Lower West Side vacation rentals

We found 200 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Lower West Side that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, including WiFi and parking. You're sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Lower West Side

Showing deals for:Nov 7 - Nov 14
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Find out more about Lower West Side

Find out more about Lower West Side

Why visit Lower West Side

  1. Urban Parks: The Lower West Side boasts beautiful parks perfect for family outings and outdoor activities.
  2. Rich Cultural Experience: Immerse yourself in the vibrant local scene filled with art, music, and community events.
  3. Historic Architecture: Explore the area’s impressive historic buildings and iconic skyscrapers that reflect Chicago's rich history.
  4. Diverse Accommodations: Enjoy a range of vacation rentals from cozy apartments to spacious homes tailored to your needs.
  5. Access to Other Neighbourhoods: Use Lower West Side as a base to explore nearby vibrant neighbourhoods and local businesses.

Popular types of accommodation around Lower West Side

Vrbo offers a diverse selection of vacation rentals in the Lower West Side, including apartments, houses, and condos. Whether you're searching for a cozy apartment in West Side Chicago or a spacious private home with a pool, we have options to suit your needs. Choose the perfect accommodation for your getaway and enjoy transparency, savings, and reassurance as you explore this vibrant neighbourhood.

  • Apartments: The most sought-after choice for vacation rentals in Lower West Side, ideal for solo travellers or groups seeking a comfortable stay.
  • Houses: A popular option for families and friends, offering a homely atmosphere and ample space during your visit.
  • Condos: Favoured by those wanting a blend of convenience and luxury, condos provide modern amenities in a vibrant setting.
  • Cottages: A charming alternative for a quaint retreat, perfect for those looking to unwind in a cosy environment.
  • Resorts: The ideal choice for travellers seeking a full-service experience with various on-site amenities and activities.**

Top attractions around Lower West Side

The Lower West Side of Chicago is perfect for family getaways and outdoor adventures, featuring urban parks, historic buildings, and impressive skyscrapers. This vibrant area offers a rich cultural experience for travellers seeking city-themed activities. Don’t miss the opportunity to indulge in sightseeing around Chicago, ensuring your visit is filled with memorable moments and local charm.

  1. McCormick Place: A premier event and conference venue, McCormick Place boasts a modern design and state-of-the-art facilities. It's ideal for business gatherings, trade shows, and conventions, fostering a vibrant professional atmosphere.
  2. Grant Park: This expansive urban park is perfect for families and outdoor enthusiasts. With lush gardens, walking paths, and stunning city views, it's a great spot for picnics, leisure activities, and public events.
  3. Art Institute of Chicago: Renowned for its vast collection of art, this museum offers a rich cultural experience. Explore masterpieces from various periods, including Impressionist works and ancient artifacts, all in a beautifully designed space.

Things to do recommended for couples

For a romantic getaway in Lower West Side, explore the vibrant House of Blues for live music, enjoy a meal at the historic Michael Jordan Restaurant with its charming atmosphere, or dance the night away at Aragon Ballroom. Each spot promises a memorable experience for couples.

Things to do recommended for families

Families can explore the excitement at Soldier Field, enjoy nature at Northerly Island Natural Area, or unwind at The East Bank Club, all conveniently located 4.8km from Lower West Side. These experiences offer a blend of sports, wellness, and relaxation for a memorable vacation.

Things to do recommended for groups

Groups visiting Lower West Side, Chicago can enjoy a captivating show at the Chicago Theatre, catch a film at Film Row Cinema, or share laughter at Second City. Each venue offers a unique blend of culture and entertainment, perfect for creating memorable experiences together.

What do I need to keep in mind when booking a vacation around Lower West Side

If you’re planning a trip with a group, family, or pets, or if you're interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Lower West Side with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Lower West Side with young kids: Travelling with young children can be quite the undertaking. It's important to prioritize their comfort and safety, along with ensuring access to 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 Lower West Side: For many families, a vacation wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most 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 Lower West Side: If you’re in search of vacation rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly locate and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Lower West Side

Exploring the Lower West Side of Chicago offers a vibrant blend of culture and urban charm. This family-friendly neighbourhood is perfect for those seeking outdoor adventures amidst stunning scenery and artistic vibes. Nearby, the rich tapestry of Chicago’s other neighbourhoods invites visitors to delve into the local business scene while enjoying the warmth of community. From the energetic streets to unique parks, Lower West Side is a fantastic base for an unforgettable Chicago experience.

  • Downtown Chicago: Downtown Chicago is a bustling urban hub located 6.4km from the Lower West Side. Known for its impressive skyline and vibrant atmosphere, this area attracts visitors with its family-friendly activities and outdoor experiences. Explore iconic shopping districts, catch a performance at a renowned theatre, or enjoy thrilling events at the arena entertainment facilities. Key landmarks include the famous tourist precinct, sports stadiums, and various cultural attractions, making Downtown Chicago a must-visit for anyone looking to immerse themselves in the city's dynamic spirit.
  • Heart of Chicago: Just 161m from the Lower West Side, the Heart of Chicago is a charming neighbourhood that offers a unique blend of family fun, city life, and outdoor experiences. Visitors can enjoy entertaining events at local arenas, shop at quaint boutiques, and discover educational opportunities in this vibrant community. Notable attractions include a sprawling urban park and sports facilities, ensuring there’s something for everyone. This close-knit neighbourhood is perfect for those who want to enjoy the essence of Chicago while remaining conveniently close to the Lower West Side.
  • Pilsen: Pilsen, located 1.6km from the Lower West Side, is a culturally rich neighbourhood celebrated for its artistic vibe and community spirit. Visitors flock to Pilsen for family outings, outdoor enjoyment, and a taste of the city's vibrant culture. Here, you can explore educational venues, lively shopping areas, and a variety of entertainment options. The neighbourhood is home to beautiful urban parks and sports facilities, making it ideal for both relaxation and recreation. Pilsen’s unique character and welcoming atmosphere make it a delightful stop during your Chicago adventure.

Best time to go to Lower West Side

If you're planning a trip to Lower West Side, 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.

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 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 simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay, which can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of 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 offers a user-friendly platform for you to plan new adventures, continue from where you last stopped, or manage your travel arrangements. You can easily access your saved or booked properties, neatly sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Lower West Side?
Apartments are the most popular kind of vacation rental in Lower West Side, according to our data. Even if you've got something else in mind, Vrbo has vacation homes in many sizes and shapes. Take a look at our options to find your ideal fit.
How much does it cost to rent a vacation rental in Lower West Side?
The average price for a vacation rental in Lower West Side is determined by a number of factors, such as property type, length of stay and time of year. Whether you're dreaming about a sprawling villa with lots of bedrooms or a comfy cabin ideal for just you and the kids, just enter your travel dates to discover stays with amazing value.
How much does it cost to rent a beach house in Lower West Side?
When you travel and the style and size of the property will determine the cost of your beachside escape. Type in your Lower West Side travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your rental.
Are there pet-friendly vacation rentals in Lower West Side?
Pack a tug toy and treats for your canine companion because Lower West Side has 18 properties that throw open their doors to pets. Let your four-legged friend have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check the "Pets allowed" filter box.
What are popular rental amenities in Lower West Side?
When it comes to rental amenities that guests are searching for in Lower West Side, a fireplace, a firepit and a nearby river are the most popular. With Vrbo vacation rentals, there are options to fit your taste and style, whether you're going on a vacation with friends, relatives or even pets.
Are there large group vacation rentals in Lower West Side?
Take your pick of six Vrbo vacation rentals in Lower West Side that can accommodate five or more people. You'll get all the privacy and space you need to spend time with the people you're vacationing with — and nobody else.
Are there vacation rentals in Lower West Side that welcome kids?
With 18 family-friendly vacation properties to pick from in Lower West Side, now is an awesome time to introduce the little ones to the joys of travel. Just check our "Properties good for families" filter to find stays that feature conveniences perfect for families on the move, such as extra bedrooms, outdoor spaces, bunk beds and entertainment areas.
What are the top attractions for families in Lower West Side?
Keep your kids busy at these leading family-friendly attractions in Lower West Side:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom vacation rentals in Lower West Side?
You'll find three one-bedroom properties in Lower West Side to choose from. A one-bedroom vacation home is a great choice if it's only you and your partner or if you're flying solo. Throw in more privacy, space and convenience compared to a hotel, and you'll be sure to have a memorable trip.
Can I find two-bedroom vacation rentals in Lower West Side?
You can pick from 10 two-bedroom properties in Lower West Side. Settle the kids into the second room or fill it with a couple of your favorite people. There's enough space for whoever's lucky enough to be coming along for the ride.
Are there vacation rentals with WiFi in Lower West Side?
There are 14 vacation rentals with WiFi in Lower West Side. If you'd like to disconnect from the world while on vacation, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Lower West Side?
Lower West Side has 17 vacation rentals where you'll be able to kick back in air-conditioned comfort. To book a property on Vrbo offering this perk, enter your dates of travel and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Lower West Side?
The minimum age permitted can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Lower West Side you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Lower West Side for?
The amount of time you can book a Lower West Side vacation home for is down to the property. Simply enter your preferred travel dates to view options offering longer term stays. They have all you require to make your extended getaway more convenient and comfortable, such as laundries and air conditioning. Some properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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