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Vacation rentals in Downtown Chicago

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Vacation rentals for every style

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Popular amenities for Downtown Chicago vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Downtown Chicago apartment rentals

Top guest favorite
A modern living space features sleek furnishings, including a spacious dining table with chairs and a comfortable sectional sofa. Natural light floods the room through large windows, enhancing the clean design. A game table adds a recreational element to this inviting area.
Apartment in Chicago
5 out of 5 average rating, 10 reviews

Pristine Gold Coast 3BD|2BA | Free Parking| Beach.

Superhost
A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.
Apartment in Chicago
4.93 out of 5 average rating, 69 reviews

Loop Loft-Subway & Art Institute

Guest favorite
A modern living room features a gray sofa adorned with plush pillows, accompanied by stylish accent chairs. A coffee table sits centrally on a textured rug, while a large window bathes the space in natural light, showcasing decorative plants and contemporary wall art.
Apartment in Chicago
4.92 out of 5 average rating, 386 reviews

Bright, Modern Apartment in a Vintage Greystone

Guest favorite
A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.
Apartment in Chicago
4.89 out of 5 average rating, 244 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Top guest favorite
The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.
Apartment in Chicago
4.98 out of 5 average rating, 123 reviews

Belmont Pleasures - hot tub / arcade gaming room

Superhost
A distinctive brick building is featured, showcasing an art deco facade and ornate fire escapes. Large windows line the upper floors, while a storefront with glass doors occupies the ground level, displaying signage for the South Loop Club. Urban surroundings are visible.
Apartment in Chicago
4.71 out of 5 average rating, 35 reviews

South Loop Studio Hotel(205)

Guest favorite
A spacious studio includes a queen-size bed with blue and white bed linens, a comfortable armchair, and a small dining table. A flat-screen TV is mounted on the wall, and a large window is adorned with dark curtains, allowing natural light to fill the room.
Apartment in Chicago
4.84 out of 5 average rating, 644 reviews

Great Location! Gold Coast! 07

Guest favorite
A well-equipped kitchen is visible, featuring modern appliances and cabinetry. A comfortable seating area includes a dark sofa with accent pillows and a matching ottoman. Soft lighting creates a calming ambience, complemented by a decorative wall art piece above the couch.
Apartment in Chicago
5 out of 5 average rating, 13 reviews

Chicago Addison St. 1 bed/1 bath condo, Garden Lvl

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Downtown Chicago condo rentals

Top guest favorite
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.
Condo in Chicago
4.99 out of 5 average rating, 285 reviews

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

Guest favorite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in Chicago
4.96 out of 5 average rating, 119 reviews

Lovely top floor 2BR/2BA, steps from everything!

Superhost
A bright studio apartment features a spacious bed covered with a blue blanket. A light-colored sofa is positioned next to a closet, while a doorway leads to a modern bathroom. Large windows allow natural light to fill the space.
Condo in Chicago
4.86 out of 5 average rating, 119 reviews

Cabin 308 at 747 Lofts

Guest favorite
A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.
Condo in Oak Park
4.94 out of 5 average rating, 248 reviews

Picture Perfect 3Bed Steps from Train and FLW

Guest favorite
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.
Condo in Chicago
4.94 out of 5 average rating, 130 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Superhost
A vibrant living area is highlighted by a deep blue sofa and a colorful area rug. A large wall-mounted television is positioned across from the seating, and modern artwork decorates the walls. The adjoining kitchen is visible in the background, showcasing sleek cabinetry and new appliances.
Condo in Chicago
4.84 out of 5 average rating, 203 reviews

3D Tour! Designer Condo near Logan Square

Guest favorite
A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in Chicago
4.92 out of 5 average rating, 350 reviews

Susie's Space. 2BR easy parking & pet friendly

Guest favorite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in Chicago
4.98 out of 5 average rating, 167 reviews

Spacious 4 Bedroom Condo

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Other great vacation rentals in Downtown Chicago

Guest favorite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in Chicago
4.99 out of 5 average rating, 110 reviews

Lovely Garden Studio in Chicago

Guest favorite
A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Sunny Penthouse - Oakwood Beach

Guest favorite
An open living space features soft bamboo flooring, accented by a modern couch. Natural light streams through a skylight and two gabled windows. A decorative wall clock adds charm, while a potted plant complements the serene atmosphere. The adjacent sleeping areas are visible in the background.
Guest suite in Chicago
4.93 out of 5 average rating, 14 reviews

Urban Penthouse- Lux Rain Shower, Church View

A modern high-rise building showcases a sleek façade of glass and steel, reflecting the surrounding urban environment. The structure features multiple floors with large windows, providing ample natural light. Trees line the street, contributing to the vibrant city atmosphere.
Apartment in Chicago
4.73 out of 5 average rating, 133 reviews

Kasa | Studio Near Museum Campus | South Loop

Guest favorite
An open living space features a sleek kitchen with modern appliances and a granite island with stools. Natural light fills the room through tall windows, illuminating the dining area with a round table and black chairs. A comfortable gray sofa is positioned nearby, enhancing the inviting layout.
Apartment in Chicago
5 out of 5 average rating, 15 reviews

Panoramic 2BR Penthouse in the Sky | Roof Deck

A spacious living area features large windows allowing natural light to fill the room. A white sectional sofa is adorned with textured pillows and a throw. A circular table with two upholstered chairs complements a soft area rug, while indoor plants add a touch of greenery.
Apartment in Chicago
5 out of 5 average rating, 4 reviews

Modern Design 3 Bedroom Dandelion Apartment

A spacious bedroom is highlighted by a large bed with crisp white linens. Flanking the bed are two wooden nightstands, each topped with unique lamps. A cozy bench is positioned at the foot of the bed, and large windows provide natural light.
Apartment in Chicago
4.7 out of 5 average rating, 293 reviews

Sonder Onterie | King Studio Apartment

A spacious living area features a sectional sofa with a modern design, paired with a coffee table. Large windows offer expansive city views, while a patterned rug adds warmth. Decorative elements include a glass bar cart and various art pieces, contributing to a contemporary ambiance.
Apartment in Chicago
5 out of 5 average rating, 3 reviews

Modern 2BR South Loop Apt, McCormick & Wintrust

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Frequently Asked Questions

  • How is the weather in Downtown Chicago?

    Downtown Chicago experiences a diverse climate. Summers can be hot, typically reaching 85°F (29°C), while winter temperatures can drop to around 20°F (-6°C), often accompanied by snow. The transitional seasons, spring and fall, offer more moderate weather, making them pleasant times to visit.

  • What are some of the best things to do in Downtown Chicago?

    There's no shortage of activities in Downtown Chicago. Explore the Art Institute of Chicago, walk alongside the Chicago River, or enjoy a stroll in Millennium Park. You can also marvel at the city's skyline from the Willis Tower's Skydeck or take a boat cruise on Lake Michigan.

  • What is the best time of year to visit Downtown Chicago?

    The summer months, from June to August, are a great time to explore Downtown Chicago as the city comes alive with a range of cultural events including Lollapalooza, the Chicago Air and Water Show, and the Jazz Festival. However, the city also offers distinctive charm during the winter season, with events like the Magnificent Mile Lights Festival and the Winter WonderFest.

  • What are the best places to stay in Downtown Chicago?

    Guests enjoy staying in several areas in Downtown Chicago. The Loop, Chicago's central business district, is known for its bustling atmosphere and close proximity to many attractions. River North, with its art galleries and fashion outlets, is also popular. Streeterville, near Navy Pier and Magnificent Mile, is another preferred location.

  • What are the best places to visit in Downtown Chicago?

    There are many popular places to visit in Downtown Chicago. These include the Navy Pier, with its iconic Ferris wheel, the Art Institute of Chicago, known for its impressive collection, and the historic Chicago Theatre. Don't miss a walk down the Magnificent Mile for shopping and dining.

  • What are some hiking trails in Downtown Chicago?

    While Downtown Chicago is primarily urban, there are lovely trails to explore. The 18-mile (29 km) Lakefront Trail along Lake Michigan is a favorite among locals and visitors. The Chicago Riverwalk also provides a scenic urban hike through the heart of the city.

  • What are some family activities to do in Downtown Chicago?

    Families in Downtown Chicago can explore a multitude of engaging activities. Visit the Shedd Aquarium or the Field Museum for an educational outing, enjoy outdoor fun at Maggie Daley Park, or discover the wonders of space at the Adler Planetarium.

  • What are some of the best day trip ideas in Downtown Chicago?

    For day trips, consider exploring the natural beauty of the Chicago Botanic Garden or the historical architecture in Oak Park, both within a short drive from Downtown. Alternatively, the Indiana Dunes National Park, 50 miles (80 km) away, offers an escape to nature.

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