Vacation rentals in Chicago
Find and book unique accommodation on Airbnb
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 Jun
$302 NZD per night
5.0 out of 5 average rating, 288 reviews
Guest favourite
Apartment 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 Dec
$823 NZD per night
4.86 out of 5 average rating, 148 reviews
Guest favourite
Apartment 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 Jul
$230 NZD per night
4.98 out of 5 average rating, 102 reviews
Holiday rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
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
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Rentals with a patio Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- House rentals Chicago
- Bed and breakfasts Chicago
- Mansion rentals Chicago
- Rentals with lake access Chicago
- Rentals with a fireplace Chicago
- Rentals with a sauna Chicago
- Cottage rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with a home theatre Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Monthly Rentals Chicago
- Apartment rentals Chicago
- Wheelchair accessible rentals Chicago
- Waterfront rentals Chicago
- Hotel rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with pools Chicago
- Fitness-friendly rentals Chicago
- Condo rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with breakfast Chicago
- Townhouse rentals Chicago
- Rentals with a balcony Chicago
- Rentals with beach access Chicago
- Rentals with an accessible height bed Chicago
- Pet-friendly rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom