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Compare 499 Vacation Homes in Wheeling with updated reviews, rates, and availability.

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Interior

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stunning / Spacious 6BD Home + garage - Bucktown!
Private kitchen

Stunning / Spacious 6BD Home + garage - Bucktown!

9.4 out of 10, Exceptional, (28)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (21)
"The property was perfect for me and my buddies for a football weekend!"
Great 3 bedroom rental unit near Logan Square
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Room

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.4 out of 10, Exceptional, (17)
"Very clean"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Belmont House, Classy & Chic/walk to Wrigley Field
Interior

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (41)
"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "
Belmont House, Classy & Chic/walk to Wrigley Field
Chicago Riverhouse with private fenced in oasis
Escape to your private outdoor oasis, available May-October. Lounge on the illuminating sofa, sway in the hammock, gather around the table for 8, fire up the grill – all within the serenity of a fenced-in retreat

Chicago Riverhouse with private fenced in oasis

9.8 out of 10, Exceptional, (18)
"Great location for needing to be around the north park area, my grandmother easily maneuvered (87 y/o), and our 4 y/o loved watching TV on the projector. Easy parking, easy access to downtown. If you need to be in the area I’d definitely recommend staying here!"
Chicago Riverhouse with private fenced in oasis
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Living area

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

10.0 out of 10, Exceptional, (6)
"Stayed here with six others for a girls trip.The house was beautifully decorated, beds were comfy, and the backyard was such a nice spot to hang out in during our downtime. We loved how much space we had and the attention to the vibes. Adam was super helpful and responsive before and during our stay. We all wished our trip was longer!"
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Spacious 5-bedroom house with movie room, game room and more!
Living area

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!
Lake/Beach Getaway (Remodeled)
Children's area

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (28)
"excellent location - very clean - close to everything we wanted to visit - owners very helpful only 20 min from Antioch where we had our family reunion - this is the 2nd year we have stayed here - very happy - lake visable from front windows - beds comfy - kitchen completely stocked - great sunsets - easy walking in the area - shopping close by wonderful rental"
Lake/Beach Getaway (Remodeled)
Breathtaking home close to Schaumburg, Chicago
Exterior

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (45)
"We had unexpected changes last minute for Thanksgiving and our Host was so great and accommodating. The space was roomy and beautiful with the rooms flowing into each other so little groups of people could talk and nosh and enjoy the food and company. The light coming in from the windows and the backyard is a little piece of nature to enjoy. At our request, our wonderful host even snuck in to start a fire for us in the firepit, making it even more homey. My husband, myself, my sister, and my...
Breathtaking home close to Schaumburg, Chicago
Cheery 2+bedroom home with free parking on premises
Living area

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (32)
"My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend."
Cheery 2+bedroom home with free parking on premises
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Libertyville Vacation Rental | 3BR | 3BA | 2,700 Sq Ft | Step-Free Access

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (16)
"We rented this house to stay for my daughter’s graduation from Navy Boot Camp. It was an easy drive in and ample room for everyone. The host was awesome and attentive to our needs. Honestly, we didn’t really have any needs, but we used party poppers in the house and wanted to be able to clean them up, but we couldn’t find the broom. Being from California, I was super nervous about being cold, but as soon as we walked in the house, it was super warm and felt so cozy. The heated floors are...
Riverfront Libertyville Retreat w/ Outdoor Kitchen
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Living area

3-bedroom house WiFi in lovely Waukegan Near Gurnee

2.0 star property
4.6 out of 10, (12)
"Cute little house at all the necessities convenient to Naval base where we spent most of our time"
3-bedroom house WiFi in lovely Waukegan Near Gurnee
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
Exterior

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.2 out of 10, Wonderful, (7)
"We had a mini cousin reunion with family who drove in from different states. No one here has a house big enough to have all of us, so this was the perfect option. The house was lovely, neighborhood very nice, easy to get to, and the host was gracious making us feel like we were all at home. I’d give it 10/5 stars if I could!"
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
First floor living room with leather couch, smart cable TV, and Alexa speaker.

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (120)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Living area

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (161)
"Well located. Large common areas. Plenty of bedrooms. Food and specialty stores including Whole Foods, Paulina’s Meat Market, Asian Markets) within driving distance. Mass transit nearby. A park across the street on which we played our 55 th Annual Turkey Bowl."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Interior

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
Living area

Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!

10.0 out of 10, Exceptional, (11)
"It was a great house with needed amenities and lots of space. Great location not far from downtown. Host was great to communicate with."
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
Pet-Friendly Bartlett Farmhouse w/ Deck!
Bartlett Vacation Rental | 4BR | 2BA | Stairs Required | 3,100 Sq Ft

Pet-Friendly Bartlett Farmhouse w/ Deck!

9.8 out of 10, Exceptional, (6)
"This was the perfect place for us to gather for the holidays. We definitely enjoyed our stay!"
Pet-Friendly Bartlett Farmhouse w/ Deck!
Comfy King bed, Free Wi-Fi, Home in Des Plaines

Comfy King bed, Free Wi-Fi, Home in Des Plaines

10.0 out of 10, Exceptional, (3)
"This home was tidy and beautiful. It fit all of us so perfectly and we were able to spend quality time together with our sailor!! We had no problems with this property and the manager was very responsive! Thank you so much!"
The price is AED 661
AED 1,862 total
includes taxes & fees
15 Jan - 16 January 2025
Comfy King bed, Free Wi-Fi, Home in Des Plaines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Wheeling

Wrigley/Southport Corridor Garden Oasis +parking!
Living area

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!
Stunning 3 BR in prime Chicago location
Living area

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (83)
"Very close to the train. Good location "
Stunning 3 BR in prime Chicago location
Stunning / Spacious 6BD Home + garage - Bucktown!
Private kitchen

Stunning / Spacious 6BD Home + garage - Bucktown!

9.4 out of 10, Exceptional, (28)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.