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.

  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 :) 


$53 per night
SUPERHOST
  1. Private room
  2. South Chicago
Room H6
$25 per night
  1. Private room
  2. McKinley Park
Cozy Private Bedroom w/ Queen Bed & 5min to Metro

Recently renovated, enjoy the comfort of staying on a brand-new home. Brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix included memory-foam mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more! Easy access to public transportation. Convenient location close to downtown Chicago, Chinatown, White Sox, Pilsen, South Loop & McCormick Convention Center.

$53 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
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Downtown Chicago vacation rentals

  1. Private room
  2. Wicker Park
Simple and Convenient
$76 per night
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
$54 per night
  1. Private room
  2. Near West Side
Cozy room in newly finished ultra modern aptmnt.
$36 per night
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 6
$47 per night
  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan
$42 per night
SUPERHOST
  1. Private room
  2. South Chicago
Room B5
$24 per night
SUPERHOST
  1. Private room
  2. Chicago
B5Hotel quality room near Downtown, CTA,McCormick
$43 per night
  1. Private room
  2. Woodlawn
Master Bedroom in Spacious and Comfy Chicago Condo
$40 per night
  1. Private room
  2. Chicago
Private Bedroom near Downtown Chicago Chinatown
$38 per night
  1. Private room
  2. Maywood
Room 4: The Maywood Manor (Twin Bed, 1 Guest)
$31 per night
  1. Private room
  2. Bridgeport
Rustic Private BR - 5 min to Chinatown & Downtown
$42 per night
  1. Private room
  2. Little Italy
Private Room in Great Location to City
$56 per night

Chicago summer vacation rentals

SUPERHOST
  1. Private room
  2. Chinatown
Hotel quality room near Downtown,CTA, McCormick
$48 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Great location. Free parking.
$98 per night
  1. Private room
  2. Douglas Park
Frida 2720 (2F)
$40 per night
  1. Private room
  2. East Rogers Park
Loft Style Private Apt (1 Room- 420 Friendly)
$53 per night
  1. Private room
  2. Bridgeport
Private Room A5 by Chinatown
$35 per night
  1. Private room
  2. Bridgeport
Self Check-in 8 min Downtown Chicago
$42 per night
SUPERHOST
  1. Private room
  2. Pilsen Historic District
In the heart of Pilsen, Self Check In
$51 per night
  1. Private room
  2. East Rogers Park
#4 Historic Chicago Home - Private Single Bedroom
$48 per night
SUPERHOST
  1. Private room
  2. McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
$41 per night
SUPERHOST
  1. Private room
  2. McKinley Park
Downtown Chicago 8 minutes away New Queen Bed
$44 per night
  1. Entire rental unit
  2. Bridgeport
1 Bedroom Apartment by McCormick Place & Chinatown
$64 per night
  1. Private room
  2. Chicago
New Queen bed near Downtown Chicago Chinatown
$44 per night

Chicago holiday vacation rentals

  1. Private room
  2. Woodlawn
5min walk to UnivOfChgo. MODERN Luxe
$42 per night
SUPERHOST
  1. Private room
  2. Bridgeport
10min to UIC, 5min to Sox Field and Soldier Field
$44 per night
SUPERHOST
  1. Private room
  2. McKinley Park
New Queen Bed near Downtown Chicago
$44 per night
  1. Private room
  2. Chicago
New Queen bed near Chinatown Downtown Chicago
$54 per night
  1. Private room
  2. Brighton Park
Room 12- Midway Pershing Inn 2 beds Private Room
$42 per night
  1. Private room
  2. McKinley Park
Cleanest & Newest place near Downtown Chicago
$41 per night
SUPERHOST
  1. Private room
  2. Woodlawn
Quiet Room #3
$35 per night
  1. Private room
  2. Little Italy
Lovely private bedroom in Fantastic location
$73 per night
  1. Private room
  2. Near West Side
B3 - Chicago Next to Downtown - Room
$62 per night
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 2
$58 per night
  1. Private room
  2. Bridgeport
R2 Prime New House Perfect for your stay
$53 per night
  1. Private room
  2. McKinley Park
Large Couple Bedroom w/ Queen Bed & 5min to Metro
$54 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.


How do I get around Chicago?

Both of Chicago’s international airports, O’Hare (ORD) and Chicago Midway (MDW), have excellent public transit links. O’Hare is 18 miles from the city center, and the CTA train leaves directly from the airport and takes about 50 minutes to reach centrally-located vacation homes in Chicago. Chicago Midway is about 13 miles from the city center, and the CTA train leaves directly from the airport and takes about 30 minutes. Shuttles, taxis and rideshares are also available from either airport, but traffic is often congested, making the trains a bit more convenient.

Once you arrive, Chicago is a walkable city with one of the country’s best public transit systems, so you can easily take advantage of the trains and buses. Cabs and ride-hailing services are also plentiful around town.


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.