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Holiday rentals in Montrose Beach

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Top-rated holiday rentals in Montrose Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern living area features a spacious orange sofa and a wooden coffee table positioned on a light rug. A large flat-screen television is mounted on the wall, with a stylish lamp and potted plant nearby. An open kitchen with white cabinetry and stainless-steel appliances is visible in the background.
Flat in Chicago
4.99 out of 5 average rating, 113 reviews

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

Guest favourite
A light-filled living area features a modern sofa adorned with textured cushions. Three tall windows frame a view of the outdoors, enhancing the natural lighting. A wooden coffee table sits centrally, complemented by a decorative bowl and a small table lamp.
Flat in Chicago
4.85 out of 5 average rating, 385 reviews

Contemporary Apartment Near Wrigley Field w/ Yard

Rediscover the history of this vintage 120 year old home. Indulge in comfort and style in a quiet modern design retreat featuring a monochrome interior contrasted with warm woods, an open-plan living and dining space, and a raised wood deck. Down comforters, nice towels and linens + stylish design and comfort You will have access to the entire space - 3 bedrooms, 2 bathrooms, living room, dining room, kitchen, back deck, and back yard. Text or call me and I will respond as soon as possible.

Top guest favourite
The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.
Guest suite in Chicago
4.96 out of 5 average rating, 392 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.

Top guest favourite
A well-maintained garden unit is framed by a neatly arranged wooden fence. A covered porch with wooden railings offers a welcoming entryway. Snow blankets the small garden at the front, and the surrounding buildings display a mix of brick and stone facades.
Flat in Chicago
4.93 out of 5 average rating, 232 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Top guest favourite
A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.
Apartment in Chicago
4.98 out of 5 average rating, 226 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Guest favourite
A spacious living area is highlighted by a light-colored sofa adorned with various cushions. A round coffee table sits in front, complemented by a cozy armchair. The open kitchen is visible in the background, featuring modern appliances and a warm wood finish.
Flat in Chicago
4.93 out of 5 average rating, 107 reviews

1-Bedroom Apt by Andersonville & Lakefront

Spacious, sunny 1-bedroom apartment in peaceful, historic Edgewater neighborhood of Chicago. Overlooks park and is short walk from Thorndale Red Line "L" station, the beach, Whole Foods, and shops, restaurants, and bars in Andersonville. Ideal for up to 4 people, has queen-size bed in bedroom and sleeper sofa in living room. Kitchen is fully equipped with gas stove, microwave, fridge, coffee machine, and utensils. Free high-speed WiFi. Smart TV. Clean and comfortable with modern touches.

Superhost
A compact studio showcases a full-size bed with plush pillows and a gray blanket. A vibrant red refrigerator stands next to stainless steel appliances. A wall-mounted flat-screen TV is visible, along with light blue curtains framing the window that overlooks an outdoor space.
Flat in Chicago
4.8 out of 5 average rating, 197 reviews

Dapper Uptown Studio near the Lake

Welcome to this beautifully renovated, 200 sq ft studio located in the Uptown neighborhood. This apartment has access to a shared fitness area, backyard/garden, and comfy work station. The building is a block from the Red Line train and is walking distance to neighborhood restaurants, bars, shops, and cafes. This apartment is perfect for remote workers or solo travelers looking to be in a nice neighborhood close to the city! Check in is completely contactless with a keypad & door code.

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, 318 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 spacious living room features a cozy seating area with two leather sofas facing a modern TV stand. A light-colored coffee table is positioned between the sofas, and a decorative painting hangs above the fireplace. Large windows with blinds allow natural light to fill the space.
Flat in Chicago
4.89 out of 5 average rating, 110 reviews

Elegant 2-bed/2-bath in the heart of Uptown

Spacious high-quality 2-bed/2-bath in the heart of Uptown Chicago. Minutes walk from Lakeshore drive, Lakefront/beach, Recreation parks, the Riviera, Aragon Ballroom, and the Green Mill Cocktail Lounge (Al Capone's fave). You can drive 10 minutes to Downtown-Chicago or jump on the Redline, a Chicago L-train classic, which is a short stop to Wrigleyville (go Cubs!), the Loop, and more. Guest have access to the entire condo as well as parking garage.

Top guest favourite
A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.
Apartment in Chicago
4.98 out of 5 average rating, 328 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Top guest favourite
Flat in Chicago
4.94 out of 5 average rating, 213 reviews

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.

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
4.92 out of 5 average rating, 106 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.

Popular amenities for Montrose Beach holiday rentals

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