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Holiday lettings & accommodation in Chicago

Find 4.368 available offers from 4 partners
Anytime
1 guest
Anytime
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Recommended holiday lettings in Chicago

Find your perfect holiday home, apartment or cottage in Chicago from just 2.270 ₹ per night!

House Mayfair
-50%
7 Feb - 14 Feb
House ∙ 6 guests ∙ 2 bedrooms
139 m² House
Mayfair, Chicago, Illinois, United States
₹48,609₹43,158
per night
Agoda
₹48,609₹43,158
per night
View deal
Agoda
Villa Douglas
19 Apr - 26 Apr
Free cancellation
Villa ∙ 6 guests ∙ 2 bedrooms
1200 m² Villa
Douglas, Chicago, Illinois, United States
₹28,512
per night
Agoda
₹28,512
per night
View deal
Agoda
House McKinley Park
19 Jul - 26 Jul
Free cancellation
House ∙ 2 guests ∙ 1 bedroom
56 m² House
McKinley Park, Chicago, Illinois, United States
₹15,985
per night
Agoda
₹15,985
per night
View deal
Agoda
Apartment Tri-Taylor
12 Jul - 19 Jul
Free cancellation
Apartment ∙ 4 guests ∙ 2 bedrooms
111 m² Apartment
Tri-Taylor, Chicago, Illinois, United States
₹27,730
per night
Agoda
₹27,730
per night
View deal
Agoda
Apartment West Town
-16%
23 Mar - 30 Mar
Free cancellation
Apartment ∙ 3 guests ∙ 1 bedroom
600 m² Apartment
West Town, Chicago, Illinois, United States
₹17,251₹16,819
per night
Agoda
₹17,251₹16,819
per night
View deal
Agoda
Apartment West Loop Gate
-41%
21 Jun - 28 Jun
Free cancellation
Apartment ∙ 6 guests ∙ 2 bedrooms
1000 m² Apartment
West Loop Gate, Chicago, Illinois, United States
₹1,50,421₹76,818
per night
Agoda
₹1,50,421₹76,818
per night
View deal
Agoda
Apartment South Loop
12 Jul - 19 Jul
Apartment ∙ 10 guests ∙ 3 bedrooms
200 m² Apartment
South Loop, Chicago, Illinois, United States
₹71,949
per night
Agoda
₹71,949
per night
View deal
Agoda
Apartment Jefferson Park
12 Jul - 19 Jul
Free cancellation
Apartment ∙ 2 guests ∙ 1 bedroom
60 m² Apartment
Jefferson Park, Chicago, Illinois, United States
₹11,943
per night
Outstanding
Agoda
₹11,943
per night
View deal
Agoda
Apartment Grand Boulevard
12 Jul - 19 Jul
Free cancellation
Apartment ∙ 6 guests ∙ 3 bedrooms
111 m² Apartment
Grand Boulevard, Chicago, Illinois, United States
₹23,488
per night
Agoda
₹23,488
per night
View deal
Agoda
House Fifth City
6 Jul - 13 Jul
Free cancellation
House ∙ 5 guests ∙ 3 bedrooms
139 m² House
Fifth City, Chicago, Illinois, United States
₹22,954
per night
Agoda
₹22,954
per night
View deal
Agoda
Apartment The Gap
-27%
31 Mar - 7 Apr
Free cancellation
Apartment ∙ 4 guests ∙ 2 bedrooms
93 m² Apartment
The Gap, Chicago, Illinois, United States
₹40,537₹35,949
per night
Agoda
₹40,537₹35,949
per night
View deal
Agoda
Apartment Mayfair
-17%
5 Jul - 12 Jul
Free cancellation
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment
Mayfair, Chicago, Illinois, United States
₹30,675₹30,723
per night
Agoda
₹30,675₹30,723
per night
View deal
Agoda
Apartment Heart of Chicago
19 Jul - 26 Jul
Free cancellation
Apartment ∙ 6 guests ∙ 2 bedrooms
65 m² Apartment
Heart of Chicago, Chicago, Illinois, United States
₹27,541
per night
Outstanding
Agoda
₹27,541
per night
View deal
Agoda
Apartment North Kenwood
12 Jul - 19 Jul
Apartment ∙ 4 guests ∙ 2 bedrooms
135 m² Apartment
North Kenwood, Chicago, Illinois, United States
₹19,313
per night
Agoda
₹19,313
per night
View deal
Agoda
Apartment Park Manor
12 Jul - 19 Jul
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment
Park Manor, Chicago, Illinois, United States
₹12,031
per night
Good
Agoda
₹12,031
per night
View deal
Agoda

Holiday homes and cottages with a garden

Bed and breakfast  Magnolia Glen
5 Jan - 12 Jan
-28%
₹22,816
₹22,659 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding
Magnolia Glen, Chicago, Illinois, United States
Garden
Agoda
View deal
Bed and breakfast  Sheffield & DePaul
1 Feb - 8 Feb
-29%
₹42,337
₹24,762 per night
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms
3.8
Good
Sheffield & DePaul, Chicago, Illinois, United States
Garden
Agoda
View deal
Bed and breakfast  Magnolia Glen
25 Jan - 1 Feb
₹14,687 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding
Magnolia Glen, Chicago, Illinois, United States
Garden
Agoda
View deal
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Best holiday rental deals in Chicago

Save up to 24%

Apartment Logan Square
28 May - 4 Jun
-20%
32.521 ₹
26.076 ₹ per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Logan Square, Chicago, Illinois, United States
Free cancellation
Agoda
View deal
Apartment West Town
26 Jul - 2 Aug
-15%
30.517 ₹
25.911 ₹ per night
Apartment ∙ 6 guests ∙ 3 bedrooms
West Town, Chicago, Illinois, United States
Free cancellation
Agoda
View deal
Apartment Logan Square
28 Jun - 5 Jul
-24%
43.550 ₹
33.188 ₹ per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Logan Square, Chicago, Illinois, United States
Free cancellation
Agoda
View deal

Budget-friendly Holiday Homes in Chicago

Find Fantastic yet Cheap Lettings

Apartment Roscoe Village
6 Feb - 13 Feb
-57%
₹29,003
₹26,547 per night
Apartment ∙ 10 guests ∙ 1 bedroom
4.3
Very good
Roscoe Village, Chicago, Illinois, United States
Agoda
View deal
House Douglas
7 Feb - 14 Feb
-79%
₹33,006
₹16,986 per night
House ∙ 6 guests ∙ 3 bedrooms
Douglas, Chicago, Illinois, United States
Agoda
View deal
Apartment West Town
2 Aug - 9 Aug
₹22,124 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding
West Town, Chicago, Illinois, United States
Free cancellation
Agoda
View deal

Top-Rated Lettings and Properties in Chicago

Book Holiday Letting Offers with the Highest User Rating

Bed and breakfast Bridgeport
4 Jan - 11 Jan
-25%
₹35,682
₹26,761 per night
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent
Bridgeport, Chicago, Illinois, United States
Agoda
View deal
Bed and breakfast Old Town
5 Jan - 12 Jan
-46%
₹28,852
₹17,104 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
4.8
Outstanding
Old Town, Chicago, Illinois, United States
Agoda
View deal
Bed and breakfast Wicker Park
4 Jan - 11 Jan
-39%
₹40,737
₹19,713 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom
4.8
Outstanding
Wicker Park, Chicago, Illinois, United States
Agoda
View deal

Customer ratings and reviews

How are reviews collected?
Abdullah N.
Guest verified by HomeToGo

I will definitely rent it out next time, best place to get if you want to visit chicago. 25-30 mins away from Downtown Chicago. Luxury and got so much Room for kids to play around. You can get 12/13 beds easily.

Reviewed on 2/12/2024 | Family
Flat South Austin
from 28.647 ₹ per night
HomeToGo
Flat ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
View deal
from 28.647 ₹ per night
Flat ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent(3 ratings)
South Austin, Chicago, Illinois, United States
HomeToGo
View deal

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Verified reviews

Verified reviews

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Smart search made simple

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Chicago

  • WiFi (4.008)
  • Pool (940)
  • Kitchen (2.097)
  • TV (3.944)
  • Air conditioning (4.291)
  • Parking (1.417)
  • Washing machine (1.689)
  • Pet-friendly (2.480)
  • Balcony/patio (893)
  • Microwave (1.568)
  • Dishwasher (1.121)
  • No smoking (3.732)

Price and Availability Index for Chicago

Click on any bar to see price and availability information

Holiday Letting Price Information in Chicago

Rental availability information in Chicago

Information about holiday rentals in Chicago

🏡 Holiday homes available 4.368 rentals
💳 Discounts available up to 75%
🌙 Nightly prices from 2.270 ₹
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly rentals 2.474 properties
🏊 Holiday rentals with pools 942 properties
2.933.319 reviews
Chicago holiday rentals have an average rating of 4.1/5 across 2.933.319 reviews left by travellers.
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