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Old Town Chicago holiday lettings

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August 2025

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Discover a selection of 19 homes, 17 apartments and other holiday rentals in Old Town Chicago that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a hot tub and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Level Chicago – Old Town

Sleeps 8

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Why visit Old Town Chicago

Historic charm: Old Town Chicago boasts a rich history, featuring beautifully preserved architecture and cultural landmarks.
Family-friendly attractions: The area offers numerous activities suitable for families, ensuring a delightful experience for all ages.
Vibrant streets: Explore lively streets filled with shops, restaurants, and entertainment options that capture the essence of city life.
Outdoor adventures: Enjoy nearby urban parks and scenic spots ideal for leisurely strolls and outdoor activities.
Comfortable accommodations: A variety of stylish apartments and homes provide a perfect base for your Chicago adventure.

Popular types of accommodation around Old Town Chicago

Explore the charm of Old Town Chicago with a variety of vacation rentals tailored to your needs. Whether you prefer chic apartments, spacious private homes, or modern condos, there’s something for everyone. Our selection of Old Town apartments offers the perfect base for your adventures, ensuring comfort and convenience during your stay. Discover the ideal apartment rental in Chicago and make your visit unforgettable.

Apartments: The most sought-after choice for holiday stays in Old Town Chicago, offering a range of styles and amenities for a comfortable experience.
Houses: A popular option for those seeking a homely atmosphere, perfect for families and groups.
Condos: These modern dwellings provide a blend of convenience and luxury, highly favoured by visitors.
Cottages: Charming and quaint, cottages offer a unique retreat amidst the vibrant city.
Villas: Spacious and luxurious, villas are ideal for those looking to indulge during their stay.**

Top attractions near Old Town Chicago

Old Town Chicago is perfect for family getaways, outdoor adventures, and city-themed holidays. Visitors can explore a vibrant mix of skyscrapers, urban parks, and lively streets. The area offers a rich cultural experience, making it ideal for families and travellers seeking a taste of city life. Don't miss the chance to discover the attractions that Old Town has to offer, ensuring an enjoyable visit for all.

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.
Navy Pier: A popular lakeside destination, featuring stunning views of Lake Michigan, amusement rides, and lively entertainment, making it a friendly spot for families and tourists alike.
Millennium Park: A beautiful urban park that showcases art installations, gardens, and a concert pavilion, ideal for leisurely strolls and family picnics in the heart of the city.

Things to do recommended for couples

For a romantic getaway in Old Town Chicago, indulge in live music at the House of Blues, savour a meal at the historic Michael Jordan Restaurant, or enjoy a concert at the Aragon Ballroom. Each venue offers a unique atmosphere perfect for couples to create lasting memories.

Things to do recommended for families

Families visiting Old Town Chicago can catch a thrilling game at Wrigley Field, unwind in the serene Northerly Island Natural Area, or enjoy the wellness facilities at the East Bank Club, all within a short distance from each other for a delightful family outing.

Things to do recommended for groups

Experience the vibrant culture of Chicago by visiting the iconic Chicago Theatre, just 1.2km from Old Town. Enjoy a laugh at the Second City comedy club nearby, or indulge in some retail therapy at the 900 North Michigan Shops, only 621m away, perfect for families and groups.

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

If you’re travelling with a group, as a family, with pets, or planning an extended stay, be sure to apply the appropriate filters to reflect your preferences. Here are some helpful booking tips for using Vrbo.

Traveling to Old Town Chicago with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
Traveling to Old Town Chicago with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
Taking your pets with you to Old Town Chicago: For many, a family holiday wouldn't feel complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer 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 holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Old Town Chicago

Old Town Chicago offers a delightful blend of family-friendly attractions, vibrant streets, and scenic spots perfect for outdoor adventures. As you explore this charming neighbourhood, you'll encounter friendly locals and an inviting atmosphere. Nearby areas also boast urban vibes and delightful scenery, providing a rich experience for any traveller. With its historic charm and modern amenities, Old Town is an ideal base for discovering the best of Chicago's neighbourhoods.

Chicago: Chicago is a bustling metropolis situated a mere 1.2km from Old Town Chicago. This vibrant city offers a rich tapestry of experiences, from family-friendly attractions to outdoor adventures. Visitors can indulge in shopping at local boutiques, catch a thrilling game at one of the renowned sports facilities, or explore educational venues. Notable landmarks include the impressive stadiums that host major sports events and a lively tourist precinct, making Chicago a must-visit destination for a diverse array of activities.
Downtown Chicago: Just 1.2km from Old Town Chicago, Downtown Chicago is a dynamic neighbourhood that encapsulates the city's urban charm. This area is perfect for families and those looking for a city-themed experience, with an abundance of shopping options and an impressive array of theatres. Visitors can enjoy the vibrant atmosphere of the tourist precinct, take in a game at one of the local stadiums, or explore the nearby sports facilities. Downtown Chicago is a hub of activity that guarantees an exciting day out.
Magnificent Mile: Located only 621m from Old Town Chicago, the Magnificent Mile is a renowned shopping and entertainment district. This neighbourhood attracts families and city explorers alike, offering a delightful mix of outdoor experiences and cultural attractions. Visitors can shop at high-end retailers, enjoy various educational opportunities, and experience the lively arena entertainment. With its proximity to tourist precincts and sports facilities, Magnificent Mile is an essential stop for anyone looking to soak in the essence 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.

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 simple

Are you keen to save on your upcoming adventure? Being open to adjusting your travel dates can lead to significant savings, as prices can vary quite a bit. Additionally, opting for a longer stay often results in substantial discounts. To discover the perfect Vrbo accommodation that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new journeys, pick up from where you last left off, or manage and review your travel arrangements. Your previously saved and booked properties are now easily accessible in the Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Old Town Chicago?

According to our research, houses are considered the most popular type of property in Old Town Chicago. But as you might expect, everyone's idea of an awesome stay differs. Vrbo has holiday homes in a variety of shapes and sizes, so you're sure to find the best fit for your needs.

How much does it cost to rent a holiday rental in Old Town Chicago?

Property type, length of stay and time of year are among the factors that can determine the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy country cottages to sprawling luxury villas, all Vrbo holiday rentals offer incredible value.

How much does it cost to rent a beach house in Old Town Chicago?

The average price for a holiday rental close to the beach in Old Town Chicago will depend on when you'll be there and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.

Are there pet-friendly holiday rentals in Old Town Chicago?

Yes. There are. You can choose from 25 stays that welcome pets in Old Town Chicago on Vrbo. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to book a place where Rover can join in the fun.

What are popular rental amenities in Old Town Chicago?

When it comes to rental amenities that guests prefer in Old Town Chicago, a fireplace, nearby museums and a firepit rank the highest. With Vrbo holiday rentals, you'll discover options to fit your style and taste, whether you're travelling with relatives, friends or even pets.

Are there large group holiday rentals in Old Town Chicago?

Old Town Chicago has 10 holiday rentals that can host 10 or more guests. These properties come with the space and privacy you need to share good times with loved ones.

Are there holiday rentals in Old Town Chicago that welcome kids?

Bring the entire family together for an adventure in Old Town Chicago at one of our 25 family-friendly holiday properties. A lot of these stays provide conveniences that are ideal for trips with the kids, including full kitchens, living rooms and entertainment units. Just click on the "Properties good for families" filter and decide on your favourite.

What are the top attractions for families in Old Town Chicago?

There's a ton of amazing things to do and see with the family in Old Town Chicago, including:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom holiday rentals in Old Town Chicago?

Yes, you'll find five one-bedroom properties in Old Town Chicago to pick from. A one-bedroom holiday home is a superb choice if it's just you and your sweetheart or if you're holidaying alone. Toss in more space, privacy and convenience compared to a regular hotel, and you've got yourself a getaway to remember.

Can I find two-bedroom holiday rentals in Old Town Chicago?

You can pick from six two-bedroom holiday homes in Old Town Chicago. Give your little ones the second room or maybe fill it with a couple of your best friends. There's enough space for whoever's fortunate enough to come along for the ride.

Are there holiday rentals with WiFi in Old Town Chicago?

Whether you want to keep up with world events, look over emails or post a pic to social media, there are 16 holiday homes with WiFi in Old Town Chicago. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.

How can I find holiday rentals with air conditioning in Old Town Chicago?

Decide on your travel dates and then use our filters to search for holiday rentals with ac in Old Town Chicago on Vrbo. With 23 air-conditioned properties available here, you can look forward to a comfortable and cool stay.

How old do you have to be to rent a holiday rental in Old Town Chicago?

The minimum required age is typically 16, 18 or 21. It can change across properties on Vrbo, so check the rules of your preferred Old Town Chicago stay before booking your escape.

How long can I rent a holiday rental in Old Town Chicago for?

The amount of time you can rent an Old Town Chicago holiday home for depends on each property. Simply tap in your travel dates to see available options offering extended stays. They feature all you require to make your extended trip more comfortable and convenient, like air conditioning and kitchens. Some holiday homes might also offer weekly or monthly discounted prices, so you can hang around longer for less.