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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.

  1. Private room
  2. Woodlawn
Master Bedroom in Spacious and Comfy Chicago Condo

Welcoming and Cozy home for up to 2 guests. City Living! Located in the University of Chicago area. EASILY ACCESSIBLE to EVERYWHERE in the Chicago! 5-10 minutes from UC, 15 minutes from South Loop and downtown Chicago . Use the kitchen and its appliances, your own personal bathroom, TV, hi-speed Wifi, laundry & parking. Meaningful conversation (if you want it).

G$6,251 per night
  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan

I used to be a live-in host, but since the pandemic I host visitors while I'm away traveling, so you will have the place all to yourself! The guestroom is SUNNY & peaceful, with balcony overlooking a lush yard, set back from street = QUIET. Available for 3-6 week stays. Equivalent to a large studio apartment + kitchen + bath. 1 block from Loyola U., 3 blocks to CTA Red Line train, 4 blocks to beaches! Second floor walk-up, bed is a full-sized FUTON (firm Japanese mattress).

G$8,792 per night
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Attractive Private Room in Wicker Park

The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located in a vibrant part of Wicker Park close to the train station giving easy access to other areas of Chicagoland.

G$10,406 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Downtown Chicago vacation rentals

SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #206 at 747 Lofts
G$13,607 per night
  1. Private room
  2. Lake View
Contemporary, private suite w fireplace
G$13,458 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
G$7,716 per night
  1. Private room
  2. Near West Side
Cozy room in newly finished ultra modern aptmnt.
G$6,789 per night
SUPERHOST
  1. Entire rental unit
  2. Uptown
Stylish studio at Uptown by Red Line
G$14,534 per night
SUPERHOST
  1. Private room
  2. River North
Restoring Chicago speakeasy of the 1920s room 3A
G$20,634 per night
  1. Entire rental unit
  2. West Town
New Spot in West Town
G$18,541 per night
SUPERHOST
  1. Entire guesthouse
  2. Bridgeport
Private Studio in Bridgeport, Chicago
G$14,924 per night
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Bright Private Room in Wicker Park
G$10,615 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #207 at 747 Lofts
G$15,072 per night
SUPERHOST
  1. Private room
  2. River North
Restoring Chicago Speakeasy from 1920's Room 1A
G$21,562 per night
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
G$6,280 per night

Chicago beach vacation rentals

SUPERHOST
  1. Private room
  2. Uptown
Private 1 Bedroom, full bathroom, Queensize Bed.
G$10,467 per night
  1. Entire rental unit
  2. Magnificent Mile
DOWNTOWN STUDIO BY RUSH STREET -GOLD COAST CENTER
G$23,984 per night
SUPERHOST
  1. Private room
  2. Lincoln Square
Basic accomodation equipped for short terms stays.
G$11,095 per night
  1. Private room
  2. North Park
Cozy East room
G$9,481 per night
SUPERHOST
  1. Entire rental unit
  2. Gold Coast
Lively Stay Steps from North Ave Beach
G$30,653 per night
SUPERHOST
  1. Private room
  2. Edgewater
Modern, Super-CLEAN, Garden Level Bedroom 3
G$8,164 per night
SUPERHOST
  1. Private room
  2. The Loop
Luxury high-rise One Bedroom One-Private bathroom
G$13,607 per night
  1. Private room
  2. East Rogers Park
Steps from the Beach Top-Floor Vintage Walk-Up
G$16,328 per night
SUPERHOST
  1. Entire rental unit
  2. Evanston
✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
G$31,162 per night
  1. Entire rental unit
  2. Chicago
Entire Rental Unit •1 BD•Cozy•Luxury•5 mins fr DT
G$23,326 per night
SUPERHOST
  1. Entire rental unit
  2. East Rogers Park
Private flat on Historic Eastlake Terrace
G$34,540 per night
SUPERHOST
  1. Entire townhouse
  2. Magnificent Mile
Historic luxury Townhouse in Downtown Chicago
G$116,138 per night

Chicago summer vacation rentals

SUPERHOST
  1. Private room
  2. West Town
Stylish & Bright 1PBR STAYCATION SPACE For You
G$10,406 per night
  1. Entire rental unit
  2. Bridgeport
1 Bedroom Apartment by McCormick Place & Chinatown
G$12,740 per night
SUPERHOST
  1. Entire home
  2. Bridgeport
Free parking, close to public transit, dining
G$15,700 per night
SUPERHOST
  1. Entire guest suite
  2. Avondale
Cozy 1 BR in Logan Square - Steps from Blue Line
G$18,631 per night
SUPERHOST
  1. Private room
  2. Chinatown
Hotel quality private room near downtown RedLine
G$9,600 per night
SUPERHOST
  1. Entire rental unit
  2. Near West Side
MedDistrict Spacious Renovated 1br Apt MONTHLY
G$15,700 per night
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Charming Private Room in Wicker Park
G$10,109 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #305 at 747 Lofts
G$14,444 per night
  1. Private room
  2. Bridgeport
R1 Prime New House Perfect for your stay
G$8,882 per night
SUPERHOST
  1. Private room
  2. River North
Restoring Chicago speakeasy of the 1920s. Room 4A
G$20,934 per night
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
G$10,586 per night
SUPERHOST
  1. Private room
  2. Near North Side
★ DOWNTOWN CHICAGO ★ The Blue Room
G$16,119 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.