Vacation Rentals By Owner In Chicago, IL

$177.97

Luxury Furnished 2-bedroom Loft- walking distance to UIC and Medical district

Chicago, Illinois, United States

Modern Furnished 2BR/1BA luxury loft in University Village. Minutes from Downtown, Illinois Medical District, UIC, University of Chicago, West Loop, and Pilsen. Located in a peaceful, family-oriented condo building. Ideal for travel nurses, doctors, and professionals. Spacious loft layout with in-unit washer and dryer. Parking space is also available for convenience. Midterm stay requested. No short term allowed.

2

Bed

1

Bath

3

Sleeps

$146.0

/ Nightly

Apartment

Amazing Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this cheery one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped Streeterville home with stunning high floor views over the city. (ID #CHI412)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your beautiful living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this Streeterville apartment has to offer. brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryer in buildingbr - Elevatorbr - Swimming poolbr - Washing machine in buildingbr - Pets allowedbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is located in Streeterville, only a 5 minute walk from The Loop. One of the fastest-developing neighborhoods in Chicago, Streeterville extends out into Lake Michigan and attracts a blend of young professionals, students, and tourists. A plethora of amenities and activities exist for every lifestyle. From Navy Pier activities to luxury shopping on Michigan Avenue, it is a walkable community with easy access to entertainment.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - The apartment is in a busy location, so it will be noisy when your windows are open

Bed

Bath

Sleeps

$270.43

/ Nightly

Condo

Affordable Apartment- Perfect for family time or a good time in Chicago.

Chicago, Illinois, United States

Open floor plan apartment with 2 bedrooms, 1 den/office with desk. Located in a quiet and clean family-oriented neighborhood (Hermosa). Great place to stay to attend one of the many concerts and festivals in the Chicago area. Short drive or bike ride to nearest 606 entrance. Cermak grocery store 2 blocks down. Aldi, Burlington, Cook Brothers, and Dollar Tree also close by. Queen air mattress included with the rental. Additional sleeping space can be arranged for bigger groups at an additional cost.

2

Bed

1

Bath

6

Sleeps

$137.0

/ Nightly

Apartment

Lovely Lincoln Park Studio w/ W/D, walk to L & New City, by Blueground

Chicago, Illinois, United States

Discover the best of Chicago, with this studio apartment in Goose Island with views over the city. It’ll be easy to simply show up and start living in this airy furnished apartment with its fully equipped kitchen, beautiful living room, and our dedicated, on-the-ground support. (ID #CHI304)brbrDesigned with you in mindbrbrAs with any Blueground apartment, you’ll find a thoughtfully designed space complete with beautiful furniture and a fully equipped kitchen in this studio property. And, thanks to our superior quality mattresses, fully stocked linens, and towels, you can relax knowing you’ll always feel comfortably at home. When you’re ready for some fun, you can take in the Chicago vibes or bring the entertainment to you with the premium wireless speaker or smart TV. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Double Bed, 55in/140cmbrbrAmenitiesbrbrBuilding amenities unique to this studio apartment include an on-site:brbr - Dryerbr - Elevatorbr - Washing machinebr - LoungebrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment faces the streetbr - This apartment's central location means it can be noisy at times

1

Bed

1

Bath

2

Sleeps

$231.0

/ Nightly

Apartment

Spacious Gold Coast 1BR, w/ W/D, Gym nr Magnificent Mile by Blueground

Chicago, Illinois, United States

Feel at home wherever you choose to live with Blueground. You’ll love this lovely Gold Coast furnished one bedroom apartment with its modern decor, fully equipped kitchen, and pretty living room with great balcony views. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI221)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your spacious living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this Gold Coast apartment has to offer. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryerbr - Elevatorbr - Game roombr - Washing machinebr - Loungebr - Pets allowedbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is in the historic Gold Coast district. The area is located just north of downtown Chicago, nestled against the Lake Michigan shoreline. Considered one of the most affluent neighborhoods in the country, the Gold Coast is every upscale shopper’s dream. The retail revelry on Oak and Rush Streets includes swanky boutiques and rare, designer fashions. There are many celebrated restaurants to try, including Michelin-starred winners and classic Chicago steakhouses. Amongst the prestigious hotels and celebrated eateries, there is a trove of booming nightlife hot spots and high-energy events.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - Some apartments in this building are undergoing remodeling; construction sounds may occasionally be heardbr - This apartment includes access to a private terrace

1

Bed

1

Bath

2

Sleeps

$147.59

/ Nightly

Apartment

River North w/King Bed, Lake & Skyline Views

Chicago, Illinois, United States

Unbeatable River North location just steps from Michigan Avenue, Northwestern and Loyola. This full condo features a fully-equipped kitchen with everything you need for your home away from home. The bedroom has a super comfortable king-size bed with luxury bamboo linens and a 55 LED with AppleTV. The living room as a buttery-soft leather sectional, 65 LED with AppleTV and smart home features including voice-activated shades. Building requires a separate lease agreement to be signed.

1

Bed

1

Bath

2

Sleeps

$313.5

/ Nightly

Hotel

Modern Queen Stay! Pet Friendly Accommodation w/ Gym Access | Chicago Riverwalk!

Chicago, Illinois, United States

The eco-friendly boutique hotel features a prime location in River NorthbrbrThis listing is for a room within a hotel.brbr✦ Your room is 235 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $74 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $26.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. USD 100 per pet, per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that the Urban Fee (Resort Fee) will be collected at the hotel.

1

Bed

1

Bath

4

Sleeps

$235.89

/ Nightly

Hotel

Pet Friendly Queen Unit! Near Chicago Attractions!

Chicago, Illinois, United States

The eco-friendly boutique hotel features a prime location in River NorthbrbrThis listing is for a room within a hotel.brbr✦ Your room is 183 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $74 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $26.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. USD 100 per pet, per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that the Urban Fee (Resort Fee) will be collected at the hotel.

1

Bed

1

Bath

2

Sleeps

$663.09

/ Nightly

Condo

Luxury 3 bedroom in Chicago, minutes from downtown and steps from Lake Michigan

Chicago, Illinois, United States

Discover the perfect blend of style, comfort, and convenience in this beautifully remodeled 3-bedroom, 2.5-bathroom home. Just minutes from downtown and steps from the shores of Lake Michigan, this spacious retreat offers a thoughtfully designed layout ideal for families, friends, or peaceful getaways.brbrEnjoy high-end finishes, modern furnishings, and an open-concept living space that invites relaxation and connection. Whether you're sipping coffee on the porch, preparing meals in the gourmet kitchen, or unwinding in the serene bedrooms, every detail is crafted for a memorable stay.brbrHighlights:brbr3 spacious bedrooms with premium beddingbr2.5 modern bathrooms with luxury fixturesbrFully equipped kitchen with stylish designbrCozy living area perfect for gatheringsbrPrivate outdoor space for relaxationbrPrime location near Lake Michigan and downtown attractionsbrPerfect for family vacations, weekend retreats, or extended stays—your luxury escape awaits.

Bed

Bath

Sleeps

$325.32

/ Nightly

Apartment

Stylish Urban Retreat 3 Bedroom Newly Remodeled

Chicago, Illinois, United States

This newly remodeled 3 bedroom 1 bath apartment is the stylish urban chic apartment for you! Perfect for exploring Chicago! The closest metro station (the green line) is only a 2 minute walk which can take you anywhere you want to go in Downtown. The closest beach and access to the lake is 5 minutes by car.brBedroom 1 has a King bed, bedroom 2 Queen sized bed and bedroom 3 has 2 Twin beds. Brand new pillow top mattresses will provide you comfort and relaxation after a long day of exploring the city. Sheets, towels, pillows, and extra blankets are provided. The AC works great for those humid summer months, while the heater keeps you cozy during a winter storm. brbrThere are lots of restaurants, grocery stores and coffee shops nearby all within walking distance.

3

Bed

1

Bath

6

Sleeps

$464.7

/ Nightly

Apartment

Modern Apt Near the Loop

Chicago, Illinois, United States

Stay comfortably in Chicago at this 4-Queen size bedroom apartment. Each bedroom features a queen bed, ensuring a pleasant night's sleep for all guests. With amenities like WiFi, heating, and AC, you'll have everything you need for a tremendous stay. The property also includes a washing machine for added convenience. It's easy to see why you'll be able to unwind at our place.

4

Bed

2

Bath

8

Sleeps

$441.69

/ Nightly

Hotel

Spacious Family-Friendly 2BR near McCormick & Zoo

Chicago, Illinois, United States

Welcome to your modern retreat in the heart of Chicago’s vibrant South Loop! This stylish 2-bedroom, 2-bathroom suite is designed for comfort, convenience, and connection—perfect for business travelers, families, or groups attending events at McCormick Place just steps away . Enjoy sweeping city skyline views a fully stocked kitchen , gym access , blazing fast Wi-Fi , optional on-site parking , and room to sleep up to 8 guests in style and comfort .brbrbrOur space combines urban elegance with homely charm . Featuring high ceilings, tall windows , and custom furnishings , this suite gives you all the vibes of downtown life—with extra comfort.brbr Sleeping arrangements:br2 Queen beds with fresh linens br 1 Comfy sofa bedbr 1 Queen air mattress (set up upon request)brbrAmenities you’ll love:br Fully equipped kitchenbr Central AC & Heating brLightning-fast Wi-Fibr 4K Smart TV with Netflixbr In-unit washer & dryerbr Fitness center accessbr Elevator buildingbr EV charging stationsbrbr Prime Location Perks:br 7-min walk to McCormick Placebr5–10 min Uber to Soldier Field, Museum Campus, Grant Park & Downtownbr Surrounded by top restaurants, bars & cafés br Walkscore: 92brbr You’ll love the balance of convenience, modern style, and local flair this suite offers .

2

Bed

2

Bath

8

Sleeps

$355.0

/ Nightly

Apartment

Gorgeous River North 1BR, nr L Stop, Riverwalk & Loop, by Blueground

Chicago, Illinois, United States

Discover the best of Chicago, with this one bedroom apartment in River North with balcony views over the city. It’ll be easy to simply show up and start living in this furnished apartment with its fully equipped kitchen, living room, and our dedicated, on-the-ground support. (ID #CHI1037)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your stylish living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this River North apartment has to offer. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - LoungebrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished apartment is located in River North, Chicago’s most trendy neighborhood. The bridges combined with the river walk offer incredible views. Nearby on Michigan Avenue is the city’s premier shopping area. One of the neighborhood’s biggest assets is the walk-to-work appeal. Young professionals, who live and work in the area, can quickly get to the office in the morning and just as easily enjoy an after-work drink, as the area is considered a premier entertainment center. Don’t miss a stroll on Kinzie and Hubbard streets. Merchandise Mart, the iconic building with showrooms, shops, and office space, is only a 5 minute walk. The Loop is just across the bridge and is about 5 minute walk.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - Building requires 48h to confirm the booking and validate the required documents

1

Bed

1

Bath

2

Sleeps

$446.6

/ Nightly

Private Vacation Home

A home away from home!

Chicago, Illinois, United States

brbrbrvacation rental cleaning protocolbrMajor surfaces are sanitized and disinfected. Major surfaces include countertops, kitchen and laundry appliances, table surfaces, bath fixtures, faucets, mirrors, door knobs, light switches, interior railings, remote controls, fireplace tools, etc.brbrCarpets and floors are vacuumed. Hardwood and tile floors are mopped with appropriate cleaners.brbrKitchen, bathrooms and bedrooms are refreshed with clean linens.brbrbr2000 Sq ft. duplex, (first and second floors), three bedrooms, two full baths, laundry room, fireplace, hardwood floors, full kitchen w/granite counter tops and adjacent dining area, dishwasher, central air & heat, cozy rear courtyard w/patio and garden.brbrLocated in one of the most desired neighborhoods in Chicago. Close to North Ave Beach, Lincoln Park (includes the Zoo, Conservatory and Caldwell Lily Pond), Museums, etc. brbrYou will love my place because of the neighborhood, the comfy beds, the full kitchen, etc. My place is good for business travelers, families or solo adventurers and can accommodate up to six guests. Stroll the quiet, safe neighborhood and admire the stately homes in a historic setting. brbrbrTags: 60614, Pets, Pet Friendly, Old Town Triangle, Lincoln Park, Lakeview, historic, landmark, lake front, lakefront, Lake Michigan, Gold Coast, Streeterville, Second City, Zanies Comedy Club, Navy Pier, Cubs, White Sox, Bears, Bulls, Blackhawks.

Bed

Bath

Sleeps

$487.06

/ Nightly

Apartment

Urban Oasis in Roscoe Village! Pet friendly and family friendly!

Chicago, Illinois, United States

Welcome to your stylish home away from home in the heart of Roscoe Village, Chicago’s charming “village within the city”! Our newly renovated 3-bedroom, 2 Bath apartment combines modern comforts with the cozy, vibrant spirit of one of the city’s most beloved neighborhoods.brbrStep outside and immerse yourself in the lively Roscoe Village scene! Whether you're grabbing a coffee at a charming café, exploring unique shops, or enjoying a night out at a local bar, everything you need is right here. This apartment is pet friendly and offers your own private laundry facilities. Parking is available- just make sure to confirm at the time of booking! Please note: this apartment is on the third floor, so there are stairs.

Bed

Bath

Sleeps

$602.76

/ Nightly

Apartment

Spacious 4BR Chicago Apt Near McCormick Place & Chinatown with Gym & Rooftop

Chicago, Illinois, United States

Welcome to your Chicago home base in the heart of the South Loop. This modern 4-bedroom, 3-bathroom apartment comfortably sleeps up to 8 guests and is thoughtfully designed for families, group trips, business travelers, and extended stays. Just minutes from Downtown Chicago, McCormick Place, and major attractions, this home combines city convenience with everyday comfort.brbrHere, your stay feels calm, organized, and effortless—perfect for both relaxing and staying productive.brbrWhat It Feels Like to Stay HerebrbrStart your morning in a quiet, light-filled apartment, preparing breakfast in the fully equipped kitchen before heading out to explore the city or attend nearby events. In the evening, gather in the spacious living room with a comfortable standard sofa—ideal for conversation, relaxing, or winding down together after a full day.brbrWhen you want a change of scenery, head to the spacious rooftop with plenty of seating, perfect for bonding with family and friends. For work or study, the lobby lounge offers a peaceful environment with seating, a microwave, and printer access—making remote work simple and stress-free. A fully equipped gym is also available to help you keep your routine while traveling.brbrThe ApartmentbrbrDesigned for comfort and functionality, the apartment features:brbr• Four private bedrooms with queen-size bedsbr• Three full bathrooms for easy group livingbr• Spacious living room with a standard sofa (no sofa bed)br• Fully equipped kitchen with modern appliances and cookwarebr• Dining area for shared meals or remote workbr• In-unit washer and dryerbr• Central heating and air conditioningbr• High-speed Wi-Fi throughoutbrbrModern finishes and a clean, open layout create a welcoming space that feels like home.brbrPremium Building AmenitiesbrRooftop Terracebrbr• Large rooftop with ample seatingbr• Ideal for relaxing, bonding, and enjoying time togetherbrbrLobby Lounge & Work Areabrbr• Comfortable seating to relax or wait before check-inbr• Dedicated space for working or studyingbr• Microwave available for guest usebr• Printer access for business travelersbrbrFitness Centerbrbr• On-site gym available for guest usebrbrAdditional Amenitiesbrbr• Elevator accessbr• Stylish, well-maintained common areasbrbrPrime South Loop LocationbrbrYou’ll be close to Chicago’s top destinations, including:brbr• McCormick Place Convention Center (approximately 8–10 minutes)br• Soldier Fieldbr• Museum Campus (Field Museum, Shedd Aquarium, Adler Planetarium)br• Grant Park and Millennium Parkbr• Chicago Riverwalk and Navy Pierbr• Downtown Chicago and The LoopbrbrSurrounded by restaurants, cafés, grocery stores, Target, Walgreens, CVS, and easy access to CTA trains and buses.brbrParkingbrbr• Paid on-site parking available in the building for $40 per nightbrbrGuest AccessbrbrGuests have full private access to the entire apartment and shared access to the rooftop, gym, lobby lounge, elevator, and all building amenities.brbrImportant Informationbrbr• Check-in: 4:00 PMbr• Check-out: 10:00 AMbr• Keyless self check-inbr• Sleeps up to 8 guestsbr• No sofa bed in the living roombr• High-speed Wi-Fi suitable for work and streamingbr• In-unit washer and dryerbrbrIdeal Forbrbr• Families and group staysbr• Business travelers and remote workersbr• Convention and event attendeesbr• Long-term and extended staysbrbrBook your stay today and enjoy a spacious South Loop Chicago apartment that offers comfort, connection, and convenience—perfectly positioned to experience the city with ease.

Bed

Bath

Sleeps

$377.52

/ Nightly

Hotel

Stylish 2BR Cozy South Loop Suite Near McCormick

Chicago, Illinois, United States

Welcome to your chic and cozy home in the heart of Chicago’s vibrant South Loop! Just steps away from McCormick Place, this bright and modern 2-bedroom, 2-bathroom suite is perfect for families, business travelers, or friend groups exploring the city. brbrThis space is thoughtfully designed for comfort and convenience — offering plenty of room to relax, work, and enjoy all that downtown Chicago has to offer.brbr Sleeps 8 guests | Optional Parking | EV Charging | Gym AccessbrbrOur suite is not your average VRBO— it’s a premium stay in a premium location. Whether you’re here for a convention, a getaway, or an extended work trip, this home is designed to make you feel at ease and energized for the Windy City experience.brbrReady to enjoy the best of Chicago with comfort, convenience, and style br Book your stay today — and feel free to message us for special rates or long-term stay discounts! brbr Highlightsbr Prime Michigan Ave locationbr 2 Queen Beds + Sofa Bed + Queen Air Mattress (Sleeps up to 8)br Fully equipped kitchen with coffee, tea & cooking essentialsbr 4K Roku HDTV with streaming appsbr Dedicated high-speed internetbr Central heating & coolingbr In-unit washer & dryerbr Optional secured parking for $30/daybr EV charging stations on-sitebr Gym access includedbr 24/7 Security with rotating shiftsbr Large windows with city views & natural lightbr Professionally cleaned between each staybrbrbr Nearby Attractions & DistancesbrMcCormick Place – 9 min walk (0.4 miles)brSoldier Field – 5 min drive (1.2 miles)br Art Institute of Chicago – 10 min drive (2.9 km)br Field Museum – 7 min drive (2.4 km)br Shedd Aquarium & Adler Planetarium – 7–10 min drive (3.3–3.4 km)br Chicago Symphony Orchestra – 10 min drive (3 km)br Grant Park – 7 min drive (2.8 km)br 31st Street Beach & Lakefront Trail – 8 min drivebr CTA Subway Station – 5–6 min walkbr Midway Airport – 25 min drive (13 km)br Walk Score: 92 – Walker’s Paradise!brbrThis stylish urban suite features:brbr- Modern loft-style 10–12 ft ceilingsbr- Custom furnishings & tasteful décorbr- Luxury vinyl flooring & remodeled kitchenbr- Stainless steel appliances & new countertopsbr- Spacious bedroom closets – perfect for extended staysbr- Bright corner unit with large windows and natural light

Bed

Bath

Sleeps

$1563.35

/ Nightly

Apartment

Luxury Loft Collection COMBO 01/03 | Terrace

Chicago, Illinois, United States

Summary:brbrEnjoy the combination of your own 2 side-by-side private luxury lofts in Chicago's bustling River North-the city's center of main nightlife and restaurants . These two ultra high-end apartments combine for over 6,000 square feet of living and features a private elevator, private terrace, free secured parking, 24 hour doorman, 6 bedrooms/5 full bathrooms, and is perfect for all types of large groups. The cityscape views are unbeatable! is perfect for group trips.brbrbrbrThe Space:brbrOur unique one of a kind lofts are located in Chicago's newest luxury building with views overlooking the city and are the most high-end rental offering in the city. The unit comprised of 2 side-by-side luxury units, joined by elevator, sleeping 28+ people comfortably and is perfectly situated for large groups, families, events, and curated dinners. In each unit, everything flows around the spacious and open living rooms and chef's kitchens, add the floor to ceiling windows with connecting outdoor patio and the space becomes a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combos are decorated in modern contemporary art and features a large sectional, accent chairs, dining areas, smart TV (Netflix, Hulu, Etc. capable) and record player for entertainment.brbrbrbrAttached to each dining room, the chef's kitchens are outfitted with gas-powered Gaggenau ranges, Gaggenau oven and microwave, restaurant sized refrigerator and freezer, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a coffee maker, amongst otherbrbrbrbrIn addition, enjoy your own large private covered terrace with seating and dining options (provided during the nice weather), truly a unique offering and extension of the living area!brbrbrbrThese one of a kind lofts comfortably sleep 22+ people when combined and has 6 bedrooms and 5 full bathrooms. Please note, while we allow 22 people to stay in this unit, there may not be 22 regular beds and allow our guests to figure out their sleeping arrangements.brbrbrbrSleeping arrangements/room layout:brbrBedroom 1: King Bed, bathroom with soaking tub, shower, and heated floorsbrbrBedroom 2: Two full-over-full bunk bed sets, private bathroom with shower brbrBedroom 3: One full-over-full bunk bed and a standard full bed, private bathroom with tub and showerbrbrBedroom 4: King Bed, private bathroom with tub and showerbrbrBedroom 5: Two full-over-full bunks bed, private bathroom with shower and large soaking tubbrbrBedroom 6: Two side-by-side twin xl beds, full bathroom across the hallbrbrbrbrOur units are made up fresh before each guest and their group arrives. Our cleaning services that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is striped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrOther Things to Note:brbrOur building is a highly secure building with 24/7 doorman and secure covered parking garage.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.

6

Bed

6

Bath

22

Sleeps

$793.39

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king and the other feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

3

Bed

2

Bath

6

Sleeps

$561.97

/ Nightly

Hotel

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 9th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

2

Bed

1

Bath

4

Sleeps

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