Vacation Rentals in Chicago

Start comparing over 1,714 rentals in Chicago and book at the best price!

Search millions of vacation rentals
+
Compare over 600 websites
=
Find your perfect vacation rental at the best price

Popular Accommodations in Chicago

Apartment for 4 people
4.8
55 reviews
Chicago, Lake Michigan
from
$262per night
Vacation house for 8 people
8 pers., 3 bedrooms, 250yd to the beach
4.4
12 reviews
Chicago, Lake Michigan
from
$226per night
Apartment for 2 people, with balcony/terrace
4.8
100 reviews
Chicago, Lake Michigan
from
$223per night
Apartment for 2 people
2 pers., 1 bedrooms, 678ft², 6.8mi to the beach
4.5
2 reviews
Chicago, Lake Michigan
from
$145per night
Apartment for 4 people
4 pers., 2 bedrooms, 1,496ft², 6.3mi to the beach
4.9
20 reviews
Chicago, Lake Michigan
from
$329per night
Apartment for 5 people, with pool
5 pers., 2 bedrooms, 1,313ft², 6.9mi to the beach
4.2
15 reviews
Chicago, Lake Michigan
from
$493per night
Apartment for 4 people
4 pers., 1 bedrooms, 700ft², 6.2mi to the beach
5.0
9 reviews
Chicago, Lake Michigan
from
$275per night
Apartmenthotel for 2 people, with balcony/terrace
4.9
88 reviews
Chicago, Lake Michigan
from
$65per night
Apartmenthotel for 4 people, with balcony
4 pers., 2 bedrooms, 915ft², 5.4mi to the beach
4.4
3 reviews
Chicago, Lake Michigan
from
$111per night
Apartment for 6 people, with balcony
5.0
103 reviews
Chicago, Lake Michigan
from
$114per night
Vacation house for 2 people, with garden
2 pers., 1 bedrooms, 646ft², 4.1mi to the beach
5.0
20 reviews
Chicago, Lake Michigan
from
$196per night
Vacation house for 10 people
4.9
32 reviews
Chicago, Lake Michigan
from
$78per night
Apartment for 10 people
5.0
81 reviews
Chicago, Lake Michigan
from
$106per night
Apartmenthotel for 4 people
4 pers., 2 bedrooms, 915ft², 5.9mi to the beach
4.5
67 reviews
Chicago, Lake Michigan
from
$86per night
Apartment for 6 people, with pool
5.0
5 reviews
Chicago, Lake Michigan
from
$135per night
Apartmenthotel for 4 people
4 pers., 2 bedrooms, 0ft², 4.6mi to the beach
4.6
10 reviews
Chicago, Lake Michigan
from
$69per night
Apartment for 4 people, with jacuzzi and balcony
5.0
45 reviews
Chicago, Lake Michigan
from
$200per night
Vacation house for 10 people
4.4
24 reviews
Chicago, Lake Michigan
from
$70per 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

Internet 1,195
Pet allowed 137
Balcony/Terrace 518
TV 1,190
Air conditioning 1,077
Garden 205
Parking 618
Washing machine 958
Heating 1,079

Prices and availability

Prices

January
February
March
April
May
$385
Dec 07 - Dec 14
$275 per night
Dec 14 - Dec 21
$265 per night
Dec 21 - Dec 28
$275 per night
Dec 28 - Jan 04
$302 per night
Jan 04 - Jan 11
$333 per night
Jan 11 - Jan 18
$323 per night
Jan 18 - Jan 25
$269 per night
Jan 25 - Feb 01
$257 per night
Feb 01 - Feb 08
$238 per night
Feb 08 - Feb 15
$246 per night
Feb 15 - Feb 22
$309 per night
Feb 22 - Feb 29
$315 per night
Feb 29 - Mar 07
$291 per night
Mar 07 - Mar 14
$278 per night
Mar 14 - Mar 21
$329 per night
Mar 21 - Mar 28
$305 per night
Mar 28 - Apr 04
$264 per night
Apr 04 - Apr 11
$299 per night
Apr 11 - Apr 18
$311 per night
Apr 18 - Apr 25
$329 per night
Apr 25 - May 02
$314 per night
May 02 - May 09
$317 per night
May 09 - May 16
$360 per night
May 16 - May 23
$385 per night
Average price per week

Availabilities

January
February
March
April
May
72 %
Dec 07 - Dec 14
34 %
Dec 14 - Dec 21
44 %
Dec 21 - Dec 28
42 %
Dec 28 - Jan 04
42 %
Jan 04 - Jan 11
64 %
Jan 11 - Jan 18
67 %
Jan 18 - Jan 25
68 %
Jan 25 - Feb 01
70 %
Feb 01 - Feb 08
71 %
Feb 08 - Feb 15
68 %
Feb 15 - Feb 22
68 %
Feb 22 - Feb 29
72 %
Feb 29 - Mar 07
66 %
Mar 07 - Mar 14
65 %
Mar 14 - Mar 21
64 %
Mar 21 - Mar 28
66 %
Mar 28 - Apr 04
60 %
Apr 04 - Apr 11
60 %
Apr 11 - Apr 18
60 %
Apr 18 - Apr 25
59 %
Apr 25 - May 02
57 %
May 02 - May 09
53 %
May 09 - May 16
52 %
May 16 - May 23
52 %
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