Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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

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Guest favourite

Guest suite in Chicago

4.96 out of 5 average rating, 306 reviews

Augusta's Garden | Noble Square | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

9–16 May

$179 SGD per night

Guest favourite

Guest suite in Chicago

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

19–26 Sep

$191 SGD per night

Guest favourite

Flat in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

13–20 Jul

$159 SGD per night

Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

13–20 Sep

$121 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 117 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

11–18 Jul

$165 SGD per night

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 106 reviews

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.

4–11 Oct

$167 SGD per night

Guest favourite

Flat in Chicago

4.99 out of 5 average rating, 103 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

22–29 Jan

$185 SGD per night

Guest favourite

Flat in West Town

4.96 out of 5 average rating, 262 reviews

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.

23–30 Dec

$138 SGD per night

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 237 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

19–26 Dec

$142 SGD per night

Guest favourite

Guest suite in Lake View

4.95 out of 5 average rating, 175 reviews

1 mile from Wrigley Field

Private entrance In-law suite with full bathroom, kitchenette, bedroom with queen bed, living room with sleeper sofa, bathroom with tub/shower. Access to washer/dryer and back yard. 1 mile from Wrigley Field (20 min walk), steps from Southport Corridor with restaurants, bars, and shopping. 2 - 4 blocks to trains which will take you downtown. 1/2 block from Belmont bus which will take you to the lake (10 min ride). We live onsite so we are available for questions, directions, etc.

5–12 Sep

$206 SGD per night

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 265 reviews

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; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

14–21 Oct

$157 SGD per night

Superhost

Flat in Chicago

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

25 Oct – 1 Nov

$162 SGD per night