Old Town Chicago vacation rentals

Why visit Old Town Chicago

1. Historic Charm: Old Town Chicago showcases a blend of historic architecture and modern vibrancy, perfect for exploring unique boutiques and art galleries.
2. Family-Friendly Activities: The area offers a variety of attractions and parks, catering to visitors of all ages.
3. Scenic Strolls: Enjoy tree-lined streets and beautiful scenery while walking through this charming neighborhood.
4. Diverse Dining Options: Experience a range of cozy cafes and restaurants that reflect the local culture.
5. Comfortable Accommodations: Choose from stylish apartments, private homes, or luxurious condos for a perfect stay.

Popular types of accommodation around Old Town Chicago

Planning a getaway to Old Town Chicago? You're in for a treat! Explore a variety of vacation rentals, including stylish apartments, cozy private homes, and luxurious condos. Whether you're looking for modern amenities or a spacious bedroom condo, you'll find the perfect accommodation to suit your needs. Let our platform help you make the most of your stay with transparency and savings at every turn!

• Apartments: A favored choice among travelers, apartments offer spacious living areas and full amenities for a comfortable stay in Old Town Chicago.
• Houses: Ideal for families or groups, these homes provide a homey atmosphere with plenty of privacy and space.
• Condos: Condominiums combine the comforts of home with the benefits of modern facilities, making them a popular option.
• Cottages: These quaint, charming homes provide a cozy retreat, perfect for a relaxing getaway.
• Villas: Luxurious and spacious, villas offer upscale accommodations for those seeking a lavish experience.**

Top attractions near Old Town Chicago

Old Town Chicago is a fantastic destination for families and outdoor enthusiasts alike, offering a rich blend of culture and city life. Visitors can explore iconic skyscrapers, relax in urban parks, and stroll along vibrant streets. With a variety of attractions catering to diverse interests, Old Town provides memorable experiences for everyone, whether traveling solo, as a couple, or with family and friends.

1. Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, restaurants, and iconic architecture, offering a vibrant city atmosphere perfect for shopping and dining.
2. Navy Pier: This lively jetty features beautiful waterfront views, cultural attractions, and family-friendly activities, making it a great spot for art lovers and those seeking a fun day out.
3. Millennium Park: A stunning urban park that hosts public art installations and green spaces, ideal for families to enjoy outdoor activities amidst the city’s skyline.

Things to do recommended for couples

For a romantic getaway in Old Town Chicago, enjoy a concert at the House of Blues, savor a meal at the historic Michael Jordan Restaurant, or dance the night away at the Aragon Ballroom. Each venue offers a unique atmosphere perfect for couples seeking unforgettable experiences.

Things to do recommended for families

Families visiting Old Town Chicago can catch a game at Wrigley Field, explore the serene Northerly Island Natural Area, or enjoy wellness activities at The East Bank Club, all offering fun and relaxation just a short drive away.

What do I need to keep in mind when booking a vacation around Old Town Chicago

When planning your trip, whether you’re traveling with a group, family, pets, or seeking extended stays, it’s essential to prioritize your preferences. Here are some helpful Vrbo booking tips for you.

• Traveling to Old Town Chicago with a group: Think about how many bedrooms you will require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
• Traveling to Old Town Chicago with young kids: Traveling with young kids can be 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 family-friendly attractions.
• Taking your pets with you to Old Town Chicago: For many families, a vacation wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most 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 Old Town Chicago: If you're in search of vacation rentals that offer discounts 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your criteria as well.

Where to stay near Old Town Chicago

Old Town Chicago offers a vibrant mix of history and modern charm, making it an ideal destination for families and outdoor enthusiasts. Explore the historic neighborhood filled with unique boutiques, art galleries, and cozy cafes. Enjoy the friendly atmosphere as you stroll through tree-lined streets, taking in the beautiful scenery. Nearby attractions provide the perfect blend of urban excitement and family-friendly activities, making your vacation a memorable experience in this captivating part of Chicago.

• Downtown Chicago: As the vibrant core of Chicago, Downtown Chicago is a bustling hub known for its incredible shopping, dining, and entertainment options. Located 2 miles from Old Town, this area offers a family-friendly atmosphere with an array of outdoor activities. You can explore iconic landmarks such as Millennium Park, catch a show at one of the many theaters, or cheer on your favorite team at nearby sports facilities. With its stunning skyline and lively streets, Downtown Chicago promises an unforgettable urban experience.
• Magnificent Mile: Just 1 mile from Old Town, the Magnificent Mile is a world-renowned shopping district that attracts visitors from all over. This neighborhood is perfect for families and city explorers alike, with an array of boutiques, upscale shops, and dining options lining the streets. Alongside shopping, you'll find attractions like the historic Water Tower and the Museum of Contemporary Art. The Magnificent Mile offers a blend of education and entertainment, ensuring a memorable visit for all ages.
• River North: Located just 1 mile from Old Town, River North is known for its art galleries, theaters, and trendy restaurants. This energetic neighborhood is ideal for families seeking a mix of culture and enjoyment. Visitors can explore the vibrant art scene or catch a live performance at one of the local theaters. River North also boasts popular shopping venues and picturesque esplanades, making it a delightful area to wander and soak in the city's atmosphere.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, simply use our filters to narrow down options by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. Being the organizer certainly has its perks! Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash™ on qualifying stays. Sign up today and begin reaping the benefits!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board feature offers you a convenient way to plan your trips. You can easily create new itineraries, pick up where you left off, or organize your existing plans all in one place. Any properties you've saved or booked before are now accessible under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.