Holiday rentals in Montrose Beach

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”

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.

3br W/ Elevator, Patio & Laundry Near the Red Line

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its vibrant food and art scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city. If work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable. (Balcony maintained for Summer Season, Memorial Day-Labor Day)

Updated home with vintage charm

This beautifully updated 4-bed 1.5 bath home offers a seamless blend of comfort and style. Relax in the bright and inviting living room ideal for unwinding after a long day of exploring. Situated 2 blocks from the legendary Aragon theater, Riviera theater and the famed Green Mill, you’ll have entertainment at your fingertips. Lake Michigan is just a 15 minute walk. Plus the CTA Red Line is a few blocks away and with a short train ride you can easily access Wrigley field and downtown Chicago.

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 $20/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

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.

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!

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

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. Wrigley Field is a 5-minute drive. CTA's Red Line/Lawrence train station is only 1 block away. Parking decals available for guests (for parking overnight on surrounding residential streets).

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

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.

Guest Favorite | In Unit Laundry | New Renovation

1st-floor unit with an 8-step staircase to access. Welcome to your charming 1BR|1BA retreat in the heart of Andersonville! This cozy apartment offers a comfortable living space, fully equipped kitchen, central heating and AC, in-unit washer and dryer, and a peaceful bedroom for a restful stay. Just steps from vibrant shops, restaurants, and cafes, plus nearby parks, nightlife, and easy public transit access.