Vacation Home Rentals By Owner In Chicago, IL

My home was recently renovated with modern comforts while honoring thebrbroriginal vintage charm of the historic Tri-Taylor landmark neighborhood. Thebrbrlight filled space has 6 bedrooms, 2 bathrooms and can sleep up to 12 guests.brbrThe quiet street is ideal for a peaceful retreat but walkable to the MedicalbrbrDistrict; Rush Hospital is 1 mile away. Little Italy is just down Taylor Ave;brbrdowntown Chicago and the West Loop restaurant corridor are a 10-min drive.brbr(Stairs are original and moderately steep) brbrGeneral Policies: brbr brbrGuest Age Policy – Guests aged 18-24 may book on an exception basis. Pleasebrbrinclude your age, reason for booking, and who will be staying with you in yourbrbrinquiry. brbr brbrLocal Guest Policy – Local guests are permitted to book on an exception basisbrbronly. Parties, gatherings, and group events are strictly prohibited.brbrUnauthorized gatherings or events will result in termination of reservationbrbrwithout refund. brbr brbrPrimary Guest Responsibility – The booking guest must stay for the fullbrbrduration and is responsible for all guests. If booking on behalf of someonebrbrelse, please contact us to discuss exceptions. brbr brbrParking – Street parking may be available but is not guaranteed. Read allbrbrposted signs to avoid tickets or towing. To secure a spot, use parking appsbrbrlike SpotHero or ParkWhiz. brbr brbrCity Noise – Some ambient noise is part of city living. brbr**House Rules:** brbr brbrPlease respect our home and neighbors. Violations of ANY of the followingbrbrrules may result in fines and/or termination of your reservation without abrbrrefund. brbrbrbr 1. No parties or unapproved guests - Only registered guests may access the property. Parties, gatherings, and group events are strictly prohibited.brbr 2. No additional visitors - Only those listed on the reservation may enter the property. Any additional visitors must be declared and pre-approved.brbr 3. Respect quiet hours - Keep noise levels down, especially between 10:00 PM - 8:00 AM. Failure to respect quiet hours or disturbances from an unauthorized gathering will result in termination of the reservation without refund and may result in additional fines to pay city tickets or HOA fines for violations.brbr 4. Check-out on time - Please vacate the unit and return any issued keys by the agreed check-out time. Late check-outs will incur a $250 fee.brbr 5. No smoking - Smoking of any kind is prohibited inside the unit and on the building premises. Evidence of smoking, including odor, will result in a $500 remediation charge. Local laws also prohibit smoking within 15 feet of any entrance.brbr 6. Lockouts & lost keys - A $150 lockout fee applies per occurrence. Lost keys or remotes will incur a $50 replacement fee each.brbr 7. Lost & found - We are not responsible for lost items. If something is left behind, we will attempt to locate it and ship it at your expense. Please check all drawers and closets before departure.brbrbrbr brbrAdditional Policies:brbrbrbr * Guest verification - To comply with legal and security requirements, you may need to sign a rental agreement, provide a government-issued photo ID, confirm your contact details, and submit a selfie matching your ID.brbr * Guest screening - Guests must have a positive track record on the booking platform and provide details about their stay and the guests traveling with them.brbr * AutoHost verification - We conduct additional screening after booking and reserve the right to decline reservations that do not pass verification.brbrbrbr brbrBy completing your reservation, you agree to ALL policies and rules statedbrbrabove. TAX ID: R25000133465brbrbrbr

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Chicago, Illinois, United States

Bed

Bath

Sleeps

$763.23

Welcome to your cozy retreat in Ukrainian Village, Chicago! This charming home features free street parking and a relaxing patio. Located near the United Center, it's perfect for sports and concerts. Enjoy the vibrant area with nearby grocery stores, trendy bars, and delicious restaurants, all within walking distance. Experience the rich culture of Ukrainian Village while having easy access to downtown attractions. Your ideal getaway awaits! Your home away from home in Chicago with 3 bedrooms. This adorable house features three queen beds, offering plenty of space for a comfortable stay. Two bathrooms make getting ready a breeze for everyone. Guests enjoy a cozy atmosphere with heating and air conditioning to keep the temperature just right. An iron and hair dryer add convenience to your visit. Whether you’re relaxing indoors or exploring nearby, this fantastic house provides a welcoming retreat. Experience the magic of Chicago at our house.brGreat location !!!

Welcoming 3-bedroom house in vibrant Chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$555.26

Newly rehabbed single family home with parking in Chicago's popular Pilsen neighborhood. Close to transportation, 18th street restaurants, night life, and music venues like Thalia Hall and Radius. 3 bedrooms and 2 full bathrooms. Entire space features brand-new furniture, mattresses, appliances, and fixtures. Guests have access to 1 parking spot and shared basement laundry space. Space was thoughtfully designed to offer guests a relaxing stay in our hometown, Chicago! Owner occupies the separate basement apartment seasonally.

Luxury Modern home minutes from Downtown Chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$533.32

It is located in the tranquil Lincoln Square, Chicago's safest neighborhood. This 4-bedroom townhome, perfect for families or groups, guarantees relaxation and entertainment. Enjoy the versatile basement, which can double as an extra bedroom or play area, and a well-equipped game room with a 65 HDTV for fun-filled evenings.brbrStep outside to a charming patio with a BBQ grill and a serene garden - your oasis in the city. The location couldn't be better; a short walk from the CTA Brown Line, exploring the vibrant town becomes a breeze. Plus, you're near various restaurants, shops, and parks, promising delightful experiences for everyone.brbrAdditionally, two private parking spaces simplify your city visits, making this home a rare find in Chicago. Book now for a remarkable stay

Northside FAMLYNEST - Lincoln Sq - 4BR/1.5BA/2P - Rare find

Chicago, Illinois, United States

Bed

Bath

Sleeps

$906.97

That's right NO NEIGHBORS ABOVE OR BELOW - It is ALL YOURS! Rare, Private, Freestanding House right in Heart of the city's best neighborhoods! Make this 2 story Coach House your private oasis in the Windy City.brbr*Ask us about Cubs Tickets- 200 level; sets of 3-8. Also, Wrigley Concerts tickets, Bears, Sox, Blackhawks, Bulls tickets.brbr**Need game parking Ask us for our VIP parking pass 1 block from Wrigley at our sister property. Go Cubs!!brbrAll the city has to offer is just outside your door. Located in between Lincoln Ave and Southport you can walk to coffee, breakfast, lunch and dinner, bars, pubs, patio restaurants, movies, Wrigley Field and Clark and Addison is just a few blocks away.brbrMake the Wrigleyville Coach House your Chicago Home Base!brbrChicago Vacation Rental License # 2912234brbrPerfect for Groups making trips to the city for Bears, Cubs, Blackhawks Games, Special Occasions, Concerts, Festivals.brbrLocated in the Heart of the City. Close to everything. Lots of space. Super Clean, Remodeled and now with 2 full baths.brbr2 Queen sized Bedrooms on the 1st Floors plus a large Loft on 2nd Floor with 2 Queen beds, sofa sleeper and air- mattresses that can sleep many.brbrEasy Transportation- L the brown line 2 blocks. Cab's on street. Take a train from O'hare or Midway Airports.brbrKitchen with Granite and Brand New Appliancesbrbr2 BathroomsbrbrSatellite TVbrbrNew Flat Panel HDTVsbrbr'L' Train station 2 blocks away- your ticket to everywhere!brbrGroceries- Target Express next door. Everything you need and more including a Starbucks inside.brbrCoffee- Local coffee shops and bakeries nearby along with Starbucks and Dunkin Donuts a few blocks in any direction its easy to get your coffee fix..brbrExercise- Lakeview YMCA located directly behind on Lincoln with Great Children activities and cheap weekly rates for non members.brbrBreakfast- Crosby's on Southport serves a great brunch on the weekend. The Breakfast House is about a 10 minute walk down Ashland. brbrLunch- Potbelly or Tuco and Blondie on Southport or any of the local establishments on Lincoln Ave and Southport.brbrDinner- Tons to choose from in the neighborhood within walking distance. OR- take the train to State and Rush for Gibson's OR quick cab to Lincoln Park. Several great local spots with in walking distance. Our Favorite is Cafe Tapatio located just one 1 block north- best Mexican food in the city. Make sure to tell them we sent you!brbrNightlife- No reason to travel to far from home. Walk to Lincoln or Southport for neighborhood pubs and upscale night light. Start or finish your night at Avenue Tap around the corner, they do a nice job and always take good care of our guests. Wander down Lincoln Ave from there or take a quick cab or Uber to any of the hot spots on Lincoln and Clark Ave's.brbrEntertainment- Walk to Wrigley Field to see the CUBS.brbrVisit Lake Shore Drive and walk the Lincoln Park Zoo- greatest Free Zoo in the Country. Go to the Beach.brbrTake the train to Millennium Park, Grant Park, the Sears Tower or John Hancock. Quick cab to Second City or The Blue Man Group. Cab or Train to the Theatre district. Walk or Cab to Clark and Addison for fun even if the Cubs are not in town.brbrKeywords: Ryder Cup, Golf, Last Minute, Location, This Weekend, Large Groups, Wrigley, Bears, Cubs, Northwestern Wildcats, Blackhawks, Games, Special Occasions, Concerts, Festivals, Lakeview, Roscoe Village, El,L,Brown Line, Redline, O'hare, Midway, Lakeshore, Lincoln Park, Wedding, Bachelor, Bachelorette, Bar, Restaurant, Public Transportation, Private, City,Train,Cheap,Clean, Southport, Clark, Addison,Airport,House, Wrigleyville

The Original Wrigleyville Coach House- Private 2 Story House in Heart of City

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1517.45

Welcome to The Jackpot — a one-of-a-kind luxury home in Chicago designed for groups who want more than just a place to sleep. This is where your crew gathers, celebrates, and makes the kind of memories you'll be talking about for years.br brWHY GROUPS CHOOSE THE JACKPOT brbrThis isn't your typical rental — it's a 3-level luxury home built for togetherness. Whether you're celebrating a milestone, hosting a weekend reunion, or just getting your favorite people under one roof, every corner of this house was designed for your group to connect.brbrAsk us about special rates for celebrations, retreats, and photo shoots!brbrTHE BACKYARD — Your Private All-Season OasisbrbrStep outside to your personal resort. The backyard is a showstopper year-round.brbr✦ Premium 5-person hot tub with fountain jets & LED lightsbr✦ Louvered pergola — opens for sun, closes for rain/snow, with privacy curtainsbr✦ Cozy fire pit surrounded by wooden chairsbr✦ Propane BBQ grill for group cookoutsbr✦ Ambient string lights & walkway lights for the perfect eveningbrbrENTERTAINMENT — Two Dedicated Fun ZonesbrbrYou will not be bored here. The lower level has two spaces built for group fun.brbrThe Game Room & Bar:br✦ Ping pong & foosball tablesbr✦ Custom bar stocked with essentialsbr✦ Record player with vinyl collectionbr✦ Poker set & board gamesbrbrThe 4K Cinema:brbr✦ 120 projector screen — the biggest screen you've ever watched a movie onbr✦ 4K projector with all streaming apps pre-installedbr✦ Immersive AI Dolby surround soundbr✦ Two ultra-comfy memory foam couches & oversized bean bagsbr✦ The perfect spot for movie nights, game day watch parties, or winding down after a night outbrbrTHE SUN ROOM — Your Morning OasisbrbrWake up slow. This light-filled room is where your group gathers for coffee, conversation, and planning the day ahead.brbr✦ Large wicker sectional with thick cushionsbr✦ Dining table & bench seatingbr✦ Privacy curtains for a cozy feelbrbrKITCHEN & COFFEE BARbrbrA fully stocked kitchen ready for everything from morning lattes to late-night snacks.brbr✦ Full coffee & tea bar: Nespresso, milk frother, flavor pumps, premium coffee & precise electric kettlebr✦ High-end appliances: Large Ninja air fryer & morebr✦ Fridge with filtered water & ice dispenserbr✦ Fully stocked: All essential cookware, bakeware, dishes & utensilsbrbrSLEEPING — 14 Guests Across 5 Bedrooms + Cinema RoombrbrEvery bedroom has real beds. The cinema room doubles as a crash-ready lounge with two full-sized memory foam sleeper sofas.brbrTop Floor (3 private bedrooms):br✦ Bedroom 1: King bedbr✦ Bedroom 2: Queen bedbr✦ Bedroom 3: Full-sized bunk bedbrbrMain Floor:br✦ Bedroom 4: Queen bedbrbrLower Level:br✦ Bedroom 5: Two twin-over-twin bunk bedsbr✦ Cinema Room: Two full-sized memory foam sleeper sofasbrbr3 full bathrooms (one on each level) with fresh towels, hair dryers & starter toiletries.brbrTHE PERFECT CHICAGO HOME BASEbrbrThe Jackpot sits in a quiet, tree-lined North Side neighborhood — peaceful enough to enjoy your backyard hot tub at midnight, connected enough to reach everything Chicago has to offer.brbrGetting Around:br✦ Blue Line (9-min walk) — your direct line to downtown & O'Harebr✦ I-90: 4-min drivebr✦ O'Hare Airport: 13-min drivebr✦ Downtown / The Loop: 16-min drivebrbrNeighborhood Vibes:br✦ Lincoln Square (8 min): Charming shops, restaurants & European bakeriesbr✦ Logan Square (10 min): Breweries, brunch spots & craft cocktailsbr✦ Wicker Park / Bucktown (15 min): Boutiques & vibrant nightlifebr✦ Wrigleyville (15 min): Bars, rooftops & game-day energybrbrAttractions & Venues:br✦ Wrigley Field: 15-min drivebr✦ Millennium Park / The Bean: 17-min drivebr✦ United Center: 17-min drivebr✦ Museum Campus (Shedd / Field): 20-min drivebr✦ McCormick Place: 24-min drivebrbrYour Group, Your Way:brbr✦ Want a quiet night in Hot tub → fire pit → movie night in the theaterbr✦ Want to go out You're 15 minutes from River North, Wrigleyville, and Logan Squarebr✦ Need recommendations Message us — we've got the best local picks

The Jackpot - Hot Tub, Cinema, Game Room, Fire Pit, Bar, Garage - Sleeps 14

Chicago, Illinois, United States

Bed

Bath

Sleeps

$874.95

This single family home w/garage is in desirable LOGAN SQUARE - our 5 bedroom / 4 bath is a 15 minute drive away from Downtown Chicago and steps away from the new Restaurant Row on Diversey Avenue! The residential and safe neighborhood offers a great location and easy access to the highway. Ohare and Midway Airports are a 20 minute drive from the home. The California Blue Line train stop is also a 15-20 min walk from away which gives you easy access to explore downtown or the suburbs.brbrKey Features You`ll Love:brbrSpacious & Comfortable: Enjoy 2550 sq ft of thoughtfully designed living space, featuring 5 bedrooms and 4 sparkling bathrooms, providing ample room for everyone to relax.brbrModern Amenities: Step onto hardwood floors that flow through the main living areas. The updated kitchen is ready for your culinary adventures, while central heating and air conditioning ensure year-round comfort.brbrPrivate Outdoor Oasis: Unwind in your own private yard, perfect for morning coffee or evening gatherings. Enjoy the convenience of a detached 1-car garage, plus a driveway, a rare find in the city!brbrAvondale/Logan Square Vibe: Immerse yourself in one of Chicago`s most dynamic neighborhoods. Known for its `hip` and `lively` atmosphere, Avondale boasts an incredible array of acclaimed restaurants, trendy bars, local breweries, and unique shops, all within easy walking distance.brbrUnbeatable Location:brbrWalk Everywhere: With a `Very Walkable` score, explore the neighborhood on foot, discovering charming cafes, boutiques, and a strong community spirit.brbrTransit Friendly: Excellent access to public transportation, including the CTA Blue Line (Belmont, California, and Logan Square stations are minutes away), makes exploring downtown Chicago and beyond a breeze.brbrEasy Commutes: Quick access to Interstate 90 for convenient travel in and out of the city.brbrFamily & Pet-Friendly Area: This neighborhood is known for being welcoming to families and dogs, with several parks nearby, including Wrightwood Park and Humboldt Park. Be sure to inquire about our pet policy!brbrLocal Delights: Don`t miss the renowned Logan Square Farmers Market (seasonal), diverse eateries, and local community events that give this area its unique charm.brbrWhether you`re visiting for leisure, work, or to reconnect with loved ones, our Avondale bungalow offers the perfect blend of comfort, convenience, and authentic Chicago living. Book your stay today and start making unforgettable memories!brbrCheck-in is effortless and 100% contact-free. Your private access code works on all exterior door keypads, allowing you to arrive and settle in on your own schedule. We’ve designed the process to be completely autonomous, though our team is always just a message away if you need us!brbr*This home is professionally curated by Hosty Co, Chicago’s premier boutique management team. We specialize in high-touch service, 5-star aesthetics, and seamless stays.*brbr**Follow the journey: Find us on social @hosty_co_chibnb for a look at our full portfolio and `insider only` Chicago neighborhood guides.**brbrTo protect the quality of our home and the harmony of our neighborhood, we specifically host:br*Corporate Travelers seeking a refined, reliable home base.br*Families visiting for holidays or major Chicago milestones.br*Urban Explorers who value a quiet, high-end retreat.brbrBooking Requirements: We operate under a strict `Good Neighbor` policy. To ensure we are the right fit for your trip:br*Tell Us Your Story: When inquiring, please include a brief note about your trip and your group. We love knowing how to best prep the space for your arrival!br*Vetting: We prioritize guests with 100% ID verification and a track record of positive reviews.br*Zero Tolerance: To maintain our home`s integrity, parties and unauthorized gatherings are strictly prohibited.brQuiet hours - 11pm - 7ambrNo smoking of any kind indoorsbrNo shoes in the housebrNo guests outside of your group in the homebrNo events

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$648.3

Ready for your UNFORGETTABLE Chicago experience brThis luxe oasis offers the perfect blend of comfort & convenience!brEnjoy a tranquil tree-lined side street in a safe neighborhood while being conveniently between O’Hare Airport/Rosemont & Downtown Chicago. brThe modern design of this newer home paired with its world class amenities makes it one of the most desirable stays in the city. brDon’t miss your chance! Book today while your dates are still available!brMessage us about our current deals!brYou will experience all of this free with your stay:br-Ultra Plush King (2) & Queen (1) Beds br- Basement Game Space for Hours of Fun!br-4K Smart TVs Throughout the Space & in Every Bedroom.br-Your Own Private Gym br-Huge Fenced Backyard with Bonfire Pitbr-Private Deck With Gas Fire Table br-Fully-Stocked Chef's Kitchen br-Gas BBQ Grill br-2 Comfortable and Large Dedicated Work Spacesbr- Oversized Backlit Vanity Mirrors br-Full-Sized Crib in a Dedicated Spacebr- Changing Table & Baby Supplies br-Garage Parkingbr-Complimentary Shampoo, Conditioner, and Body Washbr-Quiet & Safe Neighborhood br-Convenient Location between Downtown & O’Hare Airport br-Short Distance from Rosemont, Donald E Stephens Convention Center, Fashion Outlets & O'Hare Airport br-Short Distances to Public Transit Optionsbr-Free Garage Spot, Driveway, & Street Parking br-Outdoor Games br-Puzzles & Board Games br-In-Unit Washer & Dryerbr-Black-Out Curtains In Every Bedroombr-6 Person Dining Table & Kitchen Island Seating br-Tesla Level 2 Universal EV Charger brbrIs there anything else that would make your stay amazing Send us a message, we would LOVE to help!

Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-EV Charger

Chicago, Illinois, United States

Bed

Bath

Sleeps

$678.89

Experience Chicago like a local in this 5-bedroom house. The bedrooms feature 2 full beds, 1 twin bed, and 2 double beds, ensuring a comfortable stay for all guests. With amenities like heating, AC, espresso machine and an iron, your needs are well taken care of. The 2 bathrooms are equipped with showers for your convenience. Experience the magic of Chicago at our lovely house.brTwo car garage for easy parking. Just 15 min to Chicago O’Hare international airport,Allstate Arena, Rosmont theatre, Fashion outlet , and just 5 min to Copernicus Center. Perfect for families and groups looking for comfort, space and a relaxing home base near the city. brbrBook your stay today and make lasting memories in the heart of Chicago !

5BR Family home Near O’Hare, Easy Airport & Downtown Access, Garage Parking.

Chicago, Illinois, United States

Bed

Bath

Sleeps

$468.15

This spacious, modern entire home is ideally located near McCormick Place and downtown Chicago — perfect for conferences, group travel, extended stays, and families looking for space and convenience.brbrDesigned with comfort and functionality in mind, the home features multiple bedrooms, multiple bathrooms, and open living areas that work well for groups and longer stays.brbrThe home is located in Bronzeville, offering easy access to McCormick Place, the Loop, Museum Campus, the lakefront, and major expressways. Whether you’re attending a convention, visiting family, or staying in Chicago for work, this home provides the space, privacy, and location you need.

Modern Home Near McCormick Place & Downtown - Bronzeville

Chicago, Illinois, United States

Bed

Bath

8

Sleeps

$648.99

Consider this bungalow your home away from home while you visit Chicago. This marvelous retreat features five spacious bedrooms, including three king beds, one queen, and one full bed, perfect for families or groups. With three bathrooms, everyone enjoys plenty of privacy and comfort. The space stays cozy year-round, guests can relax in a serene environment that invites rest and rejuvenation after a day of exploring. Our place will help you feel at home while you're traveling in Chicago.

Charming 5-bedroom Jefferson Park Bungalow near O’Hare

Chicago, Illinois, United States

5

Bed

Bath

10

Sleeps

$672.15

Welcome to a Private Movie Experience in this 3-story home - just 10 miles to downtown! brStep into a one-of-a-kind movie-themed stay where every room brings your favorite films to life. Whether you're planning a family getaway or group trip, this home was designed for great photos, fun & unforgettable moments!brAfter a long day exploring Chicago, enjoy a fully immersive theater experience featuring recliners, premium surround sound, light-up movie posters, & popcorn machine. Lights. Camera. Check in!

Movie-Themed Home w/ Theater - Sleeps 12 - 4BR

Chicago, Illinois, United States

4

Bed

Bath

12

Sleeps

$304.13

Your home away from home in Chicago with 4 bedrooms. This amazing house features AC, a fitness room, WiFi, and more. With 3 bathrooms and a cozy atmosphere, guests will feel right at home. Kickback, relax, and enjoy everything Chicago and our house has to offer.

Charming 4-bedroom house with AC, WiFi in wonderful Chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$727.81

Welcome to Bee's Knees - a vintage gem with a Hollywood-glam twist! This 4-BR Chicago bungalow home is the perfect getaway for a celebration or family gathering. Enjoy the luxury of having a private, fully fenced-in backyard in the city. Host your friends and family for a BBQ and get cozy by the fire. Have the peace of mind coming home to a private, secured garage. We are located in Chicago's beautiful Humboldt Park, 25 min from ORD, 10 min to downtown, 800+ Mbps WIFI, free coffee and parking!brbrKey Features:br☞ 4 Bedrooms · 2 Bathrooms · Sleeps 10 comfortablybr☞ Multi-Level Layout: Spacious and thoughtfully designed across 3 levelsbr☞ California King Primary Suite + Kids' Playroom with Nintendo Switch and TVbr☞ Backyard Retreat: Fire pit, gazebo with seating for 10, & custom-built grillbr☞ Secure Parking: Private 2-car garage + free street parkingbr☞ Family-Friendly: Baby gates, travel cribs, children’s playroom, tableware for childrenbr☞ Ultra-Fast WiFi (up to 800 Mbps), free coffee, and a themed decor vibe throughoutbr☞ Fenced-in entire property with exterior security cameras for peace of mindbr☞ 3 Smart TVsbrbrBedrooms & Layout:br☞ California King Bedroom on main floorbr☞ Stylish Bathrooms, Living Room, Fully stocked Kitchenbr☞ Kids’ Playroom w/ toys, TV, and Nintendo Switchbr☞ 2 Queen Bedrooms, 1 Bedroom with 4 Twin Beds, ☞ Laundry AreabrbrOutdoor Spaces:br☞ Private Backyard with gazebo & seating for 10br☞ Fire Pit area for cozy evenings with string lightsbr☞ Custom Grill for BBQs with gas includedbr☞ Fully fenced-in backyard – perfect for kids to run around safelybrbrOptional Wellness Add-On:brElevate your stay with personalized wellness services from Holistic Vitality. Offerings include yoga, meditation, strength training, and sound baths — all led by a seasoned professional. Perfect for group relaxation or a solo reset. Ask us for more details!brbrLocation & Accessibility:br☞ Located in Humboldt Park – rich in culture, food, and musicbr☞ 1-min walk to the bus stop | 10-min drive to Downtown | 25-min from O'Harebr☞ Close to restaurants, coffee shops, bars, and Humboldt Park's 200-acre green spacebr☞ Safety-first property with exterior security cameras and unique digital entry codes for every guest that are never given to anyone else.brbrHost Support:br☞ 500+ Stays Hosted | Superhost | 24/7 Availabilitybr☞ We take our guests' experience seriously — let us know how we can make your stay even more comfortable!

Bee's Knees - Ritzy, 1924 Chicago Bungalow

Chicago, Illinois, United States

4

Bed

Bath

10

Sleeps

$613.08

Summary:brbrWelcome to our bright and modern 4-bedroom corporate suite in the heart of Chicago. Designed for both comfort and productivity, the apartment features a spacious living area with large windows, a fully equipped kitchen, and a dining space perfect for group meals or business discussions. Each bedroom offers premium bedding, ample storage, and a clean, comfortable setup for restful nights.brbrbrbrThe Space:brbr• Master Suite: Full size bed, en-suite bathroombrbr• Guest Suite: Full size bed, en-suite bathroombrbr• Second Guest Suite: Full size bedbrbr• Third Guest Suite: Full size bedbrbr• Queen floor mattress availablebrbr• Huge windows offering spectacular views of the citybrbr•Washer & dryerbrbr• Fully-equipped kitchen brbr• Flat Screen TV/Cablebrbr• High-speed Internetbrbr• Stainless steel appliancesbrbr• Spacious, walk-in closetsbrbr• Individually controlled heat and airbrbr• Shampoo, conditioner, & body wash in bathroomsbrbr• Hair dryerbrbr• Iron/ironing boardbrbrbrbrAs part of our commitment to providing a premium experience, we offer complimentary starter items to kickstart your stay like shampoo, body wash, conditioner, hand soap, toilet paper, laundry detergent and kitchen supplies like coffee, tea, cooking oil, paper towels and seasonings. These items are thoughtfully provided to ensure you have everything you need upon arrival. However, please note that they are starter supplies and not be replenished during your stay. If you require additional supplies beyond the initial offering, we recommend local stores or delivery services for your convenience.brbrbrbrGuest Access:brbrEasy and convenient self check-in is available at this property. You’ll have full access to the apartment and building amenities during your stay.brbrbrbrThe Neighborhood:brbrPerfectly positioned at the crossroads of Old Town, Lincoln Park, and the Clybourn Corridor, this location lets you experience Chicago’s best mix of shopping, dining, and culture. Step outside to explore the New City shopping plaza, enjoy a show at the Second City Theater, or stroll along the North Branch Trail toward the lakefront. Within minutes, you’ll find stylish boutiques, gyms, Whole Foods Market, Trader Joe’s, and some of the city’s most beloved restaurants and coffee houses.brbrbrbrTransit: Multiple bus lines and the Red Line train nearby for direct access downtown and to the Loop.brbrCoffee: Sweetwaters Coffee & Tea (3 min), Printer’s Row Coffee (5 min).brbrDining: Boka, Ada Street, and Armitage Alehouse all within a short walk.brbrParks: Oz Park and the Lincoln Park Boardwalk are nearby for morning runs or weekend strolls.brbrbrbrWhether you’re here for work, leisure, or family time, you’ll love how easily connected this area is to River North nightlife, the Magnificent Mile, and Lake Michigan’s scenic paths.brbrbrbrGetting Around:brbrYou are minutes away from bus and train stops. brbrbrbrWe find some of our guests prefer to use Uber or Lyft, which is a very convenient and cheap way to get around the city.brbrbrbrOther Things to Note:brbrPlease note:brbrbrbrThis listing includes multiple 4-bedroom homes with the same layout, bed sizes, and amenities, though furnishings and décor may vary slightly. Guests will be assigned one of the available homes prior to check-in, and all homes meet the same standard shown in the photos.brbrbrbr- The building features a central HVAC system that provides year-round comfort. Heating and cooling operate seasonally to keep the temperature pleasant. Guests can adjust the in-unit temperature within the range set by the building.brbr- Building maintenance staff may occasionally need access, but we’ll always provide advance notice whenever possible.brbr- Daily housekeeping isn’t included, though it can be arranged for an additional fee.brbr- Early check-in or late check-out may be available for $149 per service, depending on availability.brbr- On-site parking is available for $69 per night, per spot. Multiple spots can be reserved based on availability. Spots are limited and fill up fast - we recommend securing yours as early as possible. Please message us with your dates to reserve.brbr- Package delivery availability may vary by building - message us for details.brbr- Date changes that shorten or move a reservation follow the standard cancellation policy.brbrbrbrFor your security and a smooth check-in process:brbr- A refundable $500 security deposit is required.brbr- A valid government-issued ID and matching credit card must be provided before check-in.brbr- A short rental agreement will be sent electronically after booking.brbr- Some buildings may require a brief background check as part of management policy.brbr- Local residents (within two hours of the property) cannot book for same-day arrival.brbrbrbrWhile we strive to offer a peaceful experience, please be aware that city or building maintenance, construction, or temporary water/elevator servicing may occasionally occur. These events are outside our control and do not qualify for compensation.brbrbrbrInteraction with Guests:brbrOur online team is available 24/7 to assist you every step of the way - from booking to checkout, ensuring a smooth and comfortable stay.

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Chicago, Illinois, United States

4

Bed

Bath

10

Sleeps

$621.63

Summary:brbrWelcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitchen, and cozy bedrooms designed for both comfort and privacy. Large windows fill the space with natural light, while modern furnishings and soft tones create a calm, welcoming feel - perfect for families, groups, or business travelers seeking room to relax and recharge.brbrbrbrThe Space:brbr• Master Suite: Double bed, en-suite bathroombrbr• Guest Suite: Double bed, en-suite bathroombrbr• Second Guest Suite: Double bedbrbr• Queen floor mattress availablebrbr• Huge windows offering spectacular views of the citybrbr• Washer & dryerbrbr• Fully-equipped kitchen brbr• Flat Screen TV/Cablebrbr• High-speed Internetbrbr• Stainless steel appliancesbrbr• Spacious, walk-in closetsbrbr• Individually controlled heat and airbrbr• Shampoo, conditioner, & body wash in bathroomsbrbr• Hair dryerbrbr• Iron/ironing boardbrbrbrbrAs part of our commitment to providing a premium experience, we offer complimentary starter items to kickstart your stay like shampoo, body wash, conditioner, hand soap, toilet paper, laundry detergent and kitchen supplies like coffee, tea, cooking oil, paper towels and seasonings. These items are thoughtfully provided to ensure you have everything you need upon arrival. However, please note that they are starter supplies and not be replenished during your stay. If you require additional supplies beyond the initial offering, we recommend local stores or delivery services for your convenience.brbrbrbrGuest Access:brbrEasy and convenient self check-in is available at this property. You’ll have full access to the apartment and building amenities during your stay.brbrbrbrThe Neighborhood:brbrPerfectly positioned at the crossroads of Old Town, Lincoln Park, and the Clybourn Corridor, this location lets you experience Chicago’s best mix of shopping, dining, and culture. Step outside to explore the New City shopping plaza, enjoy a show at the Second City Theater, or stroll along the North Branch Trail toward the lakefront. Within minutes, you’ll find stylish boutiques, gyms, Whole Foods Market, Trader Joe’s, and some of the city’s most beloved restaurants and coffee houses.brbrbrbrTransit: Multiple bus lines and the Red Line train nearby for direct access downtown and to the Loop.brbrCoffee: Sweetwaters Coffee & Tea (3 min), Printer’s Row Coffee (5 min).brbrDining: Boka, Ada Street, and Armitage Alehouse all within a short walk.brbrParks: Oz Park and the Lincoln Park Boardwalk are nearby for morning runs or weekend strolls.brbrbrbrWhether you’re here for work, leisure, or family time, you’ll love how easily connected this area is to River North nightlife, the Magnificent Mile, and Lake Michigan’s scenic paths.brbrbrbrGetting Around:brbrYou are minutes away from bus and train stops. brbrbrbrWe find some of our guests prefer to use Uber or Lyft, which is a very convenient and cheap way to get around the city.brbrbrbrOther Things to Note:brbrPlease note:brbrbrbrThis listing includes multiple 3-bedroom homes with the same layout, bed sizes, and amenities, though furnishings and décor may vary slightly. Guests will be assigned one of the available homes prior to check-in, and all homes meet the same standard shown in the photos.brbrbrbr- The building features a central HVAC system that provides year-round comfort. Heating and cooling operate seasonally to keep the temperature pleasant. Guests can adjust the in-unit temperature within the range set by the building.brbr- Building maintenance staff may occasionally need access, but we’ll always provide advance notice whenever possible.brbr- Daily housekeeping isn’t included, though it can be arranged for an additional fee.brbr- Early check-in or late check-out may be available for $149 per service, depending on availability.brbr- On-site parking is available for $69 per night, per spot. Multiple spots can be reserved based on availability. Spots are limited and fill up fast - we recommend securing yours as early as possible. Please message us with your dates to reserve.brbr- Package delivery availability may vary by building - message us for details.brbr- Date changes that shorten or move a reservation follow the standard cancellation policy.brbrbrbrFor your security and a smooth check-in process:brbr- A refundable $500 security deposit is required.brbr- A valid government-issued ID and matching credit card must be provided before check-in.brbr- A short rental agreement will be sent electronically after booking.brbr- Some buildings may require a brief background check as part of management policy.brbr- Local residents (within two hours of the property) cannot book for same-day arrival.brbrbrbrWhile we strive to offer a peaceful experience, please be aware that city or building maintenance, construction, or temporary water/elevator servicing may occasionally occur. These events are outside our control and do not qualify for compensation.brbrbrbrInteraction with Guests:brbrOur online team is available 24/7 to assist you every step of the way - from booking to checkout, ensuring a smooth and comfortable stay.

Modern 3BR Apartment Near North Ave Shops

Chicago, Illinois, United States

Bed

Bath

8

Sleeps

$236.22

Modern kitchen. Granite countertops. Can't you smell the fresh baked bread welcoming you in the door. Even if you're not the cook, great restaurants are in the immediate vicinity minutes away. Get out and explore the neighborhood with restaurants, grocery stores, cafes, and the lakefront just a short walk away. McCormick Place Expo Center is only eight minutes by public transportation. Central heating air conditioning. Keyless entry. We are committed to an enhanced cleaning and sanitation routine, and we practice social distancing and encourage Guest(s) to do the same. Exterior security cameras present: “We have security cameras on the front porch, one facing the back yard area, FreshAir Respiratory Detection System is installed in the common areas of the home and a Noise decibel monitor is present: This property has one or more devices that can assess sound level but don't record audio. ERRORS AND OMISSIONS: All information is deemed reliable but not guaranteed. We are not responsible for errors or omissions. All information provided on the VRBO / Homeaway listing was posted to the U.S. English version of the website and owner is NOT responsible for any translation errors or omissions caused by VRBO / Homeaway incorrectly translating from this original version. Guest agrees this policy supersedes VRBO / Homeaway policy.

Unique and Chic home. rooftop deck, near lakefront. Easy commute to downtown.

Chicago, Illinois, United States

Bed

Bath

Sleeps

$162.45

Enjoy Classic decor in a spacious two bedroom one bathroom. Large eat-in kitchen and laundry in the basement! Tony's grocery story 5 minutes away and Swedish Covenant Hospital. Nearby 92 Foster and 49 Western bus stops and Brown Line train Station.

Cute and Cozy 2 Bedroom

Chicago, Illinois, United States

Bed

Bath

Sleeps

$905.07

Hurry - only a few weekends left this season! Experience Chicago in style from our Villa, your private 3-story luxury retreat near the Bean.brbr! Free Private Garagebr! Hot Tubbr! 360° Roof Deck with Skyline + Willis Tower ViewsbrbrPerfect for family trips, romantic escapes, or friend getaways!br+Private keyless entrybr+Luxury KING, 2 QUEEN beds + cozy fireplacebr+Full kitchen + balconybr+ 3 Smart TVs (Netflix, Disney+, Prime)br+ Super-fast WiFibrbrBook now for your unforgettable Chicago stay!brbrKey Features:brbr- King Suite: Fireplace, Smart TV, and a spa-like steam shower.br-Queen Suite: Private access to a stunning roof deck.br- Fully stocked kitchen with a balcony.br- Coffee Bar: Equipped with a Keurig & French press.br-65 Smart TV: Netflix, Disney+, and Prime streaming.br- Super-fast WiFi for work or play.br-Private car garage for added convenience.br-Roof deck: Incredible views of the Willis Tower.br- Pet-friendly with a fenced-in backyard for your furry friends.brbrbrThis “cool, fun house” is thoughtfully designed for relaxation and entertainment. Whether you’re exploring Chicago, attending an event, or enjoying cozy nights in, this home has everything you need. From high-end amenities to breathtaking views, it promises to wow you, your family, and your friends.brbrP.S Please let us know at least 24 hours in advance if you’d like to use the hot tub. This allows us to ensure the water is clean, warm, and ready for your enjoyment. Hot tub Service Fee $75.00 brUnwind in style with our SaluSpa Hollywood AirJet Hot Tub, complete with ambient color-changing LED lights- perfect for 4 to 6 guestsbrbrbrIMPORTANT : br1) Limit Use to 5 Guests – For safety and comfort, no more than 5 people in the hot tub at a time.br2) Keep It Clean – Please NO soap, oils, bubbles, food, glassware, or smoking in or near the tub.br3) Children Under 12 – Must be supervised by an adult at all times.br4) Protect the Cover – Do not sit or stand on it. Always resecure the cover when finished.br5)Power Down After Use – Turn off jets and lights to help conserve energy.br6)Respect the Space – Excessive mess or damage may result in a $200+ cleaning or repair fee.brbrbrThank you for helping us maintain a safe and enjoyable experience for all guests! brbrbrLocation Highlights:brbr5 minutes to Fulton Market's best restaurantsbr5 minutes to United Center Arena (games & concerts)br7 minutes to Grant Park & Michigan Avenuebr10 minutes to Lake Michiganbr 7 minutes to the Medical District

Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12

Chicago, Illinois, United States

Bed