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Chicago vacation rentals

We have a choice of 735 vacation home rentals in Chicago. Find a variety of accommodation options in Chicago Loop, Lakeview and Downtown Chicago districts or close to Dearborn Station to feel the urban vibe. Enter your details and booked.net will find accommodation where you can enjoy your stay after exploring Chicago.Hide
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The largest option:
6 adults
3 bedrooms
3 beds
View on map800 yd from City Center300 yd from Chicago Theater
Offering 80 rooms with city views, the hotel is set in Chicago Loop district, just steps from Washington Square Park.
7.8
Very good30 reviews
From   US$ 196 /nightSelect
Not available
4 adults
2 bedrooms
2 beds
View on map2.6 mi from City Center300 yd from Division
This 2-bedroom apartment can accommodate up to 4 people, within a 25-minute walk from United Center.
From   US$ 154 /nightSelect
Not available
The largest option:
2 adults
1.5 mi from City Center200 yd from Water Tower Place
Offering a fully furnished kitchen with a dishwasher, coffee/tea making equipment and a stove, the venue is located 30 minutes' walking distance from the center of Chicago.
8.6
Great139 reviews
From   US$ 126 /nightSelect
Not available
The largest option:
5 adults
1.4 mi from City Center1400 yd from Chicago Riverwalk
Located within a 5-minute walk of Chicago-Brown underground station, this apartment features a sunny balcony.
7.0
Very good1 review
From   US$ 364 /nightSelect
Not available
6 adults
2 bedrooms
3 beds
1500 yd from City Center700 yd from Field Museum of Natural History
This property near Field Museum of Natural History consists of 2 bedrooms, 2 bathrooms and a kitchen for up to 6 guests.
7.0
Very good1 review
From   US$ 713 /nightSelect
Not available
6 adults
2 bedrooms
3 beds
3.5 mi from City Center600 yd from Chicago White Sox
Comprising 2 bedrooms, a fully-fitted kitchen, and a nice balcony, this 121 m² apartment is set in Bridgeport district.
7.0
Very good1 review
From   US$ 167 /nightSelect
Not available
6 adults
2 bedrooms
3 beds
1.2 mi from City Center800 yd from Michigan Avenue
Featuring a patio with tower views, the apartment is placed next to Museum of Contemporary Art.
8.0
Great1 review
From   US$ 371 /nightSelect
Not available
2 adults
1 bedroom
1 bed
3.5 mi from City Center600 yd from 35th-Bronzeville-IIT
Close to a train station, the apartment has 6 rooms with a shared kitchen and a furnished balcony.
7.0
Very good1 review
From   US$ 226 /nightSelect
Not available
1.2 mi from City Center800 yd from Michigan Avenue
In the vicinity of this superior there is The Field Museum and guests can also discover the historic area.
6.8
Nice44 reviews
From   US$ 123 /nightSelect
Not available
The largest option:
2 adults
1 bedroom
1 bed
1400 yd from City Center900 yd from Field Museum of Natural History
Offering a fully-fitted kitchen with a microwave oven, a dishwasher and coffee/tea making equipment, the venue is located 20 minutes' walking distance from the center of Chicago.
From   US$ 93 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
1700 yd from City Center900 yd from Field Museum of Natural History
Located in the natural part of Chicago, this 2-bedroom apartment has a terrace.
7.2
Very good3 reviews
From   US$ 217 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
1800 yd from City Center600 yd from Michigan Avenue
Nestled within 5-minute walk of Shops at Northbridge, the venue offers to enjoy an outdoor swimming pool.
From   US$ 299 /nightSelect
Not available
4 adults
1 bedroom
2 beds
3.9 mi from City Center600 yd from Institute Museum
This property near Cook au Vin Cooking Class consists of 1 bedrooms, 1 bathrooms and a kitchen for up to 4 guests.
From   US$ 264 /nightSelect
Not available
2 adults
1 bedroom
1 bed
4.5 mi from City Center1400 yd from Wrigley Field
Nestled in Lakeview district of the city, the venue is about 13 miles from Midway airport.
From   US$ 179 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
4.6 mi from City Center1000 yd from Wrigley Field
Placed 9 km from The Field Museum, the property consists of 2 bedrooms, 1 bathrooms and a fully-fitted kitchen.
From   US$ 171 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
6.3 mi from City Center1500 yd from University of Chicago
This apartment comes with 2 separate bedrooms along with an private bathroom and is situated near Hyde Park.
From   US$ 158 /nightSelect
Not available
3 adults
1 bedroom
1 bed
6.0 mi from City Center1.2 mi from Wrigley Field
Only few steps from Neighborhood Outreach Project, the contemporary apartment offers 1-bedroom accommodation for 3 guests.
From   US$ 83 /nightSelect
Not available
8 adults
3 bedrooms
4 beds
1600 yd from City Center1100 yd from Chicago Theater
From   US$ 492 /nightSelect
Not available
7 adults
2 bedrooms
2 beds
1100 yd from City Center1000 yd from Grant Park
This 2-bedroom apartment in an university district provides a small fridge, a microwave and a washing machine in a kitchen.
From   US$ 518 /nightSelect
Not available
The largest option:
5 adults
800 yd from City Center600 yd from Chicago Riverwalk
The hotel features an outdoor pool, boasting location 550 meters from LaSalle "L" (Blue Line) metro station while Millennium Park is within walking distance.
Select
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274 hotels found

FAQs about Chicago vacation rentals

Our FAQ covers 10 frequently asked questions about vacation homes in Chicago.

What are the best Chicago vacation rentals with free parking?
The best places providing free parking are Stylish 1Br Apt Perfect For Couple'S Getaway A4 and Cozy 2 Bed / 2 Bath In Lincoln Park, which offer free parking and complimentary private parking.
What are the best vacation rentals in Lakeview district?
Our visitors usually stay in top vacation places in such districts as — Magnificent Mile, Chicago Loop and Hyde Park.
What are the most popular luxury vacation rentals in Chicago?
These luxury accommodations will make your city escape memorable: Envitae 3Br Huge Luxury Loft In Chicago'S Best Building and Printers Paradise. Go here to see more vacation rentals.
What are the best pet-friendly vacation rentals in Chicago?
Travelers who stayed in Chicago with pets have left positive reviews about 2142 West Walton Apartment and Lowest Rates! Spacious Duplex With Free Parking!.
What are the best budget vacation rentals to book in Chicago?
Some of the top cheap apartments are:
Pilsen Roadhouse from 112US$/night;
Lang House Bed & Breakfast from 179US$/night.
Find out more favored cheap places to stay here.
How much does a 3-bedroom vacation house cost for a week?
A 3-bedroom home in Chicago costs about Swank Victorian Near United Center W/ Backdeck the top-rated option is a 283US$.
What are the most popular vacation rentals in Chicago near a beach?
If you are looking for a beach villa, Family Retreat Chicago is a great option to consider.
What are the best vacation rentals with pools in Chicago?
To enjoy a swimming pool on site, rent Envitae 2Br 1 Block To Mag Mile or 2Br/2Ba Brand New Executive Luxury Suite W/ Rooftop Pool, Gym And Balcony By Envitae. Find other popular properties featuring a pool here.
What are the most popular vacation rentals providing free Wi-Fi?
Bright South Loop Suites By Sonder and West Loop Lofts are the best vacation accommodations providing free parking.
What vacation rentals near Lincoln Park Zoo would you recommend?
Sonder North Lincoln is the most popular vacation accommodation close to the Lincoln Park Zoo, one of the top Chicago attractions.

Handpicked vacation rentals in Chicago

When on city escape, all you need is a nice apartment to relax and enjoy your time off work. We can suggest townhouses, apartments, waterfront cabins in Chicago for you. Find accommodation which suits you the most and get it booked!

Exclusive luxury places to stay in Chicago

You will enjoy the opulent atmosphere of comfortable vacation homes in Chicago. Spend your summer vacation at one of the city's most luxury places. With just a few clicks you'll get the most exclusive place to stay in Chicago.

High graded cheap vacation homes in Chicago

A penny saved is a penny earned. It is not necessary to tighten your belt to afford a nice vacation home in Chicago. Our team has checked available dates in United States received from 100+ providers and filtered nice vacation rentals in Chicago to find the best options according to your budget. Surf through!

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