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Near West Side holiday homes

We found 1,032 holiday rentals — enter your dates for availability
Select from 14 houses, 14 flats and other holiday rentals to find the perfect place for your stay in Near West Side. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Near West Side

Showing deals for:5 Feb - 12 Feb

Image gallery for River North's Rock N' Roll - In The Heart of the City

River North Luxury Living
9.6 out of 10, Exceptional, (107 reviews)
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
Price is NZ$5,786
for 7 nights, 1 apartment
NZ$827 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City

Find spaces that suit your style

  • 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 Near West Side for a holiday rental?
January is a fantastic time to visit the Near West Side of Illinois, particularly for those seeking a quieter holiday rental experience. This month allows you to enjoy the city without the hustle and bustle of peak tourist season, which typically runs from May to July. Visitors can explore the vibrant neighbourhoods, indulge in local cuisine, and experience the rich cultural scene at a more leisurely pace.

The climate in January can be quite chilly, with temperatures often hovering around -5 to 4 degrees Celsius. However, this provides a superb opportunity to appreciate indoor attractions such as museums, art galleries, and cozy cafes. The area's proximity to public transportation makes it convenient to access popular sights, ensuring you can enjoy your time without the stress of heavy crowds.

If you're looking for more budget-friendly options, consider visiting in October. This month offers a lovely autumn atmosphere, with the added bonus of fewer tourists and pleasant weather for outdoor strolls. You can admire the beautiful fall colours while exploring parks and local shops, making for a delightful getaway.

Ultimately, the best time to visit the Near West Side depends on whether you prefer a more vibrant setting with events and activities in the summer or a peaceful retreat in the quieter months.
What are the top attractions in Near West Side, Illinois, United States of America?
In the Near West Side of Chicago, visitors can explore a variety of attractions that showcase the neighbourhood's rich culture and history. The United Centre, home to the Chicago Bulls and Blackhawks, is a major draw for sports enthusiasts and often hosts concerts and events. Just a short distance away, the vibrant Taylor Street offers a taste of Italian heritage with its many restaurants and cafes.

For those interested in arts and culture, the nearby UIC Pavilion frequently hosts performances and exhibitions, while the Illinois Medical District features fascinating architecture and history. The area also provides access to the expansive Douglass Park, superb for outdoor activities, picnics, or enjoying a leisurely stroll.
Are all fees included in the Near West Side holiday homes prices shown on Bookabach?
Bookabach 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 Near West Side holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Near West Side 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 Near West Side holiday homes?
You can find great discounts on holiday homes in Near West Side on Bookabach, 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 Near West Side holiday home booking on Bookabach?
To find Near West Side holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Near West Side?
A long-stay holiday home in Near West Side 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 Bookabach?
Bookabach'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 Near West Side holiday home?
Book your Near West Side 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Near West Side?
Prices for holiday homes in Near West Side 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. Bookabach offers something for every taste and budget, from affordable homes in Near West Side to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.