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.

Guest favourite
Guest suite in Chicago
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
3–10 Sep
₹10,071 per night
5.0 out of 5 average rating, 288 reviews
Guest favourite
Flat in Chicago
Amazing Location | Stunning Views | Free Parking
You will feel on top of the world as this luxury property truly has it all. With a 24 hour doorman, heated parking in the building, hot tub, workout and rec rooms, and views not to be beat, this property is in a beautiful and safe neighborhood in Chicago. Be at Mccormick place in under five minutes or dash off to all Chicago has to offer from our perfectly located condo in our Luxury South Loop flat. Close to public transport and an easy cab ride to the airports, we look forward to your stay!
4–11 Jan
₹29,249 per night
4.86 out of 5 average rating, 148 reviews
Guest favourite
Flat in Chicago
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.
3–10 Sep
₹7,400 per night
4.98 out of 5 average rating, 102 reviews

Popular amenities for Chicago holiday rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Other great holiday rentals in Chicago

Guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
9–16 Apr
₹8,071 per night
4.97 out of 5 average rating, 258 reviews
Guest favourite
Guest suite in Lincoln Square
Cozy, Quiet, Garden Getaway!
8–15 Nov
₹8,952 per night
4.91 out of 5 average rating, 414 reviews
Guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
28 Jan – 4 Feb
₹9,091 per night
4.99 out of 5 average rating, 221 reviews
Guest favourite
Guest suite in Chicago
Augusta's Garden | Noble Square | Wicker Park
5–12 Apr
₹8,856 per night
4.96 out of 5 average rating, 303 reviews
Guest favourite
Flat in Berwyn
Berwyn Betty Apartment
19–26 Aug
₹9,666 per night
4.99 out of 5 average rating, 246 reviews
Guest favourite
Flat in Irving Park
Ravenswood Manor, Sleeps 4! Close to El and Parks
16–23 Jan
₹8,194 per night
4.89 out of 5 average rating, 171 reviews
Guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
6–13 Dec
₹10,954 per night
4.96 out of 5 average rating, 406 reviews
Guest favourite
Flat in Cicero
COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
11–18 Dec
₹8,827 per night
4.98 out of 5 average rating, 185 reviews
Guest favourite
Apartment in Chicago
Unique Lincoln Park Duplex Apt
12–19 Sep
₹13,263 per night
4.95 out of 5 average rating, 431 reviews
Guest favourite
Cabin in Griffith
Beautiful Rustic Cabin for Two!
25 Feb – 4 Mar
₹6,155 per night
4.91 out of 5 average rating, 143 reviews
Guest favourite
Flat in Chicago
King Size Sleep Number Bed in Cozy Home w/ No fees
2–9 Jan
₹7,450 per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Guest suite in Irving Park
Entire 1-bedroom Apartment in Vintage Bungalow
7–14 Aug
₹6,395 per night
4.93 out of 5 average rating, 41 reviews

Quick stats about holiday rentals in Chicago

Total rentals

11T properties

Rentals with dedicated workspaces

6.6T properties have a dedicated workspace

Rentals with a pool

1.2T properties have a pool

Pet-friendly rentals

3.3T properties allow pets

Family-friendly rentals

5T properties are a good fit for families

Total number of reviews

4.8L reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago