Vacation Rentals in Chicago

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Popular Accommodations in Chicago

Apartment for 6 people, with balcony/terrace
6 pers., 3 bedrooms, 3mi to the beach
4.9
20 reviews
Chicago, Lake Michigan
from
$463per night
Apartment for 7 people
7 pers., 3 bedrooms, 1,195ft², 6.3mi to the beach
4.9
8 reviews
Chicago, Lake Michigan
from
$266per night
Apartment for 5 people, with jacuzzi and balcony
5 pers., 2 bedrooms, 1,195ft², 1.5mi to the beach
4.9
20 reviews
Chicago, Lake Michigan
from
$216per night
Vacation house for 6 people, with garden and jacuzzi
6 pers., 3 bedrooms
4.5
4 reviews
Chicago, Lake Michigan
from
$221per night
Apartment for 2 people
4.9
12 reviews
Chicago, Lake Michigan
from
$101per night
Apartment for 4 people, with garden
4 pers., 1 bedrooms, 398ft², 2.5mi to the beach
4.8
20 reviews
Chicago, Lake Michigan
from
$138per night
Apartment for 6 people, with garden
6 pers., 3 bedrooms, 1.8mi to the beach
4.7
20 reviews
Chicago, Lake Michigan
from
$169per night
Apartment for 1 people, with pets
Chicago, Lake Michigan
from
$18per night
Apartment for 2 people, with garden
3.5
7 reviews
Chicago, Lake Michigan
from
$57per night
Vacation house for 10 people
4.4
54 reviews
Chicago, Lake Michigan
from
$70per night
Vacation house for 4 people, with garden
5.0
10 reviews
Chicago, Lake Michigan
from
$252per night
Apartment for 4 people
5.0
65 reviews
Chicago, Lake Michigan
from
$158per night
Vacation house for 6 people, with garden
4.8
8 reviews
Chicago, Lake Michigan
from
$138per night
Apartment for 14 people
14 pers., 4 bedrooms, 25,833ft², 3.9mi to the beach
5.0
83 reviews
Chicago, Lake Michigan
from
$245per night
Vacation house for 9 people
9 pers., 2 bedrooms, 1,798ft², 4mi to the beach
4.3
24 reviews
Chicago, Lake Michigan
from
$140per night
Apartment for 4 people, with garden
5.0
229 reviews
Chicago, Lake Michigan
from
$121per night
Apartment for 7 people
7 pers., 2 bedrooms, 2.3mi to the beach
4.2
7 reviews
Chicago, Lake Michigan
from
$145per night
Apartment for 10 people
10 pers., 3 bedrooms
4.2
20 reviews
Chicago, Lake Michigan
from
$87per night
Show all

Highlights in Chicago

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

Most popular in Chicago

Pool 157
Internet 1,111
Balcony/Terrace 439
TV 1,063
Air conditioning 965
Garden 235
Parking 625
Washing machine 880
Heating 918

Prices and availability

Prices

February
March
April
May
June
$398
Jan 18 - Jan 25
$223 per night
Jan 25 - Feb 01
$228 per night
Feb 01 - Feb 08
$220 per night
Feb 08 - Feb 15
$223 per night
Feb 15 - Feb 22
$272 per night
Feb 22 - Feb 29
$291 per night
Feb 29 - Mar 07
$310 per night
Mar 07 - Mar 14
$308 per night
Mar 14 - Mar 21
$312 per night
Mar 21 - Mar 28
$301 per night
Mar 28 - Apr 04
$278 per night
Apr 04 - Apr 11
$297 per night
Apr 11 - Apr 18
$291 per night
Apr 18 - Apr 25
$306 per night
Apr 25 - May 02
$309 per night
May 02 - May 09
$325 per night
May 09 - May 16
$370 per night
May 16 - May 23
$380 per night
May 23 - May 30
$398 per night
May 30 - Jun 06
$397 per night
Jun 06 - Jun 13
$384 per night
Jun 13 - Jun 20
$385 per night
Jun 20 - Jun 27
$395 per night
Jun 27 - Jul 04
$396 per night
Average price per week

Availabilities

February
March
April
May
June
61 %
Jan 18 - Jan 25
34 %
Jan 25 - Feb 01
47 %
Feb 01 - Feb 08
54 %
Feb 08 - Feb 15
47 %
Feb 15 - Feb 22
46 %
Feb 22 - Feb 29
59 %
Feb 29 - Mar 07
59 %
Mar 07 - Mar 14
56 %
Mar 14 - Mar 21
55 %
Mar 21 - Mar 28
61 %
Mar 28 - Apr 04
55 %
Apr 04 - Apr 11
57 %
Apr 11 - Apr 18
57 %
Apr 18 - Apr 25
56 %
Apr 25 - May 02
55 %
May 02 - May 09
50 %
May 09 - May 16
48 %
May 16 - May 23
48 %
May 23 - May 30
47 %
May 30 - Jun 06
45 %
Jun 06 - Jun 13
45 %
Jun 13 - Jun 20
42 %
Jun 20 - Jun 27
44 %
Jun 27 - Jul 04
49 %
Percentage of available rentals

Chicago Vacation Rentals

Elegant City Center Vacation Apartments

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.

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