Uptown vacation rentals

We found 2,112 vacation rentals — enter your dates for availability

Discover a selection of 5 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.

Vacation rentals with weekly discounts - Uptown

Showing deals for:May 15 - May 22

Image gallery for New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Room
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Chicago

9% off
Price is $2,096
$14,674 for 7 nights
All fees included
New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

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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 common type of vacation rental, with around 23 available throughout the neighborhood. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and often include access to on-site facilities like fitness centers or pools. Additionally, there are several condos and vacation houses available, offering more spacious rooms ideal for families or groups. These properties usually come with extra features such as outdoor spaces, BBQ areas, and multiple bedrooms, providing a cozy environment for travelers.
Are there any beach house rentals in Uptown?
In Uptown, Illinois, there are about 20 beach house vacation rentals available. These properties are typically located near the waterfront, providing easy access to the beach and beautiful lake views. Travelers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor decks or patios, which are superb for enjoying the fresh air and scenic surroundings. Many of these rentals are suitable for families or groups, featuring multiple bedrooms and communal spaces for gathering and relaxation.
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 rental amenities typically include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature coffee and tea makers, great for those who enjoy a warm beverage in the morning. For pet owners, a number of properties permit pets, making it easier to travel with furry companions. Additionally, service animals are welcome in most rentals. Onsite parking is another common amenity, providing convenience for guests with vehicles.
Can I find family house rentals in Uptown?
In Uptown, Illinois, there are several family-friendly vacation rentals available, totaling around 13 options. This vibrant neighborhood offers a variety of homes that cater to families looking for spacious rooms. Many of these properties feature inviting living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can enjoy themselves.

Visitors will appreciate the accessibility to nearby attractions, such as the picturesque Lake Michigan waterfront, which is great for family outings, picnics, or leisurely walks. Additionally, the neighborhood is known for its parks and recreational facilities, including playgrounds and sports fields, making it an excellent choice for families seeking both comfort and convenience during their stay.
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 come equipped with both pools and hot tubs. This vibrant neighborhood offers a mix of urban living and recreational options, making it an appealing destination for travelers. Many of these properties feature private pools, inviting hot tubs, and outdoor spaces that are superb for relaxing and entertaining.

Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and easy access to local attractions like parks, restaurants, and cultural venues.
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.
Can I book pet-friendly vacation rentals in Uptown?
Yes, there are several pet-friendly vacation rentals available in Uptown, Illinois. This vibrant neighborhood offers a variety of options for travelers looking to bring their furry friends along. Many of the rentals come equipped with amenities such as spacious living areas, modern kitchens, and outdoor spaces where pets can enjoy some fresh air.

Uptown is conveniently located near several parks, providing great opportunities for pet owners to enjoy leisurely walks and outdoor activities. The nearby Montrose Beach offers a dog-friendly area, allowing pets to frolic in the sand and surf. Additionally, the neighborhood features pet-friendly cafes and local shops, ensuring that you and your pet have a comfortable and enjoyable stay.
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 is during the peak season from July to September, when the area comes alive with vibrant activities and events. This summer period is particularly appealing to travelers looking for a blend of outdoor enjoyment and cultural experiences. With warm temperatures ranging from the mid-70s to low 80s Fahrenheit, it's an ideal time for leisurely strolls, al fresco dining, and exploring the charming local shops and parks.

July stands out as the most popular month, attracting families and friends eager to take advantage of Uptown's lively option. You can enjoy outdoor festivals, farmers' markets, and seasonal attractions that showcase the best of the community. The warm weather also makes it superb for enjoying the scenic waterfront and nearby recreational activities.

For those seeking a more budget-friendly option, consider visiting in December. While this is the low season, Uptown transforms into a cozy winter wonderland, offering unique holiday festivities and a chance to explore the area without the summer crowds. You'll find local boutiques and eateries providing a warm welcome, along with the festive spirit in the air.

Ultimately, the best time for you to book a vacation rental in Uptown will depend on whether you prefer the bustling summer scene filled with activities or the quieter, charming winter atmosphere.
Are there any remote work vacation rentals in Uptown?
In Uptown, Illinois, there are a variety of remote work vacation rentals available—approximately 26 options to choose from. This vibrant neighborhood is known for its rich cultural scene and proximity to Lake Michigan, making it an appealing choice for remote workers. Many of the rentals feature dedicated office spaces, desks, and high-speed Wi-Fi, ensuring a productive environment for those working from home. Some properties may also include additional amenities like computer monitors and comfortable workstations to enhance the remote work experience.

Beyond the work setup, travelers can enjoy the local attractions, including the beautiful Montrose Beach and the lively dining scene along Broadway Avenue. The area also boasts parks and green spaces for breaks, as well as easy access to public transportation, making it convenient to explore the rest of Chicago during downtime. 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, Illinois, United States of America?
Uptown, Illinois, is a vibrant neighborhood with several attractions that appeal to both locals and visitors. One of the most great landmarks is the historic Aragon Ballroom, known for its stunning architecture and live music events. Just a short walk away is the Uptown Theatre, an iconic venue that has hosted a variety of performances over the years, making it a must-see for entertainment enthusiasts.

For outdoor activities, Montrose Beach, located nearby, offers a sandy shoreline and scenic views of Lake Michigan, great for picnics, sunbathing, and beach sports. The nearby Montrose Harbor provides opportunities for boating and fishing, adding to the recreational options in the area.

For those interested in culture and history, the neighborhood features the Uptown Square, which is dotted with unique shops, cafes, and restaurants, reflecting the local community's character.
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 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 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.
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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