Vacation Rentals in Chicago

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Popular Accommodations in Chicago

from
$118
per night

Apartment for 3 people
3 pers., 614ft²
4.4
(49 reviews)

from
$118
per night

Apartment for 2 people
2 pers., 786ft²
4.3
(247 reviews)

from
$118
per night

Apartment for 4 people, with pets
4 pers., 506ft²
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Vacation Rentals in Chicago
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from
$197
per night

Apartment for 6 people, with pets
6 pers., 3 bedrooms, 1,389ft²

from
$147
per night

Apartment for 4 people, with pets
4 pers., 1 bedroom

from
$49
per night

Apartment for 2 people, with pool and terrace, with pets
2 pers., 1 bedroomFREE cancellation
3.8
(100 reviews)

from
$108
per night

Apartment for 5 people
5 pers., 2 bedrooms
4.7
(9 reviews)

from
$71
per night

Apartment for 5 people, child-friendly
5 pers., 2 bedrooms
3.8
(23 reviews)

from
$98
per night

Apartment for 6 people
6 pers., 3 bedrooms
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Pet-friendly Vacation Rentals
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from
$176
per night

Apartment for 7 people, with pets
7 pers., 3 bedrooms, Pets allowedFREE cancellation
4.5

from
$663
per night

Vacation rental for 10 people, with garden, with pets
10 pers., 3 bedrooms, Pets allowed
4.5
(11 reviews)

from
$159
per night

Vacation rental for 2 people, with pets
2 pers., Pets allowedFREE cancellation
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Vacation Rentals with Pool
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from
$147
per night

Vacation rental for 4 people, with sauna and terrace as well as jacuzzi and pool
4 pers., 1 bedroom, 366ft²FREE cancellation
4.4
(150 reviews)

from
$153
per night

Apartment for 4 people, with terrace and jacuzzi as well as sauna and pool
4 pers., 1 bedroom

from
$196
per night

Apartment for 8 people, with pool
8 pers., 3 bedroomsFREE cancellation
5.0
(22 reviews)
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Vacation Rentals with Internet
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from
$7
per night

Vacation apartment for 2 people, child-friendly
2 pers., 1 bedroom
2.6
(139 reviews)

from
$22
per night

Vacation apartment for 1 people
1 pers., 1 bedroom
4.7
(87 reviews)

from
$122
per night

Apartment for 6 people
6 pers., 3 bedrooms
2.8
(2 reviews)
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Vacation Rentals with Air Conditioning
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from
$50
per night

Vacation apartment for 2 people
2 pers., 1 bedroomFREE cancellation
2.8
(39 reviews)

from
$180
per night

Apartment for 6 people, with balcony, child-friendly
6 pers., 3 bedroomsFREE cancellation
0.5

from
$226
per night

Apartment for 7 people
7 pers., 3 bedrooms
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Find Vacation Rentals in Chicago

Map

Highlights Chicago

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

Most popular in Chicago

Internet 13
Pets allowed 7
Balcony/Terrace 7
TV 14
Air conditioning 4
Garden 5
Parking 9
Washing machine 12
Heating 8

Prices and availability

Prices

May
June
July
August
September
$434
Apr 03 - Apr 10
$311 per night
Apr 10 - Apr 17
$307 per night
Apr 17 - Apr 24
$292 per night
Apr 24 - May 01
$323 per night
May 01 - May 08
$331 per night
May 08 - May 15
$319 per night
May 15 - May 22
$349 per night
May 22 - May 29
$385 per night
May 29 - Jun 05
$401 per night
Jun 05 - Jun 12
$374 per night
Jun 12 - Jun 19
$387 per night
Jun 19 - Jun 26
$418 per night
Jun 26 - Jul 03
$421 per night
Jul 03 - Jul 10
$406 per night
Jul 10 - Jul 17
$393 per night
Jul 17 - Jul 24
$393 per night
Jul 24 - Jul 31
$388 per night
Jul 31 - Aug 07
$400 per night
Aug 07 - Aug 14
$410 per night
Aug 14 - Aug 21
$401 per night
Aug 21 - Aug 28
$401 per night
Aug 28 - Sep 04
$426 per night
Sep 04 - Sep 11
$434 per night
Sep 11 - Sep 18
$409 per night
Average price per week

Availabilities

May
June
July
August
September
59 %
Apr 03 - Apr 10
12 %
Apr 10 - Apr 17
40 %
Apr 17 - Apr 24
46 %
Apr 24 - May 01
46 %
May 01 - May 08
53 %
May 08 - May 15
53 %
May 15 - May 22
46 %
May 22 - May 29
46 %
May 29 - Jun 05
53 %
Jun 05 - Jun 12
59 %
Jun 12 - Jun 19
53 %
Jun 19 - Jun 26
56 %
Jun 26 - Jul 03
46 %
Jul 03 - Jul 10
46 %
Jul 10 - Jul 17
53 %
Jul 17 - Jul 24
59 %
Jul 24 - Jul 31
50 %
Jul 31 - Aug 07
53 %
Aug 07 - Aug 14
46 %
Aug 14 - Aug 21
56 %
Aug 21 - Aug 28
56 %
Aug 28 - Sep 04
43 %
Sep 04 - Sep 11
53 %
Sep 11 - Sep 18
25 %
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

How much do you pay, on average, for vacation rentals in Chicago?

The COVID-19 pandemic strongly impacted travel in 2020. Last year, rentals in Chicago had an annual average price of around $336.90 per night.

What time of year offers, on average, the best vacation rental prices in Chicago?

If it is your aim to save the maximum during your vacation to Chicago, travel in January ($270.91 per night on average), December ($285.31), or February ($297.14), to find the lowest prices for the whole year.

During which months are vacation rentals more expensive in Chicago?

At the time of booking a vacation rental in Chicago, the highest prices are usually seen in the month of August (with an average of $386.83 per night), followed by July ($383.64), and September ($368.12).

Are there usually many vacation rentals available in Chicago?

We recommend you to book in advance in Chicago as only 31% of the accommodations are free throughout the year, following the data observed in 2020.

What are the best months for a last-minute getaway?

The most available months are, on average, January (with an availability of 43%), April (42%), and June (34.75%), according to the trends observed in 2020.

When will it be harder to find an available vacation rental in Chicago?

According to data from 2020, the months with the fewest housing options available in Chicago are, in order, October (with 22.4% of available rentals), August (26.8%), and July (27.25%).

How many rentals does Holidu have in Chicago?

We have grouped together the offers from 8 different partners in Chicago, so we can offer you around 1200 properties. You're going to have a hard time choosing your favorite!

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

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