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
4–11 JunIndividual Host,
£145 per night
5.0 out of 5 average rating, 290 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!
17–24 DecIndividual Host,
£394 per night
4.86 out of 5 average rating, 148 reviews
Guest favourite
Flat 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.
24 Jun – 1 JulIndividual Host,
£111 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

Superhost
Flat in Chicago
LAKESIDE PIED `A TERRE STEPS TO BEACH
12–19 JunIndividual Host,
£151 per night
4.89 out of 5 average rating, 102 reviews
Guest favourite
Guest suite in Chicago
Private suite in Lincoln Square
12–19 NovIndividual Host,
£106 per night
4.97 out of 5 average rating, 355 reviews
Guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
20–27 NovIndividual Host,
£153 per night
4.96 out of 5 average rating, 406 reviews
Guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
24 Apr – 1 MayIndividual Host,
£113 per night
4.97 out of 5 average rating, 260 reviews
Guest favourite
Guest house in Chicago
Private, Charming, Coach House Loft in Andersonville
12–19 NovIndividual Host,
£158 per night
4.91 out of 5 average rating, 338 reviews
Guest favourite
Flat in Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
7–14 NovIndividual Host,
£122 per night
4.89 out of 5 average rating, 171 reviews
Guest favourite
Flat in Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
26 Oct – 2 NovIndividual Host,
£134 per night
4.96 out of 5 average rating, 313 reviews
Guest favourite
Home in Chicago
Paradise on the Park
29 Oct – 5 NovIndividual Host,
£158 per night
4.95 out of 5 average rating, 164 reviews
Guest favourite
Apartment in Chicago
Unique Lincoln Park Duplex Apt
12–19 SeptIndividual Host,
£186 per night
4.95 out of 5 average rating, 432 reviews
Guest favourite
Home in Chicago
Modern Home RoscoeVillage/Wrigley Free St Parking
18–25 JanIndividual Host,
£112 per night
4.94 out of 5 average rating, 203 reviews
Guest favourite
Guest suite in Chicago
Comfortable & Cozy in Bridgeport
13–20 AugIndividual Host,
£83 per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Home in Chicago
Wrigleyville Southport Studio
27 Oct – 3 NovIndividual Host,
£162 per night
4.98 out of 5 average rating, 201 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