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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
Pet friendly
Gym
BBQ grill

Pet-friendly vacation rentals in Downtown Chicago

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, 114 reviews

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

Guest favorite
The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.
Guest suite in Chicago
4.94 out of 5 average rating, 419 reviews

Peaceful Portage Park Apartment

Guest favorite
The living area features exposed brick walls and large windows offering natural light. A comfortable couch is positioned near a vintage-style pool table, complemented by a light-colored coffee table and decorative accents. A mounted flat-screen TV and a modern fireplace enhance the inviting ambiance.
Loft in Chicago
4.92 out of 5 average rating, 248 reviews

Stunning Old Town Penthouse with Private Rooftop

Guest favorite
An outdoor seating area is presented with comfortable lounge chairs facing a lush green garden. Large glass doors lead into a spacious indoor area, enhancing the flow between indoor and outdoor spaces. Modern architectural lines create a clean and inviting environment.
Apartment in Chicago
4.98 out of 5 average rating, 101 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

Guest favorite
A modern living area showcases a comfortable gray sofa with decorative pillows. A sleek coffee table is positioned in front of the sofa, accompanied by a small bowl holding a plant. Bright natural light filters through large windows, highlighting the contemporary design.
Apartment in Chicago
4.86 out of 5 average rating, 113 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Top guest favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.99 out of 5 average rating, 143 reviews

Retro Modern Bungalow (fire pit • free parking)

Guest favorite
A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.
Condo in Chicago
4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

Guest favorite
A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.
Guest suite in Chicago
4.95 out of 5 average rating, 122 reviews

Eddy Street Upstairs Apartment

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Downtown Chicago apartment rentals

Top guest favorite
Two red chairs with vibrant, embroidered cushions are positioned in a contemporary living space. A large leafy plant is placed nearby, complementing the colorful decor. A blue door and a piece of wall art featuring abstract imagery add character to the area.
Apartment in Chicago
5 out of 5 average rating, 11 reviews

2B Midcentury Artist Loft w King Bed

Guest favorite
A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.
Apartment in Chicago
5 out of 5 average rating, 8 reviews

Designer Garden Unit in Bridgeport

Guest favorite
A well-lit bedroom features a spacious bed with a blue patterned comforter. Large windows allow natural light to fill the room, and a simple desk with a chair is positioned near the window. Soft carpeted flooring complements the modern decor.
Apartment in Chicago
4.96 out of 5 average rating, 27 reviews

Luxury Loop Loft

Guest favorite
An open living space is divided into areas for relaxation and sleeping. A large bed with soft linens is showcased next to a contemporary TV stand. A sectional sofa is positioned to create a cozy sitting area, complementing the natural light filtering through the curtains.
Apartment in Chicago
4.74 out of 5 average rating, 324 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Superhost
A spacious room features a queen-size bed with crisp white bedding. A plush purple sofa sits in front of large windows, dressed with sheer curtains that allow natural light to filter in. A glass coffee table rests on a soft area rug, enhancing the modern decor.
Apartment in Chicago
4.68 out of 5 average rating, 85 reviews

McCormick Place Studio/parking/sleeps up to 4

Superhost
A concrete pier extends toward the shimmering waters of Lake Michigan, with sunlight reflecting off the surface. The edge of the pier is visible, while the surrounding buildings are partially seen in the background against a clear blue sky.
Apartment in Chicago
5 out of 5 average rating, 9 reviews

Apartment on the Lake

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
4.83 out of 5 average rating, 638 reviews

Great Location! Gold Coast! 07

Superhost
An open-concept living area features large windows that offer skyline views. A comfortable sofa and an orange accent chair are complemented by a modern dining table surrounded by stylish chairs. A neutral area rug adds warmth to the hardwood floor.
Apartment in Chicago
4.67 out of 5 average rating, 15 reviews

Walk Everywhere! 5 mins to Magnificent Mile, River

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Downtown Chicago condo rentals

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, 278 reviews

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

Guest favorite
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in Chicago
4.85 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

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, 160 reviews

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

Superhost
A modern kitchen boasts a stainless steel gas range and sleek countertops. A single-serve coffee maker is positioned next to a toaster. A carousel holder for coffee pods sits nearby, accompanied by a glass jar filled with creamers and a small container for sugar.
Condo in Chicago
4.88 out of 5 average rating, 118 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

Guest favorite
A stainless steel spice rack is displayed on a textured granite countertop. The rack holds various spice jars in a circular arrangement, labeled with names such as 'Italian Seasoning' and 'Oregano.' A sleek electric wine opener rests nearby, featuring a modern design.
Condo in Chicago
4.87 out of 5 average rating, 127 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Guest favorite
The duplex layout reveals an open living area beneath a stylishly designed lofted bedroom. Light wood flooring and a cozy seating arrangement are complemented by a textured brick wall. Large windows bring in natural light, while the kitchen area is visible with modern fixtures and seating.
Condo in Chicago
4.95 out of 5 average rating, 494 reviews

Unique Lincoln Park Duplex Apt

Superhost
The exterior of the building showcases a brick facade with large windows, framed by a vibrant blue awning featuring '747 Lofts.' The corner location is highlighted by a striking urban skyline in the background under a colorful twilight sky.
Condo in Chicago
4.76 out of 5 average rating, 149 reviews

Cabin 302 at 747 Lofts

Guest favorite
A modern kitchen displays sleek dark cabinetry and stainless steel appliances. An island countertop is accompanied by transparent bar stools, while a dining area features a black table with tall stools. A light pastel wall is adorned with a playful accent, creating an inviting space.
Condo in Chicago
4.88 out of 5 average rating, 386 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

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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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