Northwest Side Holiday Rentals from €63: Search Short-Term Rentals

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Holiday Rentals in Northwest Side

"The environment was comfortable and very clean. Great accommodations. Would stay again."

"Stayed here while I was running the Chicago marathon. Was perfect for my infant and toddler and everything we needed for the weekend. Nice neighborhood, easy parking, great communication through the stay. Would definitely stay here again."

"Great stay. Will stay again!"

includes taxes & fees

24 Nov - 25 Nov

"Easiest check in and check out process "

includes taxes & fees

22 Dec - 23 Dec

Superior Apartment, 1 Bedroom, Balcony, City View | Living area

"Nice"

includes taxes & fees

19 Dec - 20 Dec

49-inch Smart TV with digital channels, TV, streaming services

"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "

50-inch Smart TV with satellite channels

"Excellent place to stay! "

"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"

includes taxes & fees

25 Nov - 26 Nov

"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...

includes taxes & fees

24 Dec - 25 Dec

"Very convenient location, the apartment was impeccable "

includes taxes & fees

23 Dec - 24 Dec

42-inch Smart TV with digital channels, TV, streaming services

"Amazing stay!"

Free toiletries, hair dryer, towels, soap

"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"

includes taxes & fees

23 Dec - 24 Dec

"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"

includes taxes & fees

8 Dec - 9 Dec

"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."

includes taxes & fees

23 Dec - 24 Dec

"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"

"Good location clean"

"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "

includes taxes & fees

23 Dec - 24 Dec

"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "

"A big, beautiful, immaculate, wonderfully furnished space 51 floors above the city. Everything in the owner's description is true. Watching the sun rise over the lake from that height was a treat. Also being able to walk to restaurants, Navy Pier, river tours, great blues clubs, plus hop the subway just a few doors away. The door staff was very helpful in stashing our luggage on both sides of our stay (be sure to "show them some kindness" for that service). "

"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "

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"Definitely was a night to remember staying here! Very beautiful style!"

includes taxes & fees

4 Dec - 5 Dec

"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."

includes taxes & fees

24 Dec - 25 Dec

"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

includes taxes & fees

23 Dec - 24 Dec

Find out more about Northwest Side

Everything you need to know about Northwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Northwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Northwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Northwest Side holiday rentals we have selected for you start as low as €63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Northwest Side rentals

At Expedia, we put the best Northwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Northwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Northwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Northwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.