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The best vacation homes in Chicago

Check out our selection of great vacation homes in Chicago

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The Avondale Guesthouse, hotel in Chicago

The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.

Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored 9.3
9.3
Rated wonderful
Wonderful
136 reviews
Price from
$204.18
1 night, 2 adults
MAGNIFICENT NEW Home w/8 Beds & Free Parking, hotel in Chicago

MAGNIFICENT NEW Home w/8 Beds & Free Parking offers accommodations in Chicago, 3.9 miles from Wrigley Field and 4 miles from Water Tower Chicago.

Comfortable clean space which was well kept.
Scored 9.2
9.2
Rated wonderful
Wonderful
6 reviews
Price from
$330
1 night, 2 adults
A terrific house for a large group., hotel in Chicago

A terrific house for a large group. Is located in Chicago, just 7 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.

One thing we all really enjoyed was how everyone’s bedroom was somewhat close to one another as well as how the living room was big enough to do different types of games and such
Scored 8.8
8.8
Rated excellent
Excellent
6 reviews
Price from
$163.94
1 night, 2 adults
Chic Green l Near Downtown & IL Medical District, hotel in Chicago

Chic Green l Near Downtown & IL Medical District offers accommodations in Chicago, 3.1 miles from Union Station and 3.2 miles from Willis Tower.

Very responsive host. When we had issues entering the unit at checkin they were able to remotely unlock until the issue was resolved.
Scored 7.7
7.7
Rated good
Good
18 reviews
Price from
$216
1 night, 2 adults
Pearly Gates l 3 Bed l Sleeps 5 l w 2-Car Garage, hotel in Chicago

Pearly Gates l 3 Bed l Sleeps 5 l w 2-Car Garage offers accommodations in Forest Park, 10 miles from Union Station and 10 miles from Willis Tower.

house was clean and comfortable with all amenities needed
Scored 7.7
7.7
Rated good
Good
9 reviews
Price from
$174
1 night, 2 adults
4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome, hotel in Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome provides accommodations with access to spa facilities and fitness...

Scored 9.6
9.6
Rated exceptional
Exceptional
5 reviews
Lincoln Park Living - Suite 1, hotel in Chicago

Lincoln Park Living - Suite 1 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

Location, spacious, lots of beds, big kitchen, free street parking.
Scored 9.1
9.1
Rated wonderful
Wonderful
10 reviews
The Black And White Suite, hotel in Chicago

The Black And White Suite is located in Chicago, just 4.3 miles from Adler Planetarium & Astronomy Museum and 4.6 miles from Art Institute of Chicago.

It's like walking into art and everything we could have wanted for our first visit to Chicago. For jazz and blues fans, the area is perfect! Quick access to public transit and walking distance from many things.
Scored 9.0
9.0
Rated wonderful
Wonderful
5 reviews
Stunning Condo #2 - Downtown River North, hotel in Chicago

Stunning Condo #2 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

Loved everything. Great location and great value overall!!! Will definitely recommend this to friends and family.
Scored 9.2
9.2
Rated wonderful
Wonderful
18 reviews
Stunning 2 Floor Penthouse Downtown, hotel in Chicago

Stunning 2 Floor Penthouse Downtown is located in Chicago, just 1.9 miles from Water Tower Chicago and 1.9 miles from United Center.

Close to shops and subway - great location on a quiet street. We will be back. Lots of room, and kids really enjoyed the decks. Parking spot was also appreciated. Thank you!
Scored 9.2
9.2
Rated wonderful
Wonderful
13 reviews
All vacation homes in Chicago
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Chicago this month

Enjoy breakfast in Chicago!

  • Lincoln Park Living - Suite 1
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 10 reviews

    Lincoln Park Living - Suite 1 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

    Location, spacious, lots of beds, big kitchen, free street parking.

  • Stunning Condo #2 - Downtown River North
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 18 reviews

    Stunning Condo #2 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

    The location, the amount of bathrooms and bedrooms

  • Stunning 2 Floor Penthouse Downtown
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 13 reviews

    Stunning 2 Floor Penthouse Downtown is located in Chicago, just 1.9 miles from Water Tower Chicago and 1.9 miles from United Center.

    It was very spacious! I enjoyed the view from the private balcony.

  • Logan Square Oasis
    Breakfast options
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 5 reviews

    Logan Square Oasis offers accommodations in Chicago, 4.2 miles from Wrigley Field and 4.6 miles from United Center. The air-conditioned accommodation is 4.2 miles from Lincoln Park Zoo.

    Location was great. Really nice apartment with good amenities. 3 bedroom and 2 bath setup was super comfortable.

  • Spacious Row Home next Transit near Downtown w Parking
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 9 reviews

    Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United Center and 4 miles from Union Station.

    Everything was clean and comfortable for 5 adults and 11 kids

  • Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 32 reviews

    Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated vacation home in Chicago where guests can make the most of the garden and tennis court.

    The place is in a very cute neighborhood and was super clean.

  • Spacious 5-BR House near Transit w Parking
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 10 reviews

    Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago. This property offers access to a terrace, free private parking, and free Wifi.

    Excellent, it was close to downtown and the airport.

  • 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 5 reviews

    A 19-minute walk from Oak Street Beach in Chicago, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome provides accommodations with access to spa facilities and fitness...

Save money on vacation homes in Chicago – budget options available!

  • Beautiful Remodeled Penthouse Unit in Old Town
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 9 reviews

    Beautiful Remodeled Penthouse Unit in Old Town offers accommodations in Chicago, 1.4 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.

  • Lincoln Park Living - 3 Queen Beds - Sleeps 6
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 5 reviews

    Lincoln Park Living - 3 Queen Beds - Sleeps 6 is located in Chicago, just 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

  • Lincoln Park Living - Suite 2
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 8 reviews

    Lincoln Park Living - Suite 2 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

  • Suite 2 on Southport 4 Queen Beds
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 15 reviews

    Suite 2 on Southport 4 Queen Beds is located in Chicago, just 1.8 miles from Wrigley Field and 3.4 miles from 360 Chicago. The air-conditioned accommodation is 1.7 miles from Lincoln Park Zoo.

    Lokalizacja, standard apartamentu, wyposażenie lokalu

  • A terrific house for a large group.
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 6 reviews

    A terrific house for a large group. Is located in Chicago, just 7 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.

  • Chicago Home with Spacious Yard 14 Mi to Dtwn
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 9 reviews

    Chicago Home with Spacious Yard 14 Mi to Dtwn is located in Chicago, just 10 miles from Guaranteed Rate Field and 13 miles from Field Museum of Natural History.

  • The Chicago Retreat Just 10 mins from Chicago Bulls Arena

    The Chicago Retreat Just 10 mins from Chicago Bulls Arena is located in Chicago, just a 17-minute walk from United Center and 2.6 miles from Union Station.

  • West Pilsen Hideaway
    Budget options available
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    West Pilsen Hideaway offers accommodations in Chicago, 3.8 miles from Union Station and 4.3 miles from Field Museum of Natural History.

Great access to the city center! Check these vacation homes in Chicago

  • Historic luxury Townhouse in Downtown Chicago
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 8-minute walk from Water Tower Chicago and half a mile from Chicago Museum of Contemporary Art.

  • Gold coast villa with free parking garage sleeps 10
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

  • Modern SFH Near McCormick Place & Soldier Field
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Modern SFH Near McCormick Place & Soldier Field is located in Chicago, just 1.8 miles from Union Station and 1.8 miles from Willis Tower.

  • Old Town Pied-a-Terre with Private Terrace and Parking!
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    A 14-minute walk from North Avenue Beach in Chicago, Old Town Pied-a-Terre with Private Terrace and Parking! offers accommodations with access to a hot tub.

  • Luxury Retreat with Home Theater
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Luxury Retreat with Home Theater offers accommodations in Chicago, 2.2 miles from United Center and 2.5 miles from Lincoln Park Zoo.

  • Spacious Luxury Retreat 8 Bed Oasis with 6 Baths
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Spacious Luxury Retreat 8 Bed Oasis with 6 Baths offers accommodations in Chicago, 2.4 miles from Guaranteed Rate Field and 3.1 miles from Union Station.

  • The Village Inn by Dakota Gal Digs
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from Fullerton Beach and 1.8 miles from North Avenue Beach.

  • Luxe Urban Retreat Near United Center
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Luxe Urban Retreat Near United Center offers accommodations in Chicago, 3.1 miles from Union Station and 3.7 miles from Millennium Station.

  • ENTIRE BUILDING-Walk to Lincoln Park or The Beach
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    ENTIRE BUILDING-Walk to Lincoln Park or The Beach offers accommodations in Chicago, 1.9 miles from North Avenue Beach and 1.2 miles from Wrigley Field.

  • The Logandale: HUGE Mid-Century Home, sleeps 15
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 reviews

    The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.6 miles from Lincoln Park Zoo and 5.1 miles from United Center.

  • Stylish Chicago Retreat, Walk to Loyola University
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Stylish Chicago Retreat, Walk to Loyola University is located in Chicago, just a 8-minute walk from Loyola University Chicago and 3.5 miles from Wrigley Field.

  • New Modern 3BR, Gym, Workspace, Quiet Location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    New Modern 3BR, Gym, Workspace, Quiet Location is located in Chicago, just 10 miles from Wrigley Field and 11 miles from Lincoln Park Zoo.

  • Belmont Heights Oasis
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 4 reviews

    Belmont Heights Oasis offers accommodations in Chicago, 9 miles from Wrigley Field and 9.2 miles from United Center. This vacation home offers air-conditioned accommodations with a patio.

  • River North Hideaway with Amazing Views and Parking
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    River North Hideaway with Amazing Views and Parking offers accommodations in Chicago, 1.6 miles from North Avenue Beach and a 11-minute walk from 360 Chicago.

  • Luxurious classic Gold coast villa for 12 guests
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious classic Gold coast villa for 12 guests features accommodations in Chicago with a garden.

  • Chicago Treasure 4 Bed Getaway
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Chicago Treasure 4 Bed Getaway offers accommodations in Chicago, 1.9 miles from Water Tower Chicago and 2 miles from Chicago Museum of Contemporary Art.

  • Windy City Getaway - 3BR 2BA Chicago Townhouse home
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Windy City Getaway - 3BR 2BA Chicago Townhouse home is located in Chicago, just 5 miles from Wrigley Field and 6.1 miles from Lincoln Park Zoo.

  • Chicago Home Near Navy Pier and Shedd Aquarium!
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 4 reviews

    Chicago Home Near Navy Pier and Shedd Aquarium! offers accommodations in Chicago, 8.4 miles from Guaranteed Rate Field and 11 miles from Field Museum of Natural History.

  • The Avondale Guesthouse
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 136 reviews

    The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.

    The size of the apartment was large. Parking was free.

  • Beautifully Renovated House 10 mins from Downtown
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 4 reviews

    Beautifully Renovated House 10 mins from Downtown offers accommodations in Chicago, 1.5 miles from Oakwood Beach and 1.8 miles from Guaranteed Rate Field.

    La casa está muy bien ubicada a 100m del metro, Justo como en las fotos, una cocina muy grande y amplia, asador en el jardín con salita, cuarto de tv, baño en la mayoría de las recámaras….

  • The Black And White Suite
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 5 reviews

    The Black And White Suite is located in Chicago, just 4.3 miles from Adler Planetarium & Astronomy Museum and 4.6 miles from Art Institute of Chicago.

  • Chic 4-Bedroom Haven: Designer's Dream Home
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1 review

    Chic 4-Bedroom Haven: Designer's Dream Home is located in Chicago, just 1.7 miles from United Center and 3.6 miles from Union Station.

  • Spacious Bucktown Sanctuary
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1 review

    Spacious Bucktown Sanctuary is located in Chicago, just 2.8 miles from United Center and 3.4 miles from Wrigley Field.

  • Duplex Chic River North Retreat
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 3 reviews

    Duplex Chic River North Retreat offers accommodations in Chicago, 1.7 miles from North Avenue Beach and a 7-minute walk from Shops at Northbridge.

  • Luxurious Gold Coast villa with parking for up to 12 guests
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious Gold Coast villa with parking for up to 12 guests features accommodations in Chicago with a garden.

  • Upscale Penthouse Private Balcony
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    Upscale Penthouse Private Balcony is located in Chicago, just 1.7 miles from United Center and 2.5 miles from Water Tower Chicago.

  • 5 Mi to Dtwn Chicago Apartment in Garfield Park!
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    5 Mi to Dtwn Chicago Apartment in Garfield Park! offers accommodations in Chicago, 2.3 miles from United Center and 4.7 miles from Union Station.

  • Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 26 reviews

    Featuring a garden and inner courtyard views, this sustainable holiday home is well located in Chicago, close to landmarks like North Avenue Beach and Lincoln Park Zoo.

    Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also

FAQ about vacation homes in Chicago

Vacation Homes That Guests Love in Chicago

  • Avg. price/night: $158.67
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 1,884 reviews
    Very clean. Conveniently located.
    Pier Luca
    Young couple
  • Avg. price/night: $179.85
    Scored 7.2
    7.2
    Rated good
    Good
     · 364 reviews
    Convenient location, room was a decent size for a solo traveller. Entire place was very clean. The mobile phone key to unlock the doors were also very useful. I also liked the TV + aircon unit, and the view from the room.
    Patricia
    Solo traveler
  • Avg. price/night: $181.73
    Scored 7.5
    7.5
    Rated good
    Good
     · 42 reviews
    Everything about this was perfect. The cute little apartment was very clean and comfortable. Fully equipped kitchen so we were able to have breakfast in and save a few quid! The location was in a quiet and safe neighbourhood with very simple and affordable access to the city. Probably my favourite stay throughout my travels around the states thus far. The owner was very easy to contact and very helpful in regard to any questions or queries we had or any help we needed while we were there.
    Julia
    Travelers with friends
  • Avg. price/night: $281.76
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 3,339 reviews
    The design of the hotel is amazing! There is breakfast at the River North Bistro (not expensive). The room view is a must! They keep the hotel very clean all the time, and they are very welcoming! The gyn is well-equipped. The shower was strong pressured (i loved it). I would recommend to every one, great experience.
    Matheus
    Solo traveler
  • Avg. price/night: $351.24
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1,383 reviews
    The location is very good! It has a bus station 50 meters from the entrance that goes to blue line(for the Airport). The room was very clean and big. The breakfast has decaf that it is very rare.
    Lampros
    Young couple
  • Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 10 reviews
    The apartment is large, well equipped, and very clean. What we liked best of all was the fridge, where you could get cold and excellent tasting water directly from the tap, as well as ice cubes and crushed ice.
    Barbara
    Family with young children
  • Avg. price/night: $434.38
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1,745 reviews
    Location very central, very comfortable beds and very clean room
    Lucy
    Group
  • Avg. price/night: $192.09
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 4,099 reviews
    Very clean
    Marlena
    Family with young children
  • Avg. price/night: $255.93
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 5,430 reviews
    Amazing view, very clean, best location and polite staff.
    Kameliya
    Young couple
  • Scored 8.4
    8.4
    Rated very good
    Very Good
     · 13 reviews
    The unit itself was renovated and lovely. Very clean and cozy space. The host was very receptive when we brought up mild concerns (tiny leak in faucet, shower temp concerns).
    Alexandra
    Family with young children

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