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Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park
5 out of 5 average rating, 300 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Top Guest favourite
A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.
Home in North Side
4.98 out of 5 average rating, 119 reviews

Flat in Lincoln Park 2-Flat Central to Everything

Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

Top Guest favourite
A light and airy living room is showcased, featuring a comfortable sofa adorned with decorative pillows. Two armchairs are positioned nearby, and a coffee table sits at the center. Natural light filters through two windows, and a large television is mounted on the wall.
Apartment in Lincoln Park
4.96 out of 5 average rating, 139 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Top Guest favourite
A two-story white house is featured, displaying large windows that allow natural light to brighten the façade. The entrance is marked by a covered porch with steps leading up, while planters are placed on either side of the door against a tree-dappled background.
Home in Lincoln Park
4.97 out of 5 average rating, 162 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Top Guest favourite
A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.
Condo in Lake View
4.98 out of 5 average rating, 228 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

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, 195 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.

Guest favourite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in Avondale
4.96 out of 5 average rating, 143 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Top Guest favourite
A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.
Apartment in South Loop
4.91 out of 5 average rating, 203 reviews

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Guest favourite
A modern teal sectional sofa with a tufted design is positioned next to a round marble coffee table. A white fur pillow and a patterned throw are draped on the couch. A black and white cowhide rug adds texture to the wooden floor.
Condo in Old Town Triangle
4.76 out of 5 average rating, 328 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

Guest favourite
A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.
Condo in Gold Coast
4.9 out of 5 average rating, 177 reviews

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Top Guest favourite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Wicker Park
4.95 out of 5 average rating, 137 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Top Guest favourite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Condo in Fulton Market
4.96 out of 5 average rating, 265 reviews

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

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

Guest favourite
The exterior of a modern three-story bungalow is showcased, featuring a mix of brick and dark paneling. A neatly landscaped front yard includes a path leading to the entryway, flanked by lush greenery and decorative stones. The structure retains a contemporary architectural style.
Home in Berwyn
4.96 out of 5 average rating, 26 reviews

The Architectural Haven

Top Guest favourite
A contemporary living area features a large brown leather sectional sofa accompanied by decorative pillows. Behind it, a full-size murphy bed is neatly stored. Large windows allow natural light to illuminate the space, complemented by warm wood flooring and exposed brick walls.
Condo in Lake View
4.96 out of 5 average rating, 27 reviews

The Cub House | Wrigleyville + Boystown |

Guest favourite
Apartment in Magnificent Mile
4.9 out of 5 average rating, 39 reviews

Luxury Designer Penthouse 3803 | Pool | Gold Coast

Guest favourite
Apartment in The Loop
4.92 out of 5 average rating, 49 reviews

Loop 2BR w/Lake Views | 10 min to Millennium Park

Top Guest favourite
A lush garden area showcases a variety of blooming flowers surrounded by greenery. The path is lined with vibrant floral colors leading up to the brick building, which features large windows allowing natural light to fill the space.
Condo in East Rogers Park
4.97 out of 5 average rating, 77 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

Top Guest favourite
Two hanging chairs are positioned on a covered patio, surrounded by lush greenery and decorative plants. A small garden structure adds privacy, while the floor features a vibrant red surface. Ambient light filters through the overhead structure, creating a relaxed outdoor space.
Home in West Town
5 out of 5 average rating, 30 reviews

Chicago Row House Garden Apartmt

Top Guest favourite
A cozy living area features a mix of comfortable seating options, including a dark gray sofa and a brown leather chair. A stone fireplace is centered beneath a large flat-screen TV. Large windows are dressed with red curtains, allowing natural light to fill the space.
Apartment in Logan Square
4.99 out of 5 average rating, 87 reviews

Paradise on the Boulevard!

Guest favourite
A cozy sleeping area features a four-poster bed draped with sheer fabric, creating an intimate ambiance. Bedside tables are positioned on either side, each topped with lamps. Natural light filters through multiple windows, illuminating the softly colored decor and inviting warmth.
Guest suite in South Loop
4.96 out of 5 average rating, 23 reviews

Hidden Gem in South Loop

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, Monthly stays and Lake access 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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