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Vacation rentals with breakfast in Chicago

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Top-rated breakfast rentals in Chicago

Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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Home in Lake View

4.86 out of 5 average rating, 125 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 Edgewater

4.89 out of 5 average rating, 318 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.

Rental unit in Hillside

4.85 out of 5 average rating, 165 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

Home in Whiting

4.84 out of 5 average rating, 139 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

Rental unit in Logan Square

4.8 out of 5 average rating, 127 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.**

Rental unit in West Town

4.95 out of 5 average rating, 392 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, 209 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

4.89 out of 5 average rating, 285 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 Pilsen Historic District

4.81 out of 5 average rating, 203 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 South Lawndale

4.92 out of 5 average rating, 178 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 Berwyn

4.9 out of 5 average rating, 229 reviews

“Dream slice of urban homesteading.”

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.

Rental unit in Logan Square

4.89 out of 5 average rating, 160 reviews

Private 2 Bedroom Retreat

This is a cozy, private 2 bedroom apartment with everything you need to be comfortable. This is a short term rental with a 3 night minimum most of the year, but please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 30 night minimum from January 2 until the end of February, or possibly March.

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Popular amenities for Chicago breakfast rentals

Free parking on premises

Air conditioning

House rentals with breakfast

Home in Homewood

5 out of 5 average rating, 3 reviews

Classic Charm with Modern Flair

Home in West Town

4.99 out of 5 average rating, 70 reviews

Luxe SFH Bucktown Retreat with Garage Parking

Home in Irving Park

5 out of 5 average rating, 7 reviews

Cozy 4-Bedroom House with Patio

Home in Matteson

4.93 out of 5 average rating, 28 reviews

Soulful 5-Bedroom Home with Indoor Fireplace

Home in Austin

4.89 out of 5 average rating, 56 reviews

A Comfortable Stay While You are Away

Home in West Town

5 out of 5 average rating, 13 reviews

Big 4BR/3.5BA Home Near Everything!

Home in Gary

4.97 out of 5 average rating, 59 reviews

Private 5 Star 2 bedroom modern city farmhouse

Home in Logan Square

4.67 out of 5 average rating, 112 reviews

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

Apartment rentals with breakfast

Rental unit in Lincoln Square

4.78 out of 5 average rating, 283 reviews

Cozy Garden-Subterranean Apartment

Rental unit in Ukrainian Village

4.97 out of 5 average rating, 164 reviews

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

Rental unit in Lake View

4.5 out of 5 average rating, 4 reviews

City Life, Neighborhood Comfort - Studio

Rental unit in Blue Island

4.93 out of 5 average rating, 283 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

Rental unit in North Lawndale

5 out of 5 average rating, 12 reviews

Bright and full of life!

Rental unit in Evanston

4.62 out of 5 average rating, 26 reviews

Bright, Cozy & Spacious 2Bed/1 bath With Gym By NW

Rental unit in Wicker Park

4.82 out of 5 average rating, 153 reviews

Heart of Wicker Park! Location. Walk to Everything

Rental unit in Lake View

4.97 out of 5 average rating, 271 reviews

The Garden on Wayne

Bed and breakfast rentals with breakfast

Private room in Lake View

4.88 out of 5 average rating, 17 reviews

Large Room with King bed in the Lakeview

Shared room in Wheeling

17 Miles to downtown

Private room in Mokena

4.95 out of 5 average rating, 74 reviews

Private home in Mokena - Room 2

Private room in East Rogers Park

4.8 out of 5 average rating, 171 reviews

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

Private room in Evanston

4.62 out of 5 average rating, 91 reviews

Gorgeous 1 Bed (King) with Private Bathroom

Private room in East Pilsen

5 out of 5 average rating, 95 reviews

Urban Oasis Pilsen - guest room in townhouse

Private room in Norwood Park

4.76 out of 5 average rating, 308 reviews

Chicago River Room near USMLE

Hotel room in Wicker Park

4.85 out of 5 average rating, 47 reviews

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

Quick stats about vacation rentals with breakfast included in Chicago

Total rentals
420 properties
Total number of reviews
27K reviews
Family-friendly rentals
170 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
240 properties have a dedicated workspace

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