
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.

❤︎ 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

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

Fairfield Flat, Airy Vintage Rehab
This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, and Douglass Park. Pilsen and West Loop night life 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. Great for couples or friends, though parents have expressed frustration with the hard, or uneven surfaces, and the stairs.

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.

On the Boulevard in Logan Square
The space is a completely renovated two bedroom garden apartment in a vintage (1918) 7 unit building on the Boulevard in Logan Square's National Register Historic and City of Chicago Landmark Districts. Logan Square is on the northwest side of Chicago, on the CTA Blue Line, which runs from O'Hare Airport to downtown Chicago's Loop, then continues on past the University of Illinois at Chicago and the West Side Medical Center to the suburban villages of Oak Park and Forest Park.

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.

Comfy Solar & Green 2BR Near Hot Hyde Park!
Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Charming Unique 2 Bdrm Apartment in Victorian Home
My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Cozy Garden-Subterranean Apartment
JAN-FEB Special, check out lower then average prices. Our cozy Lincoln Square one bedroom apartment sleeps 2, has a fully furnished kitchen, and is close to Lincoln square shops and great restaurants/carry-out. Ample street parking & close to public transportation. Entrance to the apartment at back of building. Sorry no pets, we both have allergies and my husband has asthma and cannot tolerate pet dander.

Walk to Oak Park from a Cozy, Sun-soaked Hideaway
This is a bright and comfortable apartment that has been fully updated, but still has the historic charm of an older house (early 1900s). With an 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 bedrooms are large and on opposite ends of the apartment, which is great for privacy.
Popular amenities for Chicago breakfast rentals
House rentals with breakfast

Pardizes Suites

Historic mini mansion!

Wicker Park 7 Beds Crash Pad

West Loop Retreat: High-End, Walk to Everything

Two Kings Chicago. Royal comfort in two king beds

▌360° City Skyline Chicago ▌

Historic home The Ivy 1-min walk to Wrigley Field

Soak Up Mid-Century Style in Wrigleyville and Boystown
Apartment rentals with breakfast

Pretty Suite in Lincoln Park w/HVAC +free parking

The "Nest", unconventionally modern yet vintage.

In artistic Pilsen~Continental Breakfast~Near DWTN

Bronzeville Bohemian Loft

Edgewater escape, charming 2 BR, Rooftop Solar

Magical Treehouse Located in HEART of Old Town!

Spacious Chicago Getaway with Balcony and Parking

Spacious 1BR apartment in a central location
Bed and breakfast rentals with breakfast

Historic campus U of C Prof. mansion, top location

Historic campus house owned by U of C Prof

Sun-Filled King Room in Boutique Wicker Park B&B

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

Urban Oasis Pilsen - guest room in townhouse

Chicago River Room, near Med Ctr

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

Lovely UofC Prof mansion great on campus location
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ356 | ﺩ.ﺇ353 | ﺩ.ﺇ400 | ﺩ.ﺇ404 | ﺩ.ﺇ437 | ﺩ.ﺇ448 | ﺩ.ﺇ441 | ﺩ.ﺇ448 | ﺩ.ﺇ441 | ﺩ.ﺇ419 | ﺩ.ﺇ422 | ﺩ.ﺇ408 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about vacation rentals with breakfast included in Chicago

Total vacation rentals
Explore 370 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 27,070 verified reviews to help you choose

Family-friendly vacation rentals
150 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
360 of Chicago vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chicago rentals

4.8 Average rating
Chicago stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The 606
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