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Chicago vacation rentals

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Top-rated vacation rentals in Chicago

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

SUPERHOST
  1. Entire rental unit
  2. Bridgeport
1bed/1bath !Location! Steps to South Loop Apt

Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 28th Place & Canal St to map transit options Newly remodeled 1br with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago & steps from all that trendy Bridgeport has to offer. Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays

$25 per night
SUPERHOST
  1. Entire rental unit
  2. Lower West Side
Pilsen HofC Deluxe 2bed/1bath Apt MONTHLY

Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 23rd St. & Leavitt St. to map transit options Newly remodeled two-bedroom apartment with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago and part of all that trendy Pilsen has to offer. Managed by a seasoned team specializing in monthly furnished rentals. Per the City of Chicago ordinances, 31 night minimum on all stays

$25 per night
  1. Private room
  2. Little Italy
Private Room in Great Location to City

Private, VERY CLEAN room 5 minutes to downtown with FREE PARKING, GREEN TEA & ALOE memory foam mattress, and an EARLY check-in (11 a.m.). You will have your own door code and may arrive at ANY time and as late as you wish, EASY self check-in guaranteed. I allow LUGGAGE DROP OFF! You can store your luggage in the closet before check-in and after check-out times, you can drop it off and pick it up as early and as late as you would like. The neighborhood is extremely safe even at night :) 


$60 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 Park473 locals recommend
Photo of Navy Pier
Navy Pier306 locals recommend
Photo of Willis Tower
Willis Tower151 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago185 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago437 locals recommend

Downtown Chicago vacation rentals

  1. Private room
  2. Brighton Park
Room A pershing inn
$33 per night
SUPERHOST
  1. Entire guest suite
  2. Near West Side
MedDistrict Chic Newly Remodeled 1 bedroom MONTHLY
$40 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
Bridgeport LR Renovated Loft Studio MONTHLY
$40 per night
  1. Entire home
  2. Humboldt Park
Elegant, Bright Flat
$99 per night
SUPERHOST
  1. Private room
  2. West Town
Stylish & Charming 1PBR STAYCATION SPACE For You
$56 per night
SUPERHOST
  1. Entire guesthouse
  2. Bridgeport
Private Studio in Bridgeport, Chicago
$77 per night
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
$30 per night
SUPERHOST
  1. Private room
  2. Chicago
BRONZEVILLE OASIS I - Mins to UChicago & The Loop
$44 per night
  1. Private room
  2. Near West Side
Room T6
$35 per night
SUPERHOST
  1. Entire guest suite
  2. Bridgeport
Bridgeport LF Renovated Loft Studio MONTHLY
$40 per night
SUPERHOST
  1. Private room
  2. West Town
Stylish & Ample 1PBR STAYCATION SPACE For You
$55 per night
  1. Private room
  2. South Chicago
Room B7
$23 per night

Chicago summer vacation rentals

  1. Private room
  2. Lake View
Contemporary, private suite w fireplace
$64 per night
  1. Private room
  2. Maywood
Room 4: The Maywood Manor (Twin Bed, 1 Guest)
$43 per night
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
$50 per night
  1. Private room
  2. Lincoln Park
Goose & Fox Hostel Lincoln Park
$52 per night
  1. Private room
  2. Chicago
Homey, Energy Efficient 3 & Separate Laundry Room.
$37 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
Bridgeport 2R Renovated 2bed/1bath Apt. MONTHLY
$40 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Great location. Free parking.
$100 per night
  1. Private room
  2. Little Italy
Lovely private bedroom in Fantastic location
$65 per night
  1. Entire rental unit
  2. Avondale
Great location lots of public transportation
$80 per night
  1. Private room
  2. Brighton Park
Room 9 Pershing Inn
$48 per night
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 5
$49 per night
SUPERHOST
  1. Private room
  2. McKinley Park
SELF CHECK IN Downtown Chicago 8 minutes away
$36 per night

Chicago holiday vacation rentals

  1. Private room
  2. Bridgeport
Private Room A5 by Chinatown
$33 per night
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City
$31 per night
  1. Private room
  2. South Chicago
Room B6
$24 per night
  1. Private room
  2. Chicago
City View near Downtown Chicago Sox & Chinatown
$48 per night
  1. Private room
  2. McKinley Park
Cleanest & Newest place near Downtown Chicago
$36 per night
  1. Private room
  2. Woodlawn
Perfect Oasis 4mins walk to University & hospital
$50 per night
  1. Entire rental unit
  2. Bridgeport
1 Bedroom Apartment by McCormick Place & Chinatown
$65 per night
SUPERHOST
  1. Private room
  2. Wrigleyville
Exclusive modern room on tree lined st in Lakeview
$60 per night
SUPERHOST
  1. Private room
  2. East Garfield Park
Large bedroom near medical district and UIC
$47 per night
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 6
$47 per night
  1. Private room
  2. West Town
Great room with private bathroom
$53 per night
SUPERHOST
  1. Private room
  2. Chicago
B5Hotel quality room near Downtown, CTA,McCormick
$45 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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