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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

Superhost
A modern living room features navy blue sofas arranged around a large area rug. A wooden entertainment center with a mounted TV displays the Netflix logo. Floor-to-ceiling windows offer views of the city, and a tall plant adds a touch of greenery.
Apartment in Chicago
4.75 out of 5 average rating, 4 reviews

Luxury 1BR Michigan Suite Near McCormick | Parking

Top guest favorite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in Chicago
5 out of 5 average rating, 37 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

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, 57 reviews

Pilsen Modern Chic Retreat

Guest favorite
A well-lit living area features two comfortable sofas and a wooden coffee table. Large windows allow natural light to fill the space, complemented by neutral-colored walls. A dining table is positioned in the foreground, while a door leads to a separate bedroom area.
Apartment in Chicago
4.91 out of 5 average rating, 220 reviews

Homey 2BR-2BA steps from The Bean & Michigan Ave

Superhost
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
4.84 out of 5 average rating, 25 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

Guest favorite
A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.
Apartment in Chicago
4.97 out of 5 average rating, 29 reviews

Skyline Oasis: City & Lake Views

Guest favorite
A comfortable living area features a modern sofa, complemented by two stylish ottomans. A large window with sheer curtains provides natural light, while a wall-mounted TV is positioned for easy viewing. A piece of wall art adds a contemporary touch.
Apartment in Chicago
5 out of 5 average rating, 17 reviews

Chicago Luxury Long Term 30+

Top guest favorite
An open concept living area is captured, showcasing a modern kitchen with stainless steel appliances and gray cabinetry. A cozy sofa with textured cushions faces a large window, allowing natural light to fill the space. A sleek dining table is positioned nearby.
Apartment in Chicago
5 out of 5 average rating, 47 reviews

Fantastic West Loop 2 bedroom

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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

Top guest favorite
A dining area showcases a long wooden table surrounded by six metal wire chairs. Natural light enters through two large windows, highlighting the warm wood finishes of the space. A sideboard with glass cabinets is visible against the wall, complemented by decorative art pieces.
Condo in Chicago
4.98 out of 5 average rating, 380 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Guest favorite
A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.
Condo in Evanston
4.95 out of 5 average rating, 111 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in Chicago
4.97 out of 5 average rating, 151 reviews

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

Superhost
This studio apartment features a modern kitchen with wood cabinetry and black appliances. A small dining table with curved blue chairs and a vibrant orange sofa create an inviting living space. Natural light enters through large windows, illuminating the minimalist decor.
Condo in Chicago
4.81 out of 5 average rating, 157 reviews

Cabin 207 at 747 Lofts

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, 501 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, 106 reviews

Wicker Park/Bucktown condo with large balcony

Top guest favorite
A spacious living area is filled with natural light from multiple windows. A comfortable sofa, adorned with a decorative pillow, is positioned in the corner. A dining table and chair are visible in the background, with greenery seen through the windows.
Condo in Chicago
4.97 out of 5 average rating, 165 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

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Other great vacation rentals in Downtown Chicago

Guest favorite
A modern living area is showcased with a cozy sectional couch in a warm orange hue. A flat-screen TV is mounted above a sleek fireplace, framed by dark paneling. Two round mirrors and side tables with lamps are positioned on either side, enhancing the space's contemporary design.
Home in Chicago
5 out of 5 average rating, 12 reviews

The Modern Muse of Chicago! Close to everything!

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, 113 reviews

Lovely Garden Studio in Chicago

Top guest favorite
The exterior of a modern three-story bungalow is showcased, featuring a mix of brick and dark paneling. A neatly landscaped front yard includes a path leading to the entryway, flanked by lush greenery and decorative stones. The structure retains a contemporary architectural style.
Home in Berwyn
5 out of 5 average rating, 17 reviews

The Architectural Haven

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, 12 reviews

Sunny Penthouse - Oakwood Beach

A modern lounge area features a spacious blue sectional sofa with decorative pillows, framed artwork on the wall, and a coffee table. An expansive view of the city skyline and lake is visible through large windows. A sleek kitchen showcases stainless steel appliances and contemporary cabinetry, while a stylish bedroom includes a four-poster bed and elegant accents.
Apartment in Chicago
5 out of 5 average rating, 35 reviews

Lux Loop Retreat: Amazing Views, Free Parking

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.
Apartment in Chicago
4.8 out of 5 average rating, 304 reviews

Kasa | Studio, Walk to Grant Park | South Loop

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
4.72 out of 5 average rating, 306 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, 4 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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