
Vacation rentals with breakfast in Chicago
Find and book unique breakfast rentals on Airbnb
Quick stats about vacation rentals with breakfast included in Chicago

Total vacation rentals
Explore 510 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at G$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 35,040 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

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

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

4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
Top-rated breakfast rentals in Chicago
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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.

Cheerful Remodel Prime Location
Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

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. We will provide information on local restaurants and entertainment. 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.

Gallery Loft of Oak Park #1 Top Host in IL
Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

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.

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.

Luxurious Bronzeville Apartment with RoofTop
Your cozy getaway awaits in Chicago at this beautiful apartment. With three bedrooms featuring two queen beds and a futon, there’s plenty of space for guests to relax comfortably. The apartment includes two bathrooms, each thoughtfully equipped to make your stay easy and convenient. Whether you’re unwinding after a day of exploring or preparing for a night out, this charming spot offers a welcoming atmosphere. Enjoy all that Chicago has to offer when you stay at our place.

1,800ft² Parking Workspace W/D Full Kitch
• 1,800ft² | 167m² . My home is on the top floor of a four flat 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

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.
Popular amenities for Chicago breakfast rentals
House rentals with breakfast

Pardizes Suites

Historic mini mansion!

Little House With Big Punch-4BR/3BA

West Loop Retreat: High-End, Walk to Everything

Cozy 4-Bedroom House with Patio

Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking

▌360° City Skyline Chicago ▌

The Spa of Downtown Whiting
Apartment rentals with breakfast

Comfy Solar & Green 2BR Near Hot Hyde Park!

2 Bedroom w/LOFT + BONUS Room

Edgewater escape, charming 2 BR, Rooftop Solar

Magical Treehouse in Historic Old Town Neighborhoo

Spacious 1BR apartment in a central location

Easy, Cool, safe place to stay.

Ashland Ice Cream House

Fairfield Flat, Airy Vintage Rehab
Bed and breakfast rentals with breakfast

Historic campus U of C Prof. mansion, top location

Bright Room with a Garden View

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

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Chicago River Room, near Med Ctr

Lovely UofC Prof mansion great on campus location

(BR#1) Welcoming, warm & comfortable, 3 guests
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,918 GYD | G$23,637 GYD | G$25,101 GYD | G$23,009 GYD | G$24,892 GYD | G$25,519 GYD | G$25,101 GYD | G$25,519 GYD | G$25,101 GYD | G$26,775 GYD | G$24,892 GYD | G$24,683 GYD |
| 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 |
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- Rentals with breakfast Cook County
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Washington Park Zoo
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