
Holiday rentals in Old Town, Chicago
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Top-rated holiday rentals in Old Town, Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Old Town, Chicago holiday rentals
Other great holiday rentals in Old Town, 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 favourite

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 favourite

Flat in West Town
4.85 out of 5 average rating, 129 reviewsCondo with private terrace, free WIFI and parking
SheaRating, 5 stars1 month 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 favourite

Home in Chicago
5 out of 5 average rating, 5 reviewsBirthday?Anniversary?Showers?3500 sq ft, sleeps 16
ArissRating, 5 stars1 week ago
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favourite

Flat 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

Flat 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

Apartment 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.
Quick stats about holiday rentals in Old Town, Chicago
Total rentals
80 properties
Nightly prices starting at
£53 before taxes and fees
Total number of reviews
6.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Wilmot Mountain Ski Resort
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- The Field Museum
- Lincoln Park Zoo
- Six Flags Great America
- Promontory Point
- Museum of Science and Industry
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Villa Olivia
- Raging Waves Waterpark
- Moraine Hills State Park