Holiday rentals in Rogers Park, Chicago

5 out of 5 average rating, 140 reviews

Spacious 3BR with Parking Option, Steps to Metra!

Newly renovated, the Greenleaf is the entire second floor of a two-flat on a residential street. It has been thoughtfully designed for comfort and convenience. Great location for Loyola and Northwestern University visits or downtown sight-seeing. The Metra stop for trains to the Loop or the North Shore suburbs is ON OUR BLOCK. Lake Michigan free beaches are a mile away. Easy walk to a variety of small restaurants or 10-minute drive to Evanston or Andersonville for amazing dining and shopping.

Superhost

Flat in East Rogers Park

4.53 out of 5 average rating, 53 reviews

Exquisite Stay in N. Chi Steps From The Beach

Nestled in the vibrant and diverse North Side of Chicago, our exquisite Airbnb is the perfect retreat for travelers from around the globe. This gated building ensures peace of mind, while the beautifully landscaped entrance sets the tone for your stay. Professionally decorated, the space combines comfort and style, making you feel right at home. With 1 bedroom featuring a queen bed and a full bathroom on the 2nd floor, it’s ideal for relaxation. All travelers and pets are warmly welcome to stay.

4.97 out of 5 average rating, 123 reviews

Guest house in Chicago

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

4.94 out of 5 average rating, 65 reviews

Guest suite in Chicago

McFetridge House - Beautiful Private Garden Apt #2

Guests are invited to enjoy an immaculate & spacious private garden appt in a newly renovated historic Chicago red brick (c.1903). Comprises spacious bedroom with comfortable Queen bed, plenty of storage, cosy living area with widescreen TV (cable), desk, private bathroom, kitchenette/diner. Free Wi-Fi. Access to parking. Blocks from lake with easy access to Red line L & Metra. Close to grocery store/coffee shop and variety of nearby restaurants & bars to enjoy. Note - we have one dog.

4.98 out of 5 average rating, 108 reviews

Apartment in Chicago

The Ramblers Inn, Northside NEW Reno w/parking!

Our family 2-flat has been completely gutted to the studs renovated with new everything! This top floor 3 bed 1 bath home has CENTRAL A/C, in unit washer/dryer, and free parking on-site. This prime location is a short walk to Loyola University, beaches/playgrounds, public transportation and award-winning restaurants. Lake shore trail is less than a mile away. We are steps away from a large local grocery store. Your urban stay will feel like a relaxing retreat because of these conveniences.

5 out of 5 average rating, 132 reviews

Remodeled, Near Loyola, Beach and Subway

Stylish and sophisticated, this remodeled 3 bedroom, 2 bath private apartment is in a prime location, 3 blocks from Hartigan Beach, and 2 blocks to the Loyola Red Line "L" station to take you to Wrigley Field, downtown & many locations in between. We are 2 blocks from Loyola University & about 4 miles to Northwestern University. Located on a quiet, residential tree-lined street, we are a 2 block walk from all manner of restaurants & conveniences associated with our proximity to Loyola.

Apartment in East Rogers Park

4.97 out of 5 average rating, 60 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

Welcome to Jarvis Gardens. A hidden gem in the heart of Chicago's Rogers Park northside neighborhood, located 8 miles north of downtown. Live like a true Chicagoan in this beautifully appointed and recently renovated apartment. Just 1 block to Lake Michigan's Jarvis beach, 1/2 block to Jarvis Square (shops/restaurants/bars/wine stores), and the Jarvis Redline train to Wrigley Field or the 147 bus to the famed Michigan Avenue shopping. No car is necessary for this vacation destination.

5 out of 5 average rating, 11 reviews

Flat in East Rogers Park

Apartment on the Lake

Lakeside Retreat with Stunning Views & Direct Lake Michigan Access Serene 2-bedroom, 2-bathroom apartment, complete with a private pier offering direct access to Lake Michigan. ✨ Amenities & Features: Shared outdoor terrace Onsite parking & EV charging station Steps from scenic parks—ideal for morning strolls or picnics by the lake. Prime location: Short Drive to Downtown Chicago, Wrigley Field, and top universities like Loyola University Chicago and Northwestern University.

4.88 out of 5 average rating, 296 reviews

Beautiful Three Bedroom Apartment Near Loyola

Welcome to our beautiful 3 bedroom apartment just blocks from Loyola University. Fully furnished apartment with one queen bed, two full beds, and one pull-out futon. Amenities include full kitchen, dining room, and 2 bathrooms. WiFi, cable, 3 televisions throughout the apartment and sunroom and back yard too! Close to public transportation, the lake, and dozens of dining options within walking distance. One (1) City Street Parking Pass will be provided for each night of your stay.

4.91 out of 5 average rating, 34 reviews

cozy grand studio 2nd floor/near lake/public tran.

Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming studio apartment offers a delightful blend of modern comfort and vibrant city living. The decor welcoming and will create a pleasant atmosphere. Kitchen provides everything you need to prepare meals! Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, a variety of dining options!

4.8 out of 5 average rating, 10 reviews

Flat in East Rogers Park

3 Bed 3 Bath Lakefront Oasis, Parking Included

From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances and thoughtfully provided amenities. You will want for nothing during your stay and may not want to leave! Don't miss out on a true lakefront gem, book today!

Apartment in East Rogers Park

4.93 out of 5 average rating, 240 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Note: no full kitchen.

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Other great holiday rentals in Rogers Park, Chicago

4.96 out of 5 average rating, 190 reviews

Private room in Evanston

Welcoming Evanston Home

JoshuaRating, 5 stars1 week ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

4.95 out of 5 average rating, 39 reviews

Private Room in Rogers Park

AngelRating, 5 stars1 month ago

Rudia was a great host - responsive and helpful. The apartment was very clean but truly only stocked w minimum essentials , I’d say is best to rent if you intend to spend the majority of your time out and about. Location worked well for me, I’d most likely come back!

4.9 out of 5 average rating, 63 reviews

1 bedroom apt near Michigan Lake

DanijelRating, 5 stars6 days ago

The apartment was clean and the host was extremely friendly. We at times just struggled with finding free parking due to coming home late. Downtown is about a 20 minute drive depending on traffic. Overall great place to stay and would definitely would stay again.

Private room in East Rogers Park

4.98 out of 5 average rating, 50 reviews

Renovated Sunny Oasis Steps From the Lake

SusanRating, 5 stars6 days ago

Tammy, and her husband, Scott and their two dogs are friendly and welcoming. I would definitely recommend staying at their home. And, at the end of their block is Lake Michigan!

4.96 out of 5 average rating, 26 reviews

Loft Style Private Apt 4 (1 Room- 420 Friendly)

AminaRating, 5 stars1 week ago

I had a wonderful stay at Josh’s place! The room is even more spacious than it looks in the pictures, and the natural sunlight in the kitchen every morning was such a peaceful bonus. It’s perfect for getting good rest. Josh is an amazing host, welcoming, kind, and he went above and beyond to make me feel at home. I would definitely stay here again. It’s definitely worth what you pay for. Highly recommend!

4.96 out of 5 average rating, 54 reviews

Rogers Park Penthouse

SkyeRating, 5 stars2 weeks ago

We had a wonderful stay! The space was beautiful, clean, and exactly as described—with stunning views and tons of character. The spiral staircase was more intimidating than I expected at first, but after a few trips up and down, I felt much more comfortable (and even a little proud of myself!). Michael was awesome—super communicative, kind, and full of great recommendations for places to eat and things to do in Chicago. His son was incredibly helpful, even helping us carry some of our bags up when we arrived. On checkout day, Michael offered to help with luggage again, which was so appreciated. If you’re looking for a unique, memorable stay with thoughtful hosts, I’d definitely recommend this place. Would absolutely stay here again!

Private room in North Park

4.97 out of 5 average rating, 38 reviews

Lovely master bedroom with private bath

LenaRating, 5 stars6 days ago

The apartment was beautiful and comfortable along with being in a nice spot just outside of downtown. Samuel was also very friendly and accommodating which is a definite plus! I would definitely stay with him again.