Holiday Rentals North Side from £143: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for North Side holiday rentals

1. Logan Square Boho Getaway - Sleeps 6 - Remodeled

Avondale

"The host was very communicative. We had an issue with our AC when we arrived but he was on it immediately & had a tech over the next morning. As stated the parking is tight, and it being in Chicago it is understood. We were able to park our car on the same street where the house was on but had to wake up at 7am to move it daily as there’s only permit parking under certain hours but the park right up the street has good spaces available on the side of it. Space itself was extremely clean & all...

Mayra R.

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

2. Chic Urban Retreat Near Wrigley Field w/Parking

Lakeview

Bridget

includes taxes & fees

4 Nov - 5 Nov

A living room with a sofa, a coffee table, a chair, a radiator, and a painting on the wall.

3. 1BR Fully Equipped & Central

Lakeview

Trevor F.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with white cabinets, a gas stove, a coffee maker, and a toaster.

4. 1BR Well-Equipped Apartment

Lakeview

Annette

includes taxes & fees

26 Oct - 27 Oct

A neatly made bed with white linens, a patterned pillow, and folded towels.

5. Lush Studio Apartment

Lakeview

Brad B.

includes taxes & fees

27 Oct - 28 Oct

6. Central 1BR Retreat Apartment

Lakeview

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a large bed, a bedside table, a nightstand, a window with blinds, and a wall-mounted artwork.

7. Comfortable 3BR/2BA Haven | Ideal for Families

Avondale

Marc

includes taxes & fees

18 Oct - 19 Oct

A compact kitchen with a gas stove, wooden cabinets, a sink, and a door with blinds.

8. Relaxing 1BR | King Bed & Homey Feel

Lakeview

includes taxes & fees

26 Oct - 27 Oct

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Top North Side Hotel Reviews

The Willows Hotel

8/10 Good

"Adorable boutique hotel in a great location. The property was well maintained and provided everything needed for a quick trip to the city. Parking was convenient - there is a paid parking garage located just behind the property. There are several restaurants and shops nearby, and the train station was just a 15-minute walk away. The property offered tea and coffee throughout the day and late at night. In the evenings, they put out freshly baked cookies which was a cute touch. Room was clean and smelled great. The bed was comfortable and linen was clean. Th elevator was small but we didn't have to wait long. The only concern was how easily noise travelled into the rooms, especially for rooms next to the elevator. I am not sure if anything can be done about this - perhaps earplugs if you are a light sleeper. Next time, I would request a room that was not so close to the elevator. All that said, the property was a great value for what was provided and I would still recommend."

The Chicago Hotel Collection - Wrigleyville

8/10 Good

"The room was great very clean unique fun. The location is also very good. Lots to do. Lots of restaurants nearby things to walk to close to Wrigley Field. The check process what’s difficult had to wait like 20 minutes via several phone calls to figure out how to get in . Had to call the number on the door several times before talking to someone that explained how to get our key. Looks like the lobby decor was supposed to be shabby chic, but it was just shabby talk to some other people checking in. They were somewhat disappointed at the look of the lobby all that being said, we would stay there again due to the nice rooms and great location"

Hotel Lincoln

10/10 Excellent

"Loved everything about the hotel with the exception of the coffee shop in the lobby. They never had anything. No decaf espresso beans, no pastries, limited sparkling drinks in cold case. On the second day, it was the same thing. The barista actually referred us to a coffee shop around the corner! If I was hotel Lincoln, I would be careful recommending the coffee shop if they’re going to be so ill prepared. The restaurant in the lobby is a different story! What a great place to eat. Service was great with helpful staff and great food. M6 son who lives nearby (reason for trip) didn’t 3pm know the restaurant was there, but he does now. Very pleased with the restaurant! Thanks again for a great weekend"

The Den Hotel

10/10 Excellent

"Great location for a night. This particular room had an external bathroom, but was private to us. We just had to walk through a hallway to get to it. We did not encounter any problems or other guests. We parked in The Vic public parking structure down a couple of blocks - it was $23 to park for the night: We would definitely stay here again."

Hotel Versey Chicago Lincoln Park

10/10 Excellent

"We had a great stay overall! The staff was friendly, welcoming, and helpful, and the hotel and surrounding area were clean and felt safe. The only minor issues were with the room itself. It was quite hot, even with the window open, and the street noise was noticeable. However, we spent very little time in the room, so it wasn’t a major issue for us. One thing to note is that the parking information listed valet parking, but valet service was not available. Instead, there is a self-parking garage just a short walk from the hotel. Other than these small inconveniences, everything was great. The friendly staff, cleanliness, and safe location made for a very pleasant stay. With a cooler, quieter room and more accurate parking information, this would easily be a five-star experience. We would definitely consider staying here again! Oh and if stay go to the restaurant for a burger and tots you won't be disappointed"

Find out more about North Side

Everything you need to know about North 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 North 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 North Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North 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 North 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 North Side holiday rentals we have selected for you start as low as £143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Side rentals

At Expedia, we put the best North 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 North 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 North 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 North 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.

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Check prices for these dates

Our top choices for North Side holiday rentals

1. Logan Square Boho Getaway - Sleeps 6 - Remodeled