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Vacation rentals in Downtown Chicago

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Downtown Chicago vacation rentals

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

Downtown Chicago apartment rentals

Superhost
A modern kitchen area features a compact island with a sleek sink and metallic fixtures. A round dining table with black-and-white polka dot chairs sits against a light pink floral accent wall. Warm lighting enhances the inviting ambience of the space.
Apartment in Chicago
4.83 out of 5 average rating, 354 reviews

*Entire City Apartment 1 block to Train Park Free

Guest favorite
The living space features exposed brick walls that blend with modern kitchen elements. A spacious light-colored couch is arranged around a round black coffee table on a patterned area rug. A wall-mounted TV is visible, alongside sleek kitchen appliances, enhancing the contemporary design.
Apartment in Chicago
5 out of 5 average rating, 24 reviews

Full Luxury Home in Wrigleyville

Guest favorite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Chicago
4.95 out of 5 average rating, 134 reviews

Chic retreat near the best of Lakeview & Wrigley

Guest favorite
A spacious living area features a large sectional sofa set around a modern coffee table with a textured surface. Natural light floods in through large windows, illuminating a neutral color palette. Decorative plants and stylish furniture pieces enhance the contemporary design.
Apartment in Chicago
4.89 out of 5 average rating, 62 reviews

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Guest favorite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in Chicago
4.92 out of 5 average rating, 134 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

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
4.87 out of 5 average rating, 122 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Top guest favorite
The living room features a stone accent wall with a mounted flat-screen TV centered above a fireplace. Dark blue sofas are arranged around a light-colored ottoman, while a patterned area rug extends across the dark wood floor. Natural light enters through the nearby window.
Apartment in Chicago
4.98 out of 5 average rating, 257 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

Guest favorite
A modern living area is illuminated by natural light from large floor-to-ceiling windows. A comfortable gray sofa sits against one wall, accompanied by a coffee table. The open kitchen features a sleek marble countertop and stainless steel refrigerator, with minimalistic decor enhancing the ambiance.
Apartment in Chicago
4.9 out of 5 average rating, 68 reviews

River North | Private Balcony With In&Out Parking

Downtown Chicago house rentals

Top guest favorite
The exterior of a modern two-story bungalow is showcased, featuring gray siding and stone accents. A staircase leads to the front entrance, bordered by planters with greenery. Decorative lighting elements are mounted on either side of the entryway, adding to the home's architectural appeal.
Home in Berwyn
5 out of 5 average rating, 20 reviews

The Architectural Haven

Top guest favorite
Home in Chicago
4.98 out of 5 average rating, 111 reviews

Flat in Lincoln Park 2-Flat Central to Everything

Guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Chicago
4.95 out of 5 average rating, 138 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

Guest favorite
An outdoor area features a partially enclosed space highlighted by warm wood paneling and a large window. A grill is positioned against the wall, with a concrete floor leading toward a well-lit interior visible through glass doors.
Home in Chicago
4.96 out of 5 average rating, 181 reviews

Chicago River House -BBQ Oasis now open!

Top guest favorite
A striking, two-story brick house is presented with a dark facade and a prominent red door. Large windows provide natural light, while a set of stairs leads up to the entrance. The outdoor area features a clean pathway and surrounding minimal landscaping.
Home in Chicago
4.92 out of 5 average rating, 288 reviews

Cool Quiet Coach House, Private Access + Patio

Top guest favorite
A row of multi-story brick buildings is presented along a tree-lined sidewalk. Each unit features large windows adorned with decorative elements. Soft illumination from the interiors creates a welcoming ambiance as greenery frames the entrance, and a secured fence borders the property.
Home in Chicago
4.98 out of 5 average rating, 277 reviews

Wrigleyville Southport Studio

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
4.98 out of 5 average rating, 161 reviews

Retro Modern Bungalow | free parking | fire pit

Guest favorite
A modern living area features a dark leather sofa adorned with blue and cream cushions. A stylish coffee table with geometric design sits atop a decorative area rug. A large black and white photograph of a city skyline is displayed on the wall, complemented by a floor lamp and a side table.
Home in Chicago
4.95 out of 5 average rating, 415 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Downtown Chicago condo rentals

Guest favorite
A spacious living room features floor-to-ceiling windows that allow ample natural light, showcasing views of the city. A large gray sectional sofa is complemented by a cozy yellow armchair. A wall-mounted television is situated above a built-in fireplace, with a private balcony visible through sliding doors.
Condo in Chicago
4.95 out of 5 average rating, 124 reviews

Your perfect place looks like?

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, 164 reviews

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

Guest favorite
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
4.85 out of 5 average rating, 222 reviews

3D Tour! Designer Condo near Logan Square

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, 157 reviews

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

Guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Chicago
4.98 out of 5 average rating, 126 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

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, 163 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, 509 reviews

Unique Lincoln Park Duplex Apt

Guest favorite
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, 316 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

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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