HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

Holidaymakers searching for holiday rentals in Chicago also enquired about apartments in Midtown Manhattan, apartments in Upper East Side and apartments in Central Park North

Make a holiday rental, home, or cottage in Chicago, USA your home away from home

Holidaymakers looking for a fantastic city break might like to try Chicago in the mid-west of the United States. Located in the state of Illinois this amazing city offers many exciting things for visitors to see and do. Here visitors will find numerous different places to stay including self catering accommodation, apartments and condos.

Things to do on holiday to Chicago, USA

This is a cycling friendly city with over 100 miles of bike lanes and 50 miles of bike paths. There are many scenic areas for visitors to explore either on two wheels or by foot and there are also horse riding opportunities available here. There are beaches located along Lake Michigan for holidaymakers to relax on in the sunshine. Swimming, canoeing and kayaking can also be enjoyed on the lake. The city offers many other sporting activities including tennis and softball and there are many golf courses located in and around the city. Chicago has numerous restaurants, bars and cafes offering an excellent selection of cuisine from around the world. Self catering holidaymakers will be able to buy food and drink from stores and markets as well as gifts and souvenirs. Chicago has some upscale shopping areas such as the Magnificent Mile and State Street.

Places to visit on holiday to Chicago, USA

Chicago has many wonderful places for holidaymakers to visit including historic buildings and attractions. Tourists can visit various museums and galleries in the city such as the Adler Planetarium and Astronomy Museum, the Field Museum of Natural History and the Shedd Aquarium. As well as the museums visitors can go to the Chicago Cultural Center, which houses the city’s visitor information center, galleries and exhibit halls. Some fantastic sculptures are well worth visiting including the Glass Fountain and the Cloud Gate. Chicago has lots of parks and gardens too with Lincoln Park the second most visited city park in the U.S. Other popular attractions here include Chicago Botanic Garden and Brookfield Zoo. Holidaymakers with a head for heights can get a great view of the city from Skydeck Chicago’s The Ledge, which is 1,350 feet from the ground.

Weather in Chicago, USA

The warmest time of the year in Chicago is July with average high temperatures of almost 29 degrees centigrade. The coldest month is January when average highs are -1 degrees centigrade and average lows are almost -11 degrees. January also see the highest amount of snowfall with an average of 10.7 inches, while august is the wettest month with an average of 4.2 inches of rainfall.

Travel to Chicago, USA

Chicago O’Hare International Airport has flights from many international airports including Amsterdam (AMS), Beijing-Capital (PEK), Brussels (BRU), Dublin (DUB), Frankfurt (FRA), London-Heathrow (LHW), Madrid (MAD), Manchester (MAN), Paris-Charles de Gaulle (CDG), Rome-Fiumicino (FCO), Tokyo-Narita (NRT), Toronto-Pearson (YYZ) and Zurich (ZRH) amongst others. There are taxi and limousine services available at the airport as well as several car rental firms.

Excellent! 4.5/5
(70 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #690239vb
70
Viewed 172 times in the last 48 hours
Excellent! 4.7/5
(52 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #445608vb
52
Viewed 72 times in the last 48 hours
Wonderful! 4.9/5
(35 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
Townhome #3917584
35
Viewed 57 times in the last 48 hours
Wonderful! 4.9/5
(74 reviews)
avg/night
  • 4 BR
  • 4 BA
  • Sleeps 12
Condo #679790vb
74
Viewed 140 times in the last 48 hours
Excellent! 4.7/5
(18 reviews)
avg/night
  • Studio
  • 1 BA
  • Sleeps 2
Multiple rentals Apartment #4261388
18
Viewed 104 times in the last 48 hours
Wonderful! 4.8/5
(104 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 8
Apartment #578762vb
104
Viewed 70 times in the last 48 hours
Wonderful! 4.8/5
(58 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
Apartment #3768288
58
Viewed 47 times in the last 48 hours
Wonderful! 4.9/5
(40 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #3790035
40
Viewed 87 times in the last 48 hours
Excellent! 4.7/5
(108 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Condo #222038
108
Viewed 112 times in the last 48 hours
Wonderful! 4.8/5
(54 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #290256vb
54
Viewed 118 times in the last 48 hours
Wonderful! 4.8/5
(51 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #265424vb
51
Viewed 224 times in the last 48 hours
Wonderful! 4.8/5
(33 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #735859vb
33
Viewed 86 times in the last 48 hours
Wonderful! 4.8/5
(27 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #3795191
27
Viewed 125 times in the last 48 hours
Wonderful! 4.9/5
(52 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358013
52
Viewed 40 times in the last 48 hours
Excellent! 4.7/5
(42 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #3751630
42
Viewed 66 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3645759
7
Viewed 26 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #4172462
9
Viewed 17 times in the last 48 hours
Wonderful! 4.8/5
(59 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #296798
59
Viewed 34 times in the last 48 hours
Excellent! 4.5/5
(34 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #622632vb
34
Viewed 125 times in the last 48 hours
Excellent! 4.4/5
(16 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #836457vb
16
Viewed 32 times in the last 48 hours
Exceptional! 5/5
(35 reviews)
avg/night
  • 1 BR
  • 2 BA
  • Sleeps 2
Apartment #864022vb
35
Viewed 33 times in the last 48 hours
Wonderful! 4.9/5
(27 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #894129vb
27
Viewed 131 times in the last 48 hours
Excellent! 4.5/5
(83 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 10
Condo #400905vb
83
Viewed 48 times in the last 48 hours
Excellent! 4.6/5
(26 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #4146480
26
Viewed 14 times in the last 48 hours
Wonderful! 4.9/5
(72 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358005
72
Viewed 64 times in the last 48 hours
Wonderful! 4.9/5
(66 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3720918
66
Viewed 72 times in the last 48 hours
Excellent! 4.6/5
(45 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Apartment #3833362
45
Viewed 54 times in the last 48 hours
Exceptional! 5/5
(66 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
Apartment #627209vb
66
Viewed 49 times in the last 48 hours
Excellent! 4.6/5
(12 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #4172463
12
Viewed 101 times in the last 48 hours
Wonderful! 4.9/5
(51 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #939473
51
Viewed 42 times in the last 48 hours
Excellent! 4.7/5
(46 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 8
Apartment #3645846
46
Viewed 92 times in the last 48 hours
Wonderful! 4.9/5
(15 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #780506vb
15
Viewed 31 times in the last 48 hours
Wonderful! 4.8/5
(73 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Apartment #301852vb
73
Viewed 26 times in the last 48 hours
Wonderful! 4.8/5
(29 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #870495vb
29
Viewed 53 times in the last 48 hours
Exceptional! 5/5
(21 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #695418vb
21
Viewed 30 times in the last 48 hours
Very Good! 4.1/5
(15 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #4280611
15
Viewed 13 times in the last 48 hours
Wonderful! 4.9/5
(66 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #374687
66
Viewed 55 times in the last 48 hours
Wonderful! 4.9/5
(19 reviews)
avg/night
  • Studio
  • 1 BA
  • Sleeps 2
Condo #844695vb
19
Viewed 35 times in the last 48 hours
Wonderful! 4.9/5
(76 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358020
76
Viewed 48 times in the last 48 hours
Wonderful! 4.8/5
(48 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 5
Apartment #600158vb
48
Viewed 11 times in the last 48 hours
Wonderful! 4.9/5
(82 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 6
Apartment #225815
82
Viewed 26 times in the last 48 hours
Wonderful! 4.8/5
(46 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 6
Apartment #271945
46
Viewed 19 times in the last 48 hours
Very Good! 4.1/5
(7 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Condo #159001vb
7
Viewed 187 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 30
Condo #282940vb
2
Viewed 494 times in the last 48 hours
Very Good! 4/5
(7 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
Condo #267015
7
Viewed 457 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 30
Condo #267014
2
Viewed 243 times in the last 48 hours
Very Good! 4.2/5
(5 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
Condo #318483vb
5
Viewed 190 times in the last 48 hours
Wonderful! 4.9/5
(35 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #856957vb
35
Viewed 39 times in the last 48 hours
Exceptional! 5/5
(22 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3627370
22
Viewed 18 times in the last 48 hours
Very Good! 4.2/5
(10 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 10
Apartment #874916vb
10
Viewed 68 times in the last 48 hours

Chicago Holiday Apartments & Rentals (300+)