Photo by © City of Chicago

Lakeview holiday lettings

We found 389 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Lakeview by choosing from 28 houses, 32 flats and other holiday rentals. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Why visit Lakeview

  • Stunning lakeside views: Enjoy picturesque scenery along Lake Michigan, perfect for relaxation and outdoor activities.
  • Family-friendly attractions: Explore a variety of parks and beaches that cater to families and outdoor enthusiasts.
  • Cultural enrichment: Discover local arts, theatres, and community events that showcase Lakeview's vibrant culture.
  • Diverse accommodation options: Choose from charming cottages, spacious homes, and stylish condos for a comfortable stay.
  • Urban vibrancy: Experience a lively atmosphere with an array of dining, shopping, and entertainment options.

Popular types of accommodation around Lakeview

If you're wondering what type of accommodation awaits you in Lakeview, look no further! Our most sought-after options include charming lakeview cottages, delightful holiday cottages, spacious houses, and comfortable condos. Whether you prefer a cosy lakeside lodge or a stylish apartment, we have the perfect holiday accommodation to suit your needs and ensure a memorable stay.

  • Apartments: The top choice for holiday rentals in Lakeview, offering a range of styles and amenities to suit various preferences.
  • Houses: A popular option for those seeking comfort and space, ideal for families or groups wishing for a home-away-from-home experience.
  • Condos: Stylish and modern living spaces, perfect for couples or small groups looking for convenience and a vibrant atmosphere.
  • Cottages: Charming and quaint, these rentals provide a cosy retreat for those wanting a peaceful getaway.**

Top attractions near Lakeview

Lakeview in Chicago is an excellent destination for sports enthusiasts and families seeking outdoor adventures. With attractions like beaches, towering skyscrapers, and urban parks, it offers a vibrant mix of culture and city life. Visitors can enjoy a variety of experiences, from relaxing by the private lake to exploring local points of interest that cater to both family outings and cultural enrichment.

  • Michigan Avenue: A vibrant thoroughfare known for its bustling atmosphere, Michigan Avenue is lined with upscale shops, iconic architecture, and cultural landmarks, making it a must-visit for those seeking the essence of Chicago city life.
  • Chicago Riverwalk: This scenic promenade along the Chicago River offers a delightful outdoor experience, perfect for families. With cafes, parks, and stunning views, it’s an ideal spot for leisurely strolls and enjoying the city's beauty.
  • Loyola University Chicago: A modern campus with striking architecture, Loyola University Chicago exudes a lively energy. Visitors can appreciate its beautiful grounds and the vibrant student life that characterises this esteemed institution.

Things to do recommended for couples

For a romantic getaway in Lakeview, enjoy a concert at Lincoln Hall or the Aragon Ballroom, both offering vibrant entertainment. Treat yourselves to a delightful meal at the Historic Michael Jordan Restaurant, where the atmosphere is perfect for couples seeking a memorable dining experience.

Things to do recommended for families

During your family vacation to Lakeview, Chicago, explore the iconic Wrigley Field for a thrilling sports experience, enjoy nature at the picturesque Northerly Island Natural Area, or unwind at Hamlin Park, perfect for relaxation and play just 1.6km away.

Things to do recommended for groups

Groups visiting Lakeview can enjoy a performance at the Vic Theatre for a taste of local culture, laugh at a show at Second City, and indulge in shopping at 900 North Michigan Shops, all offering vibrant atmospheres perfect for family and friends to bond.

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

If you're travelling with a group, family, pets, or seeking longer stays, it's important to filter your options according to your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Lakeview with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Lakeview with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Lakeview: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lakeview: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. 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 your search criteria as well.

Where to stay near Lakeview

Lakeview, Chicago, offers a delightful blend of urban vibrancy and family-friendly charm, making it an ideal destination for holidaymakers. Explore the stunning lakeside views and enjoy the tranquil atmosphere that this picturesque neighbourhood provides. Nearby, you can discover the scenic beauty of the surrounding areas, perfect for outdoor adventures and creating lasting memories with loved ones. Whether you seek sports or a relaxing retreat, Lakeview promises an unforgettable experience.

  • Chicago: As a bustling metropolis situated 3.1km from Lakeview, Chicago offers a wealth of experiences for tourists and families alike. Visitors can indulge in shopping at the Magnificent Mile, enjoy a thrilling game at one of the city's famous sports arenas, or explore educational institutions that reflect the city's rich history. Notable attractions include the iconic Wrigley Field and the vibrant tourist precinct, making it a perfect base for urban exploration.
  • Downtown Chicago: Located 2.5km from Lakeview, Downtown Chicago is the city's dynamic core where culture and commerce intertwine. Families can enjoy outdoor spaces, visit theatres, and explore shopping areas that cater to all tastes. The area is home to significant landmarks, including sports facilities and bustling tourist precincts, ensuring there’s never a dull moment. A visit here promises a blend of entertainment, dining, and vibrant city life.
  • Wrigleyville: Just half a mile from Lakeview, Wrigleyville is renowned for its sports culture and lively atmosphere. This neighbourhood is a haven for families and outdoor enthusiasts, with easy access to shopping, theatres, and educational venues. The highlight is undoubtedly Wrigley Field, where you can catch a baseball game and soak in the energetic vibe. Its proximity to Lakeview makes it an ideal spot for a fun-filled day or evening out.

Best time to go to Lakeview

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly 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 SunnySlightly HighSlightly 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 SunnySlightly LowAverage
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

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a convenient space to plan new journeys, pick up where you left off, or manage and arrange your travel plans. You can easily locate the properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Lakeview?
Prices for holiday rentals in Lakeview 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 Lakeview 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 Lakeview holiday house rentals?
You can find great discounts on house rentals in Lakeview 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.
Are there any Lakeview holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lakeview with parking available—perfect for families or travellers 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 holiday rentals in Lakeview?
A long-stay holiday rental in Lakeview is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Lakeview for a holiday rental?
The best time to visit Lakeview for a holiday rental is during the peak season from May to July. This vibrant period is characterised by warm weather, bustling streets, and a lively option, making it superb for those looking to soak up the local culture and outdoor activities. July, in particular, is the most popular month, with plenty of events and festivals that showcase the area's charm, including the renowned Chicago Air and Water Show.

During these months, visitors can enjoy delightful temperatures ranging from 20 to 30 degrees Celsius, ideal for leisurely strolls along the waterfront or exploring the neighbourhood's parks and gardens. The pleasant climate also creates superb conditions for outdoor dining at local restaurants, where you can savour the flavours of the region while basking in the sunshine.

For those seeking a more budget-friendly option, consider visiting in November. While this month falls outside the busy tourist season, it offers a unique opportunity to experience Lakeview's local life without the crowds. Enjoy the peaceful atmosphere as you explore the area's shops, or indulge in the culinary delights of the local eateries.
How early should I book a Lakeview holiday rental?
Book your Lakeview holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Lakeview, Illinois, United States of America?
In Lakeview, visitors can enjoy a vibrant array of attractions that showcase both the natural beauty and cultural essence of the area. One of the most great spots is Lincoln Park, which offers expansive green spaces, scenic walking paths, and the popular Lincoln Park Zoo, making it a great destination for families and nature enthusiasts. Holiday rentals in this vicinity often provide easy access to the park's amenities.

The iconic Wrigley Field, home to the Chicago Cubs, is also located in Lakeview and is a must-visit for sports fans. The surrounding area features lively bars and restaurants that cater to game day crowds, creating a bustling atmosphere.

For those interested in a more artistic experience, the Boystown neighbourhood, known for its vibrant LGBTQ+ community, boasts a variety of shops, cafes, and nightlife options. The area is adorned with colourful murals and hosts events that celebrate diversity and inclusivity.
Can I change or cancel my Lakeview home rental booking on Vrbo?
To find Lakeview holiday 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 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 travellers 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 cosy cabin or a beach house, 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 Lakeview holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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