Holiday houses in West Loop, Chicago

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Popular amenities for West Loop, Chicago holiday rentals

Stay near West Loop, Chicago's top sights

United Center50 locals recommend
Millennium Park213 locals recommend
Magnificent Mile104 locals recommend

Other great holiday rentals in West Loop, Chicago

Guest favourite
Private room in West Town
4.88 out of 5 average rating, 305 reviews

Private BR in Condo close to Chicago Dwtwn!

LamiaRating, 5 stars1 week ago
great host and stay! saurin gave us plenty of recs, allowed us to check in early and leave our luggage because we had later flights. spacious room with ample amenities. blue line and a few buses all <10 min walk away. saurin was always very friendly and made himself available to help if we ever needed something
Superhost
Private room in River North
4.87 out of 5 average rating, 210 reviews

Chicago Speakeasy-Style Loft (Room 2B)

AnaRating, 5 stars2 days ago
Had a wonderful stay at Michael’s! Amazing location, the most unique and beautiful space, and Michael was lovely to speak with. Earplugs are also provided should you need them as the room faces the lively street, which were great! Thank you and can’t wait to come back!
Guest favourite
Apartment in West Loop
4.88 out of 5 average rating, 8 reviews

1BR Captivating Apartment

EvanRating, 5 stars5 days ago
Geo never took longer than 20 minutes to respond when needed, and found workarounds when I was having difficulties with website not working. The place was lovely, and had more than enough space. Location was great, and I didn't struggle to find parking. Thanks again for hosting!
Apartment in West Loop
4.86 out of 5 average rating, 7 reviews

Sun-Drenched 1BR Apartment

MadisonRating, 5 stars6 days ago
My husband and I loved staying at Brad’s place for our honeymoon! It was such a great location. It is right by the train so I appreciate that earplugs were provided to sleep! I would definitely recommend figuring out parking before you get there. We tried to figure it out when we got there, the spot hero app wasn’t working, it was weird! But if you have parking figured out, it’s the best place to stay! We might make this a yearly stop for us!
Apartment in West Loop
4.83 out of 5 average rating, 35 reviews

Level Junior Two Bedroom Suite | Fulton Market

AlannaRating, 5 stars3 weeks ago
Had such a great stay! Everything was very clean and all information given was thorough.
Top Guest favourite
Private room in East Pilsen
5 out of 5 average rating, 120 reviews

Urban Oasis Pilsen - guest room in townhouse

GretchenRating, 5 stars4 days ago
My friend and I enjoyed staying with them. They are a very nice couple. Very helpful. We would definitely recommend staying there to anyone in the future.
Top Guest favourite
Private room in West Town
4.94 out of 5 average rating, 34 reviews

Stylish Condo BR w/Skyline Views – Walk Score 95

StevensonRating, 5 stars2 weeks ago
Tejal was extremely responsive, sweet, and hospitable! She was always available for questions and even recommendations! Her place was very clean and lovely to stay in!
Home in West Loop
4.93 out of 5 average rating, 40 reviews

Entire lofted space in West Town

NeilRating, 5 stars1 week ago
This was a great space all to ourselves. brought the family to the city to go to the museums and it was super comfortable and felt like our own space. Great location and not far from about anywhere you wanna go.

Quick stats about holiday rentals in West Loop, Chicago

  • Total rentals

    550 properties

  • Nightly prices starting at

    $17 NZD before taxes and fees

  • Total number of reviews

    17K reviews

  • Family-friendly rentals

    240 properties are a good fit for families

  • Pet-friendly rentals

    310 properties allow pets

  • Rentals with a pool

    290 properties have a pool

Destinations to explore

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