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Holiday lettings & accommodation in Chicago

Find 2.920 available offers from 4 partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to 100 ₹
    • 100 ₹ - 199 ₹
    • From 200 ₹

  • Accommodation types

    • Apartment
    • Bed and breakfast
    • Private room

  • Distance to centre

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • WiFi
    • Pool
    • Kitchen
    • TV
    • Air conditioning
    • Parking
    • Washing machine
    • Balcony/patio
    • Microwave
    • Dishwasher
    • Fireplace
    • Hot tub
    • Garden
    • Cot
    • Sauna
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Smoking allowed
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Recommended holiday lettings in Chicago

Find your perfect holiday home, apartment or cottage in Chicago from just 5.558 ₹ per night!

Bed and breakfast Legends South
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
5430 Happy Home
Legends South, Chicago, Illinois, United States
from 3.793 ₹
per night
Very good
from 3.793 ₹
per night
View deal
Motel River North
Motel ∙ 127 guests ∙ 1 bedroom
Ohio House Motel
River North, Chicago, Illinois, United States
from 9.881 ₹
per night
from 9.881 ₹
per night
View deal
Bed and breakfast North Center
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Lyons' Suite
North Center, Chicago, Illinois, United States
from 26.349 ₹
per night
from 26.349 ₹
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Afrique Francaise de Woodlawn 2
West Woodlawn, Chicago, Illinois, United States
from 7.087 ₹
per night
from 7.087 ₹
per night
View deal
Bed and breakfast Kenwood
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Drexel Apartments, Downtown Hyde Park
Kenwood, Chicago, Illinois, United States
from 6.987 ₹
per night
Excellent
from 6.987 ₹
per night
View deal
Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
House 5863- Bed and Breakfast - Adults Only
Magnolia Glen, Chicago, Illinois, United States
from 13.773 ₹
per night
Outstanding
from 13.773 ₹
per night
View deal
Bed and breakfast Avondale
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
Prime Avondale
Avondale, Chicago, Illinois, United States
from 14.073 ₹
per night
from 14.073 ₹
per night
View deal
Bed and breakfast Rogers Park
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
Farwell dream
Rogers Park, Chicago, Illinois, United States
from 7.685 ₹
per night
from 7.685 ₹
per night
View deal
Bed and breakfast Rogers Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
The Greenleaf House
Rogers Park, Chicago, Illinois, United States
from 7.586 ₹
per night
Excellent
from 7.586 ₹
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Chateau de Woodlawn - Room III - The Dream Catcher
West Woodlawn, Chicago, Illinois, United States
from 6.787 ₹
per night
Outstanding
from 6.787 ₹
per night
View deal
Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms
Villa D' Citta
Sheffield & DePaul, Chicago, Illinois, United States
from 27.546 ₹
per night
Good
from 27.546 ₹
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Chateau de Woodlawn - Room I - La Tour Eiffel
West Woodlawn, Chicago, Illinois, United States
from 7.186 ₹
per night
from 7.186 ₹
per night
View deal
Bed and breakfast Englewood
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Simplified Living Space
Englewood, Chicago, Illinois, United States
from 5.689 ₹
per night
from 5.689 ₹
per night
View deal
Bed and breakfast West Ridge
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Olive House
West Ridge, Chicago, Illinois, United States
from 13.175 ₹
per night
from 13.175 ₹
per night
View deal
Bed and breakfast Bridgeport
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms
The Polo Inn Bridgeport U. S.A.
Bridgeport, Chicago, Illinois, United States
from 26.449 ₹
per night
Outstanding
from 26.449 ₹
per night
View deal

Holiday lettings and apartments with air conditioning

Bed and breakfast Near West Side
from 12.276 ₹ per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming Shared Condo in Prime Chicago Location, 1 Bedroom and 1 Bathroom

Near West Side, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast Magnolia Glen
from 15.869 ₹ per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Magnolia Studios

5.0
Outstanding
Magnolia Glen, Chicago, Illinois, United States
Air conditioning
View deal
Bed and breakfast West Woodlawn
from 6.887 ₹ per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chateau de Woodlawn - Room II - Le Parisienne

West Woodlawn, Chicago, Illinois, United States
Air conditioning
View deal
See all offers

Holiday rentals with wifi

Bed and breakfast Canaryville
from 5.590 ₹ per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Close to Downtown - Free Parking

Canaryville, Chicago, Illinois, United States
Internet
View deal
Bed and breakfast Woodlawn
from 10.979 ₹ per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Kenwood Apartments, Downtown Hyde Park

Woodlawn, Chicago, Illinois, United States
Internet
View deal
Bed and breakfast Bridgeport
from 11.278 ₹ per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Room 2

Bridgeport, Chicago, Illinois, United States
Internet
View deal
See all offers

Apartments and holiday lettings with a kitchen

House Oak Park
from 13.973 ₹ per night
House ∙ 9 guests ∙ 3 bedrooms

139 m² House

Oak Park, Oak Park Township, Illinois, United States
Kitchen
View deal
House Cicero
from 26.349 ₹ per night
House ∙ 6 guests ∙ 2 bedrooms

125 m² House

Cicero, Cicero Township, Illinois, United States
Kitchen
View deal
Apartment Berwyn
from 16.967 ₹ per night
Apartment ∙ 3 guests ∙ 1 bedroom

84 m² Apartment

Berwyn, Cook County, Illinois, United States
Kitchen
View deal
See all offers

Budget-friendly Holiday Homes in Chicago

Find Fantastic yet Cheap Lettings

Bed and breakfast Near West Side
from 19.163 ₹ per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities

Near West Side, Chicago, Illinois, United States
View deal
Bed and breakfast Boystown
from 11.378 ₹ per night
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

Dorothy's

Boystown, Chicago, Illinois, United States
View deal
Motel River North
from 11.378 ₹ per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel

River North, Chicago, Illinois, United States
View deal

Top-Rated Lettings and Properties in Chicago

Book Holiday Letting Offers with the Highest User Rating

Bed and breakfast Fulton Market
from 17.664 ₹ per night
Bed and breakfast ∙ 127 guests ∙ 1 bedroom

The Publishing House Bed and Breakfast

4.9
Outstanding
Fulton Market, Chicago, Illinois, United States
View deal

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Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

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Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

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 (2.841)
  • Pool (852)
  • Kitchen (572)
  • TV (2.380)
  • Air conditioning (2.812)
  • Parking (1.359)
  • Washing machine (297)
  • Pet-friendly (1.757)
  • Balcony/patio (791)
  • Microwave (739)
  • Dishwasher (222)
  • No smoking (2.841)

Information about holiday rentals in Chicago

🏡 Holiday homes available 2.920 rentals
🌙 Nightly prices from 5.558 ₹
⭐ Popular amenities Internet, Pool and Kitchen
🐾 Pet friendly rentals 1.756 properties
🏊 Holiday rentals with pools 852 properties
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