Vacation rentals in Rogers Park, Chicago

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Top-rated vacation rentals in Rogers Park, Chicago

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Guest favorite

Rental unit in Edgewater

4.89 out of 5 average rating, 323 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-BR+ liv/dining room, private entrance garden apartment, 3 blks to Red Line or Metra to downtown or Evanston, Skokie, theaters, restaurants, and parks. Edgewater has tree-lined streets, known as a quiet, safe, diverse & friendly neighborhood. Breakfast foods (coffee, tea, fruit, milk, cereal, bread, homemade jam) for starters. Has a microwave, small fridge, toaster oven & induction stovetop. Your stay reduces carbon emissions due to solar panels & heat/ac pumps.

Guest favorite

Rental unit in East Rogers Park

5 out of 5 average rating, 124 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.

Guest favorite

Rental unit in Edgewater

4.93 out of 5 average rating, 413 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Guest favorite

Condo in East Rogers Park

4.91 out of 5 average rating, 128 reviews

Magnificent Place & A Parking Space

1 Bedroom with 1 bathroom This spacious, quiet condominium is located in the Rogers Park neighborhood of Chicago, 3 minute walk from the local pubs, restaurants, shopping, and tennis court. Great for weekend trips as the beach is a quick bike ride 5 minute bike ride. Metra UP-Northwest, a 17 minute train ride to Downtown Chicago (4 min walk West to catch this train). CTA Morse Red Line Train is also available, making multiple stops on its way Downtown (5 min walk East to catch this train).

Guest favorite

Condo in East Rogers Park

4.92 out of 5 average rating, 218 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This 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. Dogs only. Parking free on street or one spot for a fee.

Guest favorite

Guest suite in Andersonville

4.96 out of 5 average rating, 343 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Guest favorite

Guesthouse in East Rogers Park

4.96 out of 5 average rating, 114 reviews

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.

Guest favorite

Rental unit in East Rogers Park

5 out of 5 average rating, 124 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.

Guest favorite

Rental unit in Andersonville

4.96 out of 5 average rating, 522 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Guest favorite

Rental unit in East Rogers Park

4.96 out of 5 average rating, 150 reviews

The Lodge Chicago

Welcome to the Lodge! A cozy, rustic and vintage Northwoods themed 700 sf apartment. Enjoy the feel of a 1960's lake cabin while being nestled on the north side of Chicago in the wonderful Edgewater/Rogers Park neighborhood. Come for the quiet while you explore the bustling city. Walking distance to the red line ‘L’, nearby restaurants, coffee shops and Lake Michigan beaches. Just a few blocks from Loyola University too!

Guest favorite

Rental unit in East Rogers Park

4.98 out of 5 average rating, 132 reviews

Vintage Charm Near Lake

This is a 3 bedroom flat located on the 2nd floor of a historic brownstone, 1 block from the beach. Guests have easy access to the beach and lakefront parks, tennis courts, Loyola University and library, Starbucks and restaurants, Jazz club, tot-lot playground and movie theater, all within walking distance. This location has easy access to downtown or the North Shore and Northwestern University using the Red Line.

Guest favorite

Rental unit in Lincoln Square

4.96 out of 5 average rating, 356 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.