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Chicago, IL vacation rentals

Search among 445 available vacation rentals in Chicago from 50+ providers

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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6 adults
2 bedrooms
3 beds
View on map1700 yd from City Center500 yd from House of Blues Chicago
Featuring the views over Lake Michigan, this property offers a rooftop outdoor pool and a game room and video games for kids.
8.0
Great7 reviews
From   US$ 152 /nightSelect
Not available
The largest option:
4 adults
View on map1100 yd from City Center500 yd from House of Blues Chicago
Placed close to Cadillac Palace Theatre, this 2-bedroom apartment with an indoor swimming pool and a steam room and a Jacuzzi will make your stay unforgettable.
8.0
Great18 reviews
From   US$ 205 /nightSelect
Not available
The largest option:
4 adults
2 bedrooms
3 beds
2.0 mi from City Center100 yd from Scales and Tales
Situated in Chicago, a 10-minute drive to McCormick Place, this villa features a nice balcony and a terrace.
7.8
Very good3 reviews
From   US$ 122 /nightSelect
Not available
Homestay
The largest option:
8 adults
1 bedroom
1 bed
6.5 mi from City Center600 yd from
The budget hotel is a good starting point to Chicago' sights including Promontory Point and Saint Edmund's Episcopal Church.
8.0
Great1 review
From   US$ 19 /nightSelect
Not available
Homestay
The largest option:
12 adults
1 bedroom
1 bed
4.4 mi from City Center600 yd from
Located 1 miles from Solid Rock MB Church, this villa offers 9 rooms.
8.2
Great3 reviews
From   US$ 154 /nightSelect
Not available
The largest option:
2 adults
1 bedroom
1 bed
4.1 mi from City Center300 yd from
Offering a shared kitchen equipped with a dishwasher, a refrigerator and a washing machine, this villa is set near Claire-Christian United Methodist Church.
7.6
Very good5 reviews
From   US$ 50 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
1.3 mi from City Center1100 yd from Field Museum of Natural History
Located in the natural part of Chicago, this 2-bedroom apartment has a terrace.
7.6
Very good4 reviews
From   US$ 217 /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.
8.0
Great4 reviews
From   US$ 713 /nightSelect
Not available
The largest option:
3 adults
1 bedroom
2 beds
1100 yd from City Center600 yd from House of Blues Chicago
Featuring a sunbathing terrace and an indoor swimming pool, this venue provides convenient access to St. Therese Chinese Catholic Church, Chicago and is within a 20-minute drive from Midway airport.
7.4
Very good2 reviews
From   US$ 85 /nightSelect
Not available
The largest option:
3 adults
1 bedroom
2 beds
1.8 mi from City Center100 yd from
Featuring a kitchen, the venue is only 2.2 km from United Center.
7.6
Very good4 reviews
From   US$ 63 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
1800 yd from City Center500 yd from House of Blues Chicago
Nestled within 5-minute walk of Shops at Northbridge, the venue offers to enjoy an outdoor swimming pool.
8.4
Great2 reviews
From   US$ 276 /nightSelect
Not available
The largest option:
5 adults
1.4 mi from City Center1400 yd from House of Blues Chicago
Located within a 5-minute walk of Chicago-Brown underground station, this apartment features a sunny balcony.
7.0
Very good3 reviews
From   US$ 364 /nightSelect
Not available
8 adults
2 bedrooms
2 beds
4.6 mi from City Center
This 2-bedroom apartment can accommodate up to 4 people, within a 30-minute walk from Guaranteed Rate Field.
9.0
Perfect3 reviews
From   US$ 110 /nightSelect
Not available
4 adults
3 bedrooms
3 beds
4.9 mi from City Center400 yd from Wrigley Field
Set 3.8 miles from Water Tower Chicago, this apartment has a kitchen and 1 bathrooms.
From   US$ 201 /nightSelect
Not available
2 adults
1 bedroom
1 bed
4.9 mi from City Center1000 yd from
St. Therese Chinese Catholic Church, Chicago is 3.2 miles from this villa that offers 1 bedrooms along with a kitchenette.
8.2
Great4 reviews
From   US$ 48 /nightSelect
Not available
The largest option:
5 adults
2 bedrooms
3 beds
3.2 mi from City Center700 yd from
Offering a fully furnished kitchen with a microwave oven, tea/coffee making equipment and a fridge, the venue is located 20 minutes' walking distance from the center of Chicago.
From   US$ 130 /nightSelect
Not available
7 adults
2 bedrooms
3 beds
7.7 mi from City Center500 yd from
Staying in this 2-bedroom apartment, nestled near Lincoln Square, guests can enjoy a sunny patio to relax after a busy day.
8.0
Great5 reviews
From   US$ 105 /nightSelect
Not available
7 adults
2 bedrooms
3 beds
4.7 mi from City Center600 yd from Wrigley Field
Situated in Lakeview district, the property comprises a kitchen and 2 bedrooms.
From   US$ 128 /nightSelect
Not available
10 adults
3 bedrooms
4 beds
8.6 mi from City Center1.3 mi from Midway Airport (MDW)
Located within a 30-minute walk to Chicago Aerial Tours in Chicago, the accommodation features 3 bedrooms for up to 10 guests.
7.6
Very good3 reviews
From   US$ 210 /nightSelect
Not available
4 adults
1 bedroom
2 beds
4.0 mi from City Center200 yd from
Located within a 5-minute walk of Indiana underground station, this apartment features a balcony.
9.0
Perfect1 review
From   US$ 102 /nightSelect
Not available

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445 hotels found

FAQs about Chicago vacation rentals

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

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.

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.

Chicago vacation rentals

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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