
Vacation rentals in West Loop, Chicago
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Top-rated vacation rentals in West Loop, Chicago
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for West Loop, Chicago vacation rentals
Other great vacation rentals in West Loop, Chicago
Superhost

Home in West Lawn
4.92 out of 5 average rating, 38 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
AshleyRating, 5 stars1 month ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favorite

Home in Elmhurst
4.86 out of 5 average rating, 22 reviewsEnamored in Elmhurst
YvonneRating, 5 stars1 month ago
This home is in a beautiful neighborhood. It was very clean and the decor was simple yet stunning. There was plenty of linen and the kitchen was stocked well enough to cook an entire meal Mark was very responsive and provided clear instructions for check in and out. I would stay here again
Guest favorite

Apartment in West Town
4.85 out of 5 average rating, 129 reviewsCondo with private terrace, free WIFI and parking
SheaRating, 5 stars4 weeks ago
Loved this place! My three friends and I had plenty of space and felt right at home. The location in West Town is perfect -- not busy or loud at all, but very easy to walk to coffee shops or restaurants in less than 10 minutes. Plus, the hosts were very friendly and accommodating!
Guest favorite

Apartment in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Superhost

Home in Cicero
4.79 out of 5 average rating, 178 reviewsSpacious whole apt near shopping and city
DenisRating, 5 stars1 week ago
Dan was cool and responsive. Home was clean as well and nothing to complain about all was good.
Guest favorite

Apartment in Irving Park
4.95 out of 5 average rating, 58 reviewsPerfect 4 BDR apt, Northside, Free parking, CUBS
ErinRating, 5 stars1 month ago
This place was just what we needed. The place was clean and cute. There were lots of good restaurants around and walkable as well as a Walgreens right around the corner. It’s off the main road so it’s easy to catch a Lyft without blocking traffic.
Quick stats about vacation rentals in West Loop, Chicago
Total rentals
550 properties
Nightly prices starting at
$10 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
- Fitness-friendly rentals West Loop
- Rentals with outdoor seating West Loop
- Rentals with a patio West Loop
- Kid-friendly rentals West Loop
- Rentals with a hot tub West Loop
- Rentals with an EV charger West Loop
- Rentals with a washer and dryer West Loop
- Apartment rentals West Loop
- Rentals with a sauna West Loop
- Rentals with a fire pit West Loop
- Pet-friendly rentals West Loop
- Rentals with a fireplace West Loop
- House rentals West Loop
- Condo rentals West Loop
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