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Lake house vacation rentals in Chicago

Find and book unique lake houses on Airbnb

Top-rated lake house rentals in Chicago

Guests agree: these lake houses are highly rated for location, cleanliness, and more.

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Home in Lake View

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.

Home in Hyde Park

5 out of 5 average rating, 11 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Home in Gold Coast

5 out of 5 average rating, 6 reviews

Gold Coast Pristine 4BR/4.5BA Home | Free Parking.

Luxurious Gold Coast Getaway – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for work or leisure, this property offers modern amenities and unforgettable comfort in the heart of downtown.

Home in Near North Side

4.96 out of 5 average rating, 26 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

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

Home in Evanston

5 out of 5 average rating, 88 reviews

Larimer Park Carriage House

IMPORTANT- PLEASE NOTE THAT THE NEIGHBORING PARK IS UNDERGOING RENOVATIONS JULY 2024-OCT 2024. IF YOU FEEL THIS MAY BE DISRUPTIVE TO YOUR TRIP, PLEASE MESSAGE HOST BEFORE BOOKING. Charming, historic carriage house only a few short blocks from Evanston's best shopping, restaurants and beaches. Home offers 2 bedrooms(Queen/King) ample closets and private ensuite bathrooms. Enjoy cooking in the fully equipped kitchen. Cozy up on the huge sectional sofa. Laundry in home + parking space!

Home in Lincoln Park

4.97 out of 5 average rating, 79 reviews

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Luxurious home in the heart of Historic Old town triangle. Fantastic location! Steps to restaurants, shops, Lincoln park Zoo, Lake Michigan, Brown line. Pristine craftsmanship throughout, with no expenses spared. Sleeps 4 people. Internet speed 1G. 3 smart TVs. Essential baby gear. Key-less self-check-in. Bicycles with locks for the guests to explore the city. Complimentary guest parking permits. Private chef is available upon request This home is perfect for business and pleasure!!

Home in West Town

4.93 out of 5 average rating, 40 reviews

Hot Tub Logan Family Designer Home

Enjoy a beautiful family home on a quiet tree-lined street designed by one of NYC's top designers -- with abundant art, lots of space for kids, and a hot tub! Freshly redesigned and between Wicker Park and Logan Square, this is a perfect location for family and just a few minutes from downtown Chicago. Luxury linens, bedding, and touches abound. Explore the elevated 606 trail, excellent restaurants within walking distance, and a work desk, 4K monitor, and playroom. And secret beach!

Home in Old Town

4.87 out of 5 average rating, 129 reviews

Huge Home *Prime Spot *Yard *Parking *Fireplace

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques, and nightlife; Lincoln Park and North ave beach from this three-level house. 5 bedrooms, 3.5 baths, 2 fully stocked kitchens, 2 car garage, back yard, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22.

Home in Downers Grove

4.96 out of 5 average rating, 23 reviews

Lakefront Getaway Home! Lots of Fun! Win.Discount$

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤

Home in Skokie

4.88 out of 5 average rating, 84 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

Home in Lincoln Park

4.84 out of 5 average rating, 157 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck!

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Popular amenities for Chicago lake house rentals

Free parking on premises

Air conditioning

Waterfront lakehouse rentals

Private room in Lake View

4.87 out of 5 average rating, 126 reviews

Renovated space in a historic row house.

Home in Kenwood

5 out of 5 average rating, 6 reviews

Gem Near Hyde Park/McCormick Place

Home in Chicago

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

Private room in East Rogers Park

4.98 out of 5 average rating, 41 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

Private room in Highland Park

5 out of 5 average rating, 10 reviews

Ladies Only Home

Private room in Uptown

4.97 out of 5 average rating, 100 reviews

Comfortable private room near Lake and transit.

Home in Chicago

4.84 out of 5 average rating, 73 reviews

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

Home in Des Plaines

4.59 out of 5 average rating, 27 reviews

House 1 minute from O'hare Airport

Pet-friendly lake house rentals

Private room in Evanston

4.78 out of 5 average rating, 37 reviews

Luxury Master Suite w/Jacuzzi

Home in Bolingbrook

4.79 out of 5 average rating, 39 reviews

Peaceful Bolingbrook Getaway

Home in Wilmette

4.67 out of 5 average rating, 3 reviews

Darling 2br basement apt private entrance, yard,FP

Home in Des Plaines

4.54 out of 5 average rating, 147 reviews

Entire House Minutes from O’Hare Airport!! By lake

Home in Winnetka

5 out of 5 average rating, 14 reviews

Chicago Northshore Winnetka 4br

Home in Westmont

4.93 out of 5 average rating, 30 reviews

Westmont,Il 4/3 on the Lake

Home in Lansing

New place to stay

Little Old Lake House

Private room in Des Plaines

4.88 out of 5 average rating, 386 reviews

R2 Cozy room in a convenient location by a river

Private lake house rentals

Home in Des Plaines

4.9 out of 5 average rating, 31 reviews

House in the Park- 5 Min from O'Hare.

Home in Andersonville

5 out of 5 average rating, 4 reviews

The Lytle House Loft

Home in Chicago

4.81 out of 5 average rating, 36 reviews

Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen

Home in Woodlawn

4.82 out of 5 average rating, 110 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

Home in Des Plaines

4.83 out of 5 average rating, 53 reviews

Full House - Amazing sunset lake park

Home in Chicago

4.88 out of 5 average rating, 17 reviews

Executive Contemporary Duplex

Home in Evanston

5 out of 5 average rating, 26 reviews

Stunning Coach House in Evanston, near Lake/NU

Destinations to explore