Vacation Rentals in Chicago

Start comparing over 2,154 rentals in Chicago and book at the best price!

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Popular Accommodations in Chicago

Vacation house for 4 people
4 pers., 3 bedrooms
5.0
1 review
Chicago, Lake Michigan
from
$173per night
Apartment for 6 people, with balcony/terrace
6 pers., 3 bedrooms
4.9
20 reviews
Chicago, Lake Michigan
from
$490per night
Vacation house for 10 people
10 pers., 2 bedrooms, 1,195ft²
Chicago, Lake Michigan
from
$273per night
Apartment for 6 people
6 pers., 3 bedrooms
5.0
1 review
Chicago, Lake Michigan
from
$284per night
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Vacation Rentals in Chicago

Apartment for 6 people
6 pers., 3 bedrooms
5.0
1 review
Chicago, Lake Michigan
from
$284per night
Apartment for 7 people
7 pers., 3 bedrooms, 1,195ft²
4.9
8 reviews
Chicago, Lake Michigan
from
$282per night
Apartment for 6 people
6 pers., 2 bedrooms
Chicago, Lake Michigan
from
$328per night
Vacation house for 6 people
6 pers., 2 bedrooms
Chicago, Lake Michigan
from
$340per night
Vacation house for 6 people, with garden and pool
6 pers., 3 bedrooms, 1,195ft²
5.0
4 reviews
Chicago, Lake Michigan
from
$206per night
Vacation house for 6 people, with jacuzzi and garden
6 pers., 3 bedrooms
4.4
4 reviews
Chicago, Lake Michigan
from
$234per night
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Vacation Rentals where Pets Allowed

Apartment for 5 people, with jacuzzi and balcony
5 pers., 2 bedrooms, 1,195ft²,
4.9
20 reviews
Chicago, Lake Michigan
from
$229per night
Vacation house for 20 people, with balcony/terrace
20 pers., 6 bedrooms, 5,490ft²,
3.6
20 reviews
Chicago, Lake Michigan
from
$615per night
Apartment for 5 people
5 pers., 3 bedrooms, 1,496ft²,
4.2
3 reviews
Chicago, Lake Michigan
from
$115per 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
$369per night
Apartment for 6 people
6 pers., 2 bedrooms
Chicago, Lake Michigan
from
$328per night
Studio for 2 people, with jacuzzi
2 pers., 1 bedroom
Chicago, Lake Michigan
from
$437per night
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Vacation Rentals with Internet

Apartment for 10 people
10 pers., 3 bedrooms
2.6
1 review
Chicago, Lake Michigan
from
$190per night
Vacation house for 6 people
6 pers., 2 bedrooms
Chicago, Lake Michigan
from
$182per night
Apartment for 3 people
3 pers., , 334ft²
2.2
4 reviews
Chicago, Lake Michigan
from
$167per night
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Highlights Chicago

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

Most popular in Chicago

Internet 1,089
Balcony/Terrace 395
TV 994
Air conditioning 946
Garden 198
Parking 596
Washing machine 920
Heating 898
Elevator 402

Prices and availability

Prices

September
October
November
December
January
$456
Aug 08 - Aug 15
$324 per night
Aug 15 - Aug 22
$325 per night
Aug 22 - Aug 29
$325 per night
Aug 29 - Sep 05
$332 per night
Sep 05 - Sep 12
$343 per night
Sep 12 - Sep 19
$344 per night
Sep 19 - Sep 26
$339 per night
Sep 26 - Oct 03
$369 per night
Oct 03 - Oct 10
$345 per night
Oct 10 - Oct 17
$351 per night
Oct 17 - Oct 24
$415 per night
Oct 24 - Oct 31
$380 per night
Oct 31 - Nov 07
$319 per night
Nov 07 - Nov 14
$320 per night
Nov 14 - Nov 21
$456 per night
Nov 21 - Nov 28
$432 per night
Nov 28 - Dec 05
$335 per night
Dec 05 - Dec 12
$308 per night
Dec 12 - Dec 19
$247 per night
Dec 19 - Dec 26
$229 per night
Dec 26 - Jan 02
$312 per night
Jan 02 - Jan 09
$370 per night
Jan 09 - Jan 16
$278 per night
Jan 16 - Jan 23
$0 per night
Average price per week

Availabilities

September
October
November
December
January
55 %
Aug 08 - Aug 15
25 %
Aug 15 - Aug 22
33 %
Aug 22 - Aug 29
37 %
Aug 29 - Sep 05
38 %
Sep 05 - Sep 12
44 %
Sep 12 - Sep 19
47 %
Sep 19 - Sep 26
48 %
Sep 26 - Oct 03
48 %
Oct 03 - Oct 10
48 %
Oct 10 - Oct 17
48 %
Oct 17 - Oct 24
53 %
Oct 24 - Oct 31
54 %
Oct 31 - Nov 07
53 %
Nov 07 - Nov 14
54 %
Nov 14 - Nov 21
55 %
Nov 21 - Nov 28
53 %
Nov 28 - Dec 05
53 %
Dec 05 - Dec 12
55 %
Dec 12 - Dec 19
55 %
Dec 19 - Dec 26
54 %
Dec 26 - Jan 02
52 %
Jan 02 - Jan 09
54 %
Jan 09 - Jan 16
55 %
Jan 16 - Jan 23
55 %
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.

FAQ: Frequently asked questions about 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!

  1. Vacation rentals
  2. USA
  3. Illinois
  4. Lake Michigan
  5. Chicago