Holiday houses 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 serene bedroom is featured, showcasing a queen-sized bed dressed with soft white linens and a light pink throw blanket. Above the bed, three framed artworks add a touch of color. A hanging side table and a bedside lamp illuminate the space.
Apartment in Uptown
4.83 out of 5 average rating, 687 reviews

Walk to Lake Michigan From a Contemporary Uptown Haven

Awaken in a comfy queen size bed, ready to explore nearby attractions. Everything needed is readily at hand in this cozy space. Start the day with a quick breakfast in a compact kitchen, then refresh under a rain shower in a gleaming white bathroom. Please note that this unit is located above a late night bar, which may add to the charm of it for some but may also pose to be a noise nuisance for light sleepers. We encourage you to read the reviews of past guests to make an informed decision. Come stay at our beautiful studio apartment in Uptown Chicago. Featuring a queen sized bed with a very comfortable memory foam mattress and clean sheets you’ll love resting your head on at the end of a long day touring the city. If you want to relax, take advantage of the white noise machine we've provided. Quirky details such as the sputnik light fixtures and bedside table swing are just a few of the fine decor used to accent the studio. The full kitchen is complete with a microwave, stove top and oven which are perfect for cooking a quick breakfast before you start your day. There is also a Keurig coffee machine as well as basic cooking utensils and supplies. The bathroom has a great shower as well as complimentary toiletries and clean towels. If you need to get some work done while vacationing, you have access to free hi-speed wifi as well as a desktop for your convenience. If you're putting off that work, go ahead and watch a movie on the complimentary Netflix provided. This studio apartment is very well kept, professionally cleaned and sanitized after each and every use. When booking this unit you will have full and private access to the entire studio apartment. The check-in and check-out process is automatic and seamless. Check-in any time after 3 pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. Should you like to store your baggage before or after your stay, we can recommend a useful app which offers affordable luggage storage around Chicago. We want to make sure you have the most convenient experience possible. There is no need to meet in person in order to enter the property, access is via self check-in. Once booked, you will be e-mailed detailed instructions for your seamless check-in process. We are readily available for questions or concerns via Airbnb messaging. Of course in case of emergency you can always reach us via phone call. Please do not text us, as we may not be able to see a text immediately. The apartment is in Uptown Chicago, walking distance to beautiful Lake Michigan. Catch a Cubs game at nearby Wrigley Field or take a train to the Loop for some great shops, museums, music venues, famous architecture, and international restaurants. The quickest and most inexpensive way to get around is via Uber or Lyft. To get downtown, It’s just a straight ride on Lakeshore Dr and you're there. With the Wilson train station just by the apartment, Public transportation is also a convenient option. Public Transportation guide to the apartment: To Wrigley Field: Two stops away on the red line from the Wilson Station not far from the apartment. To the Chicago Loop: Catch either the red or purple lines from the Wilson Station just a minute walk away from the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/

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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.
Apartment in West Rogers Park
4.99 out of 5 average rating, 110 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.

LocationFamilyHeating

Superhost
A spacious living area features an exposed brick wall complemented by large windows allowing natural light in. A sectional sofa is arranged around a round coffee table atop a patterned rug, and a modern light fixture hangs from the ceiling. A television is positioned on a clean-lined media console.
Condo in Lake View
4.87 out of 5 average rating, 151 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

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Top Guest favourite
A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.
Apartment in Lincoln Park
4.99 out of 5 average rating, 163 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

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Guest favourite
Condo in Uptown
4.91 out of 5 average rating, 210 reviews

Sunny Top-Floor Uptown Condo Near Lake & Red Line

Bright top-floor Chicago condo with fast WiFi, dedicated workspace, and easy access to Montrose Beach and the CTA. Perfect for remote workers, couples, and travelers looking to experience Chicago like a local. Enjoy a sunny living room, fully equipped kitchen and dining room, spacious primary bedroom, and serene sunroom with a full-size bed. Just steps from the lakefront and a 6-minute walk to the 24/7 Wilson Red Line. Over 1,000 sq. ft. of comfortable living space in historic Uptown.

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Top Guest favourite
A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.
Loft in Lake View
4.96 out of 5 average rating, 600 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

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Top Guest favourite
A spacious seating area is defined by a dark upholstered sofa with yellow accent pillows. A modern gold-toned coffee table sits in front, resting on a textured woven rug. Art pieces adorn the walls, contributing to the room's thoughtful design.
Apartment in Lake View
5.0 out of 5 average rating, 377 reviews

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

FamilyValueWalkability

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.
Condo in Wrigleyville
4.81 out of 5 average rating, 286 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!

FamilyValueView

Top Guest favourite
A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.
Bungalow in Lake View
4.96 out of 5 average rating, 164 reviews

Chicago Bootlegger House Sleeps 10-20

Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

FamilyValueSleep quality

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.
Condo in Uptown
4.98 out of 5 average rating, 362 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.

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Top Guest favourite
A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.
Apartment in Edgewater
4.98 out of 5 average rating, 161 reviews

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

FamilyValueQuiet

Top Guest favourite
A modern living room features a gray sofa adorned with patterned pillows, complemented by two armchairs with light upholstery. Large windows framed by blue and white striped curtains allow natural light to illuminate the space. A round wooden coffee table sits atop a textured area rug.
Apartment in Uptown
4.95 out of 5 average rating, 222 reviews

Spacious 2BR Condo + Free On-site Parking

Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants, super markets and a couple of blocks from the CTA Red Line train. Our apartment is specially designed for your comfort with all the amenities you would need during your stay along with one free parking spot! Perfect for a business trip, mini getaway, family vacation to relax and feel at home!

FamilyValueAmenities

Popular amenities for Montrose Beach holiday rentals