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Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Superhost
A spacious living area features a gray sectional sofa arranged around a wooden coffee table. Soft lighting is provided by ceiling fixtures and wall-mounted sconces. The room leads to a set of stairs, while a TV is mounted on the wall for entertainment.
Flat in Forest Park
4.85 out of 5 average rating, 166 reviews

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest favourite
The living area is furnished with a gray sofa adorned with patterned cushions, positioned next to a natural wood coffee table. A potted plant and a decorative mirror enhance the space. Two windows allow natural light to brighten the room.
Flat in Lower West Side
4.94 out of 5 average rating, 177 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Guest favourite
The exterior of a historic four-story building showcases intricate stonework and arched windows. Two blue doors with glass inserts serve as the main entrance, framed by a wooden porch that leads to the entrance. The surrounding greenery adds a touch of nature.
Loft in Lower West Side
4.71 out of 5 average rating, 165 reviews

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heart of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking only . Located near major transportation, Divvy Bike Station across the street.

Top guest favourite
A bright hallway is illuminated by natural light, showcasing a mix of art and plants. Shelves with various glassware and plants line one wall, while framed artwork featuring mountains and landscapes adds character. Light wooden flooring runs throughout the space.
Flat in Humboldt Park
4.99 out of 5 average rating, 162 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Top guest favourite
A welcoming living space features a blend of modern and natural elements. A green accent wall provides a backdrop to a cozy seating area with black chairs and a sofa. Decorative plants are placed throughout, enhancing the bright and open atmosphere.
Flat in Ukrainian Village
4.99 out of 5 average rating, 213 reviews

Bright Cozy Modern-Chic Condo in Trendy West Town

Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Top guest favourite
A cozy bedroom is featured, showcasing a tufted headboard and a spacious bed dressed in crisp white linens. Flanking the bed are two nightstands with stylish lamps. Light filters through two small windows near the ceiling, illuminating the soft gray walls.
Flat in Lincoln Park
4.96 out of 5 average rating, 466 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Top guest favourite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.98 out of 5 average rating, 186 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Top guest favourite
The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.
Flat in Noble Square
4.97 out of 5 average rating, 581 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Guest favourite
A modern living area features a gray sofa with accent chairs set beside large windows, allowing natural light. A patterned area rug covers the floor, complemented by a minimalist coffee table. Wall art adds subtle elegance, enhancing the overall inviting layout.
Flat in West Town
4.98 out of 5 average rating, 112 reviews

Spacious&Modern Condo | Near Dwtn | Secure Parking

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

Guest favourite
A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.
Flat in Maywood
4.94 out of 5 average rating, 180 reviews

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Guest favourite
The kitchen area features a modern design with wooden cabinetry and a sleek countertop. Four black bar stools are positioned at a counter, which faces an abundance of natural light from a window. The kitchen is equipped with new appliances and organized shelves for easy access.
Flat in Chicago
4.97 out of 5 average rating, 434 reviews

Peaceful River West, free parking

This Apt can be rented separately or together with Comfy River West Apt. https://abnb.me/aoJ0F64vDY This one on the the 2nd floor and one directly above on the 3rd floor. Together they will sleep 8 guest. This beautiful 2BR, 1 BA has all new furniture, all new appliances, counter tops, vanity, mirrors. Free parking in a gated lot, Level 2 EV charging available for electric cars. Shared patio/gardens and grill. Fully stocked kitchen, private washer & dryer.

Top guest favourite
Flat in Lower West Side
4.99 out of 5 average rating, 264 reviews

Simple, Comfortable Pilsen Apt w/ Artistic Touches

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Popular amenities for Chicago holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Chicago's top sights

O'Hare International Airport

145 locals recommend

Wrigley Field

2,179 locals recommend

Logan Square

235 locals recommend

United Center

345 locals recommend

Millennium Park

1,637 locals recommend

Navy Pier

2,004 locals recommend

Other great holiday rentals in Chicago

Top guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Flat in Chicago
5 out of 5 average rating, 81 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Top guest favourite
The living room features two large windows allowing natural light to fill the space. A red sofa and black armchair provide seating, with a small white table beside the couch. A green plant adds a touch of nature, and a piano stands elegantly to the side.
Private room in Streeterville
4.95 out of 5 average rating, 401 reviews

A+ location by Mag Mile, views, large sunny room

Guest favourite
A bright bedroom features a king-sized bed with plush white bedding. Natural light filters through sheer curtains at a window. A simple dresser with a floral arrangement sits adjacent to the bed, complemented by a circular mirror on the wall and a wall-mounted lamp.
Flat in Dunning
4.95 out of 5 average rating, 100 reviews

King Sleep Number Bed – No Cleaning Fee

Top guest favourite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Flat in Lower West Side
4.94 out of 5 average rating, 95 reviews

Pilsen Modern Chic Retreat

Top guest favourite
Private room in South Loop
5 out of 5 average rating, 146 reviews

Urban Oasis Pilsen - guest room in townhouse

Guest favourite
Flat in Chicago
5 out of 5 average rating, 9 reviews

The Mason - Luxe 2BR Designer Flat in Bucktown/WP

Guest favourite
A decorative lantern with a warm, flickering candle sits on a wooden table in the foreground. In the background, a black sofa is paired with light-colored throw pillows, while framed black-and-white photographs adorn the walls. Soft lighting from hanging fixtures creates a cozy ambiance.
Flat in Wicker Park
4.96 out of 5 average rating, 47 reviews

Chic 1 BR in Wicker Parl|1 FREE Garage Parking

Superhost
A light-filled studio space features a plush bed with decorative pillows, accompanied by a modern wooden dresser. A flat-screen TV is mounted on the wall, and a cozy seating area is visible nearby. The open layout includes a kitchen space in the background.
Flat in Hyde Park
4.8 out of 5 average rating, 15 reviews

Hyde Park Studio Near UChicago & Lake

When is the best time to visit Chicago?

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Frequently Asked Questions

  • What are the best places to stay in Chicago?

    Explore neighborhoods like the Loop for architecture and theater, River North for art galleries and dining, or Wicker Park for music and locally owned shops. Lincoln Park is often suggested for access to parks and museums. Each area has a distinctive vibe shaped by arts, food, and community events.

  • What are the best things to do in Chicago with kids?

    Families often explore Shedd Aquarium, the interactive exhibits at the Museum of Science and Industry, and the playful areas at Millennium Park. Maggie Daley Park has climbing walls and play gardens around the park. Chicago’s lakefront paths also invite bike rides and strolls.

  • What are some of the best things to do in Chicago?

    Explore public art at Millennium Park, admire city views from Willis Tower’s Skydeck, or step inside the Art Institute of Chicago. Neighborhoods like Pilsen and Hyde Park have murals and museums with local flavor. The city’s music scene and riverwalk are also popular.

  • How is the weather in Chicago?

    Chicago has cold, often snowy winters with temperatures near 19–33°F (-7–0°C) in January and warm, humid summers around 68–85°F (20–29°C) in July. Spring and fall bring milder, changeable weather. Layers and a windproof jacket can help with breezy days.

  • What are the best places to visit in Chicago?

    Explore the Art Institute of Chicago for world-famous collections, stroll Grant Park’s gardens, or discover Navy Pier’s rides and views. Lincoln Park Zoo and the Field Museum are frequently suggested for learning and family activities. Riverwalk paths connect public art and city life.

  • What are some hiking trails in Chicago?

    The city has paved trails like the Lakefront Trail, winding along the waterfront with parks and skyline views. North Park Village Nature Center has natural paths in a woodland setting. Jackson Park features walking trails amid gardens and lagoons.

  • What are some family activities we can do in Chicago?

    Families can enjoy Cloud Gate in Millennium Park, visit the Shedd Aquarium, or experience hands-on exhibits at the Chicago Children's Museum. Maggie Daley Park has playgrounds, gardens, and seasonal skating. The Lincoln Park Zoo is also popular for its no-fee entry.

  • What are some of the best day trip ideas from Chicago?

    Explore historic towns known for architecture and artists, unwind at nearby lakefront beaches, or visit protected forest preserves with hiking and biking. In warmer months, local farms sometimes have markets and seasonal activities. Regional parks are frequently suggested for nature outings.

  • Are there any pet friendly accommodations available in Chicago?

    Many vacation rentals welcome pets in neighborhoods like Lakeview, Logan Square, and West Loop. The city has dog-friendly parks and outdoor patios where pets can relax with their people. Always confirm pet policies with your host before booking.

  • What are some local tips for visiting Chicago?

    Layer clothing for changing lakefront weather and use public transit to explore neighborhoods beyond downtown. Try local food favorites at corner shops and explore smaller galleries or shops around Pilsen or Andersonville. Many beaches and parks are free and open to all.

  • What is Chicago known for?

    Chicago is known for its skyline, jazz and blues music roots, and locally rooted culinary traditions like deep-dish pizza and Chicago-style hot dogs. The city also has a strong history of public art and diverse neighborhoods. Architecture tours and live theater are frequently suggested.

  • What are the best hidden gems to explore in Chicago?

    Explore murals and independent coffee shops in Pilsen, or the Victorian houses and gardens in the Prairie District. The Alfred Caldwell Lily Pool and the Chicago Cultural Center’s Tiffany dome are often described as peaceful escapes. Quirky museums and bookstores also dot many neighborhoods.

  • What are the best foods to try in Chicago?

    Chicago-style deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs are frequently suggested signature foods. Try popcorn mixes, fried chicken, or savory pierogi in neighborhoods known for their food scenes. Bakeries often serve cheesecake and traditional sweets as well.

  • What should I bring for a trip to Chicago?

    Pack weather-appropriate layers, a windproof jacket, and comfortable shoes for walking. Consider an umbrella or raincoat for spring or fall visits, and sun protection in summer. If you plan to explore the lakefront, bring a refillable water bottle and sunglasses.

  • What is the nightlife in Chicago like?

    Chicago has live music venues, jazz lounges, and comedy clubs in neighborhoods like River North, Wicker Park, and Uptown. Many areas have late-night dining and lively bars. Nightlife here often centers on a mix of music, food, and local performers.

  • What are the most popular events or festivals in Chicago?

    Chicago hosts music festivals in summer, large food celebrations, and the citywide Chicago Air and Water Show. Lollapalooza and the Chicago Blues Festival draw crowds in warmer months, while winter brings holiday light displays and parades. Outdoor neighborhood street fairs run throughout the year.

  • Are there family friendly vacation rentals in Chicago?

    Many vacation rentals in Chicago are family friendly, especially in neighborhoods like Lincoln Park, Lakeview, and Bucktown. These areas are known for access to parks, playgrounds, and dining suited for all ages. Hosts often include information about local family activities.

  • When is the best time to visit Chicago?

    Late spring to early fall is often recommended for milder weather, outdoor events, and green city parks. Winter brings festive lights and ice skating but requires warm clothing. Each season has its own rhythm shaped by events and changing lakefront scenery.

Quick stats about holiday rentals in Chicago

  • Total holiday rentals

    Explore 11,110 holiday rentals in Chicago

  • Verified guest reviews

    Over 591,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,510 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 3,820 rentals that welcome pets

  • Holiday rentals with a pool

    1,270 properties feature pools

  • Rentals with dedicated workspaces

    7,040 properties have a dedicated workspace

  • Wifi availability

    10,940 of Chicago holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Lake access and Free parking on premises across Chicago rentals

  • 4.7 Average rating

    Chicago stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park

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