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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

Guest favorite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Apartment in Chicago
4.95 out of 5 average rating, 55 reviews

Pilsen Modern Chic Retreat

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
4.93 out of 5 average rating, 30 reviews

Luxury Loop Loft

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

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, 122 reviews

Belmont Pleasures - hot tub / arcade gaming room

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, 290 reviews

Sonder Onterie | King Studio Apartment

Guest favorite
A modern living area features a comfortable sectional sofa on a vibrant red rug. A minimalist coffee table sits in front of a mounted television, framed by a black shelving unit filled with books. Large windows allow natural light to fill the space, complemented by stylish artwork.
Apartment in Chicago
4.94 out of 5 average rating, 157 reviews

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6

Guest favorite
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, 14 reviews

Apartment on the Lake

A modern high-rise building is showcased, featuring a glass and brick exterior. The building has multiple stories with large windows, providing a contemporary look. Surrounding trees are visible along the street, contributing to the urban landscape.
Apartment in Chicago
4.81 out of 5 average rating, 511 reviews

Kasa | 2BD Near McCormick Place | South Loop

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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, 284 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!

Guest favorite
A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.
Condo in Chicago
4.89 out of 5 average rating, 161 reviews

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

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
4.92 out of 5 average rating, 169 reviews

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

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

Top guest favorite
A stylish living area features a white sofa with bright yellow cushions, set against exposed brick walls. A flat-screen TV is positioned above a modern fireplace. A wooden staircase leads to the upper level, while a kitchen bar with dark countertops is visible on the left.
Condo in Chicago
4.95 out of 5 average rating, 498 reviews

Unique Lincoln Park Duplex Apt

Guest favorite
A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.
Condo in Chicago
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

Superhost
A modern teal sectional sofa with a tufted design is positioned next to a round marble coffee table. A white fur pillow and a patterned throw are draped on the couch. A black and white cowhide rug adds texture to the wooden floor.
Condo in Chicago
4.76 out of 5 average rating, 310 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

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Other great vacation rentals in Downtown Chicago

Top guest favorite
A landscaped garden patio is illuminated by soft lighting, highlighting a central tree and neatly arranged plants. An outdoor dining table with several chairs stands on stone paving, creating a welcoming space for relaxation. The brick facade of the coach house is visible in the background.
Guesthouse in Chicago
4.98 out of 5 average rating, 45 reviews

Solar Victorian MCM Coach House

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

Top guest favorite
A modern living area features a spacious gray sofa complemented by patterned pillows. A sleek coffee table occupies the center, while a contemporary side table holds a small plant and lamp. Large glass doors open to the outdoor patio, allowing natural light to fill the space.
Apartment in Chicago
4.93 out of 5 average rating, 30 reviews

Stunning Duplex Condo #1 - Downtown River North

Guest favorite
A modern kitchen featuring stainless steel appliances, including a refrigerator and gas range. A spacious island with white marble countertop is surrounded by light-colored chairs. Above, stylish pendant lights provide ample illumination, while the open layout invites natural light from adjacent glass doors.
Home in Chicago
4.96 out of 5 average rating, 74 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

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

Superhost
A spacious bedroom features a king bed adorned with a decorative quilt and multiple pillows. The room is complemented by hardwood floors, an array of artworks on the walls, and a comfortable seating area with a small table. Large windows invite natural light into the space.
Private room in Chicago
4.88 out of 5 average rating, 217 reviews

Chicago Speakeasy-Style Loft (Room 2B)

Superhost
The guestroom features a spacious bed with plush bedding, complemented by a green upholstered headboard. Two armchairs sit next to a table by the window, allowing for enjoyment of city views. Light from the window enhances the warm tones throughout the room.
Hotel room in Chicago
5 out of 5 average rating, 3 reviews

Newly reno’d king room with sweet city views

Guest favorite
A modern guest room features a spacious bed with crisp white linens and a padded headboard. Natural light is filtered through a large window with an upper roller shade. A desk and chair are situated near the window, complementing the contemporary decor.
Hotel room in Chicago
4.84 out of 5 average rating, 19 reviews

Modern design and smart amenities

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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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