Vacation rentals near Willis Tower

We found 3,622 vacation rentals — enter your dates for availability

Discover a selection of private vacation rentals within easy reach of Willis Tower that provide the perfect home base for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, including WiFi and parking. You're sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Willis Tower

Showing deals for:Jun 12 - Jun 19

Image gallery for Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO

Lovely living room with sofa sleeper.
8.2 out of 10, Very Good, (16 reviews)
Very Good
(16 reviews)

Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO

Rosemont

13% off
Price is $183
$1,281 for 7 nights
All fees included
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO

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Find out more about Willis Tower

Why visit Willis Tower

  • Stunning Views: Experience breathtaking cityscapes and waterfront views from the observation deck of Willis Tower.
  • Iconic Architecture: Marvel at the impressive design of one of the tallest buildings in the United States.
  • Vibrant Downtown: Explore the energetic atmosphere of downtown Chicago, filled with shops, dining, and entertainment.
  • Family-Friendly Activities: Enjoy various attractions nearby that cater to visitors of all ages.
  • Charming Neighborhoods: Discover the local vibe in the West Town area, known for its friendly locals and unique culture.

Popular types of accommodation around Willis Tower

Your trip to Willis Tower is just around the corner, and now it’s time to find the perfect place to stay. From luxury apartments and cozy condos to spacious houses, there are plenty of options that cater to your needs. Consider the convenience of apartments near Willis Tower or the amenities of presidential towers with fitness centers. Explore your ideal vacation rental and make your stay unforgettable.

  • Apartments: The top choice for visitors to Willis Tower, offering a convenient and comfortable stay in the heart of the city.
  • Houses: A popular option for families or groups seeking a home-away-from-home experience with added privacy.
  • Condos: Ideal for those wanting modern amenities and great locations, providing a blend of comfort and luxury.
  • Cottages: A charming and cozy alternative for a more intimate getaway.
  • Villas: Spacious accommodations perfect for larger groups or families looking for a premium experience.**

Top attractions near Willis Tower

When visiting Willis Tower in Chicago, you'll find a vibrant mix of attractions, including urban parks, iconic skyscrapers, and historic buildings. Whether you're traveling solo, with family, or as part of a group, there's something for everyone to enjoy. Explore the cultural offerings and family-friendly experiences that the area has to offer, making your trip memorable and exciting.

  • Michigan Avenue: A vibrant street known for its shopping, dining, and stunning architecture, Michigan Avenue offers a quintessential Chicago experience, perfect for strolling and people-watching.
  • Millennium Park: An urban oasis featuring iconic attractions like Cloud Gate and beautiful gardens, Millennium Park is ideal for families and outdoor enthusiasts seeking relaxation and culture in the heart of the city.
  • Chicago Riverwalk: This picturesque waterfront area invites families to enjoy leisurely walks, dining, and boat tours, showcasing the city's stunning skyline and vibrant atmosphere.

Things to do recommended for couples

Looking for a romantic getaway near Willis Tower? Enjoy live music at the House of Blues Chicago just 0.7 miles away, savor a delicious meal at the Historic Michael Jordan Restaurant 1 mile away, or dance the night away at the Aragon Ballroom, 6 miles from your romantic base.

Things to do recommended for families

Families visiting Willis Tower can enjoy a game at Wrigley Field, just 5 miles away, or unwind at Northerly Island Natural Area, located 2 miles from the tower. For wellness, The East Bank Club is conveniently 0.8 miles away, offering relaxation and recreation options.

Things to do recommended for groups

Experience Chicago's vibrant culture by visiting the Chicago Theatre, just 0.7 miles from Willis Tower. Enjoy laughter at The Second City, 2 miles away, or indulge in shopping at Chicago Place Mall, 1 mile from the tower—perfect for family fun and entertainment.

*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 Willis Tower

When traveling with a group, family, pets, or planning a longer stay, it's important to filter your options based on your specific priorities. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Willis Tower with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Willis Tower with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Willis Tower: For many families, a vacation isn't truly satisfying without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Willis Tower: If you’re in search of vacation rentals that offer discounts for month-long stays, 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 parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Willis Tower

Exploring the area around Willis Tower offers a vibrant mix of urban energy and stunning scenery. Downtown Chicago is a must-visit, boasting impressive cityscapes and waterfront views that will take your breath away. Don't miss the charming West Town neighborhood, where you can enjoy a family-friendly atmosphere and meet friendly locals. With its cool vibes and rich experiences, your vacation near Willis Tower promises to be unforgettable.

  • Chicago: Chicago is a vibrant city known for its rich culture, stunning architecture, and diverse attractions. Located along the shores of Lake Michigan, it offers a unique blend of urban experiences and outdoor enjoyment. Visitors can explore iconic landmarks such as Millennium Park, the Art Institute of Chicago, and the Navy Pier. With a bustling shopping area on the Magnificent Mile, various arena entertainment options like the United Center, and a thriving theater scene, Chicago provides something for everyone. Families can enjoy a day at the Lincoln Park Zoo or take a boat tour on the Chicago River for breathtaking views of the skyline.
  • Downtown Chicago: Downtown Chicago is the heart of the city, bustling with energy and activity. As the home of Willis Tower, this neighborhood is a hub for shopping, dining, and entertainment. Visitors can explore the nearby Chicago Riverwalk, which offers scenic views and a variety of restaurants. The area is also known for its theaters, such as the Chicago Shakespeare Theater, and sports venues like the United Center. With easy access to urban parks and iconic attractions, Downtown Chicago is perfect for families and city explorers alike, providing a rich urban experience infused with outdoor opportunities.
  • The Loop: The Loop is a historic neighborhood located just a short distance from Willis Tower, making it easily accessible for visitors. Renowned for its architectural marvels and cultural institutions, The Loop features a vibrant arts scene and is home to the famous Chicago Theater. Families can enjoy a visit to Grant Park, an expansive green space perfect for picnics and outdoor activities. With an array of shopping options and proximity to major attractions like the Art Institute and the Field Museum, The Loop offers a dynamic blend of city life and recreational activities, ensuring an unforgettable experience for travelers.

Best time to go to Willis Tower

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly 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 SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Planning your next getaway and hoping to save some money? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay to enjoy even greater discounts. 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 place for your trip.

Unlock savings with One Key

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

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, keep your travel arrangements on track, and manage your bookings with ease. You’ll find your saved and reserved properties neatly categorized into Potential, Upcoming, or Current Trips. To dive into Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Willis Tower?
The best vacation rentals near Willis Tower are typically located right in Downtown Chicago. You will find a great selection of properties, primarily apartments and condos, offering convenient access to city attractions. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many of these vacation rentals feature amenities such as laundry facilities for extended stays and access to shared pools, which is great for relaxing after a day of exploring. These properties are ideal for solo travelers or small groups looking for an urban experience.
Are there any cheap vacation rentals near Willis Tower?
There are several affordable vacation rentals near Willis Tower, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around $165 per night in areas like Downtown Chicago. Some stays even drop below this price in February and March during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cozy studio apartments to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Willis Tower while keeping costs down, so you can have a comfortable stay.
What are the top vacation rentals with pools near Willis Tower?
There are over 590 vacation rentals near Willis Tower that include access to swimming pools, with options for both shared community pools and private pools. These properties, predominantly apartments and condos, are concentrated in the Downtown Chicago area. Many come fully equipped with essential amenities such as kitchens, Wi-Fi, and comfortable living spaces, making them ideal for guests, whether families or groups, seeking convenience and comfort during their stay.

When selecting your ideal property, consider the type of pool that best suits your preferences. Private pools offer an exclusive experience, great for relaxation. Shared indoor or outdoor pools often come with additional facilities like heated options, which are especially appealing during cooler months. Checking the availability and type of pool based on your travel dates will ensure a more enjoyable stay.
What are the best family vacation rentals near Willis Tower?
There are over 532 family-friendly vacation homes available near Willis Tower, primarily apartments and condos in Downtown Chicago, offering ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, full kitchens for meal preparation, and washer/dryers, which are essential for family stays. Many also provide outdoor play areas like patios or yards, along with entertainment options such as books, toys, and video games.

When selecting a vacation rental, focus on homes that offer separate spaces for adults and children to relax, and prioritize those with practical amenities like a fully equipped kitchen and laundry facilities to simplify your trip. Staying close to Willis Tower means less travel time and more opportunity to enjoy the city's attractions.
Are there any luxury vacation rentals near Willis Tower?
Near Willis Tower, guests can find several luxury vacation rentals that combine urban surroundings with modern comfort. These properties often feature amenities such as private pools, designer toiletries, premium bedding, and lake views. Many also offer the option of a private chef, ensuring a gourmet experience during your stay.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and entertainment spaces. Many of these exceptional properties are hosted by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Willis Tower?
Vacation rentals near Willis Tower offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around $165 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around $415 per night, offering more comfort and privacy. Upscale options can cost $655 or more per night, providing additional space, amenities, or premium locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Willis Tower?
When planning your stay near Willis Tower, consider properties in the Downtown Chicago area. This location places you directly amidst the bustling city center, offering convenient access to Willis Tower and many other urban attractions. Properties here are often high-rise apartments or lofts, providing stunning city views.

Another excellent option is the West Loop neighborhood. Located just west of Willis Tower, this area is known for its diverse culinary scene and trendy properties. It offers a slightly more residential feel while still being very close to the heart of the city. Properties in the West Loop provide a comfortable base for exploring the area and are a short distance from Willis Tower.

For those desiring a blend of urban convenience and a touch of historical charm, properties in the Loop are ideal. This area is directly adjacent to Willis Tower and features a mix of historic buildings and modern high-rises.
What is the cheapest month to stay near Willis Tower?
The cheapest time to find vacation rentals near Willis Tower is typically during the late Winter to early Spring (February to March). February is frequently the cheapest month, often providing various savings on vacation rentals compared to peak season rates. Guests can often find lower rates during these months, along with greater availability of properties.
Are there any lakefront vacation rentals near Willis Tower
Lakefront vacation rentals near Willis Tower offer a great mix of comfort, scenery, and outdoor adventure. Many are located along Lake Michigan, providing direct access to the water. These properties are a short drive from Willis Tower, offering convenient access to water activities such as kayaking, fishing, sailing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and fully equipped kitchens, making them ideal for families or larger groups. Guests can enjoy lake views, spot wildlife, and unwind in peaceful surroundings after exploring local attractions.
Are there any monthly vacation rentals near Willis Tower?
Vrbo offers excellent options for monthly vacation rentals near Willis Tower, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Willis Tower.
Are there any last-minute vacation rentals near Willis Tower?
Vrbo makes it simple to find last-minute vacation rentals near Willis Tower that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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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