Uptown vacation rentals

We found 2,040 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Uptown that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include parking and a hot tub. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

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Find out more about Uptown

Find out more about Uptown

Why visit Uptown

  • Beautiful Beaches: Enjoy relaxing days at the beach, perfect for sunbathing and outdoor activities.
  • Cultural Experiences: Explore vibrant neighborhoods filled with friendly locals and rich cultural attractions.
  • Urban Parks: Discover delightful parks offering a serene escape for picnics and leisure activities.
  • Family-Friendly Activities: Engage in various sports and outdoor adventures suitable for all ages.
  • Diverse Accommodations: Choose from a wide range of vacation rentals, including apartments and private homes.

Popular types of accommodation around Uptown

Uptown vacation rentals offer a diverse selection of accommodations, including apartments, houses, and condos, perfect for your stay in Chicago. Whether you're searching for uptown Chicago apartments or exploring options in downtown, we have the ideal space for you. With our transparent information and focus on savings, finding the right uptown apartment has never been easier. Discover your perfect getaway today.

  • Apartments: The top choice for travelers in Uptown, offering modern amenities and convenient locations.
  • Houses: Ideal for families or groups, providing spacious living areas and a home-like atmosphere.
  • Condos: A popular option featuring stylish living spaces, often with access to shared facilities.
  • Cottages: A quaint and cozy choice for a peaceful getaway in a charming setting.**

Top attractions near Uptown

Uptown, Chicago, is perfect for a family-friendly vacation filled with sports and outdoor activities. Visitors can enjoy attractions like the beach, modern colleges, and urban parks, offering a blend of cultural experiences and leisure. Whether you seek vibrant city life or a relaxing beach day, Uptown caters to all types of travelers looking to explore and unwind.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street offers a vibrant mix of high-end shopping, dining, and iconic architecture, making it a must-visit for the city vibes.
  • Loyola University Chicago: This modern university campus features stunning architecture and beautiful green spaces, embodying a lively atmosphere that enhances the educational experience, just a short distance from Uptown.
  • Merchandise Mart: A historic gem, this massive building is home to showrooms and exhibitions, showcasing Chicago's rich culture and design heritage, perfect for those seeking cultural vibes.

Things to do recommended for couples

Ready for a romantic getaway in Uptown? Enjoy an electrifying concert at the Aragon Ballroom or Lincoln Hall, both brimming with entertainment vibes. For a delightful dining experience, savor a meal at the Historic Michael Jordan Restaurant, where city charm meets romance just 5 miles away.

Things to do recommended for families

Experience the thrill of a Cubs game at Wrigley Field, just 1 mile from Uptown. Enjoy family-friendly activities at Hamlin Park, 2 miles away, or unwind in the serene Northerly Island Natural Area, located 8 miles from Uptown, perfect for relaxation and wellness.

Things to do recommended for groups

Experience the vibrant culture of Uptown by catching a show at the historic Riviera Theatre. For some laughs, head to Second City, just 4 miles away. Don’t miss the shopping and entertainment at 900 North Michigan Shops, located 5 miles from Uptown, perfect for group fun.

*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 Uptown

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Uptown with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily sort through these options and many more on Vrbo.
  • Traveling to Uptown with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Uptown: For many families, a vacation wouldn't feel complete without their furry companions. If that 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 Uptown: If you're in search of vacation rentals with great offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily 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 Uptown

Uptown, Chicago, offers an exciting blend of urban living and scenic beauty, making it a fantastic destination for sports enthusiasts and families alike. Discover vibrant neighborhoods filled with friendly locals, delightful parks, and various outdoor activities. Just a short trip away, downtown Chicago awaits with its iconic skyline and bustling atmosphere. Whether you're exploring Uptown's cultural gems or venturing into nearby areas, your vacation promises to be an unforgettable experience.

  • Chicago: As a bustling metropolis, Chicago is the heart of Uptown and offers a vibrant mix of family-friendly activities and urban adventures. Visitors can explore numerous shopping areas, enjoy thrilling arena entertainment, or immerse themselves in educational experiences. Iconic landmarks such as sports stadiums and tourist precincts are easily accessible, making it an exciting place to discover both culture and entertainment. Whether you're enjoying a game or strolling along the scenic waterfront, Chicago is a city that delights all who visit.
  • Downtown Chicago: Located 6 miles from Uptown, Downtown Chicago is the vibrant core of the city, known for its stunning architecture and lively atmosphere. This neighborhood offers a plethora of family-oriented activities, outdoor spaces, and city-themed experiences. With a variety of shopping areas and renowned theaters, visitors can indulge in both retail therapy and cultural performances. Attractions like sports stadiums and tourist precincts add to the excitement, ensuring that there's something for everyone in this bustling urban hub.
  • Sheridan Park: Just 0.5 miles from Uptown, Sheridan Park is a charming neighborhood that caters to families and entertainment enthusiasts alike. Known for its lively theater scene and music concerts, this area is perfect for those seeking an engaging experience. With easy access to arena entertainment and local sports facilities, visitors can enjoy a range of activities. The nearby urban park provides a serene escape, making Sheridan Park an ideal spot for relaxation and recreation amidst the city's energy.

Best time to go to Uptown

If you're planning a trip to Uptown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like November to January 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 CloudyAverageSlightly 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 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 SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Also, extending your stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner truly has its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and can earn and redeem OneKeyCash on eligible reservations. Sign up now to start enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly area to plan new trips, continue from where you last stopped, or view and manage your travel arrangements. You'll easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Uptown?
In Uptown, apartments are the most popular vacation rental choice, with around 24 available in the area. These apartments are typically located in vibrant neighborhoods close to local amenities and entertainment options. Travelers can expect features such as fully equipped kitchens, cozy living areas, and access to communal facilities like fitness centers or rooftop decks for relaxation. Additionally, there are several condos and vacation houses scattered throughout Uptown, offering more space and privacy for families or groups. These properties often include multiple bedrooms, private outdoor areas, and modern conveniences, making them ideal for longer stays.
Are there any beach house rentals in Uptown?
In Uptown, Illinois, there are about 36 beach house rentals available, primarily located near the shores of Lake Michigan. These properties often feature spacious layouts with multiple bedrooms, allowing for comfortable stays for families or groups. Many of the beach houses come with fully equipped kitchens, outdoor patios, and some may even include amenities like private decks or access to nearby parks and recreational areas.
How much does it cost to rent a vacation home in Uptown?
Prices for vacation rentals in Uptown 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 Uptown 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 Uptown vacation house rentals?
You can find great discounts on house rentals in Uptown 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 Uptown?
In Uptown, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, and coffee and tea makers for a quick energy boost. Many rentals also permit pets, accommodating travelers who wish to bring their furry companions along. Additionally, some properties feature blenders, which can be handy for making smoothies or other blended drinks. Service animals are also welcomed in many accommodations, ensuring that guests with specific needs can enjoy a comfortable stay.
Are there any family house rentals in Uptown?
In Uptown, Illinois, there are some family-friendly house rentals available, specifically around 14 options for travelers to consider. This vibrant neighborhood is known for its rich cultural scene and proximity to beautiful parks, making it an excellent choice for families looking to explore the area. Many of these properties offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and relax.

Visitors can enjoy nearby attractions such as the picturesque Montrose Beach and the scenic Montrose Harbor, great for family outings and picnics. Additionally, the area boasts local dining options and shops within walking distance.
Can I rent a vacation home with a pool or hot tub in Uptown?
In Uptown, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This vibrant neighborhood offers a mix of amenities and attractions, making it an appealing destination for travelers. Many of the properties come equipped with private pools, hot tubs, and outdoor spaces ideal for relaxation and entertaining. Additionally, you can expect features like fully equipped kitchens, spacious living areas, and modern decor, ensuring a comfortable stay.
Are there any Uptown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Uptown 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 Uptown?
Yes, you can book pet-friendly vacation rentals in Uptown, Illinois. This vibrant neighborhood offers a variety of accommodations, with around 18 options available for travelers with pets. Many of these rentals come with modern amenities, such as updated kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

Uptown is home to several parks, including the scenic Montrose Beach and the expansive Lincoln Park, which are ideal for walking your dog and enjoying the outdoors. Additionally, the area has pet-friendly cafes and shops, making it convenient for those traveling with furry companions.
Can I find long-stay vacation rentals in Uptown?
A long-stay vacation rental in Uptown 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 Uptown for a vacation rental?
The best time to visit Uptown for a vacation rental is during the summer months, particularly in July. This lively period attracts visitors eager to soak up the sun and enjoy the vibrant local culture. With temperatures typically ranging from the mid-70s to mid-80s Fahrenheit, it's an ideal time for outdoor activities, leisurely strolls along the waterfront, and exploring the diverse dining options Uptown has to offer.

The peak season extends from July to September, when tourists flock to the area to experience its many festivals, outdoor concerts, and community events. This bustling atmosphere is great for those looking to immerse themselves in local life, as the streets come alive with music, art, and food.

For travelers seeking a more budget-friendly option, consider visiting in December. While this month may be quieter, it offers a unique charm with holiday decorations and seasonal events that create a cozy, festive ambiance. You'll find fewer crowds, allowing for a more relaxed experience while still enjoying the local attractions.

Ultimately, whether you prefer the energetic vibe of summer or the tranquil beauty of winter, Uptown has something special to offer throughout the year.
Are there any remote work vacation rentals in Uptown?
In Uptown, Illinois, travelers seeking remote work vacation rentals have a variety of options available, with around 23 properties to choose from. This vibrant neighborhood is known for its diverse culture and easy access to public transportation, making it convenient for both work and exploration. Many of the rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated desks, and ergonomic chairs, ensuring a comfortable working environment.

Some properties even feature additional conveniences like safes for securing valuables and computer monitors, suiting those who require a more equipped workspace. Beyond the work setup, Uptown offers a lively atmosphere with nearby parks, local eateries, and cultural venues, allowing guests to enjoy a balanced stay that combines productivity with leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Uptown vacation rental?
Book your Uptown 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 Uptown?
In Uptown, Illinois, visitors can enjoy a variety of attractions and cultural experiences. The historic Aragon Ballroom, known for its stunning architecture and live music events, is a key highlight of the neighborhood. Just a short walk away, the Uptown Theatre, an iconic venue from the 1920s, offers a glimpse into the area's rich cinematic history.

For outdoor enthusiasts, Montrose Beach provides a lovely spot for sunbathing and picnicking, with scenic views of Lake Michigan. The nearby Montrose Point Bird Sanctuary is a peaceful area to observe migratory birds and take leisurely strolls. Additionally, the vibrant dining scene along Wilson Avenue and Broadway features an array of international cuisines, making it a great area to explore local eateries and cafes.
Can I change or cancel my Uptown home rental booking on Vrbo?
To find Uptown 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 Uptown 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.

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