Old Town Chicago vacation rentals

We found 479 vacation rentals — enter your dates for availability

Discover a selection of 12 homes, 16 apartments, and other vacation rentals in Old Town Chicago that are perfect for your trip. Vacation rentals offer the best amenities for you and your friends, family, or even pets, like parking and a TV. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.

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Find out more about Old Town Chicago

Why visit Old Town Chicago

  • Historic Charm: Old Town Chicago features beautifully preserved architecture and rich history, making it a delightful area to explore.
  • Family-Friendly Activities: The neighborhood offers various attractions suitable for all ages, ensuring fun for the whole family.
  • Vibrant Local Culture: Experience bustling cafes, unique shops, and friendly faces that embody the spirit of Chicago.
  • Outdoor Spaces: Enjoy urban parks and scenic streets perfect for leisurely strolls and outdoor activities.
  • Diverse Accommodation: Choose from stylish apartments, cozy vacation homes, and modern condos for a comfortable stay.

Popular types of accommodation around Old Town Chicago

If you're exploring your accommodation options in Old Town Chicago, you're in the right place. The most popular choices for vacation rentals here include stylish apartments, cozy houses, and modern condos. Whether you're searching for an apartment in Old Town Chicago, boutique apartments, or downtown Chicago apartments, we have a variety of options that cater to your needs and ensure a memorable stay.

  • Apartments: The top choice for travelers, providing a comfortable and convenient stay in Old Town Chicago, ideal for solo travelers or groups.
  • Houses: A favorite for families and friends, offering spacious living and a home-like atmosphere for your getaway.
  • Condos: A popular option that combines luxury and practicality, perfect for those seeking a modern urban experience.
  • Cottages: These quaint retreats offer a cozy ambiance, ideal for couples or small families looking for charm.
  • Villas: For those desiring an upscale experience, villas provide ample space and luxurious amenities in a serene setting.**

Top attractions near Old Town Chicago

Old Town Chicago is perfect for family-friendly and outdoor city vacations, offering a variety of attractions like skyscrapers, urban parks, and vibrant streets. Visitors can immerse themselves in the local culture, explore family-oriented activities, and enjoy the urban experience that this historic neighborhood has to offer. Whether you're seeking adventure or a leisurely stroll, Old Town has something for everyone to enjoy.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is famous for its shopping, dining, and stunning architecture, offering a vibrant city atmosphere just 2 miles from Old Town Chicago.
  • Navy Pier: A lively jetty featuring entertainment, dining, and scenic views of Lake Michigan, Navy Pier is a great spot for families and friends, located 2 miles away from Old Town Chicago.
  • Millennium Park: A beautiful urban park showcasing art installations, gardens, and outdoor concerts, Millennium Park is a perfect family-friendly destination, also 2 miles from Old Town Chicago.

Things to do recommended for couples

For a romantic getaway in Old Town Chicago, enjoy live music at the House of Blues, only 2 miles away, or savor a meal at the historic Michael Jordan Restaurant, also 2 miles away. Don't miss the vibrant atmosphere at the Aragon Ballroom, located 4 miles from your base.

Things to do recommended for families

Your family will love the excitement of Wrigley Field, just 3 miles away, and the serene atmosphere of Northerly Island Natural Area, located 4 miles from Old Town. For relaxation, visit The East Bank Club, only 2 miles away, offering wellness and recreational activities for everyone.

Things to do recommended for groups

Experience the vibrant culture of Old Town Chicago by catching a show at the iconic Chicago Theatre, just 2 miles away. Enjoy a hilarious evening at Second City, right in the neighborhood, or indulge in some shopping at Chicago Place Mall, located 1 mile away.

*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 Old Town Chicago

If you're traveling with a group, your family, pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Old Town Chicago with a group: Think about how many bedrooms you require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Old Town Chicago with young kids: Traveling with little ones can be tricky. It’s important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town Chicago: For many, a family vacation isn't truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly options offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Old Town Chicago: If you're seeking vacation rentals with special rates for stays of a month or more, 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 a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Old Town Chicago

Old Town Chicago is a vibrant neighborhood rich in history and charm, perfect for family-friendly adventures and outdoor activities. Explore its historic streets filled with friendly faces, bustling cafes, and unique shops. Just a short distance away, you can immerse yourself in the urban atmosphere that blends scenic beauty with a welcoming vibe, making it an ideal destination for any traveler looking to experience the essence of Chicago.

  • Chicago: Chicago is a vibrant metropolis that serves as the backdrop for Old Town Chicago. This bustling city offers a diverse range of experiences, from family-friendly attractions to outdoor adventures. Visitors can enjoy an array of shopping areas and entertainment venues, including sports arenas and educational institutions. Key landmarks nearby include major stadiums and tourist precincts, making it easy to immerse yourself in the city's rich culture and history while exploring its dynamic neighborhoods.
  • Downtown Chicago: Located 2 miles from Old Town Chicago, Downtown Chicago is the heart of the city. This lively neighborhood is a hub for family activities, outdoor excursions, and urban exploration. With a fantastic selection of shopping areas, theaters, and entertainment facilities, there's always something to see and do. Visitors can easily access local landmarks such as sports facilities and popular tourist attractions, ensuring a memorable experience while soaking in the architectural beauty of the skyline.
  • Magnificent Mile: Situated 1 mile away from Old Town Chicago, the Magnificent Mile is a renowned shopping and cultural district. This bustling area attracts families and city explorers alike, offering an exciting blend of outdoor experiences and urban charm. Visitors can stroll along the iconic avenue, discovering high-end shops, theaters, and educational venues. With proximity to various landmarks, including sports facilities and tourist precincts, the Magnificent Mile is a must-visit destination for anyone looking to experience the best of Chicago.

Best time to go to Old Town Chicago

If you're planning a trip to Old Town Chicago, 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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use space for planning your next getaway, picking up right where you left off, or organizing your travel plans. You can effortlessly view your saved or booked properties, which are neatly arranged under 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

How much does it cost to rent a vacation home in Old Town Chicago?
Prices for vacation rentals in Old Town Chicago 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 Old Town Chicago 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 Old Town Chicago vacation house rentals?
You can find great discounts on house rentals in Old Town Chicago 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 Old Town Chicago vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Town Chicago 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 find long-stay vacation rentals in Old Town Chicago?
A long-stay vacation rental in Old Town Chicago 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 Old Town Chicago for a vacation rental?
July is the most popular time to visit Old Town Chicago, as it falls within the vibrant peak season from June to August. During these warm summer months, the city buzzes with activity, inviting travelers to explore its rich cultural scene, indulge in outdoor dining, and take part in various festivals and events. The pleasant temperatures, typically ranging from the mid-60s to the low 80s Fahrenheit, create an ideal atmosphere for enjoying the charming streets and historic architecture of Old Town.

In particular, July offers an array of outdoor activities, from leisurely strolls along the picturesque Lakefront Trail to exploring the many parks and gardens that flourish in the summer sun. Additionally, Old Town is known for its lively farmers' markets and street fairs, making it a great destination for those who appreciate local culture and cuisine.

For those looking to save a bit on their vacation rental, consider visiting in November. This month presents a unique opportunity to experience the beauty of the city as it transitions into winter, with fewer crowds and a more relaxed pace. You can enjoy cozy cafes, art galleries, and the early holiday decorations that start to appear, all while discovering the charm of Old Town at a more affordable rate.

Ultimately, the best time to visit Old Town Chicago depends on whether you seek the lively energy of summer or the calm of the shoulder season.
How early should I book a Old Town Chicago vacation rental?
Book your Old Town Chicago 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 Old Town Chicago, Illinois, United States of America?
In Old Town Chicago, visitors can experience firsthand a rich cultural experience with numerous attractions. The Old Town Historic District is known for its beautifully preserved Victorian-era buildings and charming streets. One of the highlights is the St. Michael's Church, an iconic structure that adds to the neighborhood's historical character.

Nearby, the Second City, famous for its improv comedy, offers a lively entertainment option that attracts both locals and tourists alike. The neighborhood is also home to the Old Town Art Fair, showcasing local artists and craftspeople, typically held in June.

For those looking for outdoor space, Lincoln Park is just a short walk away, providing expansive green areas, walking trails, and the Lincoln Park Zoo, which is free to enter. The area also boasts a variety of boutique shops, restaurants, and cafes, making it a vibrant spot for dining and shopping.
Can I change or cancel my Old Town Chicago home rental booking on Vrbo?
To find Old Town Chicago 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 Old Town Chicago 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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