Vacation Rentals in Chicago

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Popular Accommodations in Chicago

Apartment for 20 people, with terrace
20 pers., 2 bedrooms
Chicago, Lake Michigan

from
$318
per night

Apartment for 8 people, with garden, with pets
8 pers., 2 bedrooms, 990ft²
4.4
9 reviews
Chicago, Lake Michigan

from
$136
per night

Apartment for 3 people, with pool and terrace, child-friendly
3 pers., 1 bedroom
4.0
84 reviews
Chicago, Lake Michigan

from
$57
per night

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Vacation Rentals in Chicago

Apartment for 3 people, child-friendly
3 pers., 1 bedroom
3.9
21 reviews
Chicago, Lake Michigan

from
$98
per night

Apartment for 9 people, with terrace, with pets
9 pers., 3 bedrooms
Chicago, Lake Michigan

from
$252
per night

Apartment for 12 people
12 pers., 4 bedrooms
Chicago, Lake Michigan

from
$507
per night

Vacation apartment for 2 people
2 pers., 1 bedroom
2.9
149 reviews
Chicago, Lake Michigan

from
$18
per night

Apartment for 8 people
8 pers., 2 bedrooms
4.4
31 reviews
Chicago, Lake Michigan

from
$84
per night

Vacation apartment for 1 people, child-friendly
1 pers., 1 bedroom
2.6
132 reviews
Chicago, Lake Michigan

from
$6
per night

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Vacation Rentals where Pets Allowed

Apartment for 4 people, with pets
4 pers., 2 bedrooms,
0.5
1 review
Chicago, Lake Michigan

from
$103
per night

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

from
$67
per night

Vacation house for 10 people, with garden, with pets
10 pers., 3 bedrooms,
4.1
6 reviews
Chicago, Lake Michigan

from
$272
per night

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Vacation Rentals with Pool

Resort for 4 people, with sauna and terrace as well as jacuzzi and pool
4 pers., 1 bedroom, 549ft²
4.4
141 reviews
Chicago, Lake Michigan

from
$158
per night

Apartment for 2 people, with pool and terrace as well as jacuzzi, with pets
2 pers., 1 bedroom
3.8
40 reviews
Chicago, Lake Michigan

from
$70
per night

Apartment for 8 people, with pool
8 pers., 3 bedrooms
5.0
2 reviews
Chicago, Lake Michigan

from
$222
per night

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Vacation Rentals with Internet

Vacation apartment for 2 people, child-friendly
2 pers., 1 bedroom
3.4
3 reviews
Chicago, Lake Michigan

from
$67
per night

Vacation apartment for 1 people
1 pers., 1 bedroom
4.7
81 reviews
Chicago, Lake Michigan

from
$18
per night

Vacation apartment for 2 people
2 pers., 1 bedroom
1.6
4 reviews
Chicago, Lake Michigan

from
$50
per 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 76
Pet allowed 25
Balcony/Terrace 25
TV 70
Air conditioning 63
Parking 41
Washing machine 62
Heating 64
Elevator 21

Prices and availability

Prices

November
December
January
February
March
April
$339
Oct 24 - Oct 31
$276 per night
Oct 31 - Nov 07
$277 per night
Nov 07 - Nov 14
$276 per night
Nov 14 - Nov 21
$281 per night
Nov 21 - Nov 28
$274 per night
Nov 28 - Dec 05
$276 per night
Dec 05 - Dec 12
$269 per night
Dec 12 - Dec 19
$253 per night
Dec 19 - Dec 26
$297 per night
Dec 26 - Jan 02
$313 per night
Jan 02 - Jan 09
$313 per night
Jan 09 - Jan 16
$303 per night
Jan 16 - Jan 23
$326 per night
Jan 23 - Jan 30
$306 per night
Jan 30 - Feb 06
$311 per night
Feb 06 - Feb 13
$322 per night
Feb 13 - Feb 20
$239 per night
Feb 20 - Feb 27
$236 per night
Feb 27 - Mar 06
$233 per night
Mar 06 - Mar 13
$322 per night
Mar 13 - Mar 20
$339 per night
Mar 20 - Mar 27
$259 per night
Mar 27 - Apr 03
$295 per night
Apr 03 - Apr 10
$316 per night
Average price per week

Availabilities

November
December
January
February
March
April
12 %
Oct 24 - Oct 31
12 %
Oct 31 - Nov 07
12 %
Nov 07 - Nov 14
12 %
Nov 14 - Nov 21
12 %
Nov 21 - Nov 28
12 %
Nov 28 - Dec 05
12 %
Dec 05 - Dec 12
12 %
Dec 12 - Dec 19
12 %
Dec 19 - Dec 26
12 %
Dec 26 - Jan 02
12 %
Jan 02 - Jan 09
12 %
Jan 09 - Jan 16
12 %
Jan 16 - Jan 23
12 %
Jan 23 - Jan 30
12 %
Jan 30 - Feb 06
12 %
Feb 06 - Feb 13
12 %
Feb 13 - Feb 20
12 %
Feb 20 - Feb 27
12 %
Feb 27 - Mar 06
12 %
Mar 06 - Mar 13
12 %
Mar 13 - Mar 20
12 %
Mar 20 - Mar 27
12 %
Mar 27 - Apr 03
12 %
Apr 03 - Apr 10
12 %
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!

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