Holiday rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

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

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Superhost

Apartment in Broadview

5 out of 5 average rating, 4 reviews

Quiet and Cozy 2 bedroom condo

Welcome to your tranquil retreat! This thoughtfully designed two-bedroom 1 bath condo blends modern amenities with a welcoming atmosphere, making it an ideal getaway. The living area features contemporary décor and comfortable seating. The kitchen is equipped with stainless steel appliances & granite countertops. Conveniently located near shopping, restaurants & coffee shops O’Hare & Midway airports are approximately a 25 minute drive and Downtown Chicago is approximately a 20 minute drive!

Top guest favourite

Flat in Oak Park

4.97 out of 5 average rating, 77 reviews

Treetop Oasis With Parking Walk To Town & Train

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Wow kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

Superhost

Private room in Chicago

5 out of 5 average rating, 5 reviews

Deluxe King Room · Juliette Balcony · Sono B&B

You’ll be charmed by this private guest room inside The Sono Chicago Bed and Breakfast, a newly built boutique B&B in the heart of Chicago’s historic Old Town. This listing is for one private king room with a Juliette balcony within a shared bed and breakfast. Guests enjoy their own bedroom and ensuite space. Complimentary breakfast is included each morning. We’re located on a quiet, tree-lined street and offer cozy accommodations, warm hospitality, and a welcoming sense of community.

Guest favourite

Home in Skokie

4.83 out of 5 average rating, 29 reviews

Comfy Cove: 3BR-2BT *NEW* w/ 2 Living Rooms

Welcome to our cute and cozy 3BR, 2BT home in Skokie—the perfect blend of comfort and convenience. Thoughtfully designed- this space is ideal for families, friends, or business travelers. Enjoy comfortable bedrooms, a fully equipped kitchen, and relaxing living areas that make you feel right at home. Located in a quiet neighborhood with easy access to Chicago, dining, shopping, and local attractions. Whether you’re here for a weekend getaway or an extended stay, this is the place.

Home in Norridge

4.83 out of 5 average rating, 6 reviews

Modern Ranch | 5 Min to O'Hare, 25 to Chicago

Fully renovated 3-bed 1.5-bath ranch in quiet Norridge. 5 min to O'Hare, 25 to downtown Chicago. Open-concept living with two lounge areas and mounted TVs. Modern chef's kitchen with farmhouse sink, electric range, and stainless appliances. Dining for 6 and a fenced backyard with patio. Hardwood floors throughout. King primary with desk for remote work, guest room (full), and a third bedroom for added comfort (full). Walk to Harlem Irving Plaza area. Quiet corner lot near O'Hare.

Guest favourite

The exterior of a spacious home is framed by lush greenery and carefully manicured landscaping. An inviting entrance is accentuated by a covered porch. The architectural design features multiple gabled roofs and expansive windows, allowing for natural light to fill the interior.

Flat in Oak Park

4.94 out of 5 average rating, 87 reviews

First floor of Historic Oak Park Villa, Grge:2Cars

Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

Top guest favourite

The exterior of a modern three-story bungalow is showcased, featuring a mix of brick and dark paneling. A neatly landscaped front yard includes a path leading to the entryway, flanked by lush greenery and decorative stones. The structure retains a contemporary architectural style.

Home in Berwyn

4.96 out of 5 average rating, 28 reviews

The Architectural Haven

Welcome to The Architectural Haven! Enjoy comfort and luxury in our modern Berwyn bungalow, a serene escape only 15 minutes from downtown Chicago. Nestled in a charming neighborhood, this secluded retreat offers the perfect place to relax and recharge. Our thoughtfully designed space is fully equipped with premium amenities and unique architectural touches. Every room invites you to feel at home, ensuring a memorable stay you’ll want to revisit We look forward to hosting you!

Guest favourite

A stylish living area is presented with a gray sectional sofa and a small ottoman. Natural light filters through the large windows, illuminating the neutral walls and light wood flooring. A decorative fireplace is positioned against a stone feature wall, enhancing the inviting setting.

Home in La Grange Park

4.92 out of 5 average rating, 49 reviews

Zen in La Grange Park

Relax. Recharge. Explore. Welcome to Zen, your peaceful retreat in beautiful La Grange Park. This charming 2-bedroom ranch offers the perfect blend of comfort and convenience with spacious living areas, a fully fenced backyard, and an attached 2-car garage — ideal for families, friends, or extended stays. Nestled in a quiet neighborhood, you’ll enjoy a relaxing atmosphere while being just minutes from nearby trains and bus stations that provide easy access to Downtown Chicago.

Guest favourite

The spacious living area features a light wood floor and an open layout connecting the living room and dining area. A comfortable sofa and a wooden coffee table are complemented by a dining table with dark chairs. Natural light fills the space through large windows, enhancing the modern design.

Home in Oak Park

4.98 out of 5 average rating, 40 reviews

DT Oak Park Luxe|3BR 2BA+Yard|15 min to Chicago

Welcome! Location location location! Relax in this newly renovated 3-bedroom home in the heart of the historic district. Steps from the Frank Lloyd Wright Home and Studio, Hemingway Birthplace Museum, shops, dining, and easy transit to downtown Chicago. Stylish, spotless, and family-friendly — the perfect blend of comfort and charm. No parties, events, gatherings, weapons, dangerous items or disruptive behavior allowed. Every adult must be on the reservation. No exceptions.

Guest favourite

A contemporary hotel room is presented, featuring a spacious bed with soft linens. A striking blue wall mural adds a modern touch. Natural light enters through a large window, illuminating the wooden floor and sleek furniture, including a bedside table and desk.

Hotel room in Chicago

4.92 out of 5 average rating, 59 reviews

Private Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Guest favourite

A dining area showcases a long table set for a meal, adorned with colorful dishware and a decorative centerpiece. Yellow chairs surround the table. The background features a modern kitchen with stainless steel appliances and light cabinetry, enhancing the space's welcoming atmosphere.

Home in Forest Park

4.92 out of 5 average rating, 38 reviews

Swanky Rooftop Sleeps 16 Birthday Anniversary

Welcome home! This spacious, stylish 6-bedroom, 3.5 bath accommodates up to 16 guests. Open concept featuring hardwood floors & TVs in almost every room, it’s perfect for relaxation & entertaining. Newly renovated kitchen boasts stainless steel appliances & plenty of dining space. Enjoy a private rooftop with a slight view of the city Located near Madison Ave, local dining, shopping, and the historic Frank Lloyd Wright district, this home offers comfort and convenience

Guest favourite

A charming bungalow is presented, featuring a well-maintained front porch with two seated areas. The building's exterior is adorned with light-colored stucco and decorative accents. A lush, green lawn decorates the yard, complemented by carefully arranged landscaping along the pathway leading to the entrance.

Flat in Oak Park

4.84 out of 5 average rating, 89 reviews

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!