Pet-friendly holiday rentals in Downtown Chicago

A spacious living area features a gray sofa adorned with yellow cushions, accompanied by two beige armchairs. An archway leads to a contemporary kitchen, while soft lighting and a neutral color palette create a calm atmosphere.

4.84 out of 5 average rating, 330 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history to its modern comforts. Featuring warm timber floors that connect two cozy bedrooms with queen beds to a contemporary kitchen. Each room has a TV, and the kitchen is fully stocked for your convenience. With two full bathrooms and barrier-free one-floor access, this space combines old-world charm with modern living in the vibrant heart of Lincoln Park, close to the Lakefront.

A serene garden space is presented, featuring green grass and a variety of plants and trees. Two light-colored Adirondack chairs are positioned on the lawn, surrounded by vibrant foliage. The backdrop includes brick buildings and a pathway, creating a welcoming outdoor environment.

4.8 out of 5 average rating, 200 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #2

Entire 2 bedroom apartment in art filled,wicker park building 5 min from downtown Chicago. Quick walk to shops,restaurants,public transportation,parks,night life,etc. Space includes -Nice bathroom,walk in shower -1 bdrm w/ queen size bed,tv,desk,large closet -1 bdrm w/ single bed & closet -1 sleeper couch w/ full size pullout bed & mattress pad -1 foldable twin bed -1 queen size blow up air mattress -Fully equipped kitchen -Beautiful garden -1 parking space included + parking passes available

4.97 out of 5 average rating, 160 reviews

A two-story white house is featured, displaying large windows that allow natural light to brighten the façade. The entrance is marked by a covered porch with steps leading up, while planters are placed on either side of the door against a tree-dappled background.

Home in Chicago

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.

4.99 out of 5 average rating, 146 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

4.94 out of 5 average rating, 151 reviews

A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.

Apartment in Chicago

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

4.97 out of 5 average rating, 580 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Superhost

A well-appointed bedroom features a spacious bed with plush white linens and decorative yellow pillows. A stylish blue headboard adds a pop of color, and natural light filters through large windows dressed in light curtains. A modern desk and chair are positioned nearby, completing the inviting space.

4.81 out of 5 average rating, 339 reviews

Kasa | Elevate your stay, Premium 1BD | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

4.99 out of 5 average rating, 316 reviews

The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.

Apartment in Chicago

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 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 fireplace is not operational.

4.85 out of 5 average rating, 117 reviews

Downtown Mich Ave #10 | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Double bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.

4.92 out of 5 average rating, 132 reviews

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!

Superhost

A contemporary living room features a large sectional sofa and a dark coffee table. A decorative wall art piece of a city skyline is displayed above the couch. The space includes a dining area with a round table and chairs, illuminated by overhead lighting.

4.86 out of 5 average rating, 377 reviews

Unwind in the Garden of an elegant, Modern Home

Located near the vibrant West Loop and West Town neighborhoods, this apartment offers convenient access to Chicago’s best dining, shopping, and entertainment. Downtown parks, museums, and shops are less than two miles away, and there’s a Divvy bike station and a Starbucks right across the street. Public transit options are just a short walk away. The apartment comfortably sleeps up to 5 guests (extra fee for additional guests).

Superhost

A bright living area features large windows that provide panoramic city views. A comfortable gray sofa is positioned across from a 50" smart TV, with stylish accent chairs and a round coffee table nearby. Greenery adds a touch of nature to the space.