Chicago, IL vacation rentals

Search among 1317 available vacation rentals in Chicago from 50+ providers

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1-20 out of 1317
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8 adults
3 bedrooms
5 beds
Map
4.9 mi from City Center494 yd from Viaduct Center
FromUS$ 273 /nightSelect
8.8
Great18 reviews
10 adults
3 bedrooms
3 beds
Map
2.1 mi from City Center1.1 mi from Michigan Avenue
Set 1.4 miles from Chicago-style pizza, the 3 Bedroom In Best Location Parking Fireplace Patio Home Office Pets Welcome lies in the Old Town district.
FromUS$ 699 /nightSelect
5430 Happy HomeHomestay
8.6
Great21 reviews
The largest option:
2 adults
1 bedroom
1 bed
Map
5.6 mi from City Center
Offering a sunny patio, the homestay is located within 2.3 miles of Museum of Science and Industry.
FromUS$ 42 /nightSelect
7.0
Very good3 reviews
The largest option:
5 adults
2 bedrooms
3 beds
Map
5.0 mi from City Center233 yd from Wrigley Field
The surrounding area includes Gill Park, merely an 8-minute walk away, and Addison subway station only 5 minutes by foot from the Modern 2Br Flats - Right Next To Wrigley Field & Transit - Cubs! Chicago.
FromUS$ 137 /nightSelect
8.4
Great47 reviews
The largest option:
4 adults
Map
1283 yd from City Center243 yd from Chicago Riverwalk
Featuring an indoor swimming pool together with a steam room and an indoor pool, the Oakwood 200 Squared is located within 0.4 miles of The Chicago Theatre and 0.6 miles from The Rookery Building.
FromUS$ 205 /nightSelect
8.8
Great14 reviews
7 adults
5 bedrooms
5 beds
Map
4.8 mi from City Center637 yd from Wrigley Field
The Wrigleyville Friends Unit - 5Bdrm is set approximately 11 minutes' stroll from Gallagher Way and a 15-minute walk from Sheil Park Playground.
FromUS$ 800 /nightSelect
8.4
Great3 reviews
8 adults
2 bedrooms
2 beds
Map
4.6 mi from City Center
This apartment, offering 2 bedrooms and 1 bathrooms with a tub, a separate toilet and a shower, is located in Bronzeville district.
FromUS$ 135 /nightSelect
9.0
Perfect1 review
Map
1.7 mi from City Center598 yd from McCormick Place
Nestled in South Loop district of the city, the venue is about 10 miles from Midway International airport.
FromUS$ 243 /nightSelect
8.6
Great18 reviews
5 adults
3 bedrooms
3 beds
Map
4.8 mi from City Center637 yd from Wrigley Field
FromUS$ 250 /nightSelect
8.6
Great16 reviews
4 adults
1 bedroom
2 beds
Map
2.4 mi from City Center
Set 2.2 miles from 360 Chicago Observation Deck, this apartment has a kitchen and 1 bathrooms.
FromUS$ 89 /nightSelect
8.8
Great19 reviews
4 adults
2 bedrooms
3 beds
Map
4.8 mi from City Center637 yd from Wrigley Field
While staying at the Penthouse Level, Stunning Wrigley Stay you are invited to discover Lincoln Park Conservatory, set 25 minutes' walk away, or Lincoln Park Zoo, which is about 1.6 miles away.
FromUS$ 170 /nightSelect
9.0
Perfect1 review
The largest option:
4 adults
1 bedroom
2 beds
Map
3.8 mi from City Center
While staying at the Perfect Place To Enjoy The City Or Just Relax you are invited to discover United Center, set around 2.3 miles away, or Pete's Fresh Market, which is 1.9 miles away.
FromUS$ 107 /nightSelect
4 adults
3 bedrooms
3 beds
Map
4.9 mi from City Center475 yd from Wrigley Field
While staying at the Wrigley Oasis! Steps From The Field! - 3Bd 1Ba you are invited to discover The Magnificent Mile, set a 15-minute drive away, or Whole Foods Market, which is 0.7 miles away.
FromUS$ 274 /nightSelect
7.0
Very good1 review
4 adults
2 bedrooms
3 beds
Map
3.5 mi from City Center
This 70 m² apartment with 2 bedrooms has a fully furnished kitchen, while being set 3.5 miles from the city center.
FromUS$ 133 /nightSelect
9.0
Perfect1 review
Map
6.9 mi from City Center
FromUS$ 59 /nightSelect
7.8
Very good1 review
The largest option:
10 adults
1 bedroom
3 beds
Map
5.0 mi from City Center
Situated in the Roscoe Village district, the Roscoe Village Guesthouse Chicago offers quick access to Midway International airport within 23 minutes' drive.
FromUS$ 268 /nightSelect
8.0
Great1 review
7 adults
2 bedrooms
4 beds
Map
4.8 mi from City Center637 yd from Wrigley Field
FromUS$ 492 /nightSelect
Lincoln Park GemApartment
8.0
Great1 review
Map
3.8 mi from City Center
FromUS$ 202 /nightSelect
Map
3.8 mi from City Center
FromUS$ 125 /nightSelect
8.0
Great1 review
Map
8.3 mi from City Center
Henry A. Proesel Park Pavilion is 2.6 miles from the Blue Golden Luxury Modern 3- Bedroom Apartment In Chicago and Andersonville is approximately 3.7 miles away.
FromUS$ 161 /nightSelect

FAQs about Chicago vacation rentals

Discover 10 answers from our FAQ and find your perfect vacation rentals 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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Vacation rentals in Chicago essential information

🏨 Vacation rentals in Chicago 1317
👛 Lowest price 39 USD
✍️ Vacation rentals Reviews 231
Guest reviews of hotels in Chicago