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Vacation rentals with breakfast in Downtown Chicago

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Top-rated breakfast rentals in Downtown Chicago

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Home in Chicago

4.87 out of 5 average rating, 127 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.

Rental unit in Chicago

4.89 out of 5 average rating, 324 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-BR+ liv/dining room, private entrance garden apartment, 3 blks to Red Line or Metra to downtown or Evanston, Skokie, theaters, restaurants, and parks. Edgewater has tree-lined streets, known as a quiet, safe, diverse & friendly neighborhood. Breakfast foods (coffee, tea, fruit, milk, cereal, bread, homemade jam) for starters. Has a microwave, small fridge, toaster oven & induction stovetop. Your stay reduces carbon emissions due to solar panels & heat/ac pumps.

Home in Whiting

4.85 out of 5 average rating, 142 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

Guest suite in Chicago

4.97 out of 5 average rating, 263 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!

Rental unit in Oak Park

4.94 out of 5 average rating, 169 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.

Rental unit in Chicago

4.95 out of 5 average rating, 401 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.

Rental unit in Forest Park

4.99 out of 5 average rating, 214 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.

Rental unit in Evanston

4.9 out of 5 average rating, 289 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.

Rental unit in Chicago

4.8 out of 5 average rating, 209 reviews

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.

Rental unit in Chicago

4.92 out of 5 average rating, 183 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.

Rental unit in Chicago

4.93 out of 5 average rating, 343 reviews

Wrigleyville 75 yards from Wrigley Field

Beautifully remodeled apartment steps from Wrigley Field and bars. Half block from the field and One block away from the Wrigleyville night life. The apartment is right next to all the action but just far enough for a quiet night sleep. You will be pleasantly surprised how quiet my block is one hour after the game ends. Walking distance to the beach and a block from the red line.

Rental unit in Berwyn

4.9 out of 5 average rating, 235 reviews

Family Friendly, 20 min train ride to downtown.

The perfect jumping off point for exploring Chicago, we are located in hidden gem Berwyn, just 2 blocks from the train station. Child-friendly, free parking. Our home is also the site of a micro-flower farm, with pocket forest, native garden, fruit trees and kids play house. Our first floor apartment also has a crib, high chair, bunkbeds and free street parking.

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Popular amenities for Downtown Chicago breakfast rentals

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House rentals with breakfast

Home in Chicago

4.86 out of 5 average rating, 65 reviews

Wicker Park 7 Beds Crash Pad

Home in Chicago

4.99 out of 5 average rating, 73 reviews

Luxe SFH Bucktown Retreat with Garage Parking

Home in Chicago

5 out of 5 average rating, 9 reviews

Cozy 4-Bedroom House with Patio

Home in Chicago

5 out of 5 average rating, 15 reviews

Big 4BR/3.5BA Home Near Everything!

Home in Westmont

4.89 out of 5 average rating, 74 reviews

Lil Westmont Cottage whole house and enclosed yard

Home in Chicago

4.63 out of 5 average rating, 117 reviews

5 BR / 3.5 BA Newly Built Home in Logan Square!

Home in Chicago

4.95 out of 5 average rating, 56 reviews

The Ivy at Wrigley field by Wrigleyville Oasis

Home in Chicago

4.98 out of 5 average rating, 347 reviews

Cozy garden apartment historic Jackson Bvld.

Apartment rentals with breakfast

Rental unit in Chicago

4.78 out of 5 average rating, 287 reviews

Cozy Garden-Subterranean Apartment

Rental unit in Chicago

4.97 out of 5 average rating, 168 reviews

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

Rental unit in Blue Island

4.93 out of 5 average rating, 285 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

Rental unit in Chicago

5 out of 5 average rating, 14 reviews

Bright and full of life!

Rental unit in Chicago

4.82 out of 5 average rating, 159 reviews

Heart of Wicker Park! Location. Walk to Everything

Rental unit in Chicago

4.97 out of 5 average rating, 278 reviews

The Garden on Wayne

Rental unit in Chicago

4.94 out of 5 average rating, 235 reviews

Urban Chic Apartment by the Magnificent Mile

Rental unit in Chicago

4.7 out of 5 average rating, 158 reviews

Urban Camper

Bed and breakfast rentals with breakfast

Private room in Chicago

4.85 out of 5 average rating, 324 reviews

Private room with private entrance in Boystown

Private room in Chicago

4.8 out of 5 average rating, 172 reviews

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)

Private room in Evanston

4.57 out of 5 average rating, 96 reviews

Gorgeous 1 Bed (King) with Private Bathroom

Private room in Chicago

5 out of 5 average rating, 101 reviews

Urban Oasis Pilsen - guest room in townhouse

Hotel room in Chicago

4.85 out of 5 average rating, 48 reviews

Queen Room w/ Balcony in Boutique Wicker Park B&B

Private room in Chicago

4.77 out of 5 average rating, 311 reviews

Chicago River Room near USMLE

Private room in Chicago

4.95 out of 5 average rating, 169 reviews

Twin Bedroom with Private Bathroom

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