North Side Holiday Rentals from €205: Search Short-Term Rentals

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Holiday Rentals in North Side

"Had a really nice time. Great location."

"Great communication with owner/manager. Two train stations within walking distance. Used the garage for the extra fee, worth it since we took the train everywhere. "

"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."

"This is a clean and new-looking cozy mansard on the 2 story building. We liked the large kitchen, spacious bathroom, side-loading washer/dryer and a sizable bedroom. The biggest hurdle was finding parking after 10-11 pm. There might be more parking during day time. Freddy (host) nicely provided the daily parking passes, but we had to park on the adjacent street one of our 3 nights risking to get a parking ticket for the wrong location. On our last night there was a loud music/party in the...

includes taxes & fees

1 Dec - 2 Dec

"This place is amazing. Very convenient, clean, organized & updated. Thank you for a great Chicago visit!"

"Amazing experience and location!"

"Basic unit with everything you need. "

"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "

"Great location and we enjoyed our stay. Very clean code to food drink and train. Stairs were only challenge. We would come back"

"The location is close to the bus, and then easy to the Metro. It was about a 40ish min travel to the Art Institute when we were there. Roscoe Village is picturesque. There is a Starbucks at the end of the street if you want your pumpkin spice latte, but they've also got plenty of local talent- the owner of Rudy's Bakery (try the butter cookies YUM!!)-was lovely. There were plenty of other places--we just didn't have time! We arrived on Halloween; the entire neighborhood came out on their front...

Smart TV, fireplace, DVD player, table football

"Stayed for a reunion of friends after 20 yrs. Great location in Wrigleyville. Extremely well stocked kitchen. Plenty of comfortable beds and couches. Easy and quick communication from owners."

"This is an older city home with updated bathroom and kitchen. The photos represent the property well. Plentiful street parking. We felt safe walking in the neighborhood. The owner was easy to contact and responsive. Would definitely come back!"

"Our host made everything so easy. Check in, check out couldn't have been simpler. Fluffy towels and gorgeous bathrooms. Coffee and beer waiting for us. Comfy beds and a toasty gas fireplace. A 7-11 at the end of the street for buying snacks and wine. Amazing location. Spotless! We can't wait to go back in the summer and enjoy the deck. "

"This was the perfect place for an out of town Cubs fan to stay. Very convenient to Wrigley Field and the property was in great shape and very comfortable. "

"If I could give this listing 10 stars I absolutely would!! The stay went beyond expectation's. The hosts’ were friendly and attentive. Many restaurants, shops and train are at a walking distance. Would highly recommend!"

includes taxes & fees

1 Dec - 2 Dec

"It was exactly what we were looking for- perfect size, good location. It was well stocked and clean. Surprisingly quiet being so close to the rail station. "

includes taxes & fees

2 Dec - 3 Dec

"The property "

"Great location and clean apartment. The host was very quick to respond to any question, and we had a great time on our trip "

"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "

Fridge, microwave, oven, coffee/tea maker

"We loved our visit to Chicago! So much to do! We enjoyed Frank Lloyd Wright homes in Oak Park. We had fun at Wrigley Field as the Cubs won (train ride from house to Wrigley is only 2 stops). We took the train downtown for the Architecture Tour, shopping on Michigan, taking pictures with the Bean and other stuff in Millennium Park, shopping in all the 2nd hand/vintage clothing shops in Wicker Park, eating yummy tacos at Tacombi in Wicker Park, eating at Mindy's Bakery in Wicker Park, eating...

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Other types of properties in North Side you may be interested in

"Good communal area"

includes taxes & fees

8 Dec - 9 Dec

"Clean"

includes taxes & fees

15 Dec - 16 Dec

"We enjoyed our stay.... very clean and comfortable."

includes taxes & fees

16 Dec - 17 Dec

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 €205 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.