
Holiday houses in West Loop, Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in West Loop, Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for West Loop, Chicago holiday rentals
Other great holiday rentals in West Loop, Chicago
Guest favourite

Private room in West Town
4.88 out of 5 average rating, 305 reviewsPrivate 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 reviewsChicago 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 reviews1BR 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 reviewsSun-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 reviewsLevel 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 reviewsUrban 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 reviewsStylish 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 reviewsEntire 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
- Rentals with outdoor seating West Loop
- Condo rentals West Loop
- Rentals with a patio West Loop
- Rentals with a fire pit West Loop
- Rentals with a washing machine and dryer West Loop
- Rentals with a hot tub West Loop
- Rentals with a sauna West Loop
- Kid-friendly rentals West Loop
- Fitness-friendly rentals West Loop
- Apartment rentals West Loop
- Rentals with a fireplace West Loop
- Rentals with an EV charger West Loop
- Pet-friendly rentals West Loop
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center