Holiday rentals with breakfast in Near North Side

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.

Top-Rated 3BR Near O’Hare & Rosemont | Sleeps 5

Clean, spacious 3BR home designed for a reliable, stress-free stay. Professionally maintained and consistently rated for quality and comfort. Ideal for families, business travelers, and extended stays. Bright living area, full kitchen, and comfortable space for up to 6 guests. Hosted by an experienced Superhost focused on consistency and care. Prime Location • O’Hare Airport–14 mins • Rosemont (Dining, Entertainment, Convention Center)-10 mins • Allstate Arena–13 mins • Downtown Chicago-18 mins

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!

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

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.

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.

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian Brick Building . You have 3 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

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.

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

Pretty Suite in Lincoln Park w/HVAC +free parking

Location, location, location! Located in one of Chicago’s best neighborhoods, Lincoln Park near DePaul university. 3 blocks from the CTA trains. Entire Private SUITE with small KITCHENETTE in lower level of 3 story apartment building. Access to all the shopping, restaurants and bars that Lincoln Park has to offer. Leave your car in the free, far right parking space in back of the apartment building, and explore Chicago by foot, bike, Uber or train.

In artistic Pilsen~Continental Breakfast~Near DWTN

Located in the artistic town of Pilsen; minutes away from downtown Chicago, Lake Shore drive, Shedd aquarium, United Center, UIC Pavilion and McCormick Place. Great and convenient location. Walking distance from CTA #60 bus-stop and pink line to downtown. Enjoy charming first floor, full kitchen, & bathroom. Also includes continental breakfast for first day of your stay and street parking with permit.

The "Nest", unconventionally modern yet vintage.

The "Nest" has an open floor plan with a gourmet kitchen and modern appliances, with a comfortable lounge area to make you feel right at home. The dining table can be expanded for conferences or several dinner guests. The quiet, beautifully modern bedroom is large enough to accommodate a king-sized bed and a desk area.