Holiday rentals with breakfast in North Side

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Top-rated Holiday Accommodation with Breakfast in North Side

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Guest favourite

Loft in Forest Park

4.96 out of 5 average rating, 463 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

9–16 Dec

$254 NZD per night

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 294 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-bedroom + living/dining room, private entrance garden apartment, close to: the red line to downtown or Evanston, the lake, theaters, restaurants, and parks. Edgewater is known for tree-lined streets, quiet, safe, diverse, & as a friendly neighborhood. We provide breakfast foods (coffee, tea, fresh fruit, milk, cereal, bread and homemade jam). There is a microwave, small fridge & induction stovetop. You're limiting carbon emissions with solar & heat/ac pumps.

25 Dec – 1 Jan

$290 NZD per night

Guest favourite

Guest suite in Chicago

4.97 out of 5 average rating, 225 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

9–16 Jul

$256 NZD per night

Superhost

Apartment in Chicago

4.81 out of 5 average rating, 105 reviews

Welcome Chez Moi

Enjoy the privacy and comfort of the third floor with an updated furnished 1bed/1ba apartment. The daybed in the living room turns into a full sleeper for additional guests. Patio in the rear for warm days. Walking distance from the riverfront and Hamlin Park. Roscoe Village offers lots of cute shops and restaurants. Bus/train routes take you to downtown or O’Hare in about 30-40mins. Close to I-90/I-94. Free street parking around the block. **Light complimentary breakfast for short stays.**

4–11 Sep

$250 NZD per night

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 244 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

18–25 Dec

$378 NZD per night

Guest favourite

Apartment in Chicago

4.85 out of 5 average rating, 162 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

$113 NZD per night

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

3–8 Nov

$375 NZD per night

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 105 reviews

The Crash Pad 1 min walk to Wrigley Field

Cozy Garden apartment a 1/2 a block from Wrigley Field and less than a 5-minute walk to the center of Wrigleyville where you will find dozens of shops, restaurants and Bars. Even though the apartment is close to all the action, this location is on a quiet street. Great spot to relax if you’re in town for a Cubs game or concert! 15 min walk to the lake and beaches. 15 minutes from downtown 5 min walk to 2 Rapid transit stations connecting you the rest of the city.

4–11 Dec

$372 NZD per night

Guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 120 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

15–22 Feb

$247 NZD per night

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 207 reviews

Cozy Private Coach House

This is a cozy 1 bedroom unit in a private coach house. Excellent location in the middle of trendy Logan Square! Please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 28 night minimum in the winter, until the end of February or possibly March. But I recommend putting in at least 30 days to avoid those taxes!

16–23 Sep

$348 NZD per night

Guest favourite

Guest suite in Chicago

4.91 out of 5 average rating, 420 reviews

Cozy, Quiet, Garden Getaway!

Quiet 1BD garden apartment in Northcenter/Lincoln Square. 10 minutes to the el and Lincoln Square, one of the best neighborhoods in Chicago. Full kitchen, bathroom, cable and internet. Tree lined street close to two parks and a river walk. ****WE DO NOT RENT TO FILM CREWS****

23–30 Mar

$200 NZD per night

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 251 reviews

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

23–30 Sep

$212 NZD per night