Vacation rentals in Chicago Loop

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Top-rated vacation rentals in Chicago Loop

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Lincoln Park
Explore Lincoln Park from a Polished Apartment
This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.
Mar 25 – Apr 1
$144 per night
4.99 out of 5 average rating, 189 reviews
Superhost
Apartment in The Loop
Spectacular Corner 2BR Penthouse in the Loop | Roo
This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace with 360 degree vi
Oct 19 – 26
$504 per night
4.86 out of 5 average rating, 184 reviews
Guest favorite
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!
Nov 27 – Dec 4
$373 per night
4.86 out of 5 average rating, 147 reviews

Popular amenities for Chicago Loop vacation rentals

Stay near Chicago Loop's top sights

Millennium Park1,243 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Cloud Gate473 locals recommend
Willis Tower324 locals recommend
Skydeck Chicago124 locals recommend

Other great vacation rentals in Chicago Loop

Guest favorite
Guesthouse in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
Nov 16 – 23
$122 per night
4.99 out of 5 average rating, 768 reviews
Guest favorite
Apartment in Little Italy
Spacious 2BR on Quiet St - Free Park/Late Checkout
Oct 16 – 23
$154 per night
4.98 out of 5 average rating, 190 reviews
Guest favorite
Loft in Wicker Park
Tea Studio in Wicker Park Spring Factory
Jul 13 – 20
$259 per night
4.96 out of 5 average rating, 209 reviews
Superhost
Apartment in Magnificent Mile
Lux Gold Coast Condo |Rooftop Pool, Gym, Workspace
Mar 4 – 11
$146 per night
4.81 out of 5 average rating, 113 reviews
Guest favorite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
Nov 28 – Dec 5
$132 per night
4.96 out of 5 average rating, 400 reviews
Guest favorite
Apartment in Humboldt Park
Humboldt Park Loft
Aug 15 – 22
$89 per night
4.98 out of 5 average rating, 102 reviews
Guest favorite
Apartment in West Town
iKlektik House // Robin
Aug 9 – 16
$112 per night
4.89 out of 5 average rating, 463 reviews
Guest favorite
Home in West Loop
Cozy garden apartment historic Jackson Bvld.
May 3 – 8
$157 per night
4.97 out of 5 average rating, 315 reviews
Guest favorite
Apartment in Pilsen Historic District
Modern
Mar 28 – Apr 4
$95 per night
4.89 out of 5 average rating, 239 reviews
Guest favorite
Apartment in West Town
Fully Furnished Apartment Wicker Park Free Parking
Mar 31 – Apr 5
$112 per night
4.97 out of 5 average rating, 442 reviews
Guest favorite
Loft in Pilsen Historic District
Pilsen Modernist, Creative, Lightfilled Loft
Aug 15 – 22
$152 per night
4.91 out of 5 average rating, 292 reviews
Guest favorite
Apartment in Lincoln Park
Charming renovated Victorian apartment in Old Town
Apr 18 – 25
$119 per night
4.92 out of 5 average rating, 470 reviews

Quick stats about vacation rentals in Chicago Loop

Total rentals

990 properties

Rentals with dedicated workspaces

670 properties have a dedicated workspace

Rentals with a pool

550 properties have a pool

Pet-friendly rentals

500 properties allow pets

Family-friendly rentals

330 properties are a good fit for families

Total number of reviews

29K reviews

Destinations to explore

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