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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
5–12 Aug
₹10,070 per night
5.0 out of 5 average rating, 287 reviews
Guest favourite
Flat in Chicago
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; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
20–27 Apr
₹8,525 per night
4.96 out of 5 average rating, 257 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!
27 Nov – 4 Dec
₹30,932 per night
4.86 out of 5 average rating, 147 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
Tiny home in Burr Ridge
Less is more! Pet friendly Tiny Home near Chicago!
27 Jan – 3 Feb
₹9,696 per night
4.92 out of 5 average rating, 214 reviews
Guest favourite
Treehouse in Schaumburg
Enchanted Garden Treehouse (Amenity*)
6–13 Jun
₹19,744 per night
4.93 out of 5 average rating, 702 reviews
Guest favourite
Flat in Chicago
iKlektik House // Robin
9–16 Aug
₹9,313 per night
4.89 out of 5 average rating, 463 reviews
Guest favourite
Guest house in Chicago
Private, Charming, Coach House Loft in Andersonville
25 Sep – 2 Oct
₹11,135 per night
4.91 out of 5 average rating, 338 reviews
Guest favourite
Loft in Chicago
Tea Studio in Wicker Park Spring Factory
13–20 Jul
₹21,486 per night
4.96 out of 5 average rating, 209 reviews
Guest favourite
Flat in Chicago
Explore Lincoln Park from a Polished Apartment
25 Mar – 1 Apr
₹11,906 per night
4.99 out of 5 average rating, 189 reviews
Guest favourite
Apartment in Chicago
Unique Lincoln Park Duplex Apt
9–16 Sep
₹13,261 per night
4.95 out of 5 average rating, 429 reviews
Guest favourite
Flat in Chicago
Charming Edgewater/Andersonville Garden 1 bdrm.
24–31 Oct
₹7,266 per night
4.93 out of 5 average rating, 194 reviews
Guest favourite
Flat in Chicago
Logan Square Studio
22–29 Oct
₹7,165 per night
4.87 out of 5 average rating, 477 reviews
Guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
28 Nov – 5 Dec
₹10,952 per night
4.96 out of 5 average rating, 400 reviews
Guest favourite
Flat in Chicago
Charming Gold Coast One-Bedroom Near Downtown!
8–15 Feb
₹7,566 per night
4.92 out of 5 average rating, 133 reviews
Guest favourite
Apartment in Chicago
Near Lake Michigan & Wrigley Field
25 Jun – 2 Jul
₹20,513 per night
4.98 out of 5 average rating, 187 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