The Gap vacation rentals

We found 26 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in The Gap that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. At the end of the day, you'll 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 Gap

Why visit The Gap

  • Family-friendly activities: The Gap offers a variety of enjoyable attractions suitable for all ages, making it perfect for family vacations.
  • Vibrant urban life: Experience the lively atmosphere with urban parks, historic buildings, and iconic skyscrapers throughout the neighborhood.
  • Diverse accommodations: Choose from cozy apartments, spacious vacation homes, and stylish condos to find your ideal place to stay.
  • Cultural experiences: Immerse yourself in the local culture with various events and activities that reflect the vibrant community.
  • Welcoming atmosphere: Enjoy the friendly locals and scenic surroundings that make The Gap a fantastic destination for relaxation.

Popular types of accommodation around The Gap

Planning a getaway to The Gap? The excitement begins with selecting the perfect place to stay. From cozy apartments to spacious houses and stylish condos, you'll find a variety of options to suit your needs. Explore our range of house rentals and vacation homes, complete with essential amenities to enhance your stay. Discover the ideal base for your adventures in The Gap and enjoy the comfort and convenience of your home away from home.

  • Apartments: The top choice for vacation rentals in The Gap, offering convenience and comfort for solo travelers or groups.
  • Houses: A great option for families or friends seeking a cozy and spacious stay, providing a home-like atmosphere.
  • Condos: Popular among travelers looking for modern amenities and a community vibe, ideal for short or extended stays.
  • Cottages: Charming rentals that provide a quaint escape, perfect for those wanting a peaceful retreat.
  • Villas: Luxurious accommodations that offer ample space and upscale features for an indulgent vacation experience.**

Top attractions near The Gap

The Gap in Chicago is perfect for family, business, and entertainment-themed vacations. Visitors can explore a variety of attractions, including urban parks, historic buildings, and iconic skyscrapers. Whether you're seeking cultural experiences or family-friendly activities, The Gap has something for everyone, ensuring an enjoyable visit to this vibrant area.

  • McCormick Place: As the largest convention center in North America, McCormick Place offers a bustling atmosphere filled with events, trade shows, and conferences. Its modern architecture and spacious layout provide a unique business vibe, making it a hub for professionals and visitors alike.
  • Grant Park: Known as Chicago's front yard, this urban park is perfect for families and outdoor enthusiasts. With picturesque gardens, walking paths, and stunning views of the city skyline, it’s an ideal spot for relaxation and recreation.
  • Art Institute of Chicago: A must-visit for art lovers, this renowned art museum houses an extensive collection of artworks, including pieces by Monet, Van Gogh, and Grant Wood. Its rich cultural atmosphere invites exploration and appreciation of diverse artistic expressions.

Things to do recommended for couples

Looking for a romantic getaway in Chicago? Start your evening at Grand Terrace Ballroom for a cozy dinner, then enjoy live music at the nearby House of Blues. For an unforgettable experience, take in a show at Lincoln Hall, just a short drive away. Perfect for couples.

Things to do recommended for families

Your family vacation around The Gap in Chicago can include a visit to Wrigley Field for a thrilling sports experience, a day of relaxation at Northerly Island Natural Area, or engaging activities at The East Bank Club, all offering delightful vibes for family travelers.

Things to do recommended for groups

Enjoy a night of culture and entertainment at the Chicago Theatre, just 4 miles from The Gap. For a laugh, visit Second City, located 5 miles away, perfect for families. Don’t miss shopping at the nearby Chicago Place Mall, offering a great city vibe, also 4 miles away.

*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 Gap

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

  • Traveling to The Gap with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group activities. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to The Gap with young kids: Traveling with young children can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to The Gap: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting The Gap: If you're seeking vacation rentals with special offers 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near The Gap

The Gap in Chicago offers a delightful blend of family-friendly activities and vibrant urban life. Explore beautiful properties and enjoy a perfect city break with numerous vacation rentals nearby. With its welcoming atmosphere, The Gap is ideal for both business trips and family getaways. Don't miss the chance to experience the friendly people and scenic surroundings that make this neighborhood a fantastic destination for your next vacation.

  • Chicago: As a vibrant metropolis, Chicago offers a wide array of experiences for travelers. The Gap is conveniently located within the city, making it easy to explore its rich cultural scene. Visitors can indulge in shopping at renowned retail destinations, enjoy exhilarating sports events at iconic stadiums, or immerse themselves in the arts at various theaters. Chicago is renowned for its stunning skyline, diverse neighborhoods, and delectable cuisine, making it a perfect destination for family outings and urban adventures.
  • Downtown Chicago: Located just 4 miles from The Gap, Downtown Chicago is the bustling heart of the city, drawing visitors for its dynamic atmosphere and family-friendly attractions. Here, you can explore a plethora of shopping options, catch a live performance at a theater, or watch a game at one of the famous sports facilities. The area is home to iconic landmarks and a vibrant tourist precinct, ensuring a memorable urban experience. The stunning architecture and scenic riverfront also provide a beautiful backdrop for leisurely walks.
  • Douglas: Situated a mere 0.1 mile from The Gap, Douglas is a charming neighborhood that caters to both family and business travelers. This area features a variety of entertainment options, including arena facilities and shopping areas. Douglas is notable for its proximity to event venues and convention centers, making it ideal for those attending conferences or seeking leisure activities. The neighborhood's welcoming atmosphere and convenient location make it an excellent spot to relax and enjoy the local culture.

Best time to go to The Gap

If you're planning a trip to The Gap, 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 December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 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 SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly 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 SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay, as this can lead to substantial savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a dedicated area to plan new trips, refine your existing itineraries, or manage your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out 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 Gap?
In The Gap, vacation houses are a popular choice, with several available for travelers seeking a spacious and comfortable stay. These homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. They provide an ideal setting for families or groups looking to enjoy a cozy feel while exploring the surrounding nature. Additionally, apartments are also available, offering convenient amenities such as cozy living spaces and kitchen facilities, making it easy for guests to prepare meals during their stay.
Are there any beach house rentals in The Gap?
In The Gap, Illinois, beach house rentals are available, offering a great experience for travelers seeking a lakeside getaway. The area features several vacation rentals that cater to different preferences. Many of these beach houses come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor decks or patios that provide lovely views of the nearby lake.

Travelers can expect comfortable accommodations ideal for families or groups, with some properties boasting multiple bedrooms, private outdoor spaces for barbecuing, and easy access to local parks and recreational activities.
How much does it cost to rent a vacation home in The Gap?
Prices for vacation rentals in The Gap 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 Gap 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 Gap vacation house rentals?
You can find great discounts on house rentals in The Gap 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 Gap?
In The Gap, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, and onsite parking for convenience. Many rentals are located nearby beach areas, providing easy access to outdoor activities. Additionally, travelers can expect amenities like coffee and tea makers for a cozy start to their mornings, as well as decks or patios that offer a space to relax and enjoy the surrounding environment.
Can I find family house rentals in The Gap?
In The Gap, Illinois, there are several family-friendly house rentals available. This region offers a variety of spacious rooms suitable for families, often featuring amenities such as full kitchens, comfortable living areas, and outdoor spaces for children to play. Many properties provide easy access to nearby parks and recreational areas, great for outdoor activities and family outings.

Visitors can explore the scenic beauty of the surrounding countryside or enjoy local attractions that highlight the area's charm.
Are there any The Gap vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in The Gap 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 The Gap?
A long-stay vacation rental in The Gap 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 Gap for a vacation rental?
The peak season for visiting The Gap typically spans from May to July, with July being the most popular month for travelers. This vibrant time welcomes visitors eager to immerse themselves in the area's natural beauty and outdoor activities, including hiking and exploring local parks. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, it's an ideal season for enjoying the scenic landscapes and engaging in recreational pursuits.

During this period, the community comes alive with various events and activities, providing a lively option for those looking to connect with fellow travelers and locals alike. The long daylight hours allow for ample opportunities to explore the picturesque surroundings or simply unwind in a cozy vacation rental.

For those seeking a more budget-friendly option, December presents a quieter time to visit The Gap. While temperatures can drop to the low 30s Fahrenheit, this month offers a unique charm, with the potential for winter activities and a peaceful retreat from the busier seasons. It's a wonderful opportunity to enjoy the serenity of the area and experience a different side of The Gap.

Ultimately, your choice of when to visit The Gap will depend on your preference for bustling summer activities or a tranquil winter escape.
Are there any remote work vacation rentals in The Gap?
In The Gap, Illinois, there are several vacation rentals available that cater to remote workers. These accommodations typically offer essential amenities such as high-speed internet and Wi-Fi, ensuring that you can stay connected while enjoying your getaway. Many rentals also provide dedicated workspaces, often equipped with desk and chair setups, allowing for a comfortable working environment.

The surrounding area offers a peaceful atmosphere, superb for focusing on work tasks during the day while still enjoying the beauty of the region. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a The Gap vacation rental?
Book your The Gap 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.
Can I change or cancel my The Gap home rental booking on Vrbo?
To find The Gap 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 Gap 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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