Vacation rentals with breakfast in North Side

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Top-rated breakfast rentals in North Side

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Guest favorite

A modern living room features a large, curved green sectional sofa and a blue accent chair. A round, light-colored coffee table sits at the center, complemented by decorative items. Large windows provide natural light, while an artistic light fixture enhances the space.

Home in Chicago

4.87 out of 5 average rating, 128 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Guest favorite

A well-stocked kitchen features warm wooden cabinetry and modern appliances. A round dining table, set with blue-patterned plates, comfortably accommodates four. Potted plants are placed on the countertops, while a light fixture hangs above, providing ample illumination. The tiled floor enhances the inviting space.

Apartment in Hillside

4.85 out of 5 average rating, 167 reviews

Easy, Cool, safe place to stay.

Level 1 car charging available, message me. 17 mins Ohare airport 25 mins to downtown Chicago I want you to enjoy your stay, and I don't have rules other than basic ones like noise and guest limit. Have Fun Very safe and quiet 420 might be ok, please message me* 3 Queen-size beds. One is self-iflating inside the middle closet. Well stocked kitchen 2 Private parking lot spaces. Kreuger coffee 2 tvs Netflix There is no smoking in the unit or inside building* Coin laundry is available

Guest favorite

A sandy beach scene is depicted with a lively crowd enjoying the water under a clear blue sky. Colorful inflatable structures are visible in the distance, and the city skyline is faintly seen beyond the water. Sunbathers are spread across towels on the sand, with beach chairs scattered around.

Home in Whiting

4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Superhost

The bright kitchen features modern stainless steel appliances and a spacious island with green cabinetry. The dining area includes four metal chairs. Two large windows allow natural light to fill the space, highlighting the white cabinetry and tiled backsplash.

Apartment in Chicago

4.8 out of 5 average rating, 143 reviews

Welcome to my home

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.**

Top guest favorite

The entrance is framed by lush greenery and vibrant blooming flowers, complementing the charming blue facade of the house. A decorative staircase leads to the front door, flanked by elegant iron railings and hanging planters, creating an inviting approach.

Guest suite in Chicago

4.97 out of 5 average rating, 282 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!

Guest favorite

The exterior of a historic home showcases a modernist design with distinctive architectural elements. Various materials, including stone and wood, create an organic aesthetic. Lush greenery surrounds the property, enhancing the natural setting in a quiet neighborhood.

Apartment in Oak Park

4.94 out of 5 average rating, 174 reviews

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Guest favorite

A wooden swing seat is framed by a red arbor in a quiet backyard, surrounded by tall grass and greenery. The evening sky is filled with clouds, creating a serene atmosphere. Power lines are visible in the background, adding to the neighborhood setting.

Home in Evanston

4.86 out of 5 average rating, 133 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Top guest favorite

The front room features a plush leather couch adorned with vibrant red throw blankets, complemented by a bold red and white area rug. Bright teal curtains frame the windows, allowing natural light to fill the space. A coffee table is placed centrally, surrounded by decorative plants and artwork.

Apartment in Chicago

4.95 out of 5 average rating, 424 reviews

A Vintage Pink House in the Heart of Chicago

Located in a quirky, Victorian era, pink house on a residential street in the East Village neighborhood, this unit is a charming piece of Old Chicago. This 2nd story, apartment features an eat in kitchen, a double and a single bedroom, and a front room that oozes Chicago history. Perfect for a quick weekend getaway or an extended stay. A Walk Score of 97 means you won't need a car to experience the city. Easy access to Division Blue Line, nightlife, shopping & adventure.

Top guest favorite

A well-lit living area features a light-colored sofa complemented by a rustic wooden coffee table. Large windows adorned with sheer curtains allow natural light to stream in. A vibrant red accent chair adds a pop of color, while decorative artwork hangs on the walls.

Apartment in Forest Park

4.98 out of 5 average rating, 229 reviews

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

Guest favorite

A bright hallway leads to a cozy sitting area, enhanced by large windows showcasing a stained glass panel. Light wood flooring extends throughout, with a small chair positioned invitingly. Wall hooks are visible beside the door, highlighting functional design features.

Apartment in Evanston

4.89 out of 5 average rating, 304 reviews

Ashland Ice Cream House

This 1907 farmhouse style two flat sits on one of Evanston's prettiest blocks. Freshly updated and upgraded, this 2nd floor apartment consists of two levels. The main level includes living room with a sleeper sofa, an eat in kitchen, full bath and a bedroom with a full sized bed. The second level is a finished loft with a queen bed and separate office area. Host lives in first floor unit. Blocks to CTA, Metra and shopping. Ample street parking, cable and fast wi-fi.

Guest favorite

A remodeled kitchen features wooden countertops and modern appliances, including a gas stove and hood. A small dining table is positioned in the center, with warm wood flooring extending throughout. Light streams in from the windows, highlighting the clean, minimalist design.

Apartment in Chicago

4.9 out of 5 average rating, 198 reviews

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, Lagunitas Brewery & Tap Room and Douglass Park. Pilsen and West Loop night life just a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing.

Top guest favorite

A spacious covered patio area is furnished with comfortable seating options, including a swing and sectional sofas. Potted flowers add vibrant color to the space, while warm wood tones and high ceilings create an inviting atmosphere. Large windows allow for natural light to fill the area.

Guest suite in Naperville

4.95 out of 5 average rating, 414 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.