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Apartment vacation rentals in Chicago

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Top-rated apartment rentals in Chicago

Guests agree: these apartments are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Chicago
Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
Jul 25 – Aug 1
$100 per night
Guest favorite
Apartment in Humboldt Park
Humboldt Park Loft
Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.
Jul 21 – 28
$89 per night
Guest favorite
Apartment in Chicago
Turquoise Wonder - Clean, Cozy & Stylish Apt
Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.
Jan 27 – Feb 3
$78 per night

Popular amenities for Chicago apartment rentals

Apartment rentals with air conditioning

Guest favorite
Apartment in Chicago
Designer Avondale Attic
May 6 – 13
$91 per night
Superhost
Apartment in Chicago
LAKESIDE PIED `A TERRE STEPS TO BEACH
Dec 26 – Jan 2
$105 per night
Guest favorite
Apartment in Chicago
Renovated Designer Apartment in Heart of Lincoln Square
Mar 26 – Apr 2
$87 per night
Guest favorite
Apartment in Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
Oct 18 – 25
$90 per night
Guest favorite
Apartment in Lincoln Square
Bright family-friendly Lincoln Square 2-bed 1-bath
Oct 15 – 22
$115 per night
Guest favorite
Apartment in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
Jan 21 – 28
$110 per night
Guest favorite
Apartment in Chicago
iKlektik House // Robin
Nov 2 – 9
$112 per night
Guest favorite
Apartment in Chicago
Charming Gold Coast One-Bedroom Near Downtown!
Feb 6 – 13
$90 per night
Guest favorite
Apartment in West Town
Fully Furnished Apartment Wicker Park Free Parking
Mar 31 – Apr 5
$112 per night
Guest favorite
Apartment in Berwyn
Berwyn Betty Apartment
Jul 25 – Aug 1
$114 per night
Guest favorite
Apartment in Chicago
Modern Apt with style & comfort in Pilsen Chicago
$70 per night
Guest favorite
Apartment in Oak Park
Cosmopolitan Nest in Oak Park North Side
Aug 9 – 16
$62 per night

Weekly apartment rentals

Guest favorite
Apartment in Chicago
Bright, Modern Apartment in a Vintage Greystone
Oct 16 – 23
$140 per night
Guest favorite
Apartment in Chicago
Charming renovated Victorian apartment in Old Town
Apr 16 – 23
$119 per night
Guest favorite
Apartment in Chicago
Sunny, Cozy, Colorful Andersonville
Apr 4 – 11
$129 per night
Guest favorite
Apartment in Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
Apr 23 – 30
$92 per night
Guest favorite
Apartment in Andersonville
Andersonville Cozy 1 bedroom basement suite
Apr 11 – 18
$109 per night
Guest favorite
Apartment in Chicago
Spacious 2BR on Quiet St - Free Park/Late Checkout
Oct 19 – 26
$154 per night
Guest favorite
Apartment in Chicago
Modern
May 9 – 16
$95 per night
Guest favorite
Apartment in Chicago
Sunny Logan Square Artists' home
Jan 24 – 31
$94 per night
Guest favorite
Apartment in Chicago
Historic East Village in West Town
Sep 4 – 11
$96 per night
Guest favorite
Apartment in Chicago
Lovely Andersonville Apt with Ideal Location
Oct 26 – Nov 2
$102 per night
Guest favorite
Apartment in Chicago
Explore Lincoln Park from a Polished Apartment
Oct 23 – 30
$165 per night
Guest favorite
Apartment in Chicago
Convenient local, private apt. on the Northside!
Apr 10 – 17
$92 per night

Private apartment rentals

Guest favorite
Apartment in Chicago
Ravenswood Guest House Annex
Oct 1 – 8
$79 per night
Superhost
Apartment in Near North Side
Great Location!!-12
Jan 3 – 10
$99 per night
Guest favorite
Apartment in Forest Park
Peaceful oasis in Forest Park
Apr 4 – 11
$103 per night
Guest favorite
Apartment in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Jul 22 – 29
$183 per night
Guest favorite
Apartment in Chicago
Teeny Tiny Bohemian Lodge - Clean & Affordable
May 4 – 11
$51 per night
Guest favorite
Apartment in Logan Square
Logan Square 2nd Floor Chicago Victorian
Jan 1 – 8
$98 per night
Guest favorite
Apartment in Chicago
Charming, Spacious 3BR Lakeview Apt Near Transit
Oct 14 – 21
$123 per night
Guest favorite
Apartment in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
Aug 7 – 14
$287 per night
Guest favorite
Apartment in Chicago
Remodeled Boho Chic 1 Bed in Hip Logan Square
Apr 4 – 11
$85 per night
Guest favorite
Apartment in Chicago
Chicago Charming Gem with Parking, Loop In Minutes
Mar 12 – 19
$112 per night
Guest favorite
Apartment in Chicago
Your brand new Chicago suite (unit 1F)
Oct 28 – Nov 4
$93 per night
Guest favorite
Apartment in Libertyville
131 East Park Ave. #308
Mar 15 – 22
$60 per night

Quick stats about apartment rentals in Chicago

Total rentals

6K properties

Rentals with dedicated workspaces

3.8K properties have a dedicated workspace

Rentals with a pool

780 properties have a pool

Pet-friendly rentals

2K properties allow pets

Family-friendly rentals

2.8K properties are a good fit for families

Total number of reviews

263K reviews

Destinations to explore

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