House vacation rentals in Rogers Park, Chicago

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Popular amenities for Rogers Park, Chicago house rentals

House rentals with a pool

Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars5 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
Home in Glen Ellyn
4.83 out of 5 average rating, 6 reviews

Pardizes Suites

RayRating, 5 starstoday
Lisa was the best host I've ever had. The house was amazing. Definitely #1 against every other AIR BNB I've ever stayed at before. This house was comfortable, up to date (if not ahead of its time). The atmosphere was great. The beds were comfortable. There was so much to do in that home. I honestly will do my best to stay in this home again in the future. Outstanding job Lisa. See you soon!!! Rated 10 stars.......
Guest favourite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars5 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
Top guest favourite
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars3 weeks ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Guest favourite
Home in Schaumburg
4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars4 months ago
Everything went perfect for us. We flew in from out of town, and some plans fell through. We asked Mike if it was possible to check in a couple hours early and he was very flexible. We really appreciate you and your home. Thanks for letting us stay.
Home in Logan Square
New place to stay

Stunning Home in Prime Chicago with Private Pool

Weekly house rentals

Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars1 week ago
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂
Guest favourite
Home in Glen Ellyn
4.92 out of 5 average rating, 148 reviews

Home in Glen Ellyn

LindaRating, 5 stars1 week ago
Humongous place to stay for a large group. Master bedroom was so huge! Having 5 bedrooms was great. We really enjoyed our stay.
Guest favourite
Home in Wicker Park
4.98 out of 5 average rating, 152 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars2 months ago
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.
Guest favourite
Home in Avondale
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars6 months ago
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!
Guest favourite
Home in Whiting
4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

YesyRating, 5 stars2 weeks ago
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.
Top guest favourite
Home in Lake View
4.95 out of 5 average rating, 184 reviews

Wrigleyville Greystone

ThomasRating, 5 stars1 month ago
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!
Superhost
Home in Wood Dale
4.76 out of 5 average rating, 160 reviews

Excellent Location for Vacation or Business Stays.

JamesRating, 5 stars3 months ago
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.
Guest favourite
Home in West Town
4.95 out of 5 average rating, 216 reviews

Paradise on the Park

JoannaRating, 5 stars5 days ago
Great cozy place to stay. Right across from a park and super quiet. Walkable to many restaurants and public transportation. It had every amenity including a washer and dryer. The shower is huge and the bed comfortable. Ryan’s communication was fast and precise. Would definitely stay there again!

Private house rentals

Top guest favourite
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars4 months ago
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.
Superhost
Home in Illinois Medical District
4.86 out of 5 average rating, 102 reviews

Casa PLZN Location | Entire Home | Garage Parking

AuraRating, 5 stars2 weeks ago
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

PaulRating, 5 stars3 days ago
rob and sue were great hosts. easy, timely communication. the house has everything you’ll need and is spacious and quiet, despite being close to some busy streets. walkable to diners, restaurants, and some shopping. . will definitely book again.
Top guest favourite
Home in Elmhurst
5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars1 week ago
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do
Superhost
Home in Austin
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars6 months ago
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.
Top guest favourite
Home in Wood Dale
5 out of 5 average rating, 5 reviews

Home in the Woods!

DevynRating, 5 stars1 week ago
We stayed here for my Bachelor Party. It was a golf trip, so having the Preserve at Oak Meadows right next door was great. Jazmin was responsive when we had a small issue with the code to get in. All-in-all a great place!
Guest favourite
Home in Chicago Ridge
4.92 out of 5 average rating, 127 reviews

Quiet cul-de-sac with huge fenced in backyard

JonathanRating, 5 stars1 day ago
Great experience. Tom is a great host , replies super fast and offers to help with anything needed , the house is spacious and everything is well kept.
Superhost
Home in Near West Side
4.84 out of 5 average rating, 503 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

AdelaidaRating, 5 stars3 days ago
Nice place, quiet and comfortable and we loved the neighborhood

Quick stats about house rentals in Rogers Park, Chicago

  • Total rentals

    30 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Rogers Park
  7. House rentals