Old Town Chicago holiday rentals

We found 485 holiday rentals — enter your dates for availability
Discover a selection of 13 homes, 19 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.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Old Town Chicago for a holiday rental?
The peak season for visiting Old Town Chicago falls between June and August, with July being particularly popular among travellers. This vibrant time of year attracts a mix of tourists eager to enjoy the city's lively festivals, outdoor dining, and cultural events, all while basking in warm summer temperatures that typically range from 20 to 30 degrees Celsius.During these months, you can take advantage of the bustling atmosphere, with street fairs and concerts adding to the charm of the historic neighbourhood. The iconic architecture and picturesque streets provide a superb backdrop for leisurely strolls and sightseeing, ensuring that outdoor activities are both enjoyable and comfortable.For those seeking a more budget-friendly option, consider visiting in November. This month offers a unique charm as the city transitions into the holiday season. You can explore the quieter streets, enjoy the local shops, and experience the festive decorations without the summer crowds, all while taking advantage of lower rental rates.Ultimately, the best time to visit Old Town Chicago for a holiday rental hinges on your preferences—whether you're drawn to the lively summer vibe or the peaceful ambiance of late autumn.
What are the top attractions in Old Town Chicago, Illinois, United States of America?
In Old Town Chicago, visitors can immerse themselves in a variety of attractions that highlight the neighbourhood's rich history and vibrant culture. The Old Town Historic District is a key highlight, featuring beautifully preserved Victorian-era buildings and the iconic St. Michael's Church. Nearby, the famous Second City comedy club offers a unique entertainment experience with live performances that have launched many careers in comedy.For those interested in shopping and dining, Wells Street is lined with an vibrant mix of boutiques, cafes, and restaurants, making it a great spot to explore local flavours and unique finds. The area is also home to the Old Town Art Fair, held annually, which showcases local artists and craftspeople.Additionally, the nearby Lincoln Park provides ample green space for outdoor activities, with attractions like the Lincoln Park Zoo and the beautiful Conservatory enhancing the area's appeal. Visitors can enjoy leisurely strolls through the park while taking in the natural beauty and wildlife.
Are all fees included in the Old Town Chicago holiday homes prices shown on Stayz?
Stayz 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.
Are there any Old Town Chicago holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old Town Chicago with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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 any discounts for Old Town Chicago holiday homes?
You can find great discounts on holiday homes in Old Town Chicago on Stayz, 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.
Can I change or cancel my Old Town Chicago holiday home booking on Stayz?
To find Old Town Chicago holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Town Chicago?
A long-stay holiday home in Old Town Chicago is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Old Town Chicago holiday home?
Book your Old Town Chicago holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Town Chicago?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Town Chicago to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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