Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Guest favourite

Guest suite in Chicago

5.0 out of 5 average rating, 292 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 Chicago

4.94 out of 5 average rating, 189 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.

3–10 Jul

$152 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 116 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.

2–9 Jul

$154 SGD per night

Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 110 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*

17–24 Aug

$120 SGD per night

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 105 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.

23–30 Jun

$167 SGD per night

Guest favourite

Flat in Chicago

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.

1–8 Dec

$131 SGD per night

Guest favourite

Loft in Chicago

4.96 out of 5 average rating, 414 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

6–13 Feb

$206 SGD per night

Superhost

Flat in Chicago

4.89 out of 5 average rating, 105 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!

14–21 Jan

$163 SGD per night

Guest favourite

Flat in Cicero

4.98 out of 5 average rating, 200 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

11–18 Nov

$167 SGD per night

Guest favourite

Guest suite in Chicago

4.94 out of 5 average rating, 176 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

19–26 Aug

$154 SGD per night

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 328 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

2–9 Oct

$197 SGD per night

Guest favourite

Flat in Chicago

4.86 out of 5 average rating, 214 reviews

Garden Apartment in the Historic Heart of the City

Welcome to a unique historic block in the heart of the city! Surrounded by Madison/Randolph Street night life, Little Italy, Greek Town, and the United Center, you would be surprised how peaceful this little block can be. Enjoy a serene walk in the neighborhood, or walk through to any of these great attractions.

29 Sep – 6 Oct

$129 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Chicago holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chicago's top sights

Millennium Park1,243 locals recommend

O'Hare International Airport122 locals recommend

Grant Park332 locals recommend

Lincoln Park175 locals recommend

Shedd Aquarium673 locals recommend

Magnificent Mile597 locals recommend

Other great holiday rentals in Chicago

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 235 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

17–24 Nov

$142 SGD per night

Guest favourite

Guest house in Chicago

4.99 out of 5 average rating, 782 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

25 Oct – 1 Nov

$188 SGD per night

Guest favourite

Guest suite in Chicago

4.91 out of 5 average rating, 357 reviews

Contemporary, private suite w fireplace

5–12 Jan

$106 SGD per night

Guest favourite

Guest house in Chicago

4.95 out of 5 average rating, 366 reviews

Cozy Coach House

19–26 Aug

$152 SGD per night

Guest favourite

Flat in Oak Park

4.85 out of 5 average rating, 527 reviews

Long stays welcome@warm&cute vintage 2BR

24 Sep – 1 Oct

$148 SGD per night

Guest favourite

Guest house in Chicago

4.91 out of 5 average rating, 339 reviews

Private, Charming, Coach House Loft in Andersonville

3–10 Oct

$210 SGD per night

Guest favourite

Flat in Chicago

4.95 out of 5 average rating, 21 reviews

Lincoln Square Oasis - Bright, clean studio

17–24 Jan

$113 SGD per night

Guest favourite

Home in Berwyn

5.0 out of 5 average rating, 73 reviews

Retro Modern Bungalow | free parking | pets ok

1–8 Dec

$171 SGD per night

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Quick stats about holiday rentals in Chicago

Total rentals	10K properties
Rentals with dedicated workspaces	6.6K properties have a dedicated workspace
Rentals with a pool	1.1K properties have a pool
Pet-friendly rentals	3.3K properties allow pets
Family-friendly rentals	4.8K properties are a good fit for families
Total number of reviews	466K reviews

Holiday rentals in Chicago

Top-rated holiday rentals in Chicago

Guest suite in Chicago

Flat in Chicago

Flat in Chicago

Guest suite in Chicago

Flat in Chicago

Flat in Chicago

Loft in Chicago

Flat in Chicago

Flat in Cicero

Guest suite in Chicago

Apartment in Chicago

Flat in Chicago

Holiday rentals for every style

Houses

Flats

Cottages

Popular amenities for Chicago holiday rentals

Stay near Chicago's top sights

Other great holiday rentals in Chicago

Flat in Chicago

Guest house in Chicago

Guest suite in Chicago

Guest house in Chicago

Flat in Oak Park

Guest house in Chicago

Flat in Chicago

Home in Berwyn

Quick stats about holiday rentals in Chicago

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore