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Downtown Chicago vacation rentals

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Vacation rentals for every style

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Popular amenities for Downtown Chicago vacation rentals

Self check-in
Monthly stays
Gym
BBQ grill
Laptop-friendly workspace

Apartment rentals in Downtown Chicago

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, 8 reviews

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

Superhost
A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.
Apartment in Chicago
4.92 out of 5 average rating, 143 reviews

Modern 3BR with Private Rooftop & Free Parking

Guest favorite
The living area is furnished with a gray sofa adorned with patterned cushions, positioned next to a natural wood coffee table. A potted plant and a decorative mirror enhance the space. Two windows allow natural light to brighten the room.
Apartment in Chicago
4.95 out of 5 average rating, 152 reviews

Cute, Clean, Cozy Apartment in Pilsen

Guest favorite
A spacious living room features large floor-to-ceiling windows that invite natural light, revealing modern furnishings. A cozy sectional and accent chairs are arranged around a coffee table. The open layout connects to a dining area and a chef's kitchen, enhancing the inviting atmosphere.
Apartment in Chicago
4.92 out of 5 average rating, 75 reviews

Luxury Loft Collection 01 - Terrace - River North

Guest favorite
A contemporary living room features a tufted brown leather sofa and two light blue armchairs. A round coffee table is centered in front of a sleek fireplace, which is surrounded by a textured black wall. Open shelves display decorative items, with natural light filtering through blue drapes.
Apartment in Chicago
4.94 out of 5 average rating, 80 reviews

Fulton House #1 (2bd/ 1ba)

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, 68 reviews

Loop Loft-Subway & Art Institute

Guest favorite
A spacious living area showcases a blend of modern comfort and rustic charm. Exposed brick walls complement sleek furniture, including a large sofa and two orange armchairs. A flat-screen TV is mounted on the wall, with a circular coffee table in front. Dining chairs surround a nearby table.
Apartment in Chicago
4.91 out of 5 average rating, 22 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

Guest favorite
A cozy living area features a plush gray sofa accompanied by light-colored ottomans. A glass coffee table sits on a multicolored rug, adding warmth to the space. Natural light filters through sheer curtains, enhancing the modern design complemented by a mounted flat-screen television.
Apartment in Berwyn
5 out of 5 average rating, 5 reviews

NEW Jade Haven in Berwyn/Riverside

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Condo rentals in Downtown Chicago

Top guest favorite
A charming brick building is surrounded by lush greenery and a well-maintained garden. A gated entrance leads to a set of steps that rise to the main entrance. The bright exterior is complemented by large windows, indicating a welcoming atmosphere in a safe neighborhood.
Condo in Chicago
4.99 out of 5 average rating, 284 reviews

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

Guest favorite
A spacious rooftop deck is adorned with a large sectional sofa in blue upholstery, offering panoramic views of the surrounding skyline and Lake Michigan. Glass railings enhance the open atmosphere, providing an unobstructed sightline to the water and buildings in the distance.
Condo in Chicago
4.89 out of 5 average rating, 161 reviews

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Top guest favorite
A wooden patio area features a central fire table surrounded by four cushioned seating chairs. Glasses of wine rest on the tabletop, inviting relaxation. A partial view of neighboring roofs is visible in the background, providing a sense of privacy in this outdoor space.
Condo in Chicago
4.97 out of 5 average rating, 151 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Guest favorite
A cozy enclosed porch features large windows allowing natural light to fill the space. Two teal lounge chairs are positioned beside a small table, with colorful decorative elements scattered throughout. A patterned rug adds warmth to the floor, creating a relaxed atmosphere.
Condo in Chicago
4.92 out of 5 average rating, 349 reviews

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

Guest favorite
The brick building features a modern facade with large windows allowing for ample natural light. A well-maintained garden area is enclosed by a black iron fence. The entrance is marked by a stylish door with contemporary lighting fixtures on either side.
Condo in Chicago
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

Top guest favorite
A living room displays a large, vibrant artwork featuring a beach scene, complemented by a modern flat-screen TV mounted on the wall. Natural light filters through two windows with wooden blinds, casting soft shadows on the floor, which is adorned with a decorative area rug.
Condo in Chicago
4.97 out of 5 average rating, 809 reviews

Great location. Free parking.

Superhost
An outdoor deck area is equipped with two black woven lounge chairs and a glass table, surrounded by wooden railing and greenery. The setting offers a relaxed space for guests to enjoy time outdoors, with exposed brick walls in the background.
Condo in Chicago
4.76 out of 5 average rating, 309 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Guest favorite
An outdoor space features a wooden deck leading to a staircase, surrounded by exposed brick walls. A circular fire pit is centered among four chairs, with a hot tub and seating area visible in the background. Green shrubs accent the concrete patio.
Condo in Chicago
4.94 out of 5 average rating, 211 reviews

Private hot tub - King bed suite - Free parking

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Boutique hotel rooms in Downtown Chicago

Superhost
An entertainment area features a foosball table and a billiards table, inviting relaxation and socialization. Surrounding seating areas with tables are available for games or gatherings. Soft lighting from overhead fixtures creates a comfortable environment for guests to enjoy leisure activities.
Hotel room in Chicago
4.82 out of 5 average rating, 33 reviews

King Room in Theatre District

Superhost
A recreational area is presented, featuring a foosball table and a billiards table. The space includes comfortable seating arrangements and a dining table, illuminated by pendant lighting. The walls are adorned with artwork, creating an engaging atmosphere for social gatherings.
Hotel room in Chicago
4.75 out of 5 average rating, 63 reviews

Charming King Bedroom in Loop

Superhost
The exterior of the building is shown, featuring a clear 'HOTEL' sign prominently displayed. A tree adds natural elements to the scene, while a sidewalk is visible with people walking nearby, indicating a bustling urban environment.
Hotel room in Chicago
New place to stay

Clean & Modern • Central Location • Free Coffee!

Superhost
An outdoor rooftop space features comfortable seating arranged in a conversational layout, surrounded by greenery. A wooden pergola provides shade over the area, while decorative cushions add color. The deck's wooden flooring complements the serene setting, creating an inviting space for relaxation.
Hotel room in Chicago
4.67 out of 5 average rating, 6 reviews

1BD/1BA steps away from local shops, entertainment

A polished grand piano is positioned in a well-lit corner, featuring an open lid that reveals the strings inside. The surrounding area is decorated with slender plants, and the light wooden floor reflects the piano's elegant design.
Hotel room in Chicago
4.94 out of 5 average rating, 18 reviews

Lincoln Park Guest House

Superhost
A recreational area features a foosball table and a billiards table, complemented by a seating area with dining chairs. Soft lighting from pendant fixtures creates a relaxed atmosphere. A variety of games and books are visible on nearby shelves, inviting guests to enjoy leisure activities.
Hotel room in Chicago
4.79 out of 5 average rating, 14 reviews

Private King Room in Theatre District

Superhost
A modern communal space is highlighted by several round wooden tables and comfortable seating. Soft lighting illuminates the area, where a large television and shelves filled with books are visible. Large windows allow natural light to fill the room, creating a bright atmosphere.
Hotel room in Chicago
4.64 out of 5 average rating, 45 reviews

Private King Bedroom in Heart of Downtown Chicago

A grand lobby is highlighted by ornate ceilings and detailed arches, creating an upscale ambiance. Elegant seating arrangements consist of plush chairs and stylish tables, all set against polished marble floors. Decorative plants and floral displays add a touch of vibrancy to the space.
Hotel room in Chicago
4.43 out of 5 average rating, 826 reviews

Standard Double Room

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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.

Destinations to explore

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  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago