Vacation Rentals in Chicago

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Best vacation rental deals in Chicago

Sat, 03/13 - Sat, 03/20
Apartment for 6 people, with balcony
2 pers., , 495ft²
4.3
153 reviews

7 nights
$1,636

$2,670-39%
Fri, 07/02 - Sun, 07/04
Vacation house for 2 people, with pets
2 pers.

2 nights
$503

$778-35%
Sun, 01/24 - Tue, 01/26
Apartment for 3 people, with terrace and pool, child-friendly
3 pers., 1 bedroom, 517ft²
5.0
1 review

2 nights
$332

$353-6%

Vacation Rentals in Chicago

Apartment for 3 people
3 pers., , 603ft²
4.3
26 reviews
Chicago, Lake Michigan

from
$118
per night

Apartment for 4 people, with pets
4 pers., , 646ft²
Chicago, Lake Michigan

from
$118
per night

Apartment for 4 people, with pets
4 pers., 1 bedroom
Chicago, Lake Michigan

from
$118
per night

Studio for 2 people
2 pers., , 495ft²
4.3
153 reviews
Chicago, Lake Michigan

from
$107
per night

Vacation house for 6 people, with terrace and pool, child-friendly
6 pers., 3 bedrooms, 1,195ft²
5.0
7 reviews
Chicago, Lake Michigan

from
$174
per night

Apartment for 6 people, with pets
6 pers., 3 bedrooms
Chicago, Lake Michigan

from
$172
per night

Vacation house for 5 people
5 pers., 2 bedrooms
5.0
2 reviews
Chicago, Lake Michigan

from
$89
per night

Apartment for 2 people
2 pers., 1 bedroom, 538ft²
3.8
2 reviews
Chicago, Lake Michigan

from
$101
per night

Vacation house for 10 people
10 pers., 2 bedrooms, 1,195ft²
1.3
1 review
Chicago, Lake Michigan

from
$224
per night

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Pet-friendly Vacation Rentals

Apartment for 6 people
6 pers., 3 bedrooms, Pets allowed
Chicago, Lake Michigan

from
$75
per night

Apartment for 8 people, child-friendly
8 pers., 3 bedrooms, Pets allowed
5.0
4 reviews
Chicago, Lake Michigan

from
$219
per night

Vacation house for 8 people, with garden, with pets
8 pers., 4 bedrooms, Pets allowed
Chicago, Lake Michigan

from
$2,598
per night

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Vacation Rentals with Pool

Apartment for 6 people, with pool
6 pers., 2 bedrooms
5.0
1 review
Chicago, Lake Michigan

from
$326
per night

Studio for 3 people, with terrace and pool, child-friendly
3 pers., 1 bedroom, 517ft²
5.0
1 review
Chicago, Lake Michigan

from
$88
per night

Apartment for 8 people, with balcony and pool
8 pers., 3 bedrooms, 1,841ft²
Chicago, Lake Michigan

from
$690
per night

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Vacation Rentals with Internet

Apartment for 6 people
6 pers., 3 bedrooms
Chicago, Lake Michigan

from
$99
per night

Apartment for 2 people
2 pers., 1 bedroom, 581ft²
5.0
1 review
Chicago, Lake Michigan

from
$119
per night

Apartment for 6 people
6 pers., 3 bedrooms
4.4
2 reviews
Chicago, Lake Michigan

from
$224
per night

Show all

Highlights Chicago

  • World class galleries and museums
  • Sporting spectacles
  • Beautiful skyline
  • Lakefront setting
  • Good public transportation
  • Shopping

Most popular in Chicago

Pool 202
Internet 1,013
Balcony/Terrace 293
TV 955
Air conditioning 898
Parking 488
Washing machine 878
Heating 882
Elevator 460

Prices and availability

Prices

February
March
April
May
June
July
$465
Jan 23 - Jan 30
$297 per night
Jan 30 - Feb 06
$288 per night
Feb 06 - Feb 13
$280 per night
Feb 13 - Feb 20
$291 per night
Feb 20 - Feb 27
$294 per night
Feb 27 - Mar 06
$279 per night
Mar 06 - Mar 13
$303 per night
Mar 13 - Mar 20
$290 per night
Mar 20 - Mar 27
$254 per night
Mar 27 - Apr 03
$310 per night
Apr 03 - Apr 10
$348 per night
Apr 10 - Apr 17
$347 per night
Apr 17 - Apr 24
$327 per night
Apr 24 - May 01
$379 per night
May 01 - May 08
$367 per night
May 08 - May 15
$289 per night
May 15 - May 22
$351 per night
May 22 - May 29
$422 per night
May 29 - Jun 05
$420 per night
Jun 05 - Jun 12
$395 per night
Jun 12 - Jun 19
$365 per night
Jun 19 - Jun 26
$376 per night
Jun 26 - Jul 03
$465 per night
Jul 03 - Jul 10
$460 per night
Average price per week

Availabilities

February
March
April
May
June
July
50 %
Jan 23 - Jan 30
35 %
Jan 30 - Feb 06
39 %
Feb 06 - Feb 13
42 %
Feb 13 - Feb 20
44 %
Feb 20 - Feb 27
47 %
Feb 27 - Mar 06
47 %
Mar 06 - Mar 13
50 %
Mar 13 - Mar 20
45 %
Mar 20 - Mar 27
45 %
Mar 27 - Apr 03
45 %
Apr 03 - Apr 10
46 %
Apr 10 - Apr 17
44 %
Apr 17 - Apr 24
43 %
Apr 24 - May 01
43 %
May 01 - May 08
43 %
May 08 - May 15
43 %
May 15 - May 22
43 %
May 22 - May 29
43 %
May 29 - Jun 05
43 %
Jun 05 - Jun 12
42 %
Jun 12 - Jun 19
42 %
Jun 19 - Jun 26
38 %
Jun 26 - Jul 03
38 %
Jul 03 - Jul 10
38 %
Percentage of available rentals

Chicago Vacation Rentals

Elegant City Center Vacation Homes

America’s third largest city, Chicago is full of wonderful vacation rental options. For example, if you look inside the Loop, you’ll find plenty of upscale apartment properties, with multiple bathrooms, bedrooms and huge living areas – all within walking distance of the subway and major attractions.

Choose a Lakefront Vacation Home or a Suburban Villa

You don’t need to stay in the center of Chicago. One of the great things about the city is the beautiful shorefront of Lake Michigan. Check out lakefront neighborhoods like Lincoln Park, the Near North Side or Gold Coast. Or look inland to roomy vacation rental options in affluent suburbs like Wheaton or Itasca. There’s no shortage of fantastic accommodation possibilities in the Windy City.

Vacationing in Chicago

A Lakefront Metropolis with Incredible Energy

Chicago is clustered around the southern curve of Lake Michigan in the state of Illinois, roughly a quarter of the distance from New York to California. The gateway to the Midwest, Chicago is easy to reach thanks to O’Hare International Airport, which connects the city to every state in the US, and international destinations as well.

Find the Loop, and You’ve Found Chicago’s Downtown Center

In the city itself, the lake is an easy reference point. Chicago’s city center is nestled up against the lake, inside what locals call “the Loop” – which referred to the route of the elevated railway. Nowadays, the L Train network runs into the Loop from north, south, and the west, and it’s the focal point for most tourist visits.

Hundreds of Neighborhoods to Explore

However, Chicago is a massive city, with over 10 million people in the metro area. Within that area, there are plenty of sights and areas to explore, from Frank Lloyd Wright houses in Hyde Park to BrookfieldZoo. It’s all fairly spread out, so renting a car and choosing a rental home with parking space makes perfect sense.

Downtown Chicago
Downtown Chicago

Activities

A World Class Cultural Destination

Chicago has an endless array of cultural attractions. There’s a huge Blues Festival in June, the delights of the Art Institute of Chicago, the huge Field Museum and the Museum of Science. If you love art, science or music, you can’t go wrong in Chicago.

Sporting Attractions All Year-Round

Chicago is also a major sporting destination. From the NFL’s Bears to the Bulls of the NBA and Major League Baseball’s Cubs, sports fans will have an excuse to visit the city at almost any time of year.

A Superb Place if You Love to Shop

The home of Sears is a major shopping hub for the Midwest. For those who need some retail therapy, the Magnificent Mile on Michigan Avenue hosts one of the highest concentrations of boutiques in the USA, while State Street is home to huge department stores like Marshall Field's.

The famous Route 66 highway begins right outside the doors of the Art Institute of Chicago

Top 5 things to do in Chicago

1. Visit the city’s huge number of museums

Chicago’s museum collection is incredible. The Field Museum is a massive natural history center, the Art Institute hosts a huge collection of modern art, the Chicago History Museum teaches visitors about the city’s fascinating past, while the Science Museum immerses guests in the world of technology.

2. Ascend to the panoramic deck of the John Hancock Center

There’s no better place to witness the breathtaking skyline of Chicago than the observation deck of the soaring John Hancock Tower, which is accessible by a high-speed elevator (which is an attraction in itself). Be sure to take your camera.

3. Explore the Chicago Riverwalk

The south bank of the Chicago River has been turned into one of America’s finest urban walkways, with attractions like tiki bars, birdwatching tours, water taxis, wine bars and brewery pubs dotted along its route.

4. Try a Chicago deep dish pizza

Deep dish pizza is one of Chicago’s culinary specialties. If you want to try a slice, head to local institutions like Pequod’s, the Art of Pizza or Giordano’s for a pizza pie that you will never forget.

5. Head to Soldier Field, Wrigley Field or the United Center for sporting action

Chicago’s teams are all in the top bracket of their sports, so whether you love NFL, NBA, Major League Baseball or even soccer or hockey, be sure to catch a contest during your stay.

The Chicago Loop
The Chicago Loop

Useful Information

Climate

Chicago’s climate is something to think about if you are planning a visit. Because of its location at the center of the continent, Chicago experiences extremely cold winters (and the legendary wind), and hot summers. Visit in fall or late spring for the best sightseeing conditions. However, summer is festival season in Chicago, so if you are keen to attend open air music concerts, you’ll want to visit between June and September.

Getting Around

Getting around the city is fairly easy. You can travel from most suburban vacation rental home options via CTA buses or trains. If you do rely on public transportation, be sure to investigate day and week passes, as they are a great way to save money. You can also purchase City Passes to reduce the cost of visiting the major attractions.

FAQs: Vacation Rentals in Chicago

What is the average price for vacation rentals in Chicago?

At an average price of $330.49 per night, Chicago lies at the upper end of the price range for vacation rentals in the USA.

Is Chicago a good location for a last-minute getaway?

We recommend you to book in advance in Chicago as only 21% of the properties are available throughout the year, according to our 2019 data.

How many vacation rentals does Holidu have in Chicago?

We have grouped together the offers from 9 different partners in Chicago, so we can provide you with around 1800 properties. You're going to have a hard time deciding which one to go with!

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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