Chicago

Holiday bungalows in Chicago

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We found 55 Holiday bungalows in Chicago for you

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46
Hotel near Downtown Chicago,Chicago
Chicago’s Gold Coast Luxury Family Mansion. This is an open layout 7,000 SF home. Hotel style accommodations. IG: ChicagoLuxuryairbn. Please inquire for any special needs. Chauffeur, private chef, private jet access and concierge for all your needs.This is not a typical luxury rental. This is a private Gold Coast estate reserved for guests seeking absolute privacy, scale, and discretion. Set within a historic mansion and professionally hosted at a concierge level, the home offers a rare opportunity to stay in one of Chicago’s most exclusive residential properties. Designed for high-profile travelers, private gatherings, and extended luxury stays, this residence is intentionally limited to a select clientele.First floor has a spacious and open living, family, dining rooms, fully equipped kitchen and powder room. Surround sound SONOS music system throughout the entire first floor. Second floor has two master bedrooms and two full bathrooms.Third floor has two bedrooms and two bathrooms. Living room and access to 1200 SF rooftop terrace. One car garage as well as street parking with parking permits that will be provided upon request. Washer & Dryer. Housekeeping is available upon request, daily, weekly ( 24 hr notice).Guests use entire home to themselves. No restrictions. Must request garage opener if plan to park in the house garage. Valet and public transportation is available next door.One block away from the Beach, bars & restaurants. Walking distance to all the best shopping on Oak Street & Michigan Avenue. Dine out for breakfast or dinner without having to take Uber or any transportation. THE BEST location in the entire city everything at your fingertips.The home is stocked with towels, toiletry and slippers for a luxury hotel-like experience. Catering chef is available upon request to prepare meals for you and your guests at the privacy of the home. Inquire about beautiful brunches/lunches or dinners or any special requests or add ons. Home layout:Floor 1: living room, TV, family room, dining room, kitchen, powder room.Floor 2: master bedroom, king bed, pull out sofa, TV, full bathroom, walk-in closet 2nd bedroom, king bed, twin lounge bed, TV, full bathroom. Floor 3: 3rd bedroom, king bed, full bathroom4th bedroom, king bed, full bathroom. Sitting room, roof top deck. Lower level: queen bed, 2 twin beds, full bathroom, garden walk out entrance. Laundry room. 2 car garage or street parking with provided permits.About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Provide age of children.About customRules:Please provide the nature of your trip as well as names and ages of guests.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Smoking allowed outside on front yard or rooftop.About minBookingAge:Minimum age to rent: 21.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 40,Requires approval.
Outstanding
20 reviews
10/10
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33
Hotel near Rogers Park,Chicago
1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building.Conveniently located in the heart of Chicago's most popular northernmost neighborhood. The location is perfect and minutes from anywhere you may want to go in the city. Parks, coffee shops, restaurants, museums.. all just steps away! Spend your days soaking up the sun at Loyola Beach or spend the afternoon at Pottawatomie Park which are few minutes away. You'll also discover the brightly-painted murals, theaters, art galleries, and even a sculpture garden in the Glenwood Avenue Arts District.Guest Access:You’ll have access the the entire unit during your stay.Other details to note:We do not have a designated parking space. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.In case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.**HOUSE RULES**We want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.Shoes off, please. Kindly remove shoes upon entering the unit.No smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.No drugs, including marijuana.No illegal activities anywhere on the property.No parties or events.No outside visitors.No overnight guests without prior approval from the host.Food storage: Please store all food in designated areas and do not leave food out to help prevent pests.Kitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.Damages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.Checkout cleaning:Please wash dishes, return moved furniture to its original place, and take out the trash before checkout.The standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.Towels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.Lost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.Quiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.Late checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.Thank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No smoking and strictly no pets..Late checkout without approval will incur a $50 fee.,Please observe quiet hours from 10:00 PM to 8:00 AM to respect neighbors..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
113 reviews
9.4/10
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29
Hotel near Roscoe Village,Chicago
Steps away from Roscoe Village dining & shopping and a short train to the Mag Mile. Enjoy the best Chicago has to offer by visiting local micro breweries, the scenic 18-mile Lakefront Trail & beaches, and music at venues Northerly Island and Salt Shed. Eight blocks from Wrigley Field, 20 minute Uber to Soldier Field. This thoughtfully designed vacation property is ideal for weeklong visits to Chicago for weddings, family holidays, and multiple families vacationing together.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 29.About events:No events allowed.
Outstanding
76 reviews
9.8/10
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17
Hotel near Ravenswood,Chicago
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/bars, the Davis Theater and unique shopping boutiques. Start your mornings off right by taking a walk to Cafe Selmarie for a delicious breakfast, one of our favorites! Getting to Wrigleyville or downtown will be a breeze with easy access to the Brown line. Professionally designed with stylish decor, comfortable bedding, and smart TV with Netflix will make you feel right at home.Guest Access:You’ll have access the the entire unit during your stay.Other details to note:We do not have a designated parking space. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.In case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.**HOUSE RULES**We want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.Shoes off, please. Kindly remove shoes upon entering the unit.No smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.No drugs, including marijuana.No illegal activities anywhere on the property.No parties or events.No outside visitors.No overnight guests without prior approval from the host.Food storage: Please store all food in designated areas and do not leave food out to help prevent pests.Kitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.Damages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.Checkout cleaning:Please wash dishes, return moved furniture to its original place, and take out the trash before checkout.The standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.Towels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.Lost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.Quiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.Late checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.Thank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No smoking and strictly no pets..Late checkout without approval will incur a $50 fee.,Please observe quiet hours from 10:00 PM to 8:00 AM to respect neighbors..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Outstanding
264 reviews
10/10
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7
Hotel near Andersonville,Chicago
This newly constructed studio offers a stylish, modern space just steps from Clark Street—home to some of the best restaurants, bars, and local shops in the city. With sleek finishes, smart design, and brand new furnishings, this space is perfect for solo travelers or couples looking for comfort and convenience. Whether you’re here to explore the city or just enjoy a weekend getaway, you’ll love being so close to the action while still having a quiet, cozy place to call home.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Amazing
112 reviews
9.6/10
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60
Hotel near Lakeview,Chicago
Welcome to the ultimate Disco Cowboy getaway! This huge house is perfect for bach parties and friends/family trips! Located in Wrigleyville, you can walk to Cubs games, bars/restaurants, & vibrant nightlife!* Sleeps 16 comfortably - 8beds/3bathrooms* 2 free parking spots, plus plenty of free parking down Paulina* Air hockey, ping pong, basketball, bowling* Tons of space for everyone to spread out* 18 min walk to Wrigley Field & Gallagher Way* 2 min walk to coffee shops, restaurants, & bars * 23 min from O'hare Airport* 35 min from Midway AirportAbout pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Great
9.2/10
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19
Hotel near Ravenswood,Chicago
2nd-floor unit with two flights of stairs. Older building with radiant heat managed by building.Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/bars, the Davis Theater and unique shopping boutiques. Start your mornings off right by taking a walk to Cafe Selmarie for a delicious breakfast, one of our favorites! Getting to Wrigleyville or downtown will be a breeze with easy access to the Brown line. Professionally designed with stylish decor, comfortable bedding, and smart TV with Netflix will make you feel right at home.We do not have a designated parking space. There is free street parking on Eastwood Ave on a first come first serve basis. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.In case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.During your stay at our apartment you will have full and private access to the entire apartment on the 2nd floor. You will not have access to other common areas of the apartment building. Due to previous guests not following instructions we have restricted access to the back patio. You can only use the back door as an exit or entrance. You may not loiter on the back patio. None of the chairs or other items on the patio are ours so you would be disrupting our neighbors and using their property without permission. No smoking in the unit also applies to the back patio as well. Check-in any time after 3 pm and as late as 11 pm, check-out at or before 11 am.Guest Access:You’ll have access the the entire unit during your stay.**HOUSE RULES**We want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.Shoes off, please. Kindly remove shoes upon entering the unit.No smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.No drugs, including marijuana.No illegal activities anywhere on the property.No parties or events.No outside visitors.No overnight guests without prior approval from the host.Food storage: Please store all food in designated areas and do not leave food out to help prevent pests.Kitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.Damages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.Checkout cleaning:Please wash dishes, return moved furniture to its original place, and take out the trash before checkout.The standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.Towels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.Lost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.Quiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.Late checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.Thank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!License numberR21000069659About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please make sure to return the keys to the lockbox, close it securely, and scramble the code for safety..Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.,The standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty, an additional cleaning fee of up to $100 may apply..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Great
224 reviews
9.0/10
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44
Hotel near Rogers Park,Chicago
Chicago’s ONLY Urban Beach House combines the best of beach life and urban life! Perfect for couples, students, faculty, families, and vacationers who want to experience the beach house lifestyle while enjoying all of the amenities, conveniences and excitement of an urban location.Virtual tour link: https://www.smartfloorplan.com/p/t/shell5.php?id=v4507431131 W. Morse Ave. is uniquely located just steps from Lake Michigan, Loyola Park and the sandy shores of Loyola, Leone and Albion Beaches. Enjoy convenient access to the CTA Sheridan Bus, the CTA Morse Ave. “El” train station and the Metra train station at Morse Ave. Bicycle enthusiasts can rent a Divvy bicycle within a short distance of the property and explore Chicago’s premiere Lakefront path and bicycle routes. Loyola, DePaul and Northwestern Universities will find this property conveniently located to their campuses. Loyola is in walking distance and DePaul and Northwestern are a short CTA stop away. The house is surrounded by dozens of restaurants and bars, retail and a movie theater all within steps of the house. The City of Evanston, the home of Northwestern University, is a short commute and is considered the Northshore’s capital for restaurants, shopping, and nightlife.Loyola Park offers wide open sandy beaches perfect for exploring. The park is a haven for the sports enthusiast with four tennis courts, basketball courts, three baseball diamonds, sports fields, volleyball courts on the sand and land, a field house, a playground, a fitness circuit course, a nearly 2/3-mile walking trail along the beaches of Lake Michigan, and more. PROPERTY OVERVIEW: 1131 W Morse is loaded with features, including: • a large bedroom with 1 King sized bed that converts to 2 Twins (sleeps 2)• a 2nd bedroom with 1 King sized bed that converts to 2 Twins (sleeps 2)• a 3rd bedroom with 1 Queen sized bed (sleeps 1-2)• a 4th bedroom with 1 Twin sized bed (sleeps 1)• a lower level Family Room with a couch convertible to a Full bed (sleeps 1-2)• The house sleeps 8-9 people• Bedrooms can also be offices• 3 full bathrooms with newly rehabbed oversized showers • a newer chefs kitchen with granite countertops and stainless steel appliances, plenty of cookware and appliances• a large living room with decorative fireplace• a family room with bar and French doors leading to a deck• an office/game room• a fitness room with workout equipment, weights, ball and yoga mats• WIFI• two tv’s and cable (Netflix, Amazon Video, etc.)• washer/dryer with laundry supplies, ironing board and iron• front porch and 2 rear decks• complete patio furniture set• an outdoor fire pit and new 6-burner gas grill for cooking• large rear yard with yard games• direct access to the park and beach• 2 indoor garage parking spaces for an additional fee (Free street parking or two garage spaces for $15/night per space)• air conditioning• 100% smoke free• 100% pet freeBedroom DescriptionsCommodore Room: King bed can be converted to two Twin XL bedsLake Room: Twin XL beds can be converted to a King bed.Boat Room: Boat themed room with Queen bed. (sleeps 1-2)Rogers Room: Rogers Park, Chicago themed room with Twin bed and balconyCabin Room: couch convertible to a Full bed (sleeps 1-2)About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No using the indoor fireplace..No feminine products, baby wipes or other non-septic items in the toilets.,No loud noises between 10:00pm-9:00am..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 26.About events:Events allowed.Maximum event attendees: 20,Additional fees and rules apply. Please inquire..
Amazing
35 reviews
9.6/10
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13
Hotel near Rogers Park,Chicago
Welcome to this thoughtfully preserved 110 year old, original Chicago brick home, just 3 blocks from the Lake Michigan shoreline.Lots of charm and character in this storied home with a serene backyard oasis in the heart of the city! While this historical gem is the perfect private getaway for you & loved ones, its location makes it easy for you to get around.You are:1 Block to Sushi, Thai, Coffee, Jamaican, El Train, Loyola, Live Music15 min to Wrigley18 min to Michigan Ave/DowntownEvery corner of this property has been lovingly cared for to breathe new life into this storied Chicago home while still preserving its history and charm.This craftsman style home features plaster walls, an original nickel mirror on closet door, and a mix of original and period replicated hardware throughout.From the quiet, tree-line street you'll meet a grand, 2 story red brick home with a welcoming wreath on its glass and oak door.Take a journey back in time as you step onto vintage tile floors and head up the ornate wooden stairs under the art deco light fixtures to your second floor abode.Inside, the large foyer opens to the living room which has ample seating. Relax by watching a movie (Apple TV & Netflix provided) or, in the adjoining sun room, enjoy a beverage and peaceful views of the neighborhood.Down the hall, the master bedroom is on the left with two additional bedrooms on the right. Each bedroom has plenty of closet space and a ceiling fan for those that enjoy a little breeze.The hall opens to a grand dining room with expandable table that seats up to 10 so this room can comfortably accommodate just two for a romantic dinner or host a large group for a bustling family meal.Chicago is known for world class restaurants, but sometimes we all need a nice home-cooked meal, right? That's why our kitchen is fully stocked with all the spices & essentials you'll need to prepare a delicious meal of your own, if you choose to.The kitchen also features a pass-through to the dining room with generous bar seating so everyone can interact while meals are prepared.The dining room also opens to a fun sun room with a wall of windows overlooking the trees in the lovely backyard. I recommend sipping a cup of tea and spinning a record while you watch the birds. The comfy couch opens to a full-size pull-out sofa bed.The house is spacious with lots of little areas for family or friends to spend time together or do their own thing. While the home is equipped to host 8 people, we think the perfect group size is 5-6. We're happy to host all 8, but keep in mind it will be a little cozier.*Please inquire if you have a larger group as we have options to expand for up to 16 guests!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.This home is NOT childproofed at all..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
163 reviews
10/10
Check Availability
26
Hotels in Chicago
Be in Chicago and just minutes away from the suburbs. Minutes from Oak Park (Hemingway’s hometown). Close to downtown Oak Park, Elmwood Park, Forest Park, River Grove where you can enjoy great restaurant. Walk to Metra station to catch the train to downtown Chicago.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
156 reviews
9.8/10
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Frequently Asked Questions

What is the average price of a hotel in Chicago this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is TWD 11,633 per night. For a 4-star hotel, the average cost is TWD 15,070 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost TWD 36,198 per night.

How much do hotels in Chicago cost per night on weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is TWD 10,105 per night. For a 4-star hotel, you can expect to pay around TWD 14,075 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost TWD 33,726 per night on weekdays.

What are the best places to stay in Chicago?

Some of the best places to stay in Chicago are near popular attractions like Millennium Park, Willis Tower and Magnificent Mile, offering easy access to key sights and amenities.

What are the top hotels in Chicago near Millennium Park?

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from TWD 7,452), Swissotel Chicago (from TWD 7,727) and Hyatt Regency Chicago (from TWD 9,836), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

How to get good deals on hotels in Chicago?

To get the best hotel deals, try these Trip.com tips: 1. Log In Trip.com first and unlock member-only rates and Trip Coins (loyalty points). 2. Book Midweek: Sun–Thurs stays are much cheaper than weekends. 3. Set Price Alerts: Monitor price drops and rebook if needed. 4. Use “We Price Match” Policy: If you find a lower price elsewhere, Trip.com will refund the difference. 5. Avoid major holidays, conventions, and big events. 6. Check the Deals Page to see what promotions are available now on Trip.com.