for those looking to balance work and leisure. Many of these rentals come equipped with essential remote work amenities, including dedicated office spaces, high-speed Wi-Fi, desks, ergonomic chairs, and even computer monitors for a comfortable and productive work setup.

The area also offers easy access to local cafes and restaurants, providing convenient spots for coffee breaks or meals. Moreover, the proximity to parks and cultural attractions, such as the nearby Lincoln Park and the famous Second City theater, ensures that you can enjoy a variety of activities during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Old Town Triangle vacation rental?
Book your Old Town Triangle 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 Old Town Triangle?
In Old Town Triangle, visitors can appreciate the charming historic architecture and vibrant atmosphere of the neighborhood. The area is known for its beautiful Victorian homes and tree-lined streets, making it a picturesque spot for a leisurely stroll. The Old Town Art Fair, held annually, showcases local artists and craftspeople, drawing in visitors from all over.

Nearby, Lincoln Park offers access to attractions like the Lincoln Park Zoo and the Lincoln Park Conservatory, which are great for enjoying nature and wildlife. The neighborhood also boasts a variety of dining options, from cozy cafes to upscale restaurants, reflecting the diverse culinary scene of Chicago. Furthermore, the proximity to the lakefront provides opportunities for outdoor activities, including biking and walking along the scenic paths.
Can I change or cancel my Old Town Triangle home rental booking on Vrbo?
To find Old Town Triangle 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Old Town Triangle 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.