Holiday rentals in North Shore Beach

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Top-rated holiday rentals in North Shore Beach

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Guest favourite

Guest suite in East Rogers Park

4.96 out of 5 average rating, 101 reviews

1BR Historic Rogers Park/West Ridge unit- Sleeps 4

Send an inquiry before requesting booking. Quiet, tree-lined urban getaway. Separate lower level unit located in a Chicago-style bungalow near wonderful neighborhoods and restaurants. Extremely comfortable and cozy, this spot will make you forget you are in the city. Diverse restaurants to whet your appetite- Mexican, Ethiopian, Jamaican, Jewish and Indian. Take long walks to the beach (15min), to the numerous parks and or festivals and celebrations. Or cozy up to read, nap or watch a movie.

9–16 Feb

$151 SGD per night

Guest favourite

Flat in Edgewater

4.93 out of 5 average rating, 380 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.

25 Jan – 1 Feb

$124 SGD per night

Guest favourite

Flat in Edgewater

4.9 out of 5 average rating, 294 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-bedroom + living/dining room, private entrance garden apartment, close to: the red line to downtown or Evanston, the lake, theaters, restaurants, and parks. Edgewater is known for tree-lined streets, quiet, safe, diverse, & as a friendly neighborhood. We provide breakfast foods (coffee, tea, fresh fruit, milk, cereal, bread and homemade jam). There is a microwave, small fridge & induction stovetop. You're limiting carbon emissions with solar & heat/ac pumps.

20–27 Sep

$175 SGD per night

Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 292 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

18–25 Sep

$191 SGD per night

Guest favourite

Apartment in East Rogers Park

4.93 out of 5 average rating, 183 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

14–21 Jul

$205 SGD per night

Guest favourite

Flat in Lincoln Square

4.94 out of 5 average rating, 190 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

7–14 Jul

$148 SGD per night

Superhost

Flat in Andersonville

4.82 out of 5 average rating, 434 reviews

Lovely Andersonville Apt with Ideal Location

Large 1 bedroom with all the essentials and kitchen for your stay in Chicago's entertainment district. Steps away from all the amazing restaurants and shops in Andersonville, Uptown's Asia on Argyle (best Pho in the city!), and a number of music venues (Aragon, Riveria, and The Green Mill). You'll also be a short walk from Foster Beach and Chicago's Lakefront Trail, beautiful parks, and public transportation (CTA Red Line, Buses, and Metra train).

12–19 Dec

$118 SGD per night

Superhost

Flat in East Rogers Park

4.89 out of 5 average rating, 105 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

1–8 Jan

$164 SGD per night

Guest favourite

Flat in East Rogers Park

4.95 out of 5 average rating, 128 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!

27 Jun – 4 Jul

$229 SGD per night

Superhost

Flat in East Rogers Park

4.92 out of 5 average rating, 111 reviews

Private Garden Apartment GATED FREE Parking

This garden apartment is within the main house. Your cozy apartment has its own entrance with has a nice sized bedroom with queen bed, along with a living room with a coffee table, a new Crate and Barrel deep cozy sofa that can sleep a third guest, bathroom with a shower, and an office room with a desk, STOCKED mini fridge and coffee/tea station and mini oven. Free gated parking will also be available 24/7.

17–24 Jul

$208 SGD per night

Guest favourite

Guest suite in Lincoln Square

4.94 out of 5 average rating, 176 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

2–9 Oct

$141 SGD per night

Guest favourite

Flat in Andersonville

4.98 out of 5 average rating, 166 reviews

Beautiful Hollywood-Ridge Suite in Edgewater

Beautiful, complete, and private apartment/suite in a historic Chicago Greystone located in the beautiful and diverse Edgewater neighborhood. Sleeps 1-4 persons (Queen bed in master bedroom and Deluxe Memory-Foam Queen Size Sofa Sleeper in living area). Suite features guest-controlled central air and heat, 2 flat screen TVs, private bath and shower, and full access to all rooms.

26 Feb – 5 Mar

$196 SGD per night