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
29 Jul – 5 AugIndividual Host,
€ 170 per night
5.0 out of 5 average rating, 287 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.
16–23 JulIndividual Host,
€ 130 per night
4.98 out of 5 average rating, 102 reviews
Guest favourite
Flat 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.
17–24 JanIndividual Host,
€ 119 per night
4.96 out of 5 average rating, 257 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
Magnificent Mile597 locals recommend
Shedd Aquarium673 locals recommend

Other great holiday rentals in Chicago

Guest favourite
Flat in Chicago
Gracious, cool, and art-filled designer flat
12–19 MarIndividual Host,
€ 170 per night
4.94 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
Amazing Location | Stunning Views | Free Parking
17–24 DecIndividual Host,
€ 463 per night
4.86 out of 5 average rating, 148 reviews
Guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
10–17 JanIndividual Host,
€ 179 per night
4.96 out of 5 average rating, 401 reviews
Guest favourite
Apartment in Chicago
Unique Lincoln Park Duplex Apt
9–16 SepIndividual Host,
€ 219 per night
4.95 out of 5 average rating, 429 reviews
Guest favourite
Guest house in Chicago
Private, Charming, Coach House Loft in Andersonville
26 Sep – 3 OctIndividual Host,
€ 186 per night
4.91 out of 5 average rating, 338 reviews
Guest favourite
Flat in Chicago
Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village
27 Apr – 4 MayProfessional Host,
€ 171 per night
4.9 out of 5 average rating, 362 reviews
Guest favourite
Flat in Chicago
Charming Gold Coast One-Bedroom Near Downtown!
19–26 FebProfessional Host,
€ 134 per night
4.92 out of 5 average rating, 133 reviews
Guest favourite
Guest suite in Chicago
Private suite in Lincoln Square
10–17 FebIndividual Host,
€ 119 per night
4.97 out of 5 average rating, 353 reviews
Guest favourite
Flat in Chicago
Gorgeous Studio 15 Minutes From Ohare!
25 Sep – 2 OctIndividual Host,
€ 110 per night
4.98 out of 5 average rating, 108 reviews
Superhost
Flat in East Rogers Park
LAKESIDE PIED `A TERRE STEPS TO BEACH
18–25 JulIndividual Host,
€ 142 per night
4.89 out of 5 average rating, 101 reviews
Guest favourite
Treehouse in Schaumburg
Enchanted Garden Treehouse (Amenity*)
2–9 AugIndividual Host,
€ 263 per night
4.93 out of 5 average rating, 703 reviews
Guest favourite
Flat in Chicago
Charming renovated Victorian apartment in Old Town
16–23 AprIndividual Host,
€ 153 per night
4.92 out of 5 average rating, 470 reviews

Quick stats about holiday rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K reviews

Destinations to explore

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