Some info has been automatically translated. Show original language
Airbnb your place

Vacation rentals in Downtown Chicago

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

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 vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.
Apartment in Chicago
4.84 out of 5 average rating, 293 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Guest favorite
A spacious common area features large windows that allow plenty of natural light to fill the room. A modern entertainment unit is placed against a white brick wall, complemented by a comfortable sectional sofa and a round coffee table on a textured rug.
Apartment in Chicago
4.93 out of 5 average rating, 190 reviews

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Guest favorite
A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.
Apartment in Chicago
4.74 out of 5 average rating, 330 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Top guest favorite
A spacious living area features a sectional sofa with textured throw blankets, complemented by a vibrant area rug. A contemporary piece of wall art adds color to the neutral walls, while natural light enters through a nearby window. The entrance to the apartment is visible in the background.
Apartment in Chicago
4.95 out of 5 average rating, 21 reviews

Spacious New Studio: Kitchenette, Laundry & Office

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 modern kitchen area features open wooden shelves displaying decorative items, including a framed picture and potted greenery. Below, a stainless steel sink with a wooden cutting board is positioned next to glassware and a collection of dishware. The countertop is composed of light wood.
Apartment in Forest Park
5 out of 5 average rating, 6 reviews

Darling Flat Walk to OP

Superhost
A narrow hallway is depicted, leading to a bright living area with large windows offering views of the city. A rug is positioned on the wooden floor, and a small dining table with chairs is visible in the background. A television is mounted on the opposite wall.
Apartment in Chicago
4.9 out of 5 average rating, 30 reviews

Chic 1 BR w California King Bed |Heart of Downtown

Superhost
A spacious bedroom is equipped with two queen size beds dressed in soft gray bedding. Natural light filters through a large window, complementing the neutral-toned walls. A desk with a lamp and a mirror is placed against the wall, providing a functional workspace.
Apartment in Chicago
4.9 out of 5 average rating, 238 reviews

FREE PARKING Large 2BR2BA by Millenium Park

Show all

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

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 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, 113 reviews

Your perfect place looks like?

Superhost
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
4.84 out of 5 average rating, 205 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, 151 reviews

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

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 spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in Chicago
4.92 out of 5 average rating, 353 reviews

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

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

Show all

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
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 comfortable living area features a dark sectional sofa positioned around a round coffee table. A wall-mounted television is displayed above a modern electric fireplace. Natural light enters through a small window, while a plant and a workspace are subtly included in the room.
Guesthouse in Chicago
5 out of 5 average rating, 4 reviews

Garden Retreat in Historic Bronzeville

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

Guest favorite
A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.
Home in Chicago
4.96 out of 5 average rating, 26 reviews

Big house in the BEST Location!

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
4.71 out of 5 average rating, 302 reviews

Sonder Onterie | King Studio Apartment

Top guest favorite
An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.
Guesthouse in Chicago
5 out of 5 average rating, 10 reviews

Andersonville Luxury Pool Escape

Show all

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

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