View All Chicago IL Homes with Vacation Rental Listings

$275,000
1 Beds 1 Baths 12703556 MLS CLOSED Status
River-facing views don't get better than this. Experience front-row views of one of Chicago's most iconic urban landscapes from this coveted Marina City residence, where the Chicago River winds gracefully beneath the lights of Wacker Drive on its way to Lake Michigan. From your windows, enjoy a constantly changing panorama of passing boats, sparkling city lights, the vibrant Chicago Riverwalk, and breathtaking views stretching in both directions along the river. This highly sought-after south-facing one-bedroom is perfectly positioned in one of the building's most coveted tiers, offering a view that is nothing short of extraordinary. The bathroom retains many of its original finishes designed by renowned architect Bertrand Goldberg, preserving a unique piece of the building's history. Bring your design vision and transform this residence into a spectacular city retreat where the ever-changing river and skyline views are the centerpiece. Investor-friendly with no rental cap (12-month minimum lease required; no short-term or vacation rentals). Water heater replaced approximately 2024. Residents enjoy an exceptional array of amenities including 24/7 door staff, well equipped fitness center, spectacular roof level sundeck with sweeping views, storage, laundry room, receiving room. The building is exceptionally well maintained with approximately $8,459,942 million in reserves (as of June 2026). Recent capital improvements; The hallway renovation project has completed, and the balcony divider project is scheduled to begin later this year. Valet parking is available for just $285/month. Unit is being sold as is. Washer/dryer can be installed with approval first. Cats allowed, sorry no dogs. ***Click the virtual tour button below photos to see video of views from the balcony!!***

300 N State Street Unit #4333, Chicago

$725,000
3 Beds 2 Baths 12699009 MLS ACTIVE Status Prairie House At Central Station BLDG.
Stunning, bright and spacious NW corner home at the Prairie House in South Loop with spectacular skyline views. Open floor plan with huge living room flooded with light and featuring a gas fireplace, built-ins and motorized shades. Cooking will be a pleasure in the chef's kitchen with white cabinetry, quartz counters, stainless steel appliances (yes, a gas stove!) and a pantry. Dining area right off the kitchen leads to an awesome deck for grilling, cocktails and soaking in the unobstructed panoramic views. Hardwood floors throughout the living areas, great storage with custom closets and front loading LG in-unit washer and dryer. The primary suite features a large bedroom with a private, west facing balcony, huge bath with a tub and a separate shower and a walk-in-closet. The two additional bedrooms are spacious and can work as guest rooms or an office. Brand new carpeting installed in all 3 bedrooms. Two premier, side-by-side parking spaces are included in the price with room for your bikes. Excellent location in a super quiet enclave of townhomes east of Indiana Ave with easy access to the lakefront, Burnham Harbor, Museum Campus, Soldier's Field, Mark Twain Park and downtown. Walking distance to shopping, dining and nightlife. Meticulously maintained, full-amenity building with 24-hour doorman, sundeck, community room and fitness center, additional storage. $1.7M in reserves, no rental cap. Truly a remarkable property, living here will feel like a vacation retreat!

1515 S Prairie Avenue Unit #1214, Chicago

$1,050,000
4 Beds 2 Baths 12681007 MLS CLOSED Status
Turn-key 2-Flat in Beautiful Bowmanville! Stunning first-floor owner's unit plus a second-floor rental. Huge open full basement for expansion possibilities. All this plus a picturesque, landscaped yard and patio. Enter the building through a vintage Foyer. Unit 1 has been updated and tastefully remodeled and is currently the owner's unit. It offers 2 Bedrooms, 1 Bath, separate Living Room and Dining Rooms, a reimagined butler's built-in, and a newly remodeled Kitchen. This 'Chef's Dream' kitchen features beautiful cabinetry, dramatic marble countertops, La CornuFe dual fuel Range/Ovens, La Cornue Broche Flamberge Rotisserie, Sub Zero Refrigerator/Freezer and Beverage refrigerator. Enter Unit 2 through its private stairs and Foyer. It also has 2 Bedrooms, 1 Bath, separate Living Room and Dining Rooms, a nice butler's built-in, and Kitchen, but it also has a 3-season Sunroom. Then there are the must-see backyard garden and Patio. Full, mature perennial plantings, fountain, circular green, and designated table/sitting area. You will feel you are on a European vacation! French drains fill underground rainwater wells to replenish the fountain. Other features: Owner's installed sound insulation between the two units. Plumbing 'stack' for future second floor laundry. Two car Garage. Full tear-off new flat roof in 2010. Common Electrolux Washer and Dryer in the basement. Enjoy an excellent location. Walking distance to Peterson Metra, CTA Brown & Red Line stations, Andersonville dining, and shopping, many highly ranked public and private schools, and beautiful city and lakefront parks. Relish Bowmanville's tranquility while being close to Andersonville and Lincoln Square.

1959 W Balmoral Avenue, Chicago

$100,000
1 Baths 12553065 MLS CLOSED Status
Located in the heart of Edgewater, Unit 3E at 5757 N Sheridan offers a prime opportunity to create a custom lakeside retreat. This light-filled residence is being sold as-is, featuring a signature large wall of windows that floods the space with natural light and captures the vibrant energy of the neighborhood. Residents enjoy a vacation-like lifestyle in this doorman building, which provides the peace of mind of 24-hour security and the convenience of on-site management and engineering. The building's exceptional amenities include a gated beachfront patio complete with outdoor grills, perfect for summer entertaining. Additionally, a recently refurbished enclosed solarium and a reconstructed roof deck offer breathtaking, panoramic views of Lake Michigan and Hollywood Beach. Further building perks include on-site laundry facilities, a bike room, and a party room for resident use. For those with a vehicle, rental parking is available on-site within a secured, heated garage, offering both valet and self-park options for residents. The location is a commuter's dream and an outdoor enthusiast's paradise, with unbeatable access to public transportation via the CTA Red Line at the Bryn Mawr and Thorndale stations just a short walk away. Numerous express bus lines also stop right outside the door for a quick trip downtown. For recreation, you are steps from the starting point of the 18.5-mile Lakefront Bike Path and the sandy shores of Hollywood Beach. The vibrant Edgewater neighborhood also offers a wealth of amenities within walking distance, including Whole Foods, Mariano's, and the local shops and dining of the Bryn Mawr Historic District.

5757 N Sheridan Road Unit #3e, Chicago

$388,500
2 Beds 2 Baths 12460075 MLS CLOSED Status
Welcome to 3550 N. Lake Shore Drive, Unit 1002. This southeast corner 2-bedroom/2-bath in the South Tower has 17 windows that provides an enormous amount of natural light not to mention vacation views of the Lake, Belmont Harbor & Navy Pier! The open and expansive floor plan allows for a multitude of furniture placement and living arrangements. An updated, open cook's kitchen offers maple cabinetry, granite counter tops with a full backsplash, double sink and stainless steel appliances. There's "true" hardwood floors throughout the unit complimented with gorgeous crown molding. The second bedroom has stunning views as well and a full wall of closets...just across the hall is the 2nd bath complete with a walk-in shower and gorgeous wall and floor tile. The primary bedroom is "Huge" with plenty of space for a king size bed, night stands, dresser and sitting area...along with a walk-in closet. The updated primary bath features a deep soaking tub and contemporary vanity, lightly and mirrors. 3550 North Lake Shore Drive is a high-end, full-service building with 24-hour door staff, roof top decks, party room, fitness room, commissary, 2 laundry rooms, secure receiving room, on-site management office, and maintenance staff. Monthly valet parking is available for 160...no wait. Public transportation at your front door. Walk to the Lake, Wrigley Field, and all of East Lakeview. Assessments include heat, water, and Xfinity expanded cable. Owner pays electricity and internet. No dog and non-smoking building. No in unit washer/dryer allowed. Owners must own for 18 months before renting, but there is no "Rental Cap". Reserves are approximately 9M | No specials planned or pending. NOTE: 3550 has first right of refusal, therefore, FHA financing is not allowed.

3550 N Lake Shore Drive Unit #1002, Chicago

$193,500
1 Beds 1 Baths 12431006 MLS CLOSED Status
This high floor south tower, north facing unit is an opportunity for someone who is looking for a project and who could appreciate putting their own stamp and design on it. Yes, this unit needs work and would be considered a complete gut rehab, but the Views are absolutely stunning and amazing from this 24th floor unit...we are talking about vacation views of the Lake, Montrose Harbor, Golf Course and Wrigley Field. Similar Units have been converted into a 2-Bedroom due to the layout and amount of overall space....ask Listing Agent about details. 3550 North Lake Shore Drive is a high-end full-service building with 24-hour door staff, roof top decks, party room, fitness room, commissary, 2 laundry rooms, secure receiving room, on-site management office, and maintenance staff. Monthly valet parking is available for 160. Public transportation at your front door. Walk to the Lake, Wrigley Field, and all of East Lakeview. Assessments include heat, water, and Xfinity expanded cable. Owner pays electricity and internet. No dog and non-smoking building. No in unit washer/dryer allowed. Owners must own for 18 months before renting, but there is no "Rental Cap". NOTE: THIS UNIT IS SOLD AS-IS. Parking is managed by Pioneer Parking. Comcast is the cable provider. Reserves are approximately 9M | No specials planned or pending. NOTE: 3550 has first right of refusal, therefore, FHA financing is not allowed.

3550 N Lake Shore Drive Unit #2403, Chicago

$606,000
4 Beds 4 Baths 12361556 MLS CLOSED Status
Sold before print. Your chance to own a piece of Chicago history in rapidly appreciating Grand Boulevard! Built in the year of the world's Colombian Exhibition in nearby Jackson Park, this stunning greystone is nestled between its neighbors on Washington Park Court, a Chicago landmark block of architecturally distinct rowhouses tucked away in a quiet residential district at the southern edge of Bronzeville. Lovingly maintained and modernized, this beautiful home features a facade of Indiana limestone, original woodwork from 1893, and hardwood floors throughout the first and second floor. The home's main level flows from the front living and dining space to a massive, thoughtfully designed chef's kitchen. The original grand staircase in the entryway brings you upstairs to a bright sky-lit hallway with a spacious master bedroom featuring a newly renovated (2021) ensuite bath and west-facing bay windows that let in an abundance of natural light. The second floor also features three additional bedrooms, another full bath, and plenty of storage, including built-in bookshelves. In the finished basement, you'll find laundry, another full bath, and an open flex space currently being used as an artist's studio and cozy den, all accessible via both front and rear private entries. Outdoors, a garage rooftop deck provides a spacious venue for summer socializing. The new (2022) garage's roll-up garage door means easy access to exposed rafters, offering extra storage potential for bikes, kayaks, or other outdoor gear. Don't miss this opportunity to invest in a historic home in a prime location - less than a 10-minute drive to the lakefront, University of Chicago, or IIT, and a mere 20-minute drive in rush hour to the Loop! The Green Line and numerous CTA bus routes are steps away. On weekends, enjoy a short walk to Washington Park, shops, and restaurants along bustling 47th and 51st Streets. Enjoy neighborhood gems like the South Side Sanctuary, Boxville food and retail marketplace, Sip & Savor coffeeshop, the Bronzeville Art District, and so much more. Upcoming nearby developments include the Northwestern Medicine Bronzeville Outpatient Center and the Obama Presidential Center. Investors: buy and rent long-term or operate as a Airbnb or vacation rental. Savvy new homeowners: take advantage of this opportunity to buy while the neighborhood is still affordable!

4955 S Washington Park Court, Chicago

$315,000
6 Beds 3 Baths 12357417 MLS CLOSED Status
*Pullman Historic District* *Rare Two-Unit Property - Under Contract Before Print!* This beautifully renovated two-unit home in the historic Pullman District is a rare find and offers versatile living options. Meticulously updated from top to bottom, the property features modern finishes and thoughtful upgrades throughout. The first unit is a spacious duplex with four bedrooms and two full bathrooms, perfect for families or multi-generational living. The second unit offers two bedrooms and one bathroom, making it ideal as a rental opportunity or a cozy vacation retreat for Chicago travelers. Highlights include stunning quartz countertops with a stylish glass backsplash, ample cabinet space, and sleek stainless steel appliances. The home boasts a washer and dryer combo, decorative flooring, recessed lighting, and a well-maintained backyard-perfect for outdoor gatherings. Additional features include central air conditioning, all-new plumbing and HVAC systems, a brand-new roof, and updated flooring throughout. *Location is key!*This home is within walking distance to Pullman National Historic Park and Museum, as well as the Pullman Omniplex Stadium and Dr. Conrad Worrill Track & Field Center. Conveniently located near the Metra train station, major expressways, shopping, and dining options, offering unparalleled accessibility and lifestyle convenience. This move-in-ready home seamlessly combines historic charm with modern amenities, making it a fantastic opportunity in a highly desirable neighborhood. New owner will be looking for tenants in both units soon.

10557 S Corliss Avenue, Chicago

$320,000
2 Beds 2 Baths 12273883 MLS CLOSED Status
Welcome to 3420 N. Lake Shore Drive, Unit 16N. This high floor 2-bedroom and 1.5 bath condo that spans the length of the building from East to West offers straight on jetliner/vacation views of Belmont Harbor, The Lake, Wrigley Field and west as for as the eye can see for those amazing sunsets. PLUS, a secure heated indoor parking space is INCLUDED (35k + Value)!! The foyer has nice arched doorways that lead to the kitchen and hallway. The Cook's kitchen features gorgeous sleek contemporary cabinetry, thick granite counter tops with full backsplash and cool black stainless steel appliances including a full size dishwasher. The expansive living area provides plenty of space for several different lay-outs along with a large dining alcove. Beautiful grayish wood flooring in the main living areas and brand new carpet in the 2 bedrooms. Both of the bedrooms are large in size and can easily accommodate king-size beds with great closet space....not to mention the stunning western views. Both of the baths have been updated and the primary bath features gorgeous floor and wall time & newer vanity. The shower has multiple shower heads and a custom shower glass door. second-floor fitness room and convenient coin laundry. Building amenities include a rooftop deck, complete with grills for residents to use, 24-hr door staff and onsite maintenance available 24/7. Fantastic location near the lake, running paths, bike path, Belmont Harbor, restaurants, shops, and public transportation. Total Assessment = 747, Unit Assessment is 656 + Parking Assessment = 25.68, Cable TV/Internet (mandatory) = 65. Parking is included with the purchase of the unit, a 35,000 + value. Recent building improvements include new risers (2020), hallway renovations (2023), new roof top decking with all new furniture coming. Reserves are approximately 500,000 as of January, 2025. REMEMBER a Secure, Heated, In-Door Parking Space is include in the price. Oh...Pet Friendly...Dogs allowed but not over 50lbs. NOTE: NO FHA or VA financing allowed...building has first right of refusal. Also, NO in-unit W/D is allowed. NO Rental Cap or Restrictions!

3420 N Lake Shore Drive Unit #16N, Chicago

$550,000
2 Beds 3 Baths 12177780 MLS CLOSED Status
Excellent opportunity to own a Single Family Row Home on one of the best blocks in Lincoln Park that is currently set up for Air BnB! This 2 bedroom 2.5 bath home has gone through some amazing upgrades such as a recently finished full basement currently being used as a third bedroom along with a new full bathroom. This home has a great layout on a raised first floor with large family room, a powder room/half bath, a large open kitchen with a small deck out back behind the kitchen. The top floor has 2 generously sized bedrooms (Each fits a king sized bed). The top floor bedrooms were primarily used for Air BnB and thus one of the two bedrooms has been setup with a small kitchenette stove, a full sized dishwasher, a sink, custom shelving, stove and pantry. The top floor also has a large bathroom with jacuzzi tub and walk in shower as well as a washer/dryer combo in the bathroom. There is ladder access to a large rooftop deck that comes with the furniture and bar pictured. The finished basement also has a laundry room with storage space. This is a fantastic opportunity for an investor looking for a rental property or vacation rental. Ask about how much my client earns per night for the top floor 2 bedroom unit for Air BNB. Location is fantastic; steps from Lincoln Ave & Halsted St dining and shopping. Red, Purple, and Brown line station and Whole Foods just 2 blocks away. Easy street parking on Montana.

920 W Montana Street, Chicago

$1,560,000
4 Beds 4 Baths 12075758 MLS CLOSED Status
**SAT OH IS CANCELED** Incredible opportunity to purchase this fully updated 4Br/3.1Ba SFH on one of Bucktown's best blocks, just steps to The 606. This special home boasts a lower level at-grade with a private, front-facing entrance making it perfect for an Airbnb, nanny suite, or small business set to receive visitors - the options are endless. The main level offers a formal living room and dining room, anchored by a stylish fireplace and oversized windows letting in wonderful natural light - past the powder room is a stylish and modern kitchen with custom cabinetry, quartz countertops, tile backsplash, and an upgraded suite of high end stainless steel appliances. The rear family room walks out to a deck, and then up a short flight of stairs to a built out deck above the 2-car garage, perfect for entertaining on summer nights. Upstairs, you will find three generous bedrooms and two full, highly upgraded bathrooms, including a stunning primary suite with wrap-around windows, organized walk-in closet, and a spa-like marble bath with freestanding tub, glass shower, and double vanity. The lower level is currently used as an art studio and guest suite, but with its full sized windows and separate entrance, not only could it be used as a traditional family/TV room, but it could also function as a standalone apartment/in-law suite or even an income producing vacation rental. This location can not be beat - situated on a tree-lined street, this home offers easy access to Clybourn Metra and Damen CTA stations, several parks, and all the shopping, dining, and nightlife that Bucktown and Wicker Park have to offer.

1749 N Wood Street, Chicago

$149,000
1 Baths 11973613 MLS CLOSED Status Imperial Towers BLDG.
Truly wonderful, rarely available larger studio with beautiful finishes welcomes the next lucky buyer in this steps-to-the lake and Montrose Harbor, gorgeous full-amenity building! Very spacious, with a full wall of south facing windows, loads of natural light, and a partial view of the lake and park! Enjoy plenty of fabulous space to create areas for sleeping, dining, entertaining, working and relaxing! Boasting lovely hardwood floors, a sensational kitchen with marvelous granite counters, stainless steel refrigerator and oven, generous amount of terrific rich-colored wood cabinetry (some with pull put drawers), and an area for an eat-in table or add-in breakfast bar, etc.! Roomy bathroom features a large white vanity with a granite counter, abundant storage, bathtub and shower. Superb entry foyer, incredible closets!! Enjoy many luxuries and comforts in this highly desirable premier building, including attentive 24 hour door staff, beautiful outdoor Olympic-sized pool with vacation-like sundeck, hot tub, sauna, covered eating area with grills, community garden, large outdoor courtyard, fitness center, renovated party room, laundry areas (in each tower), rental suite available for guests, Go-Grocery with cafe in the building, dry cleaners, bike room, Amazon hub, receiving room, and onsite management and engineers. Additional storage unit can be rented, too (building fees for some amenities apply). Attached garage rental parking through LAZ parking for additional fee, and free non-metered street parking is available. Magnificent and sensationally landscaped circular driveway leads to this true Buena Park gem, with close proximity to trains, buses, Lake Shore Drive, parks, bike and walking paths, beach, golf, tennis, dining and shops galore. A most lovely haven, with easy accessibility to downtown and the wonderful variety of offerings of many nearby neighborhoods! Taxes include no exemptions. Assessments: Total = $486.06 ($406.77 + $79.29 cable/wifi). NOTE: Unit was originally listed as a combined 3 BR/3 BA units 2133-2135 (#2133 -large studio/1 BA and #2135 - 3 BR/2 BA) which maintained 2 PINS. Room dimensions are approximate. Don't miss seeing this very rare and special unit!!

4250 N Marine Drive Unit #2133, Chicago

$375,000
3 Beds 2 Baths 11859726 MLS CLOSED Status Imperial Towers BLDG.
Exceptional lake, park and sunset (S, E, and W) views from this fabulous and incredibly spacious, higher floor and rarely available 3 BR/2 BA corner unit with stunning balcony lake views! Located in a wonderful steps-to-lake full amenity building! Lined with windows, this unique, bright and stunning unit offers a most gracious flow for indulgent living, entertaining and multiple options for space utilization with large rooms and lined-with-windows LR opening to a dining area and great-sized east-facing balcony. Huge primary suite, and 1 large BR with full wall of closets is currently utilized as an office. Lovely wood floors in large entry foyer, living and dining spaces. Carpeted BRS, and truly sensational closet space throughout, including wall-to-wall closets in 2 of the BRs. White kitchen with marvelous cabinet space and SS appliances. Loads of gorgeous natural light throughout! Enjoy breathtaking lake, Montrose Harbor, south and west views from your own private balcony and windows galore! Enjoy many luxuries and comforts including additional storage, attentive 24 hour doorstaff, beautiful outdoor Olympic-sized pool with vacation-like sundeck, covered eating area with grills, community garden, large outdoor courtyard, fitness center, renovated party room, laundry areas in each tower, rental suite for guests ($125/night), Go-Grocery with cafe in the building, dry cleaners, bike room and onsite management and engineers. 1 additional storage unit, too (building fees for some amenities apply). Attached garage rental parking through LAZ parking for additional fee, and free non-metered street parking. Magnificent and sensationally landscaped circular driveway leads to this true Buena Park gem, with close proximity to trains, buses, Lake Shore Drive, parks, bike and walking paths, beach, golf, tennis, dining and shops galore. A most lovely haven, with easy accessibility to downtown and the wonderful variety of offerings of many nearby neighborhoods! Taxes include homeowner's and senior exemptions; Assessments: Total = $1202.21 ($1122.92 + $79.29 Cable). NOTE: Unit was originally listed as a combined 3 BR/3 BA unit (#2133 -large studio/1 BA and #2135 - 3 BR/2 BA) which maintained 2 PINS. Room dimensions are approximate.

4250 N Marine Drive Unit #2135, Chicago

$357,000
2 Beds 2 Baths 11848884 MLS CLOSED Status
Welcome to Unit 2301...soaring all the way to the 23rd floor, this rarely available high-floor northeast corner, south tower, 2-bedroom/2-bath offers vacation/jetliner views of the Lake, Belmont & Montrose Harbors, the Golf Course, Wrigley Field and The Drive from 17 windows....the views are truly eye-popping. This home has an enormous living space which can easily accommodate several living arrangements along with a dining room alcove. Absolutely gorgeous hard wood flooring and crown molding through out. A beautiful built-in too. The Cook's kitchen features white contemporary cabinetry, thick stone counter tops, a double undermount sink and newer stainless steel appliances The primary bedroom which can easily accommodate a king-size bed along with a separate seating area also has a full-size walk-in closet with organizers. The second bedroom is large with plenty of room for a queen-size bed and dresser or desk along with a wall of closets. Both bathrooms are modern and updated with newer vanities, thick stone counter tops and custom lighting. Beautiful wood blinds in the main living area and custom blackout shades in the bedrooms. 3550 LSD is a full-service building with 24-hour door staff, roof top decks, party room, new expanded fitness room, commissary, a secure receiving room and two laundry rooms. Sorry, no in unit washer & dryer allowed. Monthly valet parking is available for $160. Public transportation at your front door. Walk to the Lake, Wrigley and all of East Lakeview. Your assessments include your heat, water & Comcast/Xfinity expanded cable...you only pay for electric & internet. 3550 is a No Dog & Non-smoking building. Owners must own for 18 months before renting, but there's No Rental Cap. This home has been slightly lived in...and it shows. Welcome home to your own Window to the World!

3550 N Lake Shore Drive Unit #2301, Chicago

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Chicago, IL · Curated MLS Search

Homes with Vacation Rental in Chicago, IL

An editorially curated view of every active homes with vacation rental listing in Chicago, IL. Updated in real time from the local MLS, presented without the noise.

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