Holiday rentals in Montrose Beach

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Top-rated holiday rentals in Montrose Beach

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Top guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Flat in Chicago
5 out of 5 average rating, 61 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favourite
A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.
Apartment in Chicago
4.98 out of 5 average rating, 109 reviews

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Top guest favourite
An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.
Guest house in Chicago
4.96 out of 5 average rating, 28 reviews

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Guest favourite
The living room features hardwood flooring and is illuminated by natural light streaming through large bay windows. Two comfortable sofas face a coffee table, with a TV mounted on a console unit nearby. A warm and inviting atmosphere is created by the arrangement and decor.
Apartment in Chicago
4.88 out of 5 average rating, 33 reviews

Comfy and Walkable

You will be close to everything when you stay at this comfortable apartment that is close to everything but quiet and friendly. This is my home. I travel a lot and airbnb it when I'm away. It's comfortable, safe, has all the things a lived-in home has, and is in an amazing location. It's like staying at your friend's apartment in the city. If you want luxury, pay more and stay somewhere else... but this is exactly the kind of place I'm looking for when I travel and I hope you'll enjoy it too!

Guest favourite
A cozy living area is highlighted by a large, colorful mural depicting two seated figures. A comfortable sofa faces a round coffee table, with textured cushions adding interest. Two armchairs create additional seating, while large windows allow natural light to brighten the space.
Flat in Chicago
4.9 out of 5 average rating, 242 reviews

A Novel Situation at Wrigley

This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in all of rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a five minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's about a ten minute walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Flat in Chicago
5 out of 5 average rating, 4 reviews

Modern Vintage Charm in Historic Neighborhood

Nestled on a tree-lined street, just a block from restaurants and shops you will enjoy easy access to one of Chicago's premier and historic neighborhoods, Andersonville. This vintage greystone has been recently renovated with stainless steel appliances and new quartz countertops. The unit is on the second floor has tall ceilings and lots of natural light. Guests can enjoy a quiet and cozy night in, or a night out on the town. 2 beds available, accommodating up to four guests.

Guest favourite
Flat in Chicago
5 out of 5 average rating, 5 reviews

2 Room Studio on the Red Line

Enjoy this cheerful and sun-filled studio featuring two separate rooms, located within a few blocks of the Aragon Ballroom and Riviera Theater, the vibrant bars and restaurants on Clark Street in Andersonville and the Bryn Mawr business district. The lakefront trail and beaches are equally close! Convenient public transportation is just one block away, with the Berwyn Red Line providing quick access to Boystown, downtown (The Loop), and multiple bus lines nearby.

Top guest favourite
A spacious living area is furnished with a light-colored sofa, two armchairs, and an entertainment unit containing books. Soft lighting from a lamp creates a warm atmosphere. A geometric area rug adds visual interest to the carpeted floor. The sloped ceiling enhances the cozy feel of the space.
Flat in Chicago
4.97 out of 5 average rating, 304 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Guest favourite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Flat in Chicago
4.94 out of 5 average rating, 140 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Guest favourite
A well-arranged living space features a spacious bed covered with a light grey blanket. A modern couch in a dark hue is situated near the wall, complemented by colorful wall art above. Natural light filters in through a nearby window, enhancing the inviting atmosphere.
Flat in Chicago
4.94 out of 5 average rating, 83 reviews

Private studio near Wrigley

Getting to all major destinations is key while also coming back to a quiet neighborhood. Only a few steps from public transportation. The unit is attached to a single family home with your own private entrance and access to the backyard that has a gas grill and fire pit (and pups at times that like to play fetch). I am a 1 mile walk to Wrigley Field. Also had a pull out couch if need additional sleeping space.

Guest favourite
Private room in Chicago
4.82 out of 5 average rating, 369 reviews

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Superhost
The kitchen features dark wooden cabinetry and a granite countertop, complemented by stainless steel appliances including a gas stove and refrigerator. Two black stools are positioned at the island, and a small plant adds a touch of greenery to the space.
Loft in Chicago
4.83 out of 5 average rating, 75 reviews

Modern Studio apartment in Lakeview

Lake View is great and lovely neighborhood. Our space is located in the most vibrant location with great restaurants nightlife , Starbucks located right next door. This beautiful updated large Studio apartment has all you'll need during your stay in Chicago. Conveniently located 5 min away from CTA Brown line, 20 min walking distance from Wrigleyfield as well as Halsted Street Boystown neighborhood.

Popular amenities for Montrose Beach holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Montrose Beach