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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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Guest favourite
A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.
Flat in Chicago
4.9 out of 5 average rating, 586 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Top guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Flat in Chicago
5 out of 5 average rating, 315 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

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
4.99 out of 5 average rating, 107 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
An airy studio bedroom features a spacious bed with white linens and decorative pillows. Large windows allow natural light to fill the room, showcasing a cozy sitting area with a small table and chair. Framed botanical artwork adorns the walls, contributing to a calming ambiance.
Guest suite in Chicago
4.99 out of 5 average rating, 422 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

Guest favourite
Flat in Chicago
4.86 out of 5 average rating, 145 reviews

The Wrigley Suite - It's Really Sweet - Sleeps 1-4

The Wrigley Suite - It's Really Sweet! - Sleeps 1-4 Clean, hi-tech, modern unit - optimized for your stay. Work desk, convertible dining table, futon 30.3" (H) x 69.3" (W) x 34.3" (D)+ chaise lounge 60in x 31"+ queen bed in the bedroom. Living room has a convertible full sofa bed. 2 waterfall shower bathrooms. 2 Smart TVs. 1GB high speed WIFI to connect to many devices. Keurig coffee maker, variety of coffee pods! Parking permit stickers - you MUST check prior to booking for availability.

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, 251 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

Top guest favourite
A bright living area features two large windows framed by light blinds, allowing natural light to filter in. A blue sofa with decorative pillows and a vintage-style armchair are present. A round wooden coffee table is centered, adorned with a floral arrangement and a small potted plant.
Flat in Chicago
4.96 out of 5 average rating, 110 reviews

Lovely Apartment on Quaint Block in Andersonville

This private 1-bedroom garden apartment is located on a historical residential block in lovely Andersonville (Lakewood Balmoral) neighborhood. The apartment has one private bedroom with a queen bed, a living room with a door and nice queen sized sleeper-sofa, a kitchen/breakfast area and a bathroom. Located close to the heart of Andersonville/Clark Street, the area provides a fantastic variety restaurants & stores, 15 min walk to the lakefront, and plenty of transportation options.

Guest favourite
The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.
Flat in Chicago
4.74 out of 5 average rating, 1,350 reviews

Kasa | Spectacular City Views | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favourite
The living area features a mix of modern and industrial design, with exposed brick walls and hardwood flooring. A cozy sectional sofa, accented by colorful pillows, complements a stylish area rug. A kitchen area with dark cabinetry and stainless-steel appliances is visible in the background.
Apartment in Chicago
4.81 out of 5 average rating, 277 reviews

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Guest favourite
A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.
Flat in Evanston
4.9 out of 5 average rating, 132 reviews

Guest Favorite Escape Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!

Top guest favourite
A bright living area features large windows allowing natural light to fill the space. A brick fireplace serves as a focal point, complemented by framed artwork depicting cacti. Comfortable chairs and a wooden coffee table are arranged on a patterned rug, with a potted plant adding a touch of greenery.
Flat in Chicago
4.96 out of 5 average rating, 76 reviews

Wrigleyville Oasis with Huge Garage

Come stay at this gorgeous, clean, renovated apartment in beautiful Lakeview/Wrigleyville. The unit is located on a beautiful, quiet, tree-lined block, yet close to everything, including Wrigley Field. It includes a free on-site huge garage spot. The unit is a walker's paradise, with so much nearby, including great shops and restaurants, the lake, Wrigley Field, public transportation, Starbucks, Whole Foods, parks, playgrounds and more!

Guest favourite
Home in Chicago
5 out of 5 average rating, 14 reviews

Windsor Castle | 4 BR 3.5 Bath Near Lake & Wrigley

Welcome to Windsor Castle, a bright and beautifully restored Chicago greystone designed for comfort, creativity, and connection. This spacious 4-bedroom, 3.5-bathroom home offers multiple living areas, a fully stocked chef’s kitchen, a flexible library/family room with a queen sofa bed, and a backyard retreat with a fire pit. Perfect for families, remote workers, or friend getaways, the space blends style and warmth in every room.

Popular amenities for Montrose Beach holiday rentals

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