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Chicago vacation rentals

Book unique condos, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Chicago

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Entire rental unit · Chicago
Floor to Ceiling Windows 1 Bedroom Corner Unit
Keep it simple at this peaceful and centrally-located place. Just come with your bags and enjoy a beautiful stay with expanding views of the city. Walking distance from multiple fan favorites and close to public transport.
ﺩ.ﺇ740 per night
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Hotel room · Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
Freehand Hotel is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe designed by Roman & Williams in River North Chicago, just two blocks from the Magnificent Mile. Walking distance to public transportation, Navy Pier, and more. $10 nightly resort fee plus tax paid at the property For long-term stays, guests must move rooms about every 30 days.
ﺩ.ﺇ699 per night
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Hotel room · Near North Side
Traveler's Dream - 1 bed in a shared bedroom
Join us at Freehand Chicago Hotel for your travels in Chicago. Perfect for travelers here too long for a traditional hotel or for just 1 night; make us your home away from home. This listing is for one bunk for one person in a shared mixed/co-ed room with 4 bunks (up to 3 roommates). We have many options such as private standard rooms and private quad rooms. Please send us a message with any questions. $5 nightly resort fee plus tax paid at the property
ﺩ.ﺇ192 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park474 locals recommend
Photo of Navy Pier
Navy Pier307 locals recommend
Photo of Willis Tower
Willis Tower154 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago439 locals recommend
Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago191 locals recommend

Downtown Chicago vacation rentals

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SUPERHOST
Private room · Lake View
2 Twin beds with Private Bathroom
ﺩ.ﺇ147 per night
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Private room · Near South Side
Spectacular Downtown High Rise Extraordinary view
ﺩ.ﺇ118 per night
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Private room · Logan Square
P8. Next to Downtown! Best location! Small bedroom
ﺩ.ﺇ190 per night
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SUPERHOST
Entire loft · Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
ﺩ.ﺇ416 per night
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Private room · South Chicago
Room B4
ﺩ.ﺇ92 per night
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SUPERHOST
Private room · Englewood
Living in a dream (unit 2 room #5)
ﺩ.ﺇ84 per night
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Private room · Chicago
City View near Downtown Chicago Sox & Chinatown
ﺩ.ﺇ177 per night
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SUPERHOST
Entire rental unit · West Town
Great location. Free parking.
ﺩ.ﺇ367 per night
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SUPERHOST
Entire rental unit · West Town
Cabin #207 at 747 Lofts
ﺩ.ﺇ242 per night
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Entire loft · Berwyn
PrivateTudor in-law suite
ﺩ.ﺇ359 per night
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Entire rental unit · West Loop
5-min to Downtown Chicago, near Pay Parking | 1BR
ﺩ.ﺇ246 per night
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SUPERHOST
Entire loft · Irving Park
Industrial Style Chicago Loft with FREE parking
ﺩ.ﺇ331 per night

Chicago summer vacation rentals

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Private room · Near South Side
Stunning downtown High Rise apartment amazing view
ﺩ.ﺇ349 per night
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Private room · Chicago
Private Bedroom near Downtown Chicago Chinatown
ﺩ.ﺇ140 per night
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SUPERHOST
Private room · Lake View
Bright Room with a Garden View
ﺩ.ﺇ290 per night
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SUPERHOST
Private room · Oak Park
warm comfortable home with lots to offer
ﺩ.ﺇ171 per night
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SUPERHOST
Private room · Chicago
B5Hotel quality room near Downtown, CTA,McCormick
ﺩ.ﺇ165 per night
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SUPERHOST
Private room · Englewood
Work from home beauty (unit 2 room #4)
ﺩ.ﺇ154 per night
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Entire rental unit · Lake View
Adorable Studio Apartment in Lakeview
ﺩ.ﺇ248 per night
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Private room · Little Italy
Great Location Private Room-5 min to the City
ﺩ.ﺇ220 per night
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SUPERHOST
Private room · Wicker Park
Spacious & Bright Private Room in Wicker Park
ﺩ.ﺇ206 per night
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Entire rental unit · Lake View
Elevating Studio Apartment in Belmont
ﺩ.ﺇ191 per night
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SUPERHOST
Private room · Humboldt Park
Spacious PRVT Room w/ Full Bathroom - Logan Square
ﺩ.ﺇ164 per night
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Private room · Wicker Park
Bright & Spacious Penthouse in West Town
ﺩ.ﺇ165 per night

Chicago holiday vacation rentals

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Entire rental unit · West Loop
Adorable 1BR Apt in Famed West Loop
ﺩ.ﺇ246 per night
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SUPERHOST
Private room · Humboldt Park
Fashionable Room w/ full bathroom - FREE PARKING!
ﺩ.ﺇ188 per night
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SUPERHOST
Private room · Chinatown
Hotel quality room near Downtown,CTA, McCormick
ﺩ.ﺇ177 per night
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Private room · Chicago
City View near Downtown Chicago Sox Chinatown
ﺩ.ﺇ174 per night
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SUPERHOST
Private room · Lake View
British Themed Room in the Middle of Boystown
ﺩ.ﺇ276 per night
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SUPERHOST
Private room · West Town
Stylish & Bright 1PBR TWO Miles From Downtown
ﺩ.ﺇ259 per night
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Private room · Logan Square
P6. Next to Downtown! Best location
ﺩ.ﺇ175 per night
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SUPERHOST
Entire rental unit · West Town
Cabin #103 at 747 Lofts
ﺩ.ﺇ261 per night
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Private room · Logan Square
P3. Next to Downtown! Best location
ﺩ.ﺇ196 per night
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SUPERHOST
Private room · Wicker Park
Spacious & Attractive Private Room in Wicker Park
ﺩ.ﺇ248 per night
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Entire rental unit · Berwyn
Lovely 1-bedroom condominium with free designated parking on premises
ﺩ.ﺇ282 per night
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Private room · Uptown
Cossy room close to lake in Chicago
ﺩ.ﺇ174 per night

Your guide to Chicago

All About Chicago

Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.

You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.


When is the best time to stay in a vacation rental in Chicago?

Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.


What are the top things to do in Chicago?

The Art Institute of Chicago

The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.

Willis Tower

The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.

Millennium Park

Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.

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